CN1045602C - 四氢吡啶并吲哚衍生物及其药用组合物和制药用途 - Google Patents
四氢吡啶并吲哚衍生物及其药用组合物和制药用途 Download PDFInfo
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- CN1045602C CN1045602C CN95117133A CN95117133A CN1045602C CN 1045602 C CN1045602 C CN 1045602C CN 95117133 A CN95117133 A CN 95117133A CN 95117133 A CN95117133 A CN 95117133A CN 1045602 C CN1045602 C CN 1045602C
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- Prior art keywords
- indoles
- compound
- hydrogen
- tetrahydrochysene
- pyrido
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- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- UFXNNGDEYWTROW-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-pyrrolo[2,3-f]quinoline Chemical class C1C=C2N=CC=CC2=C2C1CCN2 UFXNNGDEYWTROW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 150000002475 indoles Chemical class 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- 229940093499 ethyl acetate Drugs 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- -1 sec.-propyl Chemical group 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- SEIDZCXANHJOSZ-UHFFFAOYSA-N Cl.NN.FC1=CC=CC=C1 Chemical compound Cl.NN.FC1=CC=CC=C1 SEIDZCXANHJOSZ-UHFFFAOYSA-N 0.000 description 3
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- DGCRRYPJCXBLSC-UHFFFAOYSA-N 4-(1-chloroethyl)benzimidazol-2-one Chemical compound CC(Cl)C1=CC=CC2=NC(=O)N=C12 DGCRRYPJCXBLSC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Gyroscopes (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9418326A GB9418326D0 (en) | 1994-09-12 | 1994-09-12 | Pharmaceutical compounds |
| GB9418326.6 | 1994-09-21 | ||
| GBGB9511166.2A GB9511166D0 (en) | 1995-06-02 | 1995-06-02 | Pharmaceutical compounds |
| GB9511166.2 | 1995-06-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1129219A CN1129219A (zh) | 1996-08-21 |
| CN1045602C true CN1045602C (zh) | 1999-10-13 |
Family
ID=26305611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95117133A Expired - Fee Related CN1045602C (zh) | 1994-09-12 | 1995-09-11 | 四氢吡啶并吲哚衍生物及其药用组合物和制药用途 |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0705832B1 (enExample) |
| JP (1) | JPH0881464A (enExample) |
| KR (1) | KR960010635A (enExample) |
| CN (1) | CN1045602C (enExample) |
| AT (1) | ATE247114T1 (enExample) |
| AU (1) | AU698580B2 (enExample) |
| CA (1) | CA2157998A1 (enExample) |
| CZ (1) | CZ286565B6 (enExample) |
| DE (1) | DE69531476T2 (enExample) |
| ES (1) | ES2204932T3 (enExample) |
| FI (1) | FI954243A7 (enExample) |
| HU (1) | HU219491B (enExample) |
| IL (1) | IL115236A (enExample) |
| IN (1) | IN179550B (enExample) |
| MY (1) | MY132009A (enExample) |
| NO (1) | NO305174B1 (enExample) |
| NZ (1) | NZ272961A (enExample) |
| PE (1) | PE41796A1 (enExample) |
| PH (1) | PH31631A (enExample) |
| PL (1) | PL310373A1 (enExample) |
| RU (1) | RU2146256C1 (enExample) |
| TR (1) | TR199501114A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2308362A (en) * | 1995-12-19 | 1997-06-25 | Lilly Industries Ltd | Pharmaceutical indole derivatives |
| EP0905136A1 (en) | 1997-09-08 | 1999-03-31 | Janssen Pharmaceutica N.V. | Tetrahydro gamma-carbolines |
| UA70334C2 (en) * | 1998-10-06 | 2004-10-15 | Janssen Pharmaceutica N V Jans | BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS |
| UA74826C2 (en) * | 2000-05-17 | 2006-02-15 | Ortho Mcneil Pharm Inc | ?-carboline derivatives as phosphodiesterase inhibitors |
| CA2415815A1 (en) * | 2000-07-06 | 2002-01-17 | Nigel H. Greig | Tetrahydrobenzothiazole analogues as neuroprotective agents |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US6586435B2 (en) | 2000-09-19 | 2003-07-01 | Boehringer Ingelheim Pharma Kg | Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| WO2002024661A2 (en) * | 2000-09-19 | 2002-03-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New n, n'-disubstituted benzimidazolone derivatives with affinity at the serotonin and dopamine receptors |
| CA2417082C (en) * | 2000-09-19 | 2009-11-17 | Enzo Cereda | New benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| US7183410B2 (en) | 2001-08-02 | 2007-02-27 | Bidachem S.P.A. | Stable polymorph of flibanserin |
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| BRPI0716439B8 (pt) | 2006-08-14 | 2021-05-25 | Boehringer Ingelheim Int | sistemas de liberação farmacêutico compreendendo flibanserina, processo para preparação e uso dos mesmos |
| BRPI0716436B8 (pt) | 2006-08-25 | 2021-05-25 | Boehringer Ingelheim Int | sistema de liberação controlada e método para fabricação do mesmo |
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| EP0099303A2 (fr) * | 1982-07-14 | 1984-01-25 | Roussel-Uclaf | Nouvelles benzothiopyranopyridinones et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant |
| WO1991016323A1 (fr) * | 1990-04-23 | 1991-10-31 | Rhone-Poulenc Rorer S.A. | Derives du naphtosultame antagonistes de la serotonine, leur preparation et les medicaments les contenant |
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| US4035369A (en) | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| US4636563A (en) * | 1985-09-16 | 1987-01-13 | American Home Products Corporation | Antipsychotic γ-carbolines |
-
1995
- 1995-09-07 AT AT95306253T patent/ATE247114T1/de not_active IP Right Cessation
- 1995-09-07 EP EP95306253A patent/EP0705832B1/en not_active Expired - Lifetime
- 1995-09-07 DE DE69531476T patent/DE69531476T2/de not_active Expired - Fee Related
- 1995-09-07 ES ES95306253T patent/ES2204932T3/es not_active Expired - Lifetime
- 1995-09-08 PH PH51266A patent/PH31631A/en unknown
- 1995-09-08 MY MYPI95002675A patent/MY132009A/en unknown
- 1995-09-08 HU HU9502631A patent/HU219491B/hu not_active IP Right Cessation
- 1995-09-08 AU AU30497/95A patent/AU698580B2/en not_active Ceased
- 1995-09-08 CZ CZ19952322A patent/CZ286565B6/cs not_active IP Right Cessation
- 1995-09-08 NZ NZ272961A patent/NZ272961A/en unknown
- 1995-09-11 CN CN95117133A patent/CN1045602C/zh not_active Expired - Fee Related
- 1995-09-11 IL IL115236A patent/IL115236A/en not_active IP Right Cessation
- 1995-09-11 RU RU95115522A patent/RU2146256C1/ru active
- 1995-09-11 KR KR1019950029475A patent/KR960010635A/ko not_active Ceased
- 1995-09-11 PL PL95310373A patent/PL310373A1/xx unknown
- 1995-09-11 CA CA002157998A patent/CA2157998A1/en not_active Abandoned
- 1995-09-11 JP JP7231873A patent/JPH0881464A/ja active Pending
- 1995-09-11 NO NO953575A patent/NO305174B1/no not_active IP Right Cessation
- 1995-09-11 IN IN1079CA1995 patent/IN179550B/en unknown
- 1995-09-11 FI FI954243A patent/FI954243A7/fi unknown
- 1995-09-12 TR TR95/01114A patent/TR199501114A2/xx unknown
- 1995-09-12 PE PE1995278830A patent/PE41796A1/es not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0099303A2 (fr) * | 1982-07-14 | 1984-01-25 | Roussel-Uclaf | Nouvelles benzothiopyranopyridinones et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant |
| WO1991016323A1 (fr) * | 1990-04-23 | 1991-10-31 | Rhone-Poulenc Rorer S.A. | Derives du naphtosultame antagonistes de la serotonine, leur preparation et les medicaments les contenant |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ272961A (en) | 1998-02-26 |
| ATE247114T1 (de) | 2003-08-15 |
| FI954243A7 (fi) | 1996-03-13 |
| IL115236A0 (en) | 1995-12-31 |
| DE69531476T2 (de) | 2004-06-09 |
| PL310373A1 (en) | 1996-03-18 |
| NO953575D0 (no) | 1995-09-11 |
| PE41796A1 (es) | 1996-10-21 |
| NO953575L (no) | 1996-03-13 |
| CZ232295A3 (en) | 1996-03-13 |
| EP0705832B1 (en) | 2003-08-13 |
| TR199501114A2 (tr) | 1996-10-21 |
| HU9502631D0 (en) | 1995-11-28 |
| AU3049795A (en) | 1996-03-28 |
| FI954243A0 (fi) | 1995-09-11 |
| EP0705832A1 (en) | 1996-04-10 |
| CZ286565B6 (cs) | 2000-05-17 |
| PH31631A (en) | 1999-01-12 |
| CA2157998A1 (en) | 1996-03-13 |
| CN1129219A (zh) | 1996-08-21 |
| HU219491B (hu) | 2001-04-28 |
| JPH0881464A (ja) | 1996-03-26 |
| RU2146256C1 (ru) | 2000-03-10 |
| MY132009A (en) | 2007-09-28 |
| HUT72593A (en) | 1996-05-28 |
| AU698580B2 (en) | 1998-11-05 |
| ES2204932T3 (es) | 2004-05-01 |
| KR960010635A (ko) | 1996-04-20 |
| DE69531476D1 (de) | 2003-09-18 |
| IN179550B (enExample) | 1997-10-18 |
| NO305174B1 (no) | 1999-04-12 |
| IL115236A (en) | 1998-06-15 |
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