IL103304A - History of Krabmat 3 - Isoxazolidinones Hydroxypyrrolidine - 2 - Cyclopropenic acid lozenges and analogues - Google Patents
History of Krabmat 3 - Isoxazolidinones Hydroxypyrrolidine - 2 - Cyclopropenic acid lozenges and analoguesInfo
- Publication number
- IL103304A IL103304A IL10330492A IL10330492A IL103304A IL 103304 A IL103304 A IL 103304A IL 10330492 A IL10330492 A IL 10330492A IL 10330492 A IL10330492 A IL 10330492A IL 103304 A IL103304 A IL 103304A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- hydrogen
- loweralkyl
- formula
- carbamate
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003814 drug Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000004657 carbamic acid derivatives Chemical class 0.000 title abstract description 5
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 5
- JQBCKRZQAMELAD-UHFFFAOYSA-N 1-hydroxypyrrolidin-2-one Chemical class ON1CCCC1=O JQBCKRZQAMELAD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 230000007074 memory dysfunction Effects 0.000 claims abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 38
- -1 (3aS-cis)- 1 ,2,3,3a,8,8a-hexahydro- 1 ,3a,8-trimethylpyrrolo-[2,3-b]indol-5-yl Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- RORCEARPBRSXAP-GSVOUGTGSA-N [(3R)-1-hydroxy-2-oxopyrrolidin-3-yl] carbamate Chemical compound C(N)(O[C@H]1C(N(CC1)O)=O)=O RORCEARPBRSXAP-GSVOUGTGSA-N 0.000 claims 1
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- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical class OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 abstract 1
- HCKUBNLZMKAEIN-UHFFFAOYSA-N 3-amino-1-hydroxypyrrolidin-2-one Chemical class NC1CCN(O)C1=O HCKUBNLZMKAEIN-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 7
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/769,268 US5153193A (en) | 1991-10-01 | 1991-10-01 | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL103304A0 IL103304A0 (en) | 1993-02-21 |
| IL103304A true IL103304A (en) | 1996-12-05 |
Family
ID=25084962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10330492A IL103304A (en) | 1991-10-01 | 1992-09-30 | History of Krabmat 3 - Isoxazolidinones Hydroxypyrrolidine - 2 - Cyclopropenic acid lozenges and analogues |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5153193A (ja) |
| EP (2) | EP1069125A3 (ja) |
| JP (1) | JP2703157B2 (ja) |
| KR (2) | KR100276143B1 (ja) |
| AT (1) | ATE201024T1 (ja) |
| AU (1) | AU649882B2 (ja) |
| CA (1) | CA2079548C (ja) |
| CZ (1) | CZ281982B6 (ja) |
| DE (1) | DE69231817T2 (ja) |
| DK (1) | DK0535645T3 (ja) |
| ES (1) | ES2157201T3 (ja) |
| FI (2) | FI102178B1 (ja) |
| GR (1) | GR3036334T3 (ja) |
| HU (1) | HU215120B (ja) |
| IL (1) | IL103304A (ja) |
| MX (1) | MX9205577A (ja) |
| NO (1) | NO301884B1 (ja) |
| NZ (1) | NZ244540A (ja) |
| PT (1) | PT535645E (ja) |
| RU (1) | RU2103271C1 (ja) |
| TW (1) | TW208009B (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231093A (en) * | 1991-10-01 | 1993-07-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
| IT1253007B (it) * | 1991-12-31 | 1995-07-10 | Aesculapius Farma Srl | Derivati dell'eserolina ad attivita' anticolinesterasica,procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
| US5480651A (en) * | 1992-03-16 | 1996-01-02 | Regents Of The University Of California | Composition and method for treating nicotine craving in smoking cessation |
| US6316439B1 (en) * | 1993-10-15 | 2001-11-13 | Aventis Pharamaceuticals Inc. | Galanthamine derivatives as acetylcholinesterase inhibitors |
| US6323196B1 (en) * | 1993-10-15 | 2001-11-27 | Aventis Pharmaceuticals Inc. | Galanthamine derivatives as acetylcholinesterase inhibitors |
| US6323195B1 (en) | 1993-10-15 | 2001-11-27 | Aventis Pharmaceuticals Inc. | Galanthamine derivatives as acetylcholinesterase inhibitors |
| AT403803B (de) * | 1996-04-19 | 1998-05-25 | Sanochemia Ltd | Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln |
| US5665880A (en) * | 1996-10-31 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseretholes |
| US5677457A (en) * | 1996-12-19 | 1997-10-14 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseroline ethers |
| ATE254928T1 (de) * | 1999-03-31 | 2003-12-15 | Eisai Co Ltd | Stabilisierte zusammensetzung mit nootropen wirkstoffen |
| SI1181294T1 (en) * | 2000-03-31 | 2004-08-31 | Sanochemia Pharmazeutica Aktiengesellschaft | Novel derivatives and analogues of galanthamin |
| EP1341541A4 (en) * | 2000-11-16 | 2004-11-17 | Alcon Mfg Ltd | COMBINATION THERAPY FOR LOWERING AND CONTROLLING THE EYE PRESSURE |
| US7795307B2 (en) * | 2003-10-21 | 2010-09-14 | Colucid Pharmaceuticals, Inc. | Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents |
| US7549431B1 (en) * | 2004-11-10 | 2009-06-23 | Gore Enterprise Holdings, Inc. | Protective enclosure |
| TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1974782U (de) | 1967-07-04 | 1967-12-14 | Filzfabrik Fulda G M B H & Co | Matratzenschoner. |
| 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 |
| ATE411026T1 (de) * | 1987-05-04 | 2008-10-15 | Bonnie Davis | Mittel zur behandlung der alzheimer-krankheit |
| GB8727792D0 (en) * | 1987-11-27 | 1987-12-31 | Merck Sharp & Dohme | Therapeutic agents |
| GB8823605D0 (en) * | 1988-10-07 | 1988-11-16 | Merck Sharp & Dohme | Therapeutic agents |
| US5187171A (en) * | 1989-01-09 | 1993-02-16 | G. D. Searle & Co. | Use of a glycine b partial agonist as an antipsychotic |
| US5061721A (en) * | 1989-03-15 | 1991-10-29 | G. D. Searle & Co. | Composition containing d-cycloserine and d-alanine for memory and learning enhancement or treatment of a cognitive or psychotic disorder |
| US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
-
1991
- 1991-10-01 US US07/769,268 patent/US5153193A/en not_active Expired - Fee Related
-
1992
- 1992-09-21 TW TW081107422A patent/TW208009B/zh active
- 1992-09-29 FI FI924370A patent/FI102178B1/fi active
- 1992-09-29 NZ NZ244540A patent/NZ244540A/en unknown
- 1992-09-30 PT PT92116760T patent/PT535645E/pt unknown
- 1992-09-30 AU AU26065/92A patent/AU649882B2/en not_active Ceased
- 1992-09-30 DK DK92116760T patent/DK0535645T3/da active
- 1992-09-30 EP EP00121827A patent/EP1069125A3/en not_active Withdrawn
- 1992-09-30 CZ CS922990A patent/CZ281982B6/cs not_active IP Right Cessation
- 1992-09-30 JP JP4261196A patent/JP2703157B2/ja not_active Expired - Fee Related
- 1992-09-30 KR KR1019920017878A patent/KR100276143B1/ko not_active IP Right Cessation
- 1992-09-30 DE DE69231817T patent/DE69231817T2/de not_active Expired - Fee Related
- 1992-09-30 CA CA002079548A patent/CA2079548C/en not_active Expired - Fee Related
- 1992-09-30 NO NO923803A patent/NO301884B1/no not_active IP Right Cessation
- 1992-09-30 IL IL10330492A patent/IL103304A/en not_active IP Right Cessation
- 1992-09-30 AT AT92116760T patent/ATE201024T1/de not_active IP Right Cessation
- 1992-09-30 EP EP92116760A patent/EP0535645B1/en not_active Expired - Lifetime
- 1992-09-30 ES ES92116760T patent/ES2157201T3/es not_active Expired - Lifetime
- 1992-09-30 RU SU5052874A patent/RU2103271C1/ru active
- 1992-09-30 MX MX9205577A patent/MX9205577A/es not_active IP Right Cessation
- 1992-10-01 HU HU9203129A patent/HU215120B/hu not_active IP Right Cessation
-
1998
- 1998-08-06 FI FI981710A patent/FI981710A/fi unknown
-
2000
- 2000-01-27 KR KR1020000004035A patent/KR100271416B1/ko not_active IP Right Cessation
-
2001
- 2001-08-07 GR GR20010401186T patent/GR3036334T3/el not_active IP Right Cessation
Also Published As
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