DD237510A5 - Verfahren zur herstellung von substituierten imidazo-(1,5-a)pyridin-derivaten - Google Patents

Verfahren zur herstellung von substituierten imidazo-(1,5-a)pyridin-derivaten Download PDF

Info

Publication number: DD237510A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; carboxy; alkyl; hydrogen
Prior art date: 1984-06-20

Application number

DD85277587A

Other languages

German (de)

English (en)

Inventor

Browne

Original Assignee

��`��@��k��

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.)

1984-06-20

Filing date

1985-06-20

Publication date

1986-07-16

1985-06-20 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1986-07-16 Publication of DD237510A5 publication Critical patent/DD237510A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 72
JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 323
-1 amino, ammonio Chemical class 0.000 claims abstract description 193
125000000217 alkyl group Chemical group 0.000 claims abstract description 127
150000003839 salts Chemical class 0.000 claims abstract description 87
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 81
239000001257 hydrogen Substances 0.000 claims abstract description 81
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 58
229910052736 halogen Inorganic materials 0.000 claims abstract description 58
150000002367 halogens Chemical class 0.000 claims abstract description 57
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 57
150000002431 hydrogen Chemical class 0.000 claims abstract description 53
238000002360 preparation method Methods 0.000 claims abstract description 33
230000008569 process Effects 0.000 claims abstract description 32
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 31
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
239000000203 mixture Substances 0.000 claims description 63
125000004432 carbon atom Chemical group C* 0.000 claims description 62
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
125000004093 cyano group Chemical group *C#N 0.000 claims description 42
125000003545 alkoxy group Chemical group 0.000 claims description 37
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
125000004414 alkyl thio group Chemical group 0.000 claims description 35
125000001424 substituent group Chemical group 0.000 claims description 32
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 28
125000003396 thiol group Chemical class [H]S* 0.000 claims description 28
125000003282 alkyl amino group Chemical group 0.000 claims description 26
125000004423 acyloxy group Chemical group 0.000 claims description 24
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
239000007858 starting material Substances 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
125000001589 carboacyl group Chemical group 0.000 claims description 22
150000003254 radicals Chemical class 0.000 claims description 22
229910052740 iodine Inorganic materials 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
230000002829 reductive effect Effects 0.000 claims description 14
230000002378 acidificating effect Effects 0.000 claims description 13
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 claims description 10
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 10
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 10
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
125000005110 aryl thio group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 5
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 5
125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000005237 alkyleneamino group Chemical group 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
CETYHXLCJBBAHU-UHFFFAOYSA-N 5-(4-bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1=CC(Br)=CC=C1C1N2C=NC=C2CCC1 CETYHXLCJBBAHU-UHFFFAOYSA-N 0.000 claims description 4
125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
125000005907 alkyl ester group Chemical group 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000004970 halomethyl group Chemical group 0.000 claims description 4
ZRBDYBQIBBZJBE-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC2=CN=CN12 ZRBDYBQIBBZJBE-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 2
230000007423 decrease Effects 0.000 claims 1
FSLPUIQRTFZEMT-UHFFFAOYSA-N ethyl 2-[5-(4-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-6-yl]acetate Chemical compound CCOC(=O)CC1CCC2=CN=CN2C1C1=CC=C(C#N)C=C1 FSLPUIQRTFZEMT-UHFFFAOYSA-N 0.000 claims 1
102000014654 Aromatase Human genes 0.000 abstract description 10
108010078554 Aromatase Proteins 0.000 abstract description 10
125000002252 acyl group Chemical group 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
230000005764 inhibitory process Effects 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 5
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
239000000243 solution Substances 0.000 description 116
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
239000011541 reaction mixture Substances 0.000 description 44
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
229910052938 sodium sulfate Inorganic materials 0.000 description 38
235000011152 sodium sulphate Nutrition 0.000 description 38
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000012074 organic phase Substances 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
239000002585 base Substances 0.000 description 22
239000007787 solid Substances 0.000 description 21
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
239000000284 extract Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
150000008064 anhydrides Chemical class 0.000 description 9
229940011871 estrogen Drugs 0.000 description 9
239000000262 estrogen Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
239000002775 capsule Substances 0.000 description 8
238000007363 ring formation reaction Methods 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
238000001914 filtration Methods 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000003826 tablet Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
238000009835 boiling Methods 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
150000003973 alkyl amines Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229940043279 diisopropylamine Drugs 0.000 description 5
239000008298 dragée Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
125000005905 mesyloxy group Chemical group 0.000 description 5
239000012071 phase Substances 0.000 description 5
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
239000008107 starch Substances 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD85277587A 1984-06-20 1985-06-20 Verfahren zur herstellung von substituierten imidazo-(1,5-a)pyridin-derivaten DD237510A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/622,421 US4617307A (en)	1984-06-20	1984-06-20	Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors

Publications (1)

Publication Number	Publication Date
DD237510A5 true DD237510A5 (de)	1986-07-16

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DD85277587A DD237510A5 (de)	1984-06-20	1985-06-20	Verfahren zur herstellung von substituierten imidazo-(1,5-a)pyridin-derivaten

Country Status (31)

Country	Link
US (1)	US4617307A (no)
EP (1)	EP0165904B1 (no)
JP (1)	JPS6112688A (no)
KR (1)	KR900008566B1 (no)
AT (1)	ATE62415T1 (no)
AU (1)	AU589565B2 (no)
BG (7)	BG60262B2 (no)
CA (1)	CA1276633C (no)
CS (1)	CS268672B2 (no)
CY (1)	CY1750A (no)
DD (1)	DD237510A5 (no)
DE (1)	DE3582452D1 (no)
DK (1)	DK170302B1 (no)
DZ (1)	DZ799A1 (no)
ES (6)	ES8702406A1 (no)
FI (1)	FI80694C (no)
GR (1)	GR851487B (no)
HK (1)	HK23494A (no)
HU (1)	HU202529B (no)
IE (1)	IE58070B1 (no)
IL (1)	IL75546A (no)
MA (1)	MA20459A1 (no)
MX (1)	MX9203369A (no)
NO (1)	NO162467C (no)
NZ (1)	NZ212483A (no)
PH (1)	PH23390A (no)
PL (6)	PL145103B1 (no)
PT (1)	PT80661B (no)
RO (1)	RO92583A (no)
SU (6)	SU1433413A3 (no)
ZA (1)	ZA854615B (no)

Families Citing this family (66)

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Publication number	Priority date	Publication date	Assignee	Title
US5428160A (en) *	1982-12-21	1995-06-27	Ciba-Geigy Corporation	Substituted imidazo[5-a]pyridine derviatives and other substituted bicyclic derivatives
US4889861A (en) *	1982-12-21	1989-12-26	Ciba-Geigy Corp.	Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors
US4728645A (en) *	1982-12-21	1988-03-01	Ciba-Geigy Corporation	Substituted imidazo[1,5-A]pyridine derivatives and other substituted bicyclic derivatives, useful as aromatase inhibitors
GB8510541D0 (en) *	1985-04-25	1985-05-30	Wyeth John & Brother Ltd	Heterocyclic compounds
US5171858A (en) *	1985-06-05	1992-12-15	Schering A.G.	Preparation of certain 5,6-dihydro-8-phenyl-imidazo[1,5-a]pyridines
US4749713A (en) *	1986-03-07	1988-06-07	Ciba-Geigy Corporation	Alpha-heterocycle substituted tolunitriles
US4978672A (en) *	1986-03-07	1990-12-18	Ciba-Geigy Corporation	Alpha-heterocyclc substituted tolunitriles
US4937250A (en) *	1988-03-07	1990-06-26	Ciba-Geigy Corporation	Alpha-heterocycle substituted tolunitriles
IL83163A (en) *	1986-07-18	1991-06-10	Erba Carlo Spa	Cycloalkyl-substituted 4-pyridyl derivatives,their preparation and pharmaceutical compositions containing them
GB8820730D0 (en) *	1988-09-02	1988-10-05	Erba Carlo Spa	Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation
US5057521A (en) *	1988-10-26	1991-10-15	Ciba-Geigy Corporation	Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism
CA2026792A1 (en) *	1989-11-01	1991-05-02	Michael N. Greco	(6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives
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1984
- 1984-06-20 US US06/622,421 patent/US4617307A/en not_active Expired - Lifetime
1985
- 1985-06-17 DE DE8585810279T patent/DE3582452D1/de not_active Expired - Lifetime
- 1985-06-17 AT AT85810279T patent/ATE62415T1/de not_active IP Right Cessation
- 1985-06-17 FI FI852399A patent/FI80694C/fi not_active IP Right Cessation
- 1985-06-17 EP EP85810279A patent/EP0165904B1/de not_active Expired - Lifetime
- 1985-06-18 IL IL75546A patent/IL75546A/xx not_active IP Right Cessation
- 1985-06-18 DZ DZ850130A patent/DZ799A1/fr active
- 1985-06-18 GR GR851487A patent/GR851487B/el unknown
- 1985-06-18 CA CA000484263A patent/CA1276633C/en not_active Expired - Lifetime
- 1985-06-18 CS CS854449A patent/CS268672B2/cs not_active IP Right Cessation
- 1985-06-19 BG BG70749A patent/BG60262B2/xx unknown
- 1985-06-19 HU HU852417A patent/HU202529B/hu unknown
- 1985-06-19 NO NO852474A patent/NO162467C/no unknown
- 1985-06-19 MA MA20686A patent/MA20459A1/fr unknown
- 1985-06-19 AU AU43857/85A patent/AU589565B2/en not_active Expired
- 1985-06-19 PT PT80661A patent/PT80661B/pt unknown
- 1985-06-19 RO RO85119210A patent/RO92583A/ro unknown
- 1985-06-19 ES ES544344A patent/ES8702406A1/es not_active Expired
- 1985-06-19 DK DK277685A patent/DK170302B1/da not_active IP Right Cessation
- 1985-06-19 SU SU853917403A patent/SU1433413A3/ru active
- 1985-06-19 KR KR1019850004323A patent/KR900008566B1/ko not_active IP Right Cessation
- 1985-06-19 ZA ZA854615A patent/ZA854615B/xx unknown
- 1985-06-19 IE IE152085A patent/IE58070B1/en not_active IP Right Cessation
- 1985-06-19 PH PH32427A patent/PH23390A/en unknown
- 1985-06-19 NZ NZ212483A patent/NZ212483A/xx unknown
- 1985-06-20 PL PL1985259303A patent/PL145103B1/pl unknown
- 1985-06-20 PL PL1985259306A patent/PL145104B1/pl unknown
- 1985-06-20 PL PL1985259305A patent/PL145814B1/pl unknown
- 1985-06-20 DD DD85277587A patent/DD237510A5/de not_active IP Right Cessation
- 1985-06-20 PL PL1985259307A patent/PL145105B1/pl unknown
- 1985-06-20 PL PL1985254099A patent/PL145087B1/pl unknown
- 1985-06-20 PL PL1985259304A patent/PL145348B1/pl unknown
- 1985-06-20 JP JP60133167A patent/JPS6112688A/ja active Granted
1986
- 1986-05-30 ES ES555539A patent/ES8802155A1/es not_active Expired
- 1986-05-30 ES ES555542A patent/ES8802049A1/es not_active Expired
- 1986-05-30 ES ES555541A patent/ES8800681A1/es not_active Expired
- 1986-05-30 ES ES555540A patent/ES8801262A1/es not_active Expired
- 1986-05-30 ES ES555538A patent/ES8802048A1/es not_active Expired
- 1986-07-02 SU SU864027756A patent/SU1482530A3/ru active
- 1986-07-02 SU SU864027754A patent/SU1436878A3/ru active
- 1986-07-02 SU SU864027758A patent/SU1443802A3/ru active
- 1986-07-02 SU SU864027757A patent/SU1436880A3/ru active
- 1986-07-02 SU SU864027755A patent/SU1436879A3/ru active
1992
- 1992-06-25 MX MX9203369A patent/MX9203369A/es unknown
- 1992-10-22 BG BG097012A patent/BG60352B2/bg not_active Expired - Lifetime
- 1992-10-22 BG BG097010A patent/BG60306B2/bg unknown
- 1992-10-22 BG BG097011A patent/BG60307B2/xx unknown
- 1992-10-22 BG BG097013A patent/BG60353B2/bg unknown
- 1992-10-22 BG BG097009A patent/BG60305B2/bg unknown
1993
- 1993-11-11 BG BG098213A patent/BG60402B2/bg unknown
1994
- 1994-03-17 HK HK234/94A patent/HK23494A/xx not_active IP Right Cessation
- 1994-06-03 CY CY175094A patent/CY1750A/xx unknown

Also Published As

Publication number	Publication date
DK170302B1 (da)	1995-07-31
MA20459A1 (fr)	1985-12-31
US4617307A (en)	1986-10-14
FI80694B (fi)	1990-03-30
ES555538A0 (es)	1988-03-16
PL145103B1 (en)	1988-08-31
SU1482530A3 (ru)	1989-05-23
DE3582452D1 (de)	1991-05-16
IL75546A (en)	1990-01-18
DK277685A (da)	1985-12-21
SU1443802A3 (ru)	1988-12-07
CS444985A2 (en)	1989-07-12
KR860000299A (ko)	1986-01-27
PL145105B1 (en)	1988-08-31
PL145814B1 (en)	1988-11-30
BG60402B2 (bg)	1995-02-28
DZ799A1 (fr)	2004-09-13
EP0165904A3 (en)	1987-09-09
NZ212483A (en)	1988-10-28
ES555539A0 (es)	1988-04-01
CA1276633C (en)	1990-11-20
KR900008566B1 (ko)	1990-11-24
ES8800681A1 (es)	1987-11-16
FI852399L (fi)	1985-12-21
IE851520L (en)	1985-12-20
BG60307B2 (en)	1994-07-25
JPS6112688A (ja)	1986-01-21
SU1436880A3 (ru)	1988-11-07
HUT37936A (en)	1986-03-28
SU1433413A3 (ru)	1988-10-23
BG60352B2 (bg)	1994-11-30
PL254099A1 (en)	1986-09-09
ES8802155A1 (es)	1988-04-01
EP0165904B1 (de)	1991-04-10
ES8802049A1 (es)	1988-03-16
EP0165904A2 (de)	1985-12-27
IE58070B1 (en)	1993-06-30
BG60262B1 (bg)	1994-03-31
NO852474L (no)	1985-12-23
MX9203369A (es)	1992-09-01
PL145348B1 (en)	1988-09-30
ATE62415T1 (de)	1991-04-15
JPH047746B2 (no)	1992-02-12
BG60306B2 (bg)	1994-07-25
ES555540A0 (es)	1987-12-16
ES8801262A1 (es)	1987-12-16
GR851487B (no)	1985-11-25
PL145087B1 (en)	1988-08-31
FI852399A0 (fi)	1985-06-17
CS268672B2 (en)	1990-04-11
BG60305B2 (bg)	1994-07-25
DK277685D0 (da)	1985-06-19
ES555541A0 (es)	1987-11-16
ES8702406A1 (es)	1987-01-01
PL145104B1 (en)	1988-08-31
BG60262B2 (en)	1994-03-31
NO162467C (no)	1990-01-10
FI80694C (fi)	1990-07-10
PT80661A (en)	1985-07-01
ES8802048A1 (es)	1988-03-16
ZA854615B (en)	1986-02-26
IL75546A0 (en)	1985-10-31
PH23390A (en)	1989-07-26
HK23494A (en)	1994-03-25
SU1436878A3 (ru)	1988-11-07
RO92583A (ro)	1987-11-30
HU202529B (en)	1991-03-28
SU1436879A3 (ru)	1988-11-07
NO162467B (no)	1989-09-25
CY1750A (en)	1994-06-03
ES555542A0 (es)	1988-03-16
AU4385785A (en)	1986-01-02
BG60353B2 (bg)	1994-11-30
PT80661B (en)	1987-05-04
ES544344A0 (es)	1987-01-01
AU589565B2 (en)	1989-10-19

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD237510A5 (de)	1986-07-16	Verfahren zur herstellung von substituierten imidazo-(1,5-a)pyridin-derivaten
EP0682027B1 (de)	1997-10-15	Pyrrolopyrimidinderivate mit antiproliferativer Wirkung
EP0059391B1 (de)	1985-05-08	Imidazodiazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE60016566T2 (de)	2005-12-15	Triazolopyridazinderivate als liganden für gaba-rezeptoren
DE3724164A1 (de)	1988-01-28	Neue 1,4-benzodiazepine, ihre herstellung und verwendung
EP0100906B1 (de)	1987-05-13	Tri- und tetracyclische Imidazo(1,5-a)(1,4)Benzodiazepin-1-carbonsäurederivate
EP0408509B1 (de)	1996-03-06	Substituierte Benzonitrile
EP1071670B1 (de)	2004-07-07	Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel
CH646696A5 (de)	1984-12-14	Dibenzazepine, ihre herstellung und verwendung.
EP0255028A2 (de)	1988-02-03	Neue 1,4-Benzodiazepine, ihre Herstellung und Verwendung als PAF Antagonisten
EP0490816A2 (de)	1992-06-17	Fluorverbindungen
EP0539803B1 (de)	1999-01-07	Triazaspirodecanon-Methyl-Chromane zur Bekämpfung von Erkrankungen des Zentralnervensystems
EP0298921B1 (de)	1992-12-23	1,2-Benzisoxazole und 1,2-Benzisothiazole
DE2423759A1 (de)	1974-12-19	2-(pyrrol-1-yl)-amino-4,5-dihydro1h-imidazol-derivate
DD208153A5 (de)	1984-03-28	Verfahren zur herstellung von benzodiazepinderivaten
EP0233483A2 (de)	1987-08-26	Pyrrolo[1,2-a][4,1]benzoxazepine, Verfahren zur ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie therapeutische Verwendung
EP0477141A1 (de)	1992-03-25	Heteroarylmethylbenzole-Aromatasehemmer
EP0285837A1 (de)	1988-10-12	Imidazodiazepin-Derivate
EP0273168A1 (de)	1988-07-06	Triazaspirodecanylmethylindolon-Derivate
DE2736652C2 (no)	1989-07-06
DE69707080T2 (de)	2002-05-02	Pyrrolidinonderivate und ihre Verwendung als antipsychotische Arzneimittel
DD220307A5 (de)	1985-03-27	Verfahren zur herstellung von polycyclische carbonsaeureverbindungen
EP0357043A2 (de)	1990-03-07	Imidazodiazepin-Derivate
EP0195939B1 (de)	1991-06-12	Imidazodiazepin-Derivate
EP0555825A1 (de)	1993-08-18	Imidazo 1,2-a pyridine als Angiotensin-II-Antagonisten