GB1309692A - N-substituted lactams - Google Patents
N-substituted lactamsInfo
- Publication number
- GB1309692A GB1309692A GB697870A GB697870A GB1309692A GB 1309692 A GB1309692 A GB 1309692A GB 697870 A GB697870 A GB 697870A GB 697870 A GB697870 A GB 697870A GB 1309692 A GB1309692 A GB 1309692A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- alkenyl
- hydrogen atom
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003951 lactams Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 alkynyl radical Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 206010020651 Hyperkinesia Diseases 0.000 abstract 1
- 208000000269 Hyperkinesis Diseases 0.000 abstract 1
- 206010020852 Hypertonia Diseases 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 201000003152 motion sickness Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1309692 N-Amidoaldyllactams UCB SA 19 April 1971 [13 Feb 1970] 6978/70 Addition to 1039113 Heading C2C Novel compounds of Formula I wherein X is a hydrogen atom or an alkyl, alkenyl or alkynyl radical containing 1 to 6 carbon atoms, p is a whole number of from 1 to 6, Y is a hydrogen atom or an alkyl, alkenyl or alkynyl radical containing 1 to 6 carbon atoms or a cycloalkyl radical and R<SP>1</SP> and R<SP>11</SP>, which may be the same or different, are hydrogen atoms or alkyl, alkenyl, alkynyl, cycloalkyl or aryl radicals or R<SP>1</SP> and R<SP>11</SP>, together with the nitrogen atom to which they are attached, form a heterocyclic radical which may contain further heteroatoms, with the proviso that at least one of the symbols X and Y is other than a hydrogen atom are prepared by one of the following methods: (a) a compound of formula wherein M is an alkali metal atom is reacted with a compound of formula (b) an ester of Formula IV where Alk is alkyl or (c) an acid chloride of Formula VI is reacted with the amine H.N.R<SP>1</SP>R<SP>11</SP>, and (d) an ammonium salt of formula is heated. Esters of Formula IV above are prepared by reacting the sodium derivative of the appropriate pyrrolidin-2-one with the appropriate alkyl haloalkylcarboxylate and optionally hydrolysed to the corresponding acids which may be converted into their ammonium salts and acid chlorides by reaction with ammonia or thionyl chloride respectively. Pharmaceutical compositions in conventional forms for oral, parenteral or rectal administration to be used in treatment of motion sickness, hyperkinesia, hypertonia, epilepsy and mnesic conditions comprise an above novel compound and an excipient.
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB697870A GB1309692A (en) | 1970-02-13 | 1970-02-13 | N-substituted lactams |
| FR7104195A FR2081508B2 (en) | 1970-02-13 | 1971-02-08 | |
| NLAANVRAGE7101697,A NL168830C (en) | 1970-02-13 | 1971-02-09 | PROCESS FOR PREPARING THERAPEUTIC PREPARATIONS AND PROCESS FOR PREPARING AMIDS SUITABLE FOR THESE |
| CS987A CS167911B2 (en) | 1970-02-13 | 1971-02-10 | |
| ES388135A ES388135A2 (en) | 1970-02-13 | 1971-02-10 | PROCEDURE FOR OBTAINING NITROGEN SUBSTITUTED LACTAMS. |
| BE762728A BE762728R (en) | 1970-02-13 | 1971-02-10 | NEW LACTAMES N-SUBSTITUTES |
| FI383/71A FI54916C (en) | 1970-02-13 | 1971-02-10 | FRAMEWORK FOR THERAPEUTIC TREATMENT OF NUTRITIONAL N-SUBSTITUTE 2-PYRROLIDONER |
| DK59571AA DK137451B (en) | 1970-02-13 | 1971-02-10 | Analogous process for the preparation of derivatives of 2-oxo-pyrrolidine. |
| YU306/71A YU34876B (en) | 1970-02-13 | 1971-02-10 | Process for obtaining novel n-substituted pyrrolidines |
| DE2106418A DE2106418C2 (en) | 1970-02-13 | 1971-02-11 | N-substituted 2-pyrrolidone derivatives, processes for their preparation and pharmaceuticals containing them |
| ZA710877A ZA71877B (en) | 1970-02-13 | 1971-02-11 | New n-substituted lactams |
| CH200171A CH530395A (en) | 1970-02-13 | 1971-02-11 | Process for the preparation of new N-substituted lactams |
| SU1621307A SU508185A3 (en) | 1970-02-13 | 1971-02-12 | The method of obtaining-substituted lactams |
| JP612471A JPS535301B1 (en) | 1970-02-13 | 1971-02-12 | |
| SU1893858A SU508186A3 (en) | 1970-02-13 | 1971-02-12 | The method of obtaining-substituted lactams |
| CS140674A CS167912B2 (en) | 1970-02-13 | 1971-12-10 | |
| CY72774A CY727A (en) | 1964-08-06 | 1974-03-01 | New n-substituted lactams |
| MY197472A MY7400072A (en) | 1970-02-13 | 1974-12-31 | New n-substituted lactams |
| JP13335277A JPS53130656A (en) | 1970-02-13 | 1977-11-07 | Method of producing novel nnsubstituted lactams |
| YU01445/78A YU144578A (en) | 1970-02-13 | 1978-06-19 | Process for obtaining new n-substituted pyrrolidones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB697870A GB1309692A (en) | 1970-02-13 | 1970-02-13 | N-substituted lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1309692A true GB1309692A (en) | 1973-03-14 |
Family
ID=9824325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB697870A Expired GB1309692A (en) | 1964-08-06 | 1970-02-13 | N-substituted lactams |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS535301B1 (en) |
| BE (1) | BE762728R (en) |
| CH (1) | CH530395A (en) |
| CS (2) | CS167911B2 (en) |
| DE (1) | DE2106418C2 (en) |
| DK (1) | DK137451B (en) |
| ES (1) | ES388135A2 (en) |
| FI (1) | FI54916C (en) |
| FR (1) | FR2081508B2 (en) |
| GB (1) | GB1309692A (en) |
| MY (1) | MY7400072A (en) |
| NL (1) | NL168830C (en) |
| SU (2) | SU508185A3 (en) |
| YU (2) | YU34876B (en) |
| ZA (1) | ZA71877B (en) |
Cited By (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2368275A1 (en) * | 1976-10-19 | 1978-05-19 | Ucb Sa | 2- (2-OXO-PYRROLIDINO) -ALKYLAMIDES FOR THE TREATMENT OF VASCULAR DISORDERS |
| DE2808067A1 (en) * | 1977-03-03 | 1978-09-07 | Parke Davis & Co | N- (SUBSTITUTED AMINOALKYL) -2-OXO-1- PYRROLIDINE ACETAMIDE AND METHOD FOR THE PREPARATION |
| US4221789A (en) | 1978-05-08 | 1980-09-09 | Ucb, Societe Anonyme | Lactam-N-acetic acids and their amides |
| EP0089900A1 (en) * | 1982-03-24 | 1983-09-28 | Prodes S.A. | New N-((2-oxo-1-pyrrolidinyl)acetyl)piperazines, the methods of producing such new compounds and their salts as well as pharmaceutical preparations for therapeutic use containing these compounds or salts |
| JPS60252461A (en) * | 1984-05-15 | 1985-12-13 | ユセベ ソシエテ アノニム | Antihypoxic and ischemic pharmacological composition |
| JPS60255764A (en) * | 1984-05-15 | 1985-12-17 | ユセベ ソシエテ アノニム | (r)-alpha-ethyl-2-oxo-1-pyridineacetamide, manufacture and pharmaceutical composition |
| EP0071216B1 (en) * | 1981-07-24 | 1986-12-30 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-hydroxypyrrolidin-2-one derivatives, process and intermediates for their preparation and pharmaceutical preparations containing them |
| US4670456A (en) * | 1984-05-30 | 1987-06-02 | Boehringer Ingelheim Kg | 4-Aminocarbonylaminomethyl-1-benzylpyrrolidin-2-ones as nootropic agents and as agents for treating cerebral insufficiency |
| US4929272A (en) * | 1986-09-12 | 1990-05-29 | Ciba-Geigy Corporation | N-phenyl-maleimides and N-phenyl-succinimides and their use in a herbicidal and/or plant growth regulating action |
| GB2225322A (en) * | 1988-11-23 | 1990-05-30 | Ucb Sa | The preparation of S-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| WO2001062726A3 (en) * | 2000-02-23 | 2002-01-17 | Ucb Sa | 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses |
| WO2002026705A3 (en) * | 2000-09-29 | 2002-07-11 | Eastman Chem Co | Highly enantiomerically pure lactam-substituted propanoic acid derivatives and their preparation |
| WO2002094787A1 (en) * | 2001-05-23 | 2002-11-28 | Ucb, S.A. | 2-oxo-piperidinyl- and 2-oxo-azepanyl alkanoic acid derivativ es for the treatment of epilepsy and other neurological disorders |
| WO2003014080A3 (en) * | 2001-08-10 | 2003-11-06 | Ucb Sa | Oxopyrrolidine compounds, preparation of said compounds and their use in the manufacturing of levetiracetam and analogues |
| WO2003030899A3 (en) * | 2001-10-08 | 2004-01-08 | Ucb Sa | Use of 2-oxo-1-pyrrolidine derivatives for the treatment of dyskinesia and movement disorders |
| ES2214147A1 (en) * | 2003-02-28 | 2004-09-01 | Farma-Lepori S.A. | PROCEDURE FOR OBTAINING AN ANTIEPILEPTIC AGENT. |
| EP1566376A1 (en) | 2004-02-18 | 2005-08-24 | Dr. Reddy's Laboratories Limited | Preparation of amino acid amides |
| WO2006053441A1 (en) | 2004-11-22 | 2006-05-26 | Apotex Pharmachem Inc. | Improved process for the preparation of (s)-alpha-etyl-2-oxo-1-pyrrolidineacetamide and (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| WO2006095362A1 (en) * | 2005-03-10 | 2006-09-14 | Rubamin Limited | Process for preparing levetiracetam |
| US7132552B2 (en) | 2003-02-03 | 2006-11-07 | Teva Pharmaceutical Industries, Ltd. | Process for producing levetiracetam |
| EP2147911A1 (en) | 2008-07-24 | 2010-01-27 | ZaCh System S.p.A. | Process for the preparation of levetiracetam |
| EP2308867A2 (en) | 2005-06-01 | 2011-04-13 | UCB Pharma S.A. | 2-oxo-1-pyrrolidine deriatives, processes for preparing them and their uses |
| US7939676B2 (en) | 2009-09-17 | 2011-05-10 | Zach System S.P.A. | Process for the preparation of levetiracetam |
| WO2011100373A1 (en) | 2010-02-09 | 2011-08-18 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| US8604075B2 (en) | 2008-10-16 | 2013-12-10 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| US8785661B2 (en) | 2009-05-13 | 2014-07-22 | Nektar Therapeutics | Oligome-containing pyrrolidine compounds |
| WO2014144801A1 (en) | 2013-03-15 | 2014-09-18 | Agenebio Inc. | Methods and compositions for improving cognitive function |
| CN104059010A (en) * | 2014-06-12 | 2014-09-24 | 浙江华海药业股份有限公司 | Preparation method of 2-(2-oxopyrrolidine-1-yl)-butyrate |
| WO2015110435A1 (en) | 2014-01-21 | 2015-07-30 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| EP3827820A1 (en) | 2013-03-15 | 2021-06-02 | The Johns Hopkins University | Brivaracetam for improving cognitive function |
| CN113979911A (en) * | 2021-11-12 | 2022-01-28 | 汤斌 | Method for extracting etiracetam from giant salamander peptide |
| US11369606B2 (en) | 2014-01-21 | 2022-06-28 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US11384050B1 (en) | 2021-02-03 | 2022-07-12 | Vitaworks Ip, Llc | Method for preparing levetiracetam and intermediates thereof |
| WO2024039886A1 (en) | 2022-08-19 | 2024-02-22 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
| US12528770B2 (en) | 2023-06-12 | 2026-01-20 | Suzhou Brighthope Pharmatech Co., Ltd. | Process for the production of levetiracetam and intermediates thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1045043B (en) * | 1975-08-13 | 1980-04-21 | Isf Spa | PYROLIDINE DERIVATIVES |
| IT1141287B (en) * | 1979-06-13 | 1986-10-01 | Nattermann A & Cie | PYROLIDIN ACIDS AMIDS- (2) -ON- (1) -ILALKYL-CARBOXYLS, PROCEDURE FOR THEIR PREPARATION AND MEDICINAL PRODUCTS CONTAINING THEM |
| TW544311B (en) * | 1998-08-06 | 2003-08-01 | Daiichi Seiyaku Co | Therapeutic or preventive agent for intractable epilepsies |
| CN106591179B (en) * | 2016-12-05 | 2018-07-03 | 长兴制药股份有限公司 | Methyl packing bacterium and its prepare the application on (S)-α-ethyl -2- oxygen -1- pyrrolidine acetic acid salt in selective fractionation |
| RU2663899C1 (en) * | 2017-07-19 | 2018-08-13 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Process for the preparation of 1-carbamoylmethyl-4-phenyl-2-pyrrolidone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
-
1970
- 1970-02-13 GB GB697870A patent/GB1309692A/en not_active Expired
-
1971
- 1971-02-08 FR FR7104195A patent/FR2081508B2/fr not_active Expired
- 1971-02-09 NL NLAANVRAGE7101697,A patent/NL168830C/en not_active IP Right Cessation
- 1971-02-10 FI FI383/71A patent/FI54916C/en active
- 1971-02-10 ES ES388135A patent/ES388135A2/en not_active Expired
- 1971-02-10 DK DK59571AA patent/DK137451B/en not_active IP Right Cessation
- 1971-02-10 YU YU306/71A patent/YU34876B/en unknown
- 1971-02-10 CS CS987A patent/CS167911B2/cs unknown
- 1971-02-10 BE BE762728A patent/BE762728R/en active
- 1971-02-11 CH CH200171A patent/CH530395A/en not_active IP Right Cessation
- 1971-02-11 DE DE2106418A patent/DE2106418C2/en not_active Expired
- 1971-02-11 ZA ZA710877A patent/ZA71877B/en unknown
- 1971-02-12 SU SU1621307A patent/SU508185A3/en active
- 1971-02-12 SU SU1893858A patent/SU508186A3/en active
- 1971-02-12 JP JP612471A patent/JPS535301B1/ja active Pending
- 1971-12-10 CS CS140674A patent/CS167912B2/cs unknown
-
1974
- 1974-12-31 MY MY197472A patent/MY7400072A/en unknown
-
1977
- 1977-11-07 JP JP13335277A patent/JPS53130656A/en active Granted
-
1978
- 1978-06-19 YU YU01445/78A patent/YU144578A/en unknown
Cited By (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115579A (en) | 1976-10-19 | 1978-09-19 | U C B, Societe Anonyme | Process for inhibiting blood platelet aggregation |
| FR2368275A1 (en) * | 1976-10-19 | 1978-05-19 | Ucb Sa | 2- (2-OXO-PYRROLIDINO) -ALKYLAMIDES FOR THE TREATMENT OF VASCULAR DISORDERS |
| DE2808067A1 (en) * | 1977-03-03 | 1978-09-07 | Parke Davis & Co | N- (SUBSTITUTED AMINOALKYL) -2-OXO-1- PYRROLIDINE ACETAMIDE AND METHOD FOR THE PREPARATION |
| US4221789A (en) | 1978-05-08 | 1980-09-09 | Ucb, Societe Anonyme | Lactam-N-acetic acids and their amides |
| EP0071216B1 (en) * | 1981-07-24 | 1986-12-30 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-hydroxypyrrolidin-2-one derivatives, process and intermediates for their preparation and pharmaceutical preparations containing them |
| US5034402A (en) * | 1981-07-24 | 1991-07-23 | Hoffmann-La Roche Inc. | Methods and pharmaceutical compositions using pyrrolidine derivatives |
| EP0089900A1 (en) * | 1982-03-24 | 1983-09-28 | Prodes S.A. | New N-((2-oxo-1-pyrrolidinyl)acetyl)piperazines, the methods of producing such new compounds and their salts as well as pharmaceutical preparations for therapeutic use containing these compounds or salts |
| AU574465B2 (en) * | 1984-05-15 | 1988-07-07 | Ucb | (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| US4696942A (en) * | 1984-05-15 | 1987-09-29 | Ucb Societe Anonyme | Treatment of memory impairment using (R)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| US4696943A (en) * | 1984-05-15 | 1987-09-29 | U C B Societe Anonyme | (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| AU574175B2 (en) * | 1984-05-15 | 1988-06-30 | Ucb | (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| JPS60255764A (en) * | 1984-05-15 | 1985-12-17 | ユセベ ソシエテ アノニム | (r)-alpha-ethyl-2-oxo-1-pyridineacetamide, manufacture and pharmaceutical composition |
| JPS60252461A (en) * | 1984-05-15 | 1985-12-13 | ユセベ ソシエテ アノニム | Antihypoxic and ischemic pharmacological composition |
| JPH0629186B2 (en) | 1984-05-15 | 1994-04-20 | ユセベ ソシエテ アノニム | Anti-hypoxia and ischemia pharmacological composition |
| US4670456A (en) * | 1984-05-30 | 1987-06-02 | Boehringer Ingelheim Kg | 4-Aminocarbonylaminomethyl-1-benzylpyrrolidin-2-ones as nootropic agents and as agents for treating cerebral insufficiency |
| US4929272A (en) * | 1986-09-12 | 1990-05-29 | Ciba-Geigy Corporation | N-phenyl-maleimides and N-phenyl-succinimides and their use in a herbicidal and/or plant growth regulating action |
| GB2225322A (en) * | 1988-11-23 | 1990-05-30 | Ucb Sa | The preparation of S-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| GB2225322B (en) * | 1988-11-23 | 1992-03-25 | Ucb Sa | A process for the preparation of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| CZ304420B6 (en) * | 2000-02-23 | 2014-04-30 | Ucb Pharma S.A. | 2-Oxo-1-pyrrolidine derivatives, process of their preparation and their use |
| US6806287B2 (en) | 2000-02-23 | 2004-10-19 | Ucb, S.A. | 2-oxo-1-pyrrolidine derivatives, process for preparing them and their uses |
| CN1303066C (en) * | 2000-02-23 | 2007-03-07 | Ucb公司 | 2-oxo-1-pyrrolidine derivatives, their preparation methods and uses |
| US8492416B2 (en) | 2000-02-23 | 2013-07-23 | Ucb Pharma, S.A. | 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses |
| US8034958B2 (en) | 2000-02-23 | 2011-10-11 | UOB Pharma, S.A. | 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses |
| WO2001062726A3 (en) * | 2000-02-23 | 2002-01-17 | Ucb Sa | 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses |
| EP1447399A1 (en) * | 2000-02-23 | 2004-08-18 | Ucb, S.A. | "2-oxo-1-pyrrolidine derivative and its pharmaceutical uses" |
| US6784197B2 (en) * | 2000-02-23 | 2004-08-31 | Ucb S.A. | 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses |
| EP1452524A1 (en) | 2000-02-23 | 2004-09-01 | Ucb, S.A. | "2-oxo-1-pyrrolidine derivative and its pharmaceutical uses" |
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Also Published As
| Publication number | Publication date |
|---|---|
| YU30671A (en) | 1979-10-31 |
| FR2081508A2 (en) | 1971-12-03 |
| ES388135A2 (en) | 1973-05-01 |
| BE762728R (en) | 1971-08-10 |
| FI54916C (en) | 1979-04-10 |
| SU508185A3 (en) | 1976-03-25 |
| NL7101697A (en) | 1971-08-17 |
| FI54916B (en) | 1978-12-29 |
| DE2106418C2 (en) | 1983-12-22 |
| DK137451B (en) | 1978-03-06 |
| YU34876B (en) | 1980-04-30 |
| FR2081508B2 (en) | 1975-06-06 |
| NL168830C (en) | 1982-05-17 |
| JPS53130656A (en) | 1978-11-14 |
| CH530395A (en) | 1972-11-15 |
| DK137451C (en) | 1978-07-24 |
| YU144578A (en) | 1982-10-31 |
| CS167911B2 (en) | 1976-05-28 |
| CS167912B2 (en) | 1976-05-28 |
| JPS535301B1 (en) | 1978-02-25 |
| SU508186A3 (en) | 1976-03-25 |
| NL168830B (en) | 1981-12-16 |
| MY7400072A (en) | 1974-12-31 |
| ZA71877B (en) | 1971-10-27 |
| DE2106418A1 (en) | 1971-08-19 |
| JPS5420491B2 (en) | 1979-07-23 |
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| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |