NO330456B1 - Pyrazolderivater, medisinske sammensetninger inneholdende slike, medisinsk anvendelse derav samt intermediater for samme - Google Patents

Pyrazolderivater, medisinske sammensetninger inneholdende slike, medisinsk anvendelse derav samt intermediater for samme Download PDF

Info

Publication number: NO330456B1
Authority: NO; Norway
Prior art keywords: group; methyl; pyrazole; isopropyl; alkyl
Prior art date: 2002-08-08

Application number

NO20051209A

Other languages

English (en)

Norwegian (no)

Other versions

NO20051209L (no

Inventor

Nobuhiko Fushimi

Hirotaka Teranishi

Shigeru Yonekubo

Masayuki Lsaji

Kazuo Shimizu

Toshihide Shibazaki

Original Assignee

Kissei Pharmaceutical Company Ltd

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.)

2002-08-08

Filing date

2005-03-08

Publication date

2011-04-18

2005-03-08 Application filed by Kissei Pharmaceutical Company Ltd filed Critical Kissei Pharmaceutical Company Ltd

2005-04-15 Publication of NO20051209L publication Critical patent/NO20051209L/no

2011-04-18 Publication of NO330456B1 publication Critical patent/NO330456B1/no

Links

150000003217 pyrazoles Chemical class 0.000 title claims abstract description 67
239000000203 mixture Substances 0.000 title claims description 216
239000000543 intermediate Substances 0.000 title abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 83
150000003839 salts Chemical class 0.000 claims abstract description 65
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 41
230000002401 inhibitory effect Effects 0.000 claims abstract description 32
208000002249 Diabetes Complications Diseases 0.000 claims abstract description 26
206010012655 Diabetic complications Diseases 0.000 claims abstract description 26
239000003795 chemical substances by application Substances 0.000 claims abstract description 25
125000005843 halogen group Chemical group 0.000 claims abstract description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
201000010099 disease Diseases 0.000 claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
101000716688 Homo sapiens Sodium/glucose cotransporter 1 Proteins 0.000 claims abstract description 18
102000052194 human SLC5A1 Human genes 0.000 claims abstract description 18
201000001421 hyperglycemia Diseases 0.000 claims abstract description 17
208000008589 Obesity Diseases 0.000 claims abstract description 15
235000020824 obesity Nutrition 0.000 claims abstract description 15
230000002265 prevention Effects 0.000 claims abstract description 15
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 10
229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 283
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 232
-1 4-{3-[1-carbamoyl-1-(methyl)ethylcarbamoyl]propyl}-2-methylphenyl Chemical group 0.000 claims description 194
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 89
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 68
125000003277 amino group Chemical group 0.000 claims description 65
125000001424 substituent group Chemical group 0.000 claims description 59
125000006239 protecting group Chemical group 0.000 claims description 52
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
239000003112 inhibitor Substances 0.000 claims description 47
208000002705 Glucose Intolerance Diseases 0.000 claims description 29
201000009104 prediabetes syndrome Diseases 0.000 claims description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
239000008280 blood Substances 0.000 claims description 25
210000004369 blood Anatomy 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
239000004480 active ingredient Substances 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
125000004430 oxygen atom Chemical group O* 0.000 claims description 15
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 14
206010060378 Hyperinsulinaemia Diseases 0.000 claims description 14
230000003451 hyperinsulinaemic effect Effects 0.000 claims description 14
201000008980 hyperinsulinism Diseases 0.000 claims description 14
208000031226 Hyperlipidaemia Diseases 0.000 claims description 13
208000035150 Hypercholesterolemia Diseases 0.000 claims description 12
206010020772 Hypertension Diseases 0.000 claims description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
208000006575 hypertriglyceridemia Diseases 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
201000001320 Atherosclerosis Diseases 0.000 claims description 10
208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
125000004193 piperazinyl group Chemical group 0.000 claims description 10
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 9
229930182830 galactose Natural products 0.000 claims description 9
239000002552 dosage form Substances 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
206010019280 Heart failures Diseases 0.000 claims description 7
206010030113 Oedema Diseases 0.000 claims description 7
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
238000009472 formulation Methods 0.000 claims description 6
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 6
125000004755 (C2-C7) acylamino group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
201000005569 Gout Diseases 0.000 claims description 5
201000001431 Hyperuricemia Diseases 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
230000001771 impaired effect Effects 0.000 claims description 5
238000013268 sustained release Methods 0.000 claims description 5
239000012730 sustained-release form Substances 0.000 claims description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
230000000750 progressive effect Effects 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
125000006411 1-propenylene group Chemical group [H]\C(*)=C(\[H])C([H])([H])[H] 0.000 claims description 3
208000027472 Galactosemias Diseases 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
230000000291 postprandial effect Effects 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 2
ANMVTDVBEDVFRB-UHFFFAOYSA-N 1-propan-2-ylpyrazole Chemical compound CC(C)N1C=CC=N1 ANMVTDVBEDVFRB-UHFFFAOYSA-N 0.000 claims 2
229940002612 prodrug Drugs 0.000 abstract description 7
239000000651 prodrug Substances 0.000 abstract description 7
238000004519 manufacturing process Methods 0.000 abstract description 5
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 238
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 205
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 176
239000002904 solvent Substances 0.000 description 141
239000000243 solution Substances 0.000 description 139
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 118
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
230000002829 reductive effect Effects 0.000 description 101
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
239000011541 reaction mixture Substances 0.000 description 79
238000006243 chemical reaction Methods 0.000 description 69
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 51
238000001914 filtration Methods 0.000 description 46
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
238000004440 column chromatography Methods 0.000 description 40
238000000034 method Methods 0.000 description 39
239000002198 insoluble material Substances 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
239000003480 eluent Substances 0.000 description 36
WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 35
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 35
239000008103 glucose Substances 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000000706 filtrate Substances 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
239000012044 organic layer Substances 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
230000008569 process Effects 0.000 description 31
239000000741 silica gel Substances 0.000 description 31
229910002027 silica gel Inorganic materials 0.000 description 31
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 29
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
239000012442 inert solvent Substances 0.000 description 28
239000000463 material Substances 0.000 description 27
238000010992 reflux Methods 0.000 description 27
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 26
ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 26
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000000843 powder Substances 0.000 description 26
239000007858 starting material Substances 0.000 description 26
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 25
239000000556 agonist Substances 0.000 description 25
229940079593 drug Drugs 0.000 description 25
239000003814 drug Substances 0.000 description 25
239000000284 extract Substances 0.000 description 25
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 25
230000035484 reaction time Effects 0.000 description 25
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 24
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 24
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 23
239000003623 enhancer Substances 0.000 description 23
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 22
239000011780 sodium chloride Substances 0.000 description 22
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 19
102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 19
230000009102 absorption Effects 0.000 description 19
238000010521 absorption reaction Methods 0.000 description 19
239000001257 hydrogen Substances 0.000 description 19
229910052739 hydrogen Inorganic materials 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
239000012298 atmosphere Substances 0.000 description 18
239000012267 brine Substances 0.000 description 17
229920006395 saturated elastomer Polymers 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
239000000872 buffer Substances 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 13
238000001816 cooling Methods 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
238000012360 testing method Methods 0.000 description 13
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 12
108091006277 SLC5A1 Proteins 0.000 description 12
102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 12
229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 12
CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 12
KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical class C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 description 11
206010022489 Insulin Resistance Diseases 0.000 description 11
235000019270 ammonium chloride Nutrition 0.000 description 11
239000013078 crystal Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
230000003914 insulin secretion Effects 0.000 description 11
210000000813 small intestine Anatomy 0.000 description 11
239000000725 suspension Substances 0.000 description 11
102000004877 Insulin Human genes 0.000 description 10
108090001061 Insulin Proteins 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 10
102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 10
238000009903 catalytic hydrogenation reaction Methods 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
229940125396 insulin Drugs 0.000 description 10
239000012071 phase Substances 0.000 description 10
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 9
229940123208 Biguanide Drugs 0.000 description 9
CYAYKKUWALRRPA-HTOAHKCRSA-N [(2r,3s,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O CYAYKKUWALRRPA-HTOAHKCRSA-N 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
210000000692 cap cell Anatomy 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
230000002440 hepatic effect Effects 0.000 description 9
230000002441 reversible effect Effects 0.000 description 9
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TVTJZMHAIQQZTL-WATAJHSMSA-M sodium;(2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate Chemical compound [Na+].C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C([O-])=O)CCCC1=CC=CC=C1 TVTJZMHAIQQZTL-WATAJHSMSA-M 0.000 description 1
NTDIRNUKAZNMSW-IYVGUKHKSA-M sodium;(3s,5r,6e)-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyltetrazol-5-yl)nona-6,8-dienoate Chemical compound [Na+].CN1N=NN=C1C(\C=C\[C@H](O)C[C@H](O)CC([O-])=O)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NTDIRNUKAZNMSW-IYVGUKHKSA-M 0.000 description 1
JQWYNJRCVYGLMO-GPPXSFHXSA-M sodium;5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [Na+].S1C(=O)[N-]C(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 JQWYNJRCVYGLMO-GPPXSFHXSA-M 0.000 description 1
239000008279 sol Substances 0.000 description 1
LLDXOPKUNJTIRF-QFIPXVFZSA-N solabegron Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=1)=CC=CC=1C1=CC=CC(C(O)=O)=C1 LLDXOPKUNJTIRF-QFIPXVFZSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229960000553 somatostatin Drugs 0.000 description 1
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LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 1
229950004311 sorbinil Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229960002909 spirapril Drugs 0.000 description 1
108700035424 spirapril Proteins 0.000 description 1
229960002256 spironolactone Drugs 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960000651 tasosartan Drugs 0.000 description 1
ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
229960005187 telmisartan Drugs 0.000 description 1
229960004084 temocapril Drugs 0.000 description 1
FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960001909 terazosin hydrochloride Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 1
WSWFIVDZAHHZCS-UHFFFAOYSA-N tert-butyl n-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)C(=O)N1CCNCC1 WSWFIVDZAHHZCS-UHFFFAOYSA-N 0.000 description 1
125000005922 tert-pentoxy group Chemical group 0.000 description 1
125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
229960000347 tertatolol hydrochloride Drugs 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229950000584 tezosentan Drugs 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
229940034199 thyrotropin-releasing hormone Drugs 0.000 description 1
229960002961 ticlopidine hydrochloride Drugs 0.000 description 1
MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 1
229950008411 tilisolol Drugs 0.000 description 1
229960005221 timolol maleate Drugs 0.000 description 1
RBKASMJPSJDQKY-RBFSKHHSSA-N tirilazad Chemical compound O=C([C@@H]1[C@@]2(C)CC=C3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)CN(CC1)CCN1C(N=1)=CC(N2CCCC2)=NC=1N1CCCC1 RBKASMJPSJDQKY-RBFSKHHSSA-N 0.000 description 1
229960005155 tirilazad Drugs 0.000 description 1
229950001089 todralazine Drugs 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
229960003069 tolrestat Drugs 0.000 description 1
LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
229960005461 torasemide Drugs 0.000 description 1
229960002051 trandolapril Drugs 0.000 description 1
239000012096 transfection reagent Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
229960000363 trapidil Drugs 0.000 description 1
IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
229960001288 triamterene Drugs 0.000 description 1
229960004813 trichlormethiazide Drugs 0.000 description 1
LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
229950004678 tripamide Drugs 0.000 description 1
UHLOVGKIEARANS-QZHINBJYSA-N tripamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NN2C[C@@H]3[C@H]4CC[C@H](C4)[C@@H]3C2)=C1 UHLOVGKIEARANS-QZHINBJYSA-N 0.000 description 1
108010039189 tripeptidyl-peptidase 2 Proteins 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
229960001130 urapidil Drugs 0.000 description 1
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210000002700 urine Anatomy 0.000 description 1
239000000777 urocortin Substances 0.000 description 1
229960004699 valsartan Drugs 0.000 description 1
ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
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229960001722 verapamil Drugs 0.000 description 1
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239000011534 wash buffer Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
229950006343 zenarestat Drugs 0.000 description 1
229960002769 zofenopril Drugs 0.000 description 1
229950005346 zopolrestat Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Obesity (AREA)
Cardiology (AREA)
Hematology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Heart & Thoracic Surgery (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20051209A 2002-08-08 2005-03-08 Pyrazolderivater, medisinske sammensetninger inneholdende slike, medisinsk anvendelse derav samt intermediater for samme NO330456B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2002232074		2002-08-08
JP2002321729		2002-11-05
PCT/JP2003/010048 WO2004014932A1 (ja)	2002-08-08	2003-08-07	ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体

Publications (2)

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NO20051209L NO20051209L (no)	2005-04-15
NO330456B1 true NO330456B1 (no)	2011-04-18

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US (2)	US7375087B2 (ja)
EP (1)	EP1544208B1 (ja)
JP (1)	JP4540475B2 (ja)
KR (1)	KR100985502B1 (ja)
AT (1)	ATE469161T1 (ja)
AU (1)	AU2003254847B2 (ja)
BR (1)	BRPI0313290B1 (ja)
CA (1)	CA2494179C (ja)
DE (1)	DE60332743D1 (ja)
ES (1)	ES2345250T3 (ja)
HK (1)	HK1082743A1 (ja)
IL (1)	IL166748A0 (ja)
MX (1)	MXPA05001549A (ja)
NO (1)	NO330456B1 (ja)
NZ (1)	NZ538117A (ja)
PL (1)	PL213095B1 (ja)
RU (1)	RU2356906C2 (ja)
TW (1)	TW200413401A (ja)
WO (1)	WO2004014932A1 (ja)

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EP2076503B1 (en)	2006-05-19	2013-07-17	Taisho Pharmaceutical Co., Ltd	C-phenyl glycitol compound for the treatment of diabetes
JP5230613B2 (ja)	2006-05-23	2013-07-10	テラコス・インコーポレイテッド	グルコース輸送体阻害剤およびその使用方法
CA2655937A1 (en)	2006-06-29	2008-01-03	Taisho Pharmaceutical Co., Ltd.	C-phenyl 1-thioglucitol compound
WO2008072726A1 (ja)	2006-12-14	2008-06-19	Taisho Pharmaceutical Co., Ltd.	１－フェニル１－チオ－ｄ－グルシト－ル誘導体
KR101506935B1 (ko) *	2007-04-02	2015-03-31	테라코스, 인코포레이티드	벤질릭 글리코시드 유도체 및 사용 방법
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UA101004C2 (en)	2007-12-13	2013-02-25	Теракос, Инк.	Derivatives of benzylphenylcyclohexane and use thereof
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RU2530494C2 (ru)	2008-08-22	2014-10-10	Теракос, Инк.	Способ получения ингибиторов sglt2
PT2334687E (pt) *	2008-08-28	2012-04-13	Pfizer	Derivados de dioxa-biciclo[3.2.1]octano-2,3,4-triol
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ES2345250T3 (es)	2010-09-20
IL166748A0 (en)	2006-01-15
MXPA05001549A (es)	2005-05-05
US7655632B2 (en)	2010-02-02
BRPI0313290B1 (pt)	2016-12-06
KR100985502B1 (ko)	2010-10-05
RU2005106259A (ru)	2005-08-27
CA2494179A1 (en)	2004-02-19
AU2003254847B2 (en)	2009-06-04
EP1544208B1 (en)	2010-05-26
KR20050059067A (ko)	2005-06-17
US20060166899A1 (en)	2006-07-27
PL213095B1 (pl)	2013-01-31
PL375473A1 (en)	2005-11-28
US7375087B2 (en)	2008-05-20
WO2004014932A1 (ja)	2004-02-19
ATE469161T1 (de)	2010-06-15
CA2494179C (en)	2012-04-24
NO20051209L (no)	2005-04-15
TWI341843B (ja)	2011-05-11
NZ538117A (en)	2007-01-26
DE60332743D1 (de)	2010-07-08
RU2356906C2 (ru)	2009-05-27
JPWO2004014932A1 (ja)	2005-12-02
JP4540475B2 (ja)	2010-09-08
EP1544208A4 (en)	2007-05-02
US20080312153A1 (en)	2008-12-18
AU2003254847A1 (en)	2004-02-25
BR0313290A (pt)	2005-07-05
HK1082743A1 (en)	2006-06-16
TW200413401A (en)	2004-08-01
EP1544208A1 (en)	2005-06-22

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Publication	Publication Date	Title
CA2494179C (en)	2012-04-24	Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
CA2496329C (en)	2012-05-15	Pyrazole derivatives, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
US7393838B2 (en)	2008-07-01	Glucopyranosyloxypyrazole derivatives and use thereof in medicines
JP4606876B2 (ja)	2011-01-05	ピラゾール誘導体、それを含有する医薬組成物及びその医薬用途
US7655633B2 (en)	2010-02-02	Nitrogen-containing heterocyclic derivatives, medicinal compositions containing the same and medicinal use thereof
CA2438595C (en)	2011-08-09	Glucopyranosyloxypyrazole derivatives and medicinal use thereof
US7576064B2 (en)	2009-08-18	Pyrazole derivative, drug composition containing the same and production intermediate therefor
EP1400529A1 (en)	2004-03-24	Glucopyranosyloxypyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate therefor
CA2557766A1 (en)	2005-09-15	Nitrogenous fused-ring derivatives, medicinal compositions containing the derivatives, and use thereof as drugs
US20070185197A1 (en)	2007-08-09	Phenol derivative, medicinal composition containing the same, and medicinal use thereof
EP1550668A1 (en)	2005-07-06	Pyrazole derivative, medicinal composition containing the same, medicinal use thereof and intermediate in producing the same