IL98162A - Alpha-oxopyrrolo (2,3-b) indole-5-acetic acids, esters, amides and related analogs, a process for their preparation and their use as medicaments - Google Patents
Alpha-oxopyrrolo (2,3-b) indole-5-acetic acids, esters, amides and related analogs, a process for their preparation and their use as medicamentsInfo
- Publication number
- IL98162A IL98162A IL9816291A IL9816291A IL98162A IL 98162 A IL98162 A IL 98162A IL 9816291 A IL9816291 A IL 9816291A IL 9816291 A IL9816291 A IL 9816291A IL 98162 A IL98162 A IL 98162A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- oxo
- loweralkyl
- hexahydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000001408 amides Chemical class 0.000 title description 6
- 150000002148 esters Chemical class 0.000 title description 4
- FCIMQYOEWVRZQH-UHFFFAOYSA-N 2-oxo-2-pyrrolo[2,3-b]indol-7-ylacetic acid Chemical class O=C(C(=O)O)C=1C=C2C=3C(=NC2=CC=1)N=CC=3 FCIMQYOEWVRZQH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 58
- SEOVTRFCIGRIMH-UHFFFAOYSA-N Indole-3-acetic acid Natural products C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 57
- 239000003617 indole-3-acetic acid Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- -1 oxalate ester amide Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 230000007074 memory dysfunction Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 239000004480 active ingredient Substances 0.000 claims 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52462790A | 1990-05-17 | 1990-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL98162A0 IL98162A0 (en) | 1992-06-21 |
| IL98162A true IL98162A (en) | 1994-12-29 |
Family
ID=24090019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9816291A IL98162A (en) | 1990-05-17 | 1991-05-16 | Alpha-oxopyrrolo (2,3-b) indole-5-acetic acids, esters, amides and related analogs, a process for their preparation and their use as medicaments |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0457318B1 (en16) |
| JP (1) | JPH0826024B2 (en16) |
| KR (2) | KR100215615B1 (en16) |
| AR (1) | AR247888A1 (en16) |
| AT (1) | ATE141273T1 (en16) |
| AU (1) | AU634380B2 (en16) |
| CA (1) | CA2042737A1 (en16) |
| CZ (1) | CZ280922B6 (en16) |
| DE (1) | DE69121299T2 (en16) |
| DK (1) | DK0457318T3 (en16) |
| ES (1) | ES2094768T3 (en16) |
| FI (1) | FI96689C (en16) |
| GR (1) | GR3021043T3 (en16) |
| HU (1) | HU210179B (en16) |
| IE (1) | IE76318B1 (en16) |
| IL (1) | IL98162A (en16) |
| MX (2) | MX25777A (en16) |
| NO (1) | NO177710C (en16) |
| NZ (2) | NZ238151A (en16) |
| PL (1) | PL290273A1 (en16) |
| PT (1) | PT97688B (en16) |
| ZA (1) | ZA913711B (en16) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983616A (en) * | 1990-02-01 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Hexahydropyrrolo(2,3-B)indole carbamates, ureas, amides and related compounds |
| AU634654B2 (en) * | 1990-05-11 | 1993-02-25 | Hoechst-Roussel Pharmaceuticals Incorporated | Pyrrolo(2,3-b)indole-ketones and analogs, a process for their preparation and their use as medicaments |
| AU649953B2 (en) * | 1990-06-27 | 1994-06-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Tetrahydroisoquinolinylcarbamates of 1,2,3,3A,8,8A-hexahydro-1,3A,8-trimethylpyrrolo(2,3-B)indole |
| US7229986B2 (en) | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| WO2010027334A1 (en) | 2008-09-03 | 2010-03-11 | Nanyang Technological University | Novel tricyclic chiral compounds and their use in asymmetric catalysis |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199076B (it) * | 1984-03-01 | 1988-12-30 | Consiglio Nazionale Ricerche | Derivati della fisostigmina con proprieta'di inibizione della aceticolinesterasi e relativo procedimento di produzione |
| US4791107A (en) * | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
| US4971992A (en) * | 1989-03-27 | 1990-11-20 | Hoechst-Roussel Pharmaceuticals Inc. | Carbonate derivatives of eseroline |
-
1991
- 1991-04-29 AU AU76182/91A patent/AU634380B2/en not_active Ceased
- 1991-05-14 MX MX2577791A patent/MX25777A/es unknown
- 1991-05-14 AR AR91319694A patent/AR247888A1/es active
- 1991-05-15 NZ NZ238151A patent/NZ238151A/en unknown
- 1991-05-15 NO NO911892A patent/NO177710C/no not_active IP Right Cessation
- 1991-05-15 CZ CS911429A patent/CZ280922B6/cs not_active IP Right Cessation
- 1991-05-15 FI FI912363A patent/FI96689C/fi active
- 1991-05-15 NZ NZ260210A patent/NZ260210A/en unknown
- 1991-05-16 PL PL29027391A patent/PL290273A1/xx unknown
- 1991-05-16 IE IE167891A patent/IE76318B1/en not_active IP Right Cessation
- 1991-05-16 AT AT91107942T patent/ATE141273T1/de not_active IP Right Cessation
- 1991-05-16 ZA ZA913711A patent/ZA913711B/xx unknown
- 1991-05-16 JP JP3139418A patent/JPH0826024B2/ja not_active Expired - Lifetime
- 1991-05-16 KR KR1019910007922A patent/KR100215615B1/ko not_active Expired - Fee Related
- 1991-05-16 DK DK91107942.4T patent/DK0457318T3/da active
- 1991-05-16 PT PT97688A patent/PT97688B/pt not_active IP Right Cessation
- 1991-05-16 ES ES91107942T patent/ES2094768T3/es not_active Expired - Lifetime
- 1991-05-16 DE DE69121299T patent/DE69121299T2/de not_active Expired - Fee Related
- 1991-05-16 MX MX2581691A patent/MX25816A/es unknown
- 1991-05-16 CA CA002042737A patent/CA2042737A1/en not_active Abandoned
- 1991-05-16 EP EP91107942A patent/EP0457318B1/en not_active Expired - Lifetime
- 1991-05-16 IL IL9816291A patent/IL98162A/en unknown
- 1991-05-17 HU HU911658A patent/HU210179B/hu not_active IP Right Cessation
-
1996
- 1996-09-13 GR GR960402402T patent/GR3021043T3/el unknown
-
1999
- 1999-02-03 KR KR1019990003497A patent/KR100227715B1/ko not_active Expired - Fee Related
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