UA73333C2 - Branched substituted aminoderivatives of 3-amino-1-phenyl-1n-[1,2,4]triazole, a method for the preparation thereof (variants), pharmaceutical composition and medicament based thereon - Google Patents

Branched substituted aminoderivatives of 3-amino-1-phenyl-1n-[1,2,4]triazole, a method for the preparation thereof (variants), pharmaceutical composition and medicament based thereon Download PDF

Info

Publication number: UA73333C2
Authority: UA; Ukraine
Prior art keywords: cyclopropyl; alkyl; hydrochloride; amine; propyl
Prior art date: 1999-12-17

Application number

UA2002064623A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Sanofi Aventis

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-12-17

Filing date

2000-12-14

Publication date

2005-07-15

2000-12-14 Application filed by Sanofi Aventis filed Critical Sanofi Aventis

2005-07-15 Publication of UA73333C2 publication Critical patent/UA73333C2/uk

Links

238000000034 method Methods 0.000 title claims description 17
150000001412 amines Chemical class 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
239000003814 drug Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 104
125000000217 alkyl group Chemical group 0.000 claims abstract description 76
-1 methylenedioxy group Chemical group 0.000 claims abstract description 49
125000005843 halogen group Chemical group 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 95
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
238000004519 manufacturing process Methods 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
PVPTUASRAVWKGX-UHFFFAOYSA-N 1,2-dihydrotriazol-3-amine Chemical compound NN1NNC=C1 PVPTUASRAVWKGX-UHFFFAOYSA-N 0.000 claims description 16
239000004480 active ingredient Substances 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
150000004677 hydrates Chemical class 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 claims 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
229940055764 triaz Drugs 0.000 claims 1
MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 claims 1
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract description 5
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
229910052736 halogen Inorganic materials 0.000 abstract description 3
125000003545 alkoxy group Chemical group 0.000 abstract description 2
150000002367 halogens Chemical class 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
239000000243 solution Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
229920006395 saturated elastomer Polymers 0.000 description 20
239000011780 sodium chloride Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 18
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 14
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
208000035475 disorder Diseases 0.000 description 13
239000003480 eluent Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
238000003786 synthesis reaction Methods 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 11
150000003141 primary amines Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 9
239000000725 suspension Substances 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000004054 inflammatory process Effects 0.000 description 8
150000002923 oximes Chemical class 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
230000004048 modification Effects 0.000 description 7
238000012986 modification Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
102400000739 Corticotropin Human genes 0.000 description 6
101800000414 Corticotropin Proteins 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
241000700159 Rattus Species 0.000 description 6
230000009471 action Effects 0.000 description 6
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 6
229960000258 corticotropin Drugs 0.000 description 6
239000003921 oil Substances 0.000 description 6
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 6
230000007170 pathology Effects 0.000 description 6
230000028327 secretion Effects 0.000 description 6
230000035882 stress Effects 0.000 description 6
208000019901 Anxiety disease Diseases 0.000 description 5
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
230000036506 anxiety Effects 0.000 description 5
230000006399 behavior Effects 0.000 description 5
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
229910000024 caesium carbonate Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
229910000105 potassium hydride Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
102000004196 processed proteins & peptides Human genes 0.000 description 5
150000003335 secondary amines Chemical class 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
OTANKABMTCCMOJ-UHFFFAOYSA-N 2-anilinoguanidine hydrochloride Chemical compound Cl.NC(=N)NNC1=CC=CC=C1 OTANKABMTCCMOJ-UHFFFAOYSA-N 0.000 description 4
JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 4
208000024827 Alzheimer disease Diseases 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000033228 biological regulation Effects 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000001568 sexual effect Effects 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
ILCVKEBXPLEGOY-ZLFMSJRASA-N 74434-59-6 Chemical compound CC[C@H](C)[C@@H](C(N)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)CNC(=O)[C@H]2NC(=O)CC2)CCC1 ILCVKEBXPLEGOY-ZLFMSJRASA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010006550 Bulimia nervosa Diseases 0.000 description 3
102100021752 Corticoliberin Human genes 0.000 description 3
108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
229940083963 Peptide antagonist Drugs 0.000 description 3
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000009858 acid secretion Effects 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000003542 behavioural effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000002996 emotional effect Effects 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000030136 gastric emptying Effects 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000000185 intracerebroventricular administration Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
101150109980 napA gene Proteins 0.000 description 3
210000002569 neuron Anatomy 0.000 description 3
239000012071 phase Substances 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
238000011160 research Methods 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
108010086511 sauvagine Proteins 0.000 description 3
239000000126 substance Substances 0.000 description 3
229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
VYWUMKDOVBOZFU-UHFFFAOYSA-N 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethanone Chemical compound C1=C(F)C(C)=CC=C1C(=O)CC1CC1 VYWUMKDOVBOZFU-UHFFFAOYSA-N 0.000 description 2
YMMZMIKMXJPZFX-UHFFFAOYSA-N 2-cyclopropyl-1-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1CC1 YMMZMIKMXJPZFX-UHFFFAOYSA-N 0.000 description 2
MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
239000000275 Adrenocorticotropic Hormone Substances 0.000 description 2
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
208000000103 Anorexia Nervosa Diseases 0.000 description 2
208000020446 Cardiac disease Diseases 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
206010053759 Growth retardation Diseases 0.000 description 2
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 2
208000023105 Huntington disease Diseases 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
206010062016 Immunosuppression Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
208000018737 Parkinson disease Diseases 0.000 description 2
208000005107 Premature Birth Diseases 0.000 description 2
206010036590 Premature baby Diseases 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000010171 animal model Methods 0.000 description 2
208000022531 anorexia Diseases 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000000338 anxiogenic effect Effects 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
230000000949 anxiolytic effect Effects 0.000 description 2
229940005530 anxiolytics Drugs 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000008366 benzophenones Chemical class 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000003983 crown ethers Chemical class 0.000 description 2
239000000287 crude extract Substances 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
206010061428 decreased appetite Diseases 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
206010015037 epilepsy Diseases 0.000 description 2
230000005284 excitation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
206010016256 fatigue Diseases 0.000 description 2
210000003608 fece Anatomy 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000012631 food intake Nutrition 0.000 description 2
231100000001 growth retardation Toxicity 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
210000003630 histaminocyte Anatomy 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
201000001421 hyperglycemia Diseases 0.000 description 2
230000001506 immunosuppresive effect Effects 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
210000002011 intestinal secretion Anatomy 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
230000002474 noradrenergic effect Effects 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
230000000770 proinflammatory effect Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
230000001850 reproductive effect Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
239000000777 urocortin Substances 0.000 description 2
230000008728 vascular permeability Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XFINCIOMSDNZHO-UHFFFAOYSA-N (2-chloro-4-methoxy-5-methylphenyl)hydrazine Chemical compound COC1=CC(Cl)=C(NN)C=C1C XFINCIOMSDNZHO-UHFFFAOYSA-N 0.000 description 1
GDCYWRVVKQODGO-UHFFFAOYSA-N (2-chloro-4-methoxy-5-methylphenyl)hydrazine;hydrochloride Chemical compound Cl.COC1=CC(Cl)=C(NN)C=C1C GDCYWRVVKQODGO-UHFFFAOYSA-N 0.000 description 1
WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
FMMVUADITNBALS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-cyclopropylethanone Chemical compound C=1C=C2OCOC2=CC=1C(=O)CC1CC1 FMMVUADITNBALS-UHFFFAOYSA-N 0.000 description 1
SLFNGVGRINFJLK-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methylbenzene Chemical compound CC1=CC=C(Br)C(F)=C1 SLFNGVGRINFJLK-UHFFFAOYSA-N 0.000 description 1
CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical class CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 1
FWIHMKRULOLWKW-UHFFFAOYSA-N 1-phenyl-n-propylbutan-1-amine Chemical compound CCCNC(CCC)C1=CC=CC=C1 FWIHMKRULOLWKW-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
BJEXWFRASFTKNJ-UHFFFAOYSA-N 2-anilinoguanidine Chemical class NC(=N)NNC1=CC=CC=C1 BJEXWFRASFTKNJ-UHFFFAOYSA-N 0.000 description 1
JBGVKJVTILEZNJ-UHFFFAOYSA-N 2-cyclopropyl-1-(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(=O)CC1CC1 JBGVKJVTILEZNJ-UHFFFAOYSA-N 0.000 description 1
QSBBANHYUGUUCO-UHFFFAOYSA-N 2-cyclopropyl-1-[4-(methoxymethyl)phenyl]ethanone Chemical compound C1=CC(COC)=CC=C1C(=O)CC1CC1 QSBBANHYUGUUCO-UHFFFAOYSA-N 0.000 description 1
FAUQRRGKJKMEIW-UHFFFAOYSA-N 2-cyclopropylacetonitrile Chemical compound N#CCC1CC1 FAUQRRGKJKMEIW-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
102100027708 Astrotactin-1 Human genes 0.000 description 1
UICLSIHOOJMJMH-UHFFFAOYSA-N B.O1NBCC1 Chemical compound B.O1NBCC1 UICLSIHOOJMJMH-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
244000201986 Cassia tora Species 0.000 description 1
208000018152 Cerebral disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QQKYFCAJVVQWPC-UHFFFAOYSA-N Cl.[B] Chemical compound Cl.[B] QQKYFCAJVVQWPC-UHFFFAOYSA-N 0.000 description 1
206010010144 Completed suicide Diseases 0.000 description 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
208000001640 Fibromyalgia Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010064147 Gastrointestinal inflammation Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000936741 Homo sapiens Astrotactin-1 Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
206010062767 Hypophysitis Diseases 0.000 description 1
208000005615 Interstitial Cystitis Diseases 0.000 description 1
240000007839 Kleinhovia hospita Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000948268 Meda Species 0.000 description 1
208000019022 Mood disease Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
108090000189 Neuropeptides Proteins 0.000 description 1
102000003797 Neuropeptides Human genes 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010033664 Panic attack Diseases 0.000 description 1
208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 description 1
208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
208000027520 Somatoform disease Diseases 0.000 description 1
208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
108010059705 Urocortins Proteins 0.000 description 1
102000005630 Urocortins Human genes 0.000 description 1
108010011107 Urotensins Proteins 0.000 description 1
102000026557 Urotensins Human genes 0.000 description 1
206010046851 Uveitis Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
FYOWOHMZNWQLFG-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYOWOHMZNWQLFG-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
230000036626 alertness Effects 0.000 description 1
229940124332 anorexigenic agent Drugs 0.000 description 1
230000002891 anorexigenic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
210000003403 autonomic nervous system Anatomy 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
210000001175 cerebrospinal fluid Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000037326 chronic stress Effects 0.000 description 1
206010009887 colitis Diseases 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
210000004748 cultured cell Anatomy 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
150000001912 cyanamides Chemical class 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000003826 endocrine responses Effects 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
210000003016 hypothalamus Anatomy 0.000 description 1
230000008799 immune stress Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000008676 import Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000004807 localization Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
102000006240 membrane receptors Human genes 0.000 description 1
108020004084 membrane receptors Proteins 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
HCOVEUUIZWEZBK-UHFFFAOYSA-N n-(2,2-diethoxyethyl)formamide Chemical compound CCOC(OCC)CNC=O HCOVEUUIZWEZBK-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000000955 neuroendocrine Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
208000027753 pain disease Diseases 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
230000037361 pathway Effects 0.000 description 1
NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
210000003635 pituitary gland Anatomy 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
229920000767 polyaniline Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000003938 response to stress Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
108010045994 tricholysine Proteins 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000000780 urotensin Substances 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Gynecology & Obstetrics (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (AREA)
Pregnancy & Childbirth (AREA)
Diabetes (AREA)
Nutrition Science (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

UA2002064623A 1999-12-17 2000-12-14 Branched substituted aminoderivatives of 3-amino-1-phenyl-1n-[1,2,4]triazole, a method for the preparation thereof (variants), pharmaceutical composition and medicament based thereon UA73333C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9915935A FR2802530B1 (fr)	1999-12-17	1999-12-17	Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2,4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant
PCT/FR2000/003536 WO2001044207A2 (fr)	1999-12-17	2000-12-14	Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2 4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant

Publications (1)

Publication Number	Publication Date
UA73333C2 true UA73333C2 (en)	2005-07-15

Family

ID=9553380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002064623A UA73333C2 (en)	1999-12-17	2000-12-14	Branched substituted aminoderivatives of 3-amino-1-phenyl-1n-[1,2,4]triazole, a method for the preparation thereof (variants), pharmaceutical composition and medicament based thereon

Country Status (34)

Country	Link
US (1)	US6806282B2 (ru)
EP (1)	EP1242389B1 (ru)
JP (1)	JP4146641B2 (ru)
KR (1)	KR100705525B1 (ru)
CN (1)	CN1293061C (ru)
AR (1)	AR031837A1 (ru)
AT (1)	ATE264847T1 (ru)
AU (1)	AU780711B2 (ru)
BR (1)	BR0017023A (ru)
CA (1)	CA2398772C (ru)
CO (1)	CO5251379A1 (ru)
CZ (1)	CZ302460B6 (ru)
DE (1)	DE60010126T2 (ru)
DK (1)	DK1242389T3 (ru)
EA (1)	EA004957B1 (ru)
EE (1)	EE04778B1 (ru)
ES (1)	ES2219436T3 (ru)
FR (1)	FR2802530B1 (ru)
HK (1)	HK1055947A1 (ru)
HU (1)	HUP0204080A3 (ru)
IL (2)	IL150037A0 (ru)
IS (1)	IS2315B (ru)
ME (1)	MEP12108A (ru)
MX (1)	MXPA02006033A (ru)
NO (1)	NO20022828L (ru)
PL (1)	PL203819B1 (ru)
PT (1)	PT1242389E (ru)
RS (1)	RS50289B (ru)
SK (1)	SK285994B6 (ru)
TR (2)	TR200201600T2 (ru)
TW (1)	TWI289554B (ru)
UA (1)	UA73333C2 (ru)
WO (1)	WO2001044207A2 (ru)
ZA (1)	ZA200204422B (ru)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7226920B2 (en) *	2003-08-06	2007-06-05	Vertex Pharmaceuticals Inc.	Aminotriazole compounds useful as inhibitors of protein kinases
JO3019B1 (ar)	2006-04-19	2016-09-05	Janssen Pharmaceutica Nv	ثلاثي مستبدل 4،2،1-ثلاثي زولات
JO2784B1 (en)	2007-10-18	2014-03-15	شركة جانسين فارماسوتيكا ان. في	5,3,1 - Triazole substitute derivative
US8440701B2 (en)	2007-10-18	2013-05-14	Janssen Pharmaceutica Nv	Trisubstituted 1,2,4 triazoles
MY152486A (en) *	2008-03-19	2014-10-15	Janssen Pharmaceutica Nv	Trisubstituted 1,2,4 - triazoles as nicotinic acetylcholine receptor modulators
US8779158B2 (en)	2008-05-09	2014-07-15	Janssen Pharmaceutica Nv	Trisubstituted pyrazoles as acetylcholine receptor modulators
EP2629616A4 (en) *	2010-10-21	2014-03-26	Merck Sharp & Dohme	SUBSTITUTED AMINO-TRIAZOLYL-PDE10-HEMMER
PL3096756T3 (pl)	2014-01-21	2024-10-28	Neurocrine Biosciences, Inc.	Antagonisty receptora CRF1 do leczenia wrodzonego przerostu nadnerczy
CN104059027B (zh) *	2014-07-01	2015-10-28	河北大学	一类含1,2,4-三唑的(e)-甲氧基亚氨基苯乙酸甲酯类化合物及其制备方法和用途
WO2020115555A2 (en)	2018-12-07	2020-06-11	Neurocrine Biosciences, Inc.	Crf1 receptor antagonist, pharmaceutical formulations and solid forms thereof for the treatment of congenital adrenal hyperplasia
CA3155177A1 (en) *	2019-09-25	2021-04-01	Oncoarendi Therapeutics S.A.	Process for the production of 5-(4-((2s,5s)-5-(4-chlorobenzyl)-2-methylmorpholino)piperidin-1-yl)-1h-1,2,4-triazol-3-amine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3869167D1 (de) *	1987-03-27	1992-04-23	Kumiai Chemical Industry Co	Phenyltriazol-derivate und insectizid.
US5795905A (en) *	1995-06-06	1998-08-18	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods relating thereto
FR2763337B1 (fr) *	1997-05-13	1999-08-20	Sanofi Sa	Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant

1999
- 1999-12-17 FR FR9915935A patent/FR2802530B1/fr not_active Expired - Fee Related
2000
- 2000-12-14 EE EEP200200331A patent/EE04778B1/xx not_active IP Right Cessation
- 2000-12-14 ME MEP-121/08A patent/MEP12108A/xx unknown
- 2000-12-14 DE DE60010126T patent/DE60010126T2/de not_active Expired - Lifetime
- 2000-12-14 HU HU0204080A patent/HUP0204080A3/hu unknown
- 2000-12-14 ES ES00988916T patent/ES2219436T3/es not_active Expired - Lifetime
- 2000-12-14 US US10/149,499 patent/US6806282B2/en not_active Expired - Lifetime
- 2000-12-14 CZ CZ20022099A patent/CZ302460B6/cs not_active IP Right Cessation
- 2000-12-14 JP JP2001544697A patent/JP4146641B2/ja not_active Expired - Lifetime
- 2000-12-14 BR BR0017023-2A patent/BR0017023A/pt active Search and Examination
- 2000-12-14 AT AT00988916T patent/ATE264847T1/de active
- 2000-12-14 RS YUP-439/02A patent/RS50289B/sr unknown
- 2000-12-14 CN CNB00819078XA patent/CN1293061C/zh not_active Expired - Fee Related
- 2000-12-14 EA EA200200523A patent/EA004957B1/ru not_active IP Right Cessation
- 2000-12-14 TR TR2002/01600T patent/TR200201600T2/xx unknown
- 2000-12-14 AU AU25259/01A patent/AU780711B2/en not_active Ceased
- 2000-12-14 MX MXPA02006033A patent/MXPA02006033A/es active IP Right Grant
- 2000-12-14 DK DK00988916T patent/DK1242389T3/da active
- 2000-12-14 KR KR1020027007736A patent/KR100705525B1/ko not_active IP Right Cessation
- 2000-12-14 EP EP00988916A patent/EP1242389B1/fr not_active Expired - Lifetime
- 2000-12-14 UA UA2002064623A patent/UA73333C2/uk unknown
- 2000-12-14 SK SK850-2002A patent/SK285994B6/sk not_active IP Right Cessation
- 2000-12-14 WO PCT/FR2000/003536 patent/WO2001044207A2/fr active IP Right Grant
- 2000-12-14 CO CO00095200A patent/CO5251379A1/es not_active Application Discontinuation
- 2000-12-14 PT PT00988916T patent/PT1242389E/pt unknown
- 2000-12-14 PL PL355811A patent/PL203819B1/pl not_active IP Right Cessation
- 2000-12-14 CA CA2398772A patent/CA2398772C/fr not_active Expired - Fee Related
- 2000-12-14 IL IL15003700A patent/IL150037A0/xx active IP Right Grant
- 2000-12-14 TR TR2004/01775T patent/TR200401775T4/xx unknown
- 2000-12-15 AR ARP000106666A patent/AR031837A1/es not_active Application Discontinuation
2001
- 2001-01-29 TW TW089126997A patent/TWI289554B/zh not_active IP Right Cessation
2002
- 2002-05-04 IL IL150037A patent/IL150037A/en not_active IP Right Cessation
- 2002-05-28 IS IS6402A patent/IS2315B/is unknown
- 2002-06-03 ZA ZA200204422A patent/ZA200204422B/en unknown
- 2002-06-13 NO NO20022828A patent/NO20022828L/no not_active Application Discontinuation
2003
- 2003-11-11 HK HK03108164A patent/HK1055947A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE264847T1 (de)	2004-05-15
WO2001044207A3 (fr)	2001-12-20
SK285994B6 (sk)	2008-01-07
JP4146641B2 (ja)	2008-09-10
CA2398772C (fr)	2011-07-05
US20030162771A1 (en)	2003-08-28
KR100705525B1 (ko)	2007-04-10
IS6402A (is)	2002-05-28
IL150037A0 (en)	2002-12-01
NO20022828L (no)	2002-08-19
PT1242389E (pt)	2004-08-31
IS2315B (is)	2007-11-15
TR200201600T2 (tr)	2002-10-21
KR20020061002A (ko)	2002-07-19
MEP12108A (en)	2010-06-10
DE60010126T2 (de)	2005-04-28
HUP0204080A2 (hu)	2003-04-28
CA2398772A1 (fr)	2001-06-21
PL203819B1 (pl)	2009-11-30
YU43902A (sh)	2005-03-15
HK1055947A1 (en)	2004-01-30
EP1242389A2 (fr)	2002-09-25
MXPA02006033A (es)	2003-01-28
US6806282B2 (en)	2004-10-19
SK8502002A3 (en)	2003-02-04
WO2001044207B1 (fr)	2002-06-06
AU2525901A (en)	2001-06-25
EP1242389B1 (fr)	2004-04-21
FR2802530B1 (fr)	2002-02-22
ZA200204422B (en)	2003-11-26
EA004957B1 (ru)	2004-10-28
DE60010126D1 (de)	2004-05-27
RS50289B (sr)	2009-09-08
CZ20022099A3 (cs)	2002-09-11
AR031837A1 (es)	2003-10-08
AU780711B2 (en)	2005-04-14
IL150037A (en)	2007-02-11
EA200200523A1 (ru)	2002-12-26
WO2001044207A2 (fr)	2001-06-21
NO20022828D0 (no)	2002-06-13
DK1242389T3 (da)	2004-08-09
PL355811A1 (en)	2004-05-17
EE200200331A (et)	2003-06-16
TR200401775T4 (tr)	2004-09-21
TWI289554B (en)	2007-11-11
WO2001044207A8 (fr)	2001-07-12
JP2003516975A (ja)	2003-05-20
BR0017023A (pt)	2002-12-03
CO5251379A1 (es)	2003-02-28
ES2219436T3 (es)	2004-12-01
CZ302460B6 (cs)	2011-06-01
EE04778B1 (et)	2007-02-15
FR2802530A1 (fr)	2001-06-22
CN1434808A (zh)	2003-08-06
CN1293061C (zh)	2007-01-03
HUP0204080A3 (en)	2005-01-28

Publication	Publication Date	Title
EP1478363B1 (en)	2009-01-14	Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (vr1) receptor
CA2503884C (en)	2011-07-05	Cyclic sulfamides for inhibition of gamma-secretase
EP1902034B1 (en)	2011-03-30	Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
CA2539042A1 (en)	2005-04-07	Gamma-secretase inhibitors
UA74066C2 (en)	2005-10-17	Derivatives of 4,5-dihydro-1n-pyrazole with antagonistic activity relative to receptors of canabis-1, a method for the preparation trhereof, a pharmaceutical composition and a method for treatment
EP1560580A1 (en)	2005-08-10	Sulfonamides, sulfamates and sulfamides as gamma-secretase inhibitors
AU2007316605A1 (en)	2008-05-15	1,2,4-triazole derivatives as sigma receptor inhibitors
UA73333C2 (en)	2005-07-15	Branched substituted aminoderivatives of 3-amino-1-phenyl-1n-[1,2,4]triazole, a method for the preparation thereof (variants), pharmaceutical composition and medicament based thereon
JPS58180481A (ja)	1983-10-21	新規なピペリジン誘導体
JP2024009948A (ja)	2024-01-23	Ｐ３００／ｃｂｐｈａｔ阻害剤及びそれらの使用の方法
JP2000504039A (ja)	2000-04-04	アミノチアゾール誘導体、その製造方法およびそれを含有してなる医薬組成物
EA005159B1 (ru)	2004-12-30	Производные аминотиазола и их применение в качестве лигандов рецепторов крф
FI76076B (fi)	1988-05-31	Foerfarande foer framstaellning av farmakologiskt vaerdefulla heterocykliska foereningar.
WO2008034644A2 (en)	2008-03-27	Process for making anastrozole
TW200522964A (en)	2005-07-16	5-aryl-pyrimidine derivatives
US6166033A (en)	2000-12-26	2-carbonylthiazole derivatives and use of the same
US4343801A (en)	1982-08-10	1,2,4-Triazine derivatives, and their production and use
SK59995A3 (en)	1995-10-11	Process for preparing enantiomerically pure 6-£(4-chlorophenyl) (1h-triazol-1,2,4-triazol-1-yl) methyl\|-1-methyl-1h-benzotriazole, intermediates for its production and method of its production
WO1999047513A1 (en)	1999-09-23	Heteroaromatic derivatives
EP0030835A1 (en)	1981-06-24	Derivatives of 2-substituted-6-phenyl-3(2H)pyridazinone, their production and pharmaceutical compositions containing them
JPS5953482A (ja)	1984-03-28	ピリダジノン誘導体