GB1367598A - Derivatives of delta 1-pyrroline their method of preparation and their applications - Google Patents
Derivatives of delta 1-pyrroline their method of preparation and their applicationsInfo
- Publication number
- GB1367598A GB1367598A GB2110173A GB2110173A GB1367598A GB 1367598 A GB1367598 A GB 1367598A GB 2110173 A GB2110173 A GB 2110173A GB 2110173 A GB2110173 A GB 2110173A GB 1367598 A GB1367598 A GB 1367598A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- phenyl
- radical
- atom
- formula
- 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
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- FPUIMUBIGILNNL-UHFFFAOYSA-N 5-methyl-2-oxo-4-phenylpyrrolidine-3-carboxylic acid Chemical compound CC1NC(=O)C(C(O)=O)C1C1=CC=CC=C1 FPUIMUBIGILNNL-UHFFFAOYSA-N 0.000 abstract 1
- FCFHNVZGACYFTM-UHFFFAOYSA-N 5-methyl-4-phenyl-1,3-dihydropyrrol-2-one Chemical compound C1C(=O)NC(C)=C1C1=CC=CC=C1 FCFHNVZGACYFTM-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 230000005792 cardiovascular activity Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 1
- 229940040102 levulinic acid Drugs 0.000 abstract 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- WGSVFWFSJDAYBM-BQYQJAHWSA-N phenyl-2-nitropropene Chemical compound [O-][N+](=O)C(/C)=C/C1=CC=CC=C1 WGSVFWFSJDAYBM-BQYQJAHWSA-N 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- VIANBEAUACIOKY-UHFFFAOYSA-M sodium;3-ethoxy-3-oxopropanoate Chemical class [Na+].CCOC(=O)CC([O-])=O VIANBEAUACIOKY-UHFFFAOYSA-M 0.000 abstract 1
- -1 triethyloxonium tetrafluoroborate Chemical compound 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7215636A FR2186236B1 (enrdf_load_stackoverflow) | 1972-05-03 | 1972-05-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1367598A true GB1367598A (en) | 1974-09-18 |
Family
ID=9097884
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2110173A Expired GB1367598A (en) | 1972-05-03 | 1973-05-03 | Derivatives of delta 1-pyrroline their method of preparation and their applications |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS4947366A (enrdf_load_stackoverflow) |
BE (1) | BE798779A (enrdf_load_stackoverflow) |
CH (1) | CH566981A5 (enrdf_load_stackoverflow) |
DE (1) | DE2321950A1 (enrdf_load_stackoverflow) |
ES (1) | ES414289A1 (enrdf_load_stackoverflow) |
FR (1) | FR2186236B1 (enrdf_load_stackoverflow) |
GB (1) | GB1367598A (enrdf_load_stackoverflow) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2143234A (en) * | 1983-07-06 | 1985-02-06 | Shinogi Seiyaku Kabushiki Kais | (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives |
US4699918A (en) * | 1983-01-28 | 1987-10-13 | Laboratoires Jacques Logeais | 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same |
US5854234A (en) * | 1993-10-21 | 1998-12-29 | G. D. Searle & Co. | Amidino dervatives useful as nitric oxide synthase inhibitors |
US5883251A (en) * | 1995-04-20 | 1999-03-16 | G. D. Searle & Co. | Azepine derivatives useful as nitric oxide synthase inhibitors |
US5945408A (en) * | 1996-03-06 | 1999-08-31 | G.D. Searle & Co. | Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors |
US5958958A (en) * | 1997-07-22 | 1999-09-28 | G.D. Searle & Co. | 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors |
US6344473B1 (en) | 2000-08-07 | 2002-02-05 | G.D. Searle & Co. | Imidazoles useful as nitric oxide synthase inhibitors |
US6489323B1 (en) | 1998-06-10 | 2002-12-03 | G.D. Searle & Co. | Heterobicyclic and tricyclic nitric oxide synthase inhibitors |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50140080A (enrdf_load_stackoverflow) * | 1974-04-25 | 1975-11-10 | ||
DE3149776C2 (de) * | 1981-12-16 | 1985-11-14 | Daimler-Benz Ag, 7000 Stuttgart | Ventilführungsanordnung für ein die Verbindung einer Abgashauptleitung einer Brennkraftmaschine mit einer Abgasnebenleitung beherrschendes Tellerventil |
JPS6222757A (ja) * | 1985-07-22 | 1987-01-30 | Daicel Chem Ind Ltd | 置換アニリノ−2−ピロリン誘導体 |
WO1992010475A1 (en) * | 1990-12-13 | 1992-06-25 | E.I. Du Pont De Nemours And Company | Novel heterocyclic amidines and guanidines as plant fungicides |
SE520050C2 (sv) | 2000-03-30 | 2003-05-13 | Bertil Johansson | Sammansatt projektil samt patron innehållande sådan projektil |
LV14346B (lv) * | 2009-11-05 | 2011-07-20 | Grindeks, A/S | 2-(4-Fenil-5-metil-2-oksopirolidin-1-il)-acetamīda 4R,5S-enantiomērs ar nootropo aktivitāti |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3632604A (en) * | 1970-04-09 | 1972-01-04 | Sandoz Ag | 2-substituted-4-phenyl and substituted phenyl-1-pyrrolines |
-
1972
- 1972-05-03 FR FR7215636A patent/FR2186236B1/fr not_active Expired
-
1973
- 1973-04-26 BE BE130469A patent/BE798779A/xx unknown
- 1973-05-02 ES ES414289A patent/ES414289A1/es not_active Expired
- 1973-05-02 CH CH622773A patent/CH566981A5/xx not_active IP Right Cessation
- 1973-05-02 DE DE19732321950 patent/DE2321950A1/de active Pending
- 1973-05-03 GB GB2110173A patent/GB1367598A/en not_active Expired
- 1973-05-04 JP JP4918173A patent/JPS4947366A/ja active Pending
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4699918A (en) * | 1983-01-28 | 1987-10-13 | Laboratoires Jacques Logeais | 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same |
GB2143234A (en) * | 1983-07-06 | 1985-02-06 | Shinogi Seiyaku Kabushiki Kais | (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives |
US6046211A (en) * | 1993-10-21 | 2000-04-04 | G.D. Searle & Co. | Amidino derivatives useful as nitric oxide synthase inhibitors |
US5854234A (en) * | 1993-10-21 | 1998-12-29 | G. D. Searle & Co. | Amidino dervatives useful as nitric oxide synthase inhibitors |
US6448286B1 (en) | 1993-10-21 | 2002-09-10 | G.D. Searle & Co. | Imino pyrrolidine derivatives useful as nitric oxide synthase inhibitors |
US6071906A (en) * | 1993-10-21 | 2000-06-06 | G. D. Searle & Co. | Imidino piperidine derivatives useful as nitric oxide synthase inhibitors |
US5883251A (en) * | 1995-04-20 | 1999-03-16 | G. D. Searle & Co. | Azepine derivatives useful as nitric oxide synthase inhibitors |
US6043261A (en) * | 1995-04-20 | 2000-03-28 | G. D. Searle & Co. | Pyrrolodino imidines useful as nitric oxide synthase inhibitors |
US5945408A (en) * | 1996-03-06 | 1999-08-31 | G.D. Searle & Co. | Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors |
US5981556A (en) * | 1997-07-22 | 1999-11-09 | G.D. Searle & Co. | 1,3-diazolino and 1,3-diazolidino heterocycles as useful nitric oxide synthase inhibitors |
US5958958A (en) * | 1997-07-22 | 1999-09-28 | G.D. Searle & Co. | 1,2,4-oxa diazolino and 1,24-oxa diazolidion heterocycles as useful nitric oxide synthase inhibitors |
US6136829A (en) * | 1997-07-22 | 2000-10-24 | G.D. Searle & Co. | Oxathiadiazole derivatives usful as iNOS inhibitors |
US6489323B1 (en) | 1998-06-10 | 2002-12-03 | G.D. Searle & Co. | Heterobicyclic and tricyclic nitric oxide synthase inhibitors |
US6344473B1 (en) | 2000-08-07 | 2002-02-05 | G.D. Searle & Co. | Imidazoles useful as nitric oxide synthase inhibitors |
Also Published As
Publication number | Publication date |
---|---|
ES414289A1 (es) | 1976-01-16 |
CH566981A5 (enrdf_load_stackoverflow) | 1975-09-30 |
DE2321950A1 (de) | 1973-11-15 |
FR2186236B1 (enrdf_load_stackoverflow) | 1975-08-01 |
BE798779A (fr) | 1973-08-16 |
FR2186236A1 (enrdf_load_stackoverflow) | 1974-01-11 |
JPS4947366A (enrdf_load_stackoverflow) | 1974-05-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
PCNP | Patent ceased through non-payment of renewal fee |