HUT67662A - Process for producing new 4-androsteno[4,5-b]pyrrol derivatives and pharmaceutical compositions containing them - Google Patents
Process for producing new 4-androsteno[4,5-b]pyrrol derivatives and pharmaceutical compositions containing them Download PDFInfo
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- HUT67662A HUT67662A HU9401003A HU9401003A HUT67662A HU T67662 A HUT67662 A HU T67662A HU 9401003 A HU9401003 A HU 9401003A HU 9401003 A HU9401003 A HU 9401003A HU T67662 A HUT67662 A HU T67662A
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- 238000000034 method Methods 0.000 title claims description 28
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 133
- 239000000203 mixture Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229940011871 estrogen Drugs 0.000 claims description 13
- 239000000262 estrogen Substances 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 8
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010014733 Endometrial cancer Diseases 0.000 claims description 3
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003886 aromatase inhibitor Substances 0.000 claims description 3
- 230000020176 deacylation Effects 0.000 claims description 3
- 238000005947 deacylation reaction Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 208000011803 breast fibrocystic disease Diseases 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000002357 endometrial effect Effects 0.000 claims description 2
- 201000000079 gynecomastia Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 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 2
- 230000002611 ovarian Effects 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 229940122815 Aromatase inhibitor Drugs 0.000 claims 2
- YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical compound C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000015124 ovarian disease Diseases 0.000 claims 1
- 230000002028 premature Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 102000014654 Aromatase Human genes 0.000 description 7
- 108010078554 Aromatase Proteins 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 229960005471 androstenedione Drugs 0.000 description 4
- 238000005899 aromatization reaction Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- 239000012043 crude product Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- -1 saccirose Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
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- 239000001632 sodium acetate Substances 0.000 description 3
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- 229940032147 starch Drugs 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- KQRGETZTRARSMA-DAELLWKTSA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-6-methylidene-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 KQRGETZTRARSMA-DAELLWKTSA-N 0.000 description 2
- PYTDABYDYFETHL-RDVHEEPHSA-N (8r,9s,10r,13s,14s)-4-amino-10,13-dimethyl-6-methylidene-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1N PYTDABYDYFETHL-RDVHEEPHSA-N 0.000 description 2
- FFKIBVHZKFTRIU-RDVHEEPHSA-N (8r,9s,10r,13s,14s)-4-azido-10,13-dimethyl-6-methylidene-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1N=[N+]=[N-] FFKIBVHZKFTRIU-RDVHEEPHSA-N 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
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- FHPZOWOEILXXBD-UHFFFAOYSA-N phenylseleninyl benzeneseleninate Chemical compound C=1C=CC=CC=1[Se](=O)O[Se](=O)C1=CC=CC=C1 FHPZOWOEILXXBD-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Pyrrole Compounds (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929217035A GB9217035D0 (en) | 1992-08-11 | 1992-08-11 | Androst-4-eno(4,5-b)pyrrole derivatives and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU9401003D0 HU9401003D0 (en) | 1994-07-28 |
| HUT67662A true HUT67662A (en) | 1995-04-28 |
Family
ID=10720180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9401003A HUT67662A (en) | 1992-08-11 | 1993-08-05 | Process for producing new 4-androsteno[4,5-b]pyrrol derivatives and pharmaceutical compositions containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5457097A (enExample) |
| EP (1) | EP0608404B1 (enExample) |
| JP (1) | JPH07500119A (enExample) |
| CN (1) | CN1086220A (enExample) |
| AT (1) | ATE136036T1 (enExample) |
| AU (1) | AU662077B2 (enExample) |
| CA (1) | CA2120726A1 (enExample) |
| DE (1) | DE69302007T2 (enExample) |
| DK (1) | DK0608404T3 (enExample) |
| ES (1) | ES2088289T3 (enExample) |
| FI (1) | FI941635A7 (enExample) |
| GB (1) | GB9217035D0 (enExample) |
| GR (1) | GR3019729T3 (enExample) |
| HU (1) | HUT67662A (enExample) |
| IL (1) | IL106597A (enExample) |
| MX (1) | MX9304852A (enExample) |
| MY (1) | MY108957A (enExample) |
| NZ (1) | NZ254805A (enExample) |
| TW (1) | TW276257B (enExample) |
| WO (1) | WO1994004554A1 (enExample) |
| ZA (1) | ZA935769B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510340A (en) * | 1992-06-12 | 1996-04-23 | Sri International | Antihypercholesterolemic compounds and related pharmaceutical compositions and methods of use |
| CA2794565C (en) | 2010-04-08 | 2018-08-21 | Emory University | Substituted androst-4-ene diones |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3032551A (en) * | 1961-05-25 | 1962-05-01 | Syntex Sa | Pyrrolo(3', 2'-2, 3)-androstanes and process therefor |
| US3282928A (en) * | 1964-04-23 | 1966-11-01 | American Cyanamid Co | 1, 11-iminoestratetraenes |
| GB8503940D0 (en) * | 1985-02-15 | 1985-03-20 | Erba Farmitalia | 4-substituted androstendione derivatives |
| GB8617107D0 (en) * | 1986-07-14 | 1986-08-20 | Erba Farmitalia | 6-/7-methylenandrosta-1 4-diene-3 17-dione derivatives |
| GB8622330D0 (en) * | 1986-09-17 | 1986-10-22 | Erba Farmitalia | 4-substituted 6-alkylidenandrostene-3,17-dione derivatives |
| GB8721384D0 (en) * | 1987-09-11 | 1987-10-21 | Erba Farmitalia | 17-substituted andro-sta-1 4-dien-3-one derivatives |
-
1992
- 1992-08-11 GB GB929217035A patent/GB9217035D0/en active Pending
-
1993
- 1993-07-19 US US08/092,789 patent/US5457097A/en not_active Expired - Fee Related
- 1993-08-05 NZ NZ254805A patent/NZ254805A/en unknown
- 1993-08-05 AT AT93917746T patent/ATE136036T1/de not_active IP Right Cessation
- 1993-08-05 JP JP6505839A patent/JPH07500119A/ja active Pending
- 1993-08-05 ES ES93917746T patent/ES2088289T3/es not_active Expired - Lifetime
- 1993-08-05 DE DE69302007T patent/DE69302007T2/de not_active Expired - Fee Related
- 1993-08-05 AU AU47072/93A patent/AU662077B2/en not_active Ceased
- 1993-08-05 HU HU9401003A patent/HUT67662A/hu unknown
- 1993-08-05 EP EP93917746A patent/EP0608404B1/en not_active Expired - Lifetime
- 1993-08-05 DK DK93917746.5T patent/DK0608404T3/da active
- 1993-08-05 WO PCT/EP1993/002080 patent/WO1994004554A1/en not_active Ceased
- 1993-08-05 CA CA002120726A patent/CA2120726A1/en not_active Abandoned
- 1993-08-05 IL IL106597A patent/IL106597A/xx not_active IP Right Cessation
- 1993-08-09 TW TW082106387A patent/TW276257B/zh active
- 1993-08-09 ZA ZA935769A patent/ZA935769B/xx unknown
- 1993-08-10 MX MX9304852A patent/MX9304852A/es unknown
- 1993-08-10 MY MYPI93001588A patent/MY108957A/en unknown
- 1993-08-10 CN CN93109285A patent/CN1086220A/zh active Pending
-
1994
- 1994-04-08 FI FI941635A patent/FI941635A7/fi not_active Application Discontinuation
-
1996
- 1996-04-23 GR GR960401114T patent/GR3019729T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL106597A0 (en) | 1993-12-08 |
| JPH07500119A (ja) | 1995-01-05 |
| FI941635A0 (fi) | 1994-04-08 |
| US5457097A (en) | 1995-10-10 |
| ES2088289T3 (es) | 1996-08-01 |
| DE69302007D1 (de) | 1996-05-02 |
| AU662077B2 (en) | 1995-08-17 |
| GR3019729T3 (en) | 1996-07-31 |
| DE69302007T2 (de) | 1996-08-29 |
| GB9217035D0 (en) | 1992-09-23 |
| EP0608404A1 (en) | 1994-08-03 |
| EP0608404B1 (en) | 1996-03-27 |
| CA2120726A1 (en) | 1994-03-03 |
| HU9401003D0 (en) | 1994-07-28 |
| MY108957A (en) | 1996-11-30 |
| AU4707293A (en) | 1994-03-15 |
| CN1086220A (zh) | 1994-05-04 |
| DK0608404T3 (da) | 1996-04-29 |
| NZ254805A (en) | 1995-11-27 |
| FI941635A7 (fi) | 1994-04-08 |
| MX9304852A (es) | 1994-02-28 |
| TW276257B (enExample) | 1996-05-21 |
| ZA935769B (en) | 1994-03-08 |
| WO1994004554A1 (en) | 1994-03-03 |
| ATE136036T1 (de) | 1996-04-15 |
| IL106597A (en) | 1997-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFA9 | Temporary protection cancelled due to abandonment |