SU1360583A3 - Способ получени производных пирролидинона - Google Patents
Способ получени производных пирролидинона Download PDFInfo
- Publication number
- SU1360583A3 SU1360583A3 SU853900955A SU3900955A SU1360583A3 SU 1360583 A3 SU1360583 A3 SU 1360583A3 SU 853900955 A SU853900955 A SU 853900955A SU 3900955 A SU3900955 A SU 3900955A SU 1360583 A3 SU1360583 A3 SU 1360583A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- general formula
- formula
- methyl
- indicated meanings
- Prior art date
Links
- 150000004040 pyrrolidinones Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000001257 hydrogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 7
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 6
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 abstract description 6
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 abstract description 6
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 abstract description 6
- 229960002646 scopolamine Drugs 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 230000004071 biological effect Effects 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 230000001777 nootropic effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 230000006403 short-term memory Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZPROSAGHJAQREZ-UHFFFAOYSA-N 3-(aminomethyl)-1-benzylpyrrolidin-2-one Chemical compound O=C1C(CN)CCN1CC1=CC=CC=C1 ZPROSAGHJAQREZ-UHFFFAOYSA-N 0.000 description 1
- -1 4- (N-Methylpiperazinyl-carbonylaminomethyl) -benzyl pyrrolidin-2-one Chemical compound 0.000 description 1
- ZBULGGJXBMLOKD-UHFFFAOYSA-N 4-amino-1-benzylpyrrolidin-2-one Chemical compound O=C1CC(N)CN1CC1=CC=CC=C1 ZBULGGJXBMLOKD-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LCAFGJGYCUMTGS-UHFFFAOYSA-N nebracetam Chemical compound O=C1CC(CN)CN1CC1=CC=CC=C1 LCAFGJGYCUMTGS-UHFFFAOYSA-N 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843420193 DE3420193A1 (de) | 1984-05-30 | 1984-05-30 | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1360583A3 true SU1360583A3 (ru) | 1987-12-15 |
Family
ID=6237240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853900955A SU1360583A3 (ru) | 1984-05-30 | 1985-05-29 | Способ получени производных пирролидинона |
Country Status (22)
| Country | Link |
|---|---|
| US (4) | US4670456A (enExample) |
| EP (1) | EP0163260B1 (enExample) |
| JP (1) | JPS6168A (enExample) |
| KR (1) | KR850008343A (enExample) |
| AT (1) | ATE36151T1 (enExample) |
| AU (1) | AU581438B2 (enExample) |
| CA (1) | CA1255664A (enExample) |
| CS (1) | CS261883B2 (enExample) |
| DD (1) | DD235256A5 (enExample) |
| DE (2) | DE3420193A1 (enExample) |
| DK (1) | DK239685A (enExample) |
| ES (4) | ES8607926A1 (enExample) |
| FI (1) | FI78462C (enExample) |
| GR (1) | GR851306B (enExample) |
| HU (1) | HU193393B (enExample) |
| IL (1) | IL75339A (enExample) |
| NO (1) | NO852133L (enExample) |
| NZ (1) | NZ212241A (enExample) |
| PL (1) | PL144921B1 (enExample) |
| PT (1) | PT80545B (enExample) |
| SU (1) | SU1360583A3 (enExample) |
| ZA (1) | ZA854072B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2287525C2 (ru) * | 2002-03-13 | 2006-11-20 | Смитклайн Бичам Корпорейшн | Производные имидазолидина в качестве ингибиторов пептиддеформилазы |
| US8093248B2 (en) | 2007-12-05 | 2012-01-10 | Astrazeneca Ab (Publ) | Compounds useful for the treatment of conditions associated with weight gain |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3336024A1 (de) * | 1983-10-04 | 1985-04-18 | Boehringer Ingelheim KG, 6507 Ingelheim | 4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel |
| FR2597100A1 (fr) * | 1986-01-21 | 1987-10-16 | Nippon Shinyaku Co Ltd | Derives du pyroglutamide |
| US4960776A (en) * | 1987-01-28 | 1990-10-02 | A. H. Robins Company, Inc. | 4-aryl-N-(alkylaminoalkyl, heterocyclicamino and heterocyclicamino)alkyl)-1-piperazinecarboxamides |
| CA1305148C (en) * | 1987-08-19 | 1992-07-14 | Hiromu Matsumura | Carbamoylpyrrolidone derivatives and drugs for senile dementia |
| US4833139A (en) * | 1988-01-25 | 1989-05-23 | Hoechst-Roussel Pharmaceuticals, Inc. | Enhancing cholinergic activity with 5-substituted 1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinones and related compounds |
| CA1336333C (en) * | 1988-05-20 | 1995-07-18 | Davide Della Bella | Pyrrolidone-2 compounds and their use for central analgesic activity |
| JPH02137427A (ja) * | 1988-11-18 | 1990-05-25 | Du Pont Opt Electron Kk | 光電気的接続装置及び光コンセント |
| US4981974A (en) * | 1989-05-08 | 1991-01-01 | Gaf Chemicals Corporation | Polymerizable pyrrolidonyl oxazoline monomers |
| TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
| KR101419554B1 (ko) * | 2006-03-13 | 2014-07-17 | 교린 세이야꾸 가부시키 가이샤 | Ｇｓｋ３ 억제제로서 아미노퀴놀론 |
| BRPI0816798A2 (pt) * | 2007-09-11 | 2016-10-11 | Activx Biosciences Inc | composto, composição farmacêutica, métodos para inibir a ação do glicogênio sintase cinase-3, e para tratar, prevenir ou melhorar uma doença, uso de um composto, e, artigo de fabricação |
| CA2707555A1 (en) * | 2007-12-05 | 2009-06-11 | Astrazeneca Ab | Piperazines as anti-obesity agents |
| EP2321276A1 (en) * | 2008-06-04 | 2011-05-18 | AstraZeneca AB | New compounds vii |
| BRPI1008974A2 (pt) * | 2009-03-11 | 2017-06-06 | Kyorin Seiyaku Kk | composto, composição farmacêutica, e, método para tratar, prevenir ou melhorar uma doença mediada com gsk-3 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838914A (en) * | 1957-07-03 | 1958-06-17 | Olin Mathieson | Isonicotinic acid hydrazide derivatives |
| GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
| GB1309692A (en) * | 1970-02-13 | 1973-03-14 | Ucb Sa | N-substituted lactams |
| JPS4924916B1 (enExample) * | 1970-08-14 | 1974-06-26 | ||
| FR2387218A1 (fr) * | 1977-04-15 | 1978-11-10 | Ile De France | Nouveaux n-(1'-ethyl 2'-oxo 5'-pyrrolidinyl methyl) benzamides, leurs procedes de preparation et leur application comme modificateurs du comportement |
| CU21107A3 (es) * | 1978-02-10 | 1988-02-01 | Hoffmann La Roche | Pyrrolidines derivatives |
| DE3326724A1 (de) * | 1983-07-25 | 1985-02-07 | Boehringer Ingelheim KG, 6507 Ingelheim | In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte |
| DE3336024A1 (de) * | 1983-10-04 | 1985-04-18 | Boehringer Ingelheim KG, 6507 Ingelheim | 4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel |
| GB8412358D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
| US4670436A (en) * | 1986-08-29 | 1987-06-02 | Mcneilab, Inc. | Hypoglycemic 5-substituted pyrrolidinylidene compounds, compositions and use |
-
1984
- 1984-05-30 DE DE19843420193 patent/DE3420193A1/de not_active Withdrawn
-
1985
- 1985-05-23 AT AT85106343T patent/ATE36151T1/de not_active IP Right Cessation
- 1985-05-23 EP EP85106343A patent/EP0163260B1/de not_active Expired
- 1985-05-23 DE DE8585106343T patent/DE3564105D1/de not_active Expired
- 1985-05-24 US US06/738,152 patent/US4670456A/en not_active Expired - Fee Related
- 1985-05-28 PL PL1985253668A patent/PL144921B1/pl unknown
- 1985-05-28 GR GR851306A patent/GR851306B/el unknown
- 1985-05-29 IL IL75339A patent/IL75339A/xx unknown
- 1985-05-29 NO NO852133A patent/NO852133L/no unknown
- 1985-05-29 KR KR1019850003709A patent/KR850008343A/ko not_active Withdrawn
- 1985-05-29 CA CA000482660A patent/CA1255664A/en not_active Expired
- 1985-05-29 FI FI852130A patent/FI78462C/fi not_active IP Right Cessation
- 1985-05-29 ZA ZA854072A patent/ZA854072B/xx unknown
- 1985-05-29 SU SU853900955A patent/SU1360583A3/ru active
- 1985-05-29 CS CS853854A patent/CS261883B2/cs unknown
- 1985-05-29 NZ NZ212241A patent/NZ212241A/xx unknown
- 1985-05-29 PT PT80545A patent/PT80545B/pt unknown
- 1985-05-29 DD DD85276752A patent/DD235256A5/de not_active IP Right Cessation
- 1985-05-29 DK DK239685A patent/DK239685A/da not_active Application Discontinuation
- 1985-05-29 ES ES543592A patent/ES8607926A1/es not_active Expired
- 1985-05-29 HU HU852056A patent/HU193393B/hu not_active IP Right Cessation
- 1985-05-30 JP JP60117657A patent/JPS6168A/ja active Granted
- 1985-05-30 AU AU43170/85A patent/AU581438B2/en not_active Ceased
-
1986
- 1986-02-26 ES ES552409A patent/ES8801200A1/es not_active Expired
- 1986-02-26 ES ES552411A patent/ES8707928A1/es not_active Expired
- 1986-02-26 ES ES552410A patent/ES8707927A1/es not_active Expired
- 1986-12-18 US US06/943,532 patent/US4762832A/en not_active Expired - Fee Related
-
1988
- 1988-04-20 US US07/183,819 patent/US4857528A/en not_active Expired - Fee Related
-
1989
- 1989-06-12 US US07/365,169 patent/US4891378A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Hicolaus B.I.R. Drug Development Res, 2, 464 (1982). * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2287525C2 (ru) * | 2002-03-13 | 2006-11-20 | Смитклайн Бичам Корпорейшн | Производные имидазолидина в качестве ингибиторов пептиддеформилазы |
| US8093248B2 (en) | 2007-12-05 | 2012-01-10 | Astrazeneca Ab (Publ) | Compounds useful for the treatment of conditions associated with weight gain |
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