CS261883B2 - Method of new substituted pyrrolidinones production - Google Patents
Method of new substituted pyrrolidinones production Download PDFInfo
- Publication number
- CS261883B2 CS261883B2 CS853854A CS385485A CS261883B2 CS 261883 B2 CS261883 B2 CS 261883B2 CS 853854 A CS853854 A CS 853854A CS 385485 A CS385485 A CS 385485A CS 261883 B2 CS261883 B2 CS 261883B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- group
- phenyl
- carbon atoms
- benzylpyrrolidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000004040 pyrrolidinones Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 chlorocarbon ester Chemical class 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
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- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- WQKVZVGKZZWLPJ-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-2-one Chemical compound NCN1CCCC1=O WQKVZVGKZZWLPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
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- YOSIGHUZRIDPHE-UHFFFAOYSA-N n-[(1-benzyl-5-oxopyrrolidin-3-yl)methyl]-n-(4-chlorophenyl)piperazine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1N(C(=O)N1CCNCC1)CC1CC(=O)N(CC=2C=CC=CC=2)C1 YOSIGHUZRIDPHE-UHFFFAOYSA-N 0.000 description 1
- APFGGXAHGCBRSU-UHFFFAOYSA-N n-[(1-benzyl-5-oxopyrrolidin-3-yl)methyl]morpholine-2-carboxamide Chemical compound C1NCCOC1C(=O)NCC(CC1=O)CN1CC1=CC=CC=C1 APFGGXAHGCBRSU-UHFFFAOYSA-N 0.000 description 1
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- SAXDPGWLFRAGFG-UHFFFAOYSA-N n-[[1-[(2-chlorophenyl)methyl]-5-oxopyrrolidin-3-yl]methyl]-n-methylpiperazine-1-carboxamide Chemical compound C1CNCCN1C(=O)N(C)CC(CC1=O)CN1CC1=CC=CC=C1Cl SAXDPGWLFRAGFG-UHFFFAOYSA-N 0.000 description 1
- MOGYYMMKAORNKQ-UHFFFAOYSA-N n-methyl-n-[[1-[(4-methylphenyl)methyl]-5-oxopyrrolidin-3-yl]methyl]piperazine-1-carboxamide Chemical compound C1CNCCN1C(=O)N(C)CC(CC1=O)CN1CC1=CC=C(C)C=C1 MOGYYMMKAORNKQ-UHFFFAOYSA-N 0.000 description 1
- LCAFGJGYCUMTGS-UHFFFAOYSA-N nebracetam Chemical compound O=C1CC(CN)CN1CC1=CC=CC=C1 LCAFGJGYCUMTGS-UHFFFAOYSA-N 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000009467 reduction Effects 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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- 229940113147 shellac Drugs 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 230000004936 stimulating effect Effects 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (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 (2)
| Publication Number | Publication Date |
|---|---|
| CS385485A2 CS385485A2 (en) | 1988-06-15 |
| CS261883B2 true CS261883B2 (en) | 1989-02-10 |
Family
ID=6237240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS853854A CS261883B2 (en) | 1984-05-30 | 1985-05-29 | Method of new substituted pyrrolidinones production |
Country Status (22)
| Country | Link |
|---|---|
| US (4) | US4670456A (en, 2012) |
| EP (1) | EP0163260B1 (en, 2012) |
| JP (1) | JPS6168A (en, 2012) |
| KR (1) | KR850008343A (en, 2012) |
| AT (1) | ATE36151T1 (en, 2012) |
| AU (1) | AU581438B2 (en, 2012) |
| CA (1) | CA1255664A (en, 2012) |
| CS (1) | CS261883B2 (en, 2012) |
| DD (1) | DD235256A5 (en, 2012) |
| DE (2) | DE3420193A1 (en, 2012) |
| DK (1) | DK239685A (en, 2012) |
| ES (4) | ES8607926A1 (en, 2012) |
| FI (1) | FI78462C (en, 2012) |
| GR (1) | GR851306B (en, 2012) |
| HU (1) | HU193393B (en, 2012) |
| IL (1) | IL75339A (en, 2012) |
| NO (1) | NO852133L (en, 2012) |
| NZ (1) | NZ212241A (en, 2012) |
| PL (1) | PL144921B1 (en, 2012) |
| PT (1) | PT80545B (en, 2012) |
| SU (1) | SU1360583A3 (en, 2012) |
| ZA (1) | ZA854072B (en, 2012) |
Families Citing this family (16)
| 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 |
| ES2043943T3 (es) * | 1988-05-20 | 1994-01-01 | Zambon Spa | Procedimiento para la preparacion de compuestos con actividad analgesica central. |
| 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 |
| TWI294778B (en) * | 2002-03-13 | 2008-03-21 | Smithkline Beecham Corp | Peptide deformylase inhibitors |
| PT2383271E (pt) * | 2006-03-13 | 2013-10-10 | Kyorin Seiyaku Kk | Aminoquinolonas como inibidores de gsk-3 |
| CN101855228B (zh) * | 2007-09-11 | 2012-10-24 | 杏林制药株式会社 | 作为gsk-3抑制剂的氰基氨基喹诺酮和四唑并氨基喹诺酮 |
| AU2008333173A1 (en) * | 2007-12-05 | 2009-06-11 | Astrazeneca Ab | Piperazines as anti-obesity agents |
| CN102015668A (zh) | 2007-12-05 | 2011-04-13 | 阿斯利康(瑞典)有限公司 | 用作瘦蛋白受体调节剂的哌嗪衍生物及其用途 |
| US20110275670A1 (en) * | 2008-06-04 | 2011-11-10 | Emma Chapman | New Compounds VII |
| MX2011009414A (es) * | 2009-03-11 | 2011-10-19 | Kyorin Seiyaku Kk | 7-cicloalquiloaminoquinolonas como inhibidores de 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 (en, 2012) * | 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 EP EP85106343A patent/EP0163260B1/de not_active Expired
- 1985-05-23 AT AT85106343T patent/ATE36151T1/de not_active IP Right Cessation
- 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 CA CA000482660A patent/CA1255664A/en not_active Expired
- 1985-05-29 FI FI852130A patent/FI78462C/fi not_active IP Right Cessation
- 1985-05-29 KR KR1019850003709A patent/KR850008343A/ko not_active Withdrawn
- 1985-05-29 NO NO852133A patent/NO852133L/no unknown
- 1985-05-29 HU HU852056A patent/HU193393B/hu not_active IP Right Cessation
- 1985-05-29 SU SU853900955A patent/SU1360583A3/ru active
- 1985-05-29 PT PT80545A patent/PT80545B/pt unknown
- 1985-05-29 NZ NZ212241A patent/NZ212241A/xx unknown
- 1985-05-29 ZA ZA854072A patent/ZA854072B/xx unknown
- 1985-05-29 ES ES543592A patent/ES8607926A1/es not_active Expired
- 1985-05-29 IL IL75339A patent/IL75339A/xx unknown
- 1985-05-29 DD DD85276752A patent/DD235256A5/de not_active IP Right Cessation
- 1985-05-29 CS CS853854A patent/CS261883B2/cs unknown
- 1985-05-29 DK DK239685A patent/DK239685A/da not_active Application Discontinuation
- 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 ES552410A patent/ES8707927A1/es not_active Expired
- 1986-02-26 ES ES552411A patent/ES8707928A1/es not_active Expired
- 1986-02-26 ES ES552409A patent/ES8801200A1/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
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