GB1057289A - New pyrrolidine derivatives - Google Patents
New pyrrolidine derivativesInfo
- Publication number
- GB1057289A GB1057289A GB52230/65A GB5223065A GB1057289A GB 1057289 A GB1057289 A GB 1057289A GB 52230/65 A GB52230/65 A GB 52230/65A GB 5223065 A GB5223065 A GB 5223065A GB 1057289 A GB1057289 A GB 1057289A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazinyl
- compounds
- methyl
- dimethoxyphenyl
- pyrrolidine
- 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
- 150000003235 pyrrolidines Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 amino, hydrazino, guanidino Chemical group 0.000 abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- PGARGBKSHAFMLE-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrrole-2-carboxamide Chemical compound COC=1C=C(C=CC1OC)C1=NC(CC1)C(=O)N PGARGBKSHAFMLE-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- DHKAVYNXQVBNAA-UHFFFAOYSA-N [5-(3,4-dimethoxyphenyl)-1-methylpyrrolidin-2-yl]methanamine Chemical compound CN1C(CCC1C1=CC(=C(C=C1)OC)OC)CN DHKAVYNXQVBNAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000001262 anti-secretory effect Effects 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 230000005792 cardiovascular activity Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- GVCMDRGAPUSRTC-UHFFFAOYSA-N methyl 5-(3,4-dimethoxyphenyl)-1-methylpyrrolidine-2-carboxylate Chemical compound CN1C(CCC1C1=CC(=C(C=C1)OC)OC)C(=O)OC GVCMDRGAPUSRTC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US244903A US3164597A (en) | 1962-12-17 | 1962-12-17 | 5-carboxylic acid-2-phenyl-pyrrolines, corresponding pyrrolidines and functional derivatives thereof |
| US417517A US3250771A (en) | 1962-12-17 | 1964-12-10 | 5-monocarbocyclic aryl-n-lower alkyl-2-pyrrolidine carboxylic acid, esters, amides and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1057289A true GB1057289A (en) | 1967-02-01 |
Family
ID=26936869
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52231/65A Expired GB1057290A (en) | 1962-12-17 | 1965-12-09 | New pyrrolidine derivatives |
| GB52230/65A Expired GB1057289A (en) | 1962-12-17 | 1965-12-09 | New pyrrolidine derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52231/65A Expired GB1057290A (en) | 1962-12-17 | 1965-12-09 | New pyrrolidine derivatives |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3250771A (en:Method) |
| DE (2) | DE1545924A1 (en:Method) |
| FR (4) | FR1464233A (en:Method) |
| GB (2) | GB1057290A (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127369A (en) * | 1980-02-15 | 1981-10-06 | Mitsui Toatsu Chem Inc | Nevel piperazine compound, its preparation and utilization |
| HU189214B (en) * | 1983-01-20 | 1986-06-30 | Alkaloida Vegyeszeti Gyar,Hu | Process for preparing pyrroline and pyrrolidine carboxamide derivatives |
| DE3473442D1 (de) * | 1983-01-21 | 1988-09-22 | Alkaloida Vegyeszeti Gyar | New alkyl diamine derivatives |
| FR2663026B1 (fr) * | 1990-06-07 | 1992-08-07 | Synthelabo | Derives de [(1-arylpyrrolidin-2-yl) methyl] piperazine, leur preparation et leur application en therapeutique. |
| US5876464A (en) * | 1998-02-17 | 1999-03-02 | Bristol-Myers Squibb Company | Hair dyeing with N-(4-aminophenyl) prolineamide, couplers, and oxidizing agents |
| GB0423356D0 (en) * | 2004-10-21 | 2004-11-24 | Merck Sharp & Dohme | Therapeutic agents |
| US20090099201A1 (en) * | 2007-05-22 | 2009-04-16 | David Robert Bolin | Diacylglycerol Acyltransferase Inhibitors |
| US8058299B2 (en) * | 2007-05-22 | 2011-11-15 | Via Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8153644B2 (en) * | 2007-05-22 | 2012-04-10 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8115011B2 (en) * | 2007-05-22 | 2012-02-14 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8211884B2 (en) * | 2008-08-06 | 2012-07-03 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8324385B2 (en) * | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| WO2010065310A1 (en) * | 2008-12-03 | 2010-06-10 | Via Pharmaceuticals, Inc | Inhibitors of diacylglycerol acyltransferase |
| US8211914B2 (en) * | 2008-12-17 | 2012-07-03 | Madrigal Pharmaceuticals, Inc. | Inhibitors of diacylglycerol acyltransferase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3164597A (en) * | 1962-12-17 | 1965-01-05 | Geigy Chem Corp | 5-carboxylic acid-2-phenyl-pyrrolines, corresponding pyrrolidines and functional derivatives thereof |
-
1964
- 1964-12-10 US US417517A patent/US3250771A/en not_active Expired - Lifetime
-
1965
- 1965-12-09 GB GB52231/65A patent/GB1057290A/en not_active Expired
- 1965-12-09 GB GB52230/65A patent/GB1057289A/en not_active Expired
- 1965-12-09 DE DE19651545924 patent/DE1545924A1/de active Pending
- 1965-12-09 DE DE19651545925 patent/DE1545925A1/de active Pending
- 1965-12-10 FR FR41776A patent/FR1464233A/fr not_active Expired
- 1965-12-10 FR FR41775A patent/FR1473934A/fr not_active Expired
-
1966
- 1966-03-09 FR FR52753A patent/FR5287M/fr not_active Expired
- 1966-03-09 FR FR52752A patent/FR5259M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1057290A (en) | 1967-02-01 |
| FR1473934A (fr) | 1967-03-24 |
| FR1464233A (fr) | 1966-12-30 |
| US3250771A (en) | 1966-05-10 |
| DE1545924A1 (de) | 1970-01-08 |
| FR5259M (en:Method) | 1967-07-24 |
| DE1545925A1 (de) | 1970-01-08 |
| FR5287M (en:Method) | 1967-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1057289A (en) | New pyrrolidine derivatives | |
| GB1022032A (en) | Basic ethers | |
| GB1176092A (en) | Improvements in or relating to Substituted Piperidinoalkylthianaphthenes and Benzofurans | |
| DE3170937D1 (en) | 2-(1,4-benzodioxan-2-ylalkyl) imidazoles, their preparation and pharmaceutical compositions containing them | |
| GB1018985A (en) | Benzoxacycloalkanemethylamines | |
| GB993525A (en) | Substituted propanolamines and process for preparing the same | |
| GB1096351A (en) | Improvements in or relating to piperazine derivatives | |
| GB915259A (en) | 4-halo-3-sulfamoylbenzoic acid esters and methods for producing same | |
| GB1109848A (en) | New dibenzocycloheptadiene derivatives and process for their preparation | |
| GB858140A (en) | The preparation of new basic phenothiazine derivatives | |
| GB1113802A (en) | Improvements in or relating to substituted quinolines and the manufacture thereof | |
| GB1350520A (en) | Bis-basic esters and amides of xanthene and xanthone | |
| GB1204946A (en) | Improvements in or relating to sulphon anilides and the manufacture thereof | |
| GB1340637A (en) | Dibenzocycloheptadioxolan derivatives | |
| GB1015921A (en) | Benzamides | |
| ES355267A1 (es) | Metodo para producir una n-(fenoxifenil) sulfamida. | |
| GB1193534A (en) | Novel Benzazocine Derivatives, the Preparation thereof and Compositions Containing the same | |
| GB897052A (en) | Improvements in and relating to n-heterocyclic compounds | |
| GB1046226A (en) | Substituted tetrahydroquinolines | |
| GB1049824A (en) | Hexahydropyridobenzodiazepine derivatives | |
| GB920859A (en) | Substituted triphenylmethanols | |
| GB983608A (en) | Novel des-a-steroid compounds, and processes for their preparation | |
| GB986875A (en) | The manufacture of halogeno-alkylidene tricyclic compounds and the conversion thereof | |
| SE8206230D0 (sv) | Novel cyclic imines, their preparation and pharmaceutical compositions containing the same | |
| GB1042490A (en) | Phenoxyalkylaminoguanidines |