AP401A - Condensed indole derivatives as 5H4-receptor antagonists. - Google Patents
Condensed indole derivatives as 5H4-receptor antagonists. Download PDFInfo
- Publication number
- AP401A AP401A APAP/P/1993/000494A AP9300494A AP401A AP 401 A AP401 A AP 401A AP 9300494 A AP9300494 A AP 9300494A AP 401 A AP401 A AP 401A
- Authority
- AP
- ARIPO
- Prior art keywords
- indole
- alkyl
- compound according
- hydrogen
- treated
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 4
- 150000002475 indoles Chemical class 0.000 title description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 4
- 239000002464 receptor antagonist Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- -1 polymethylene chain Polymers 0.000 claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 14
- 239000003523 serotonin 4 antagonist Substances 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
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- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
- 235000019502 Orange oil Nutrition 0.000 description 9
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- HBQIITMSFPSBAF-UHFFFAOYSA-N 1,2-dihydro-[1,3]thiazolo[3,2-a]indole-4-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=C2N1CCS2 HBQIITMSFPSBAF-UHFFFAOYSA-N 0.000 description 8
- UNFSNTCNFIQMSM-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N)=C2N1CCCO2 UNFSNTCNFIQMSM-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
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- KBSNNUAQCDKOLL-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]indole-4-carboxylic acid Chemical compound C1=CC=C2N(C=CS3)C3=C(C(=O)O)C2=C1 KBSNNUAQCDKOLL-UHFFFAOYSA-N 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
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- DEWPDCSLWTYBEZ-UHFFFAOYSA-N (1-butylpiperidin-4-yl)methyl 1h-indole-3-carboxylate Chemical compound C1CN(CCCC)CCC1COC(=O)C1=CNC2=CC=CC=C12 DEWPDCSLWTYBEZ-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
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- IMKKVSYOKTZVBO-UHFFFAOYSA-N methyl pyrimido[1,2-a]indole-10-carboxylate Chemical compound C1=CC=NC2=C(C(=O)OC)C3=CC=CC=C3N21 IMKKVSYOKTZVBO-UHFFFAOYSA-N 0.000 description 5
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- OEKWLWGLAKDLIY-UHFFFAOYSA-N ethyl 2-[2-(5-chloropentanoylamino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1NC(=O)CCCCCl OEKWLWGLAKDLIY-UHFFFAOYSA-N 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/452—Piperidinium derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929205428A GB9205428D0 (en) | 1992-03-12 | 1992-03-12 | Pharmaceuticals |
| GB929218846A GB9218846D0 (en) | 1992-09-05 | 1992-09-05 | Pharmaceuticals |
| GB929227045A GB9227045D0 (en) | 1992-12-29 | 1992-12-29 | Pharmaceuticals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9300494A0 AP9300494A0 (en) | 1993-04-30 |
| AP401A true AP401A (en) | 1995-08-29 |
Family
ID=27266092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1993/000494A AP401A (en) | 1992-03-12 | 1993-03-10 | Condensed indole derivatives as 5H4-receptor antagonists. |
Country Status (29)
| Country | Link |
|---|---|
| EP (2) | EP0884319B1 (cs) |
| JP (1) | JP2831467B2 (cs) |
| KR (1) | KR100282730B1 (cs) |
| CN (2) | CN1043893C (cs) |
| AP (1) | AP401A (cs) |
| AT (2) | ATE266033T1 (cs) |
| AU (1) | AU671102B2 (cs) |
| CA (1) | CA2131797C (cs) |
| CY (1) | CY2510B1 (cs) |
| CZ (1) | CZ286194B6 (cs) |
| DE (2) | DE69333504T2 (cs) |
| DK (2) | DK0630376T3 (cs) |
| ES (2) | ES2132223T3 (cs) |
| FI (1) | FI107158B (cs) |
| GR (1) | GR3030668T3 (cs) |
| HU (1) | HU219121B (cs) |
| IL (1) | IL105003A (cs) |
| MA (1) | MA22819A1 (cs) |
| MX (1) | MX9301348A (cs) |
| MY (1) | MY110110A (cs) |
| NO (1) | NO303638B1 (cs) |
| NZ (1) | NZ249565A (cs) |
| PT (1) | PT884319E (cs) |
| RU (1) | RU2104279C1 (cs) |
| SG (1) | SG50693A1 (cs) |
| SI (1) | SI9300114B (cs) |
| SK (1) | SK281423B6 (cs) |
| UA (1) | UA41311C2 (cs) |
| WO (1) | WO1993018036A1 (cs) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5852014A (en) * | 1992-03-12 | 1998-12-22 | Smithkline Beecham P.L.C. | Condensed indole derivatives as 5HT4 -receptor antagonists |
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1993
- 1993-03-10 DK DK93905561T patent/DK0630376T3/da active
- 1993-03-10 KR KR1019940703167A patent/KR100282730B1/ko not_active Expired - Fee Related
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- 1993-03-10 RU RU94040864A patent/RU2104279C1/ru not_active IP Right Cessation
- 1993-03-10 WO PCT/GB1993/000506 patent/WO1993018036A1/en active IP Right Grant
- 1993-03-10 DK DK98114130T patent/DK0884319T3/da active
- 1993-03-10 SK SK1078-94A patent/SK281423B6/sk not_active IP Right Cessation
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- 1993-03-10 IL IL10500393A patent/IL105003A/en not_active IP Right Cessation
- 1993-03-10 AP APAP/P/1993/000494A patent/AP401A/en active
- 1993-03-10 ES ES93905561T patent/ES2132223T3/es not_active Expired - Lifetime
- 1993-03-10 MA MA23113A patent/MA22819A1/fr unknown
- 1993-03-10 ES ES98114130T patent/ES2219813T3/es not_active Expired - Lifetime
- 1993-03-10 SI SI9300114A patent/SI9300114B/sl active Search and Examination
- 1993-03-10 CZ CZ19942210A patent/CZ286194B6/cs not_active IP Right Cessation
- 1993-03-10 AT AT93905561T patent/ATE180785T1/de active
- 1993-03-10 MY MYPI93000436A patent/MY110110A/en unknown
- 1993-03-10 EP EP98114130A patent/EP0884319B1/en not_active Expired - Lifetime
- 1993-03-10 SG SG1996008846A patent/SG50693A1/en unknown
- 1993-03-10 EP EP93905561A patent/EP0630376B1/en not_active Expired - Lifetime
- 1993-03-10 NZ NZ249565A patent/NZ249565A/en not_active IP Right Cessation
- 1993-03-11 MX MX9301348A patent/MX9301348A/es not_active IP Right Cessation
- 1993-03-11 CN CN93102648A patent/CN1043893C/zh not_active Expired - Fee Related
- 1993-05-22 CN CN93107234A patent/CN1085083A/zh active Pending
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1994
- 1994-09-09 NO NO943348A patent/NO303638B1/no not_active IP Right Cessation
- 1994-09-12 FI FI944204A patent/FI107158B/fi not_active IP Right Cessation
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1999
- 1999-06-30 GR GR990401755T patent/GR3030668T3/el unknown
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2005
- 2005-04-12 CY CY0500021A patent/CY2510B1/xx unknown
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| GB1566307A (en) * | 1975-12-19 | 1980-04-30 | Hoechst Ag | Indole derivatives of amides and amino esters and process for their manufacture |
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| EP0485962A2 (en) * | 1990-11-16 | 1992-05-20 | Syntex (U.S.A.) Inc. | New tricyclic compounds |
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