GB1153670A - Isoquinoline Derivatives and preparation thereof - Google Patents
Isoquinoline Derivatives and preparation thereofInfo
- Publication number
- GB1153670A GB1153670A GB5537167A GB5537167A GB1153670A GB 1153670 A GB1153670 A GB 1153670A GB 5537167 A GB5537167 A GB 5537167A GB 5537167 A GB5537167 A GB 5537167A GB 1153670 A GB1153670 A GB 1153670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- carboxyl
- formula
- esterified
- substituted
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,153,670. Pyrrolo-isoquinolines. SIPHAR S.A. 5 Dec., 1967 [7 Dec., 1966], No. 55371/67. Heading C2C. Novel pyrrole [2,1-a] isoquinolines of the general Formula I in which the pyrrole ring may be unsaturated or saturated, R<SP>1</SP> is a hydrogen atom or a carboxyl or esterified carboxyl group, R<SP>2</SP> is an alkyl, cycloalkyl, aryl, carboxyl, esterified carboxyl, carboxymethyl, esterified carboxymethyl, carboxyamide or substituted carboxyamide group, R<SP>3</SP> is a hydrogen atom or a carboxyl or esterified carboxyl group, or R<SP>2</SP> and R<SP>3</SP> when taken together may form the anhydride of the corresponding dicarboxylic acid, and salts and addition compounds thereof, with pharmacologically acceptable organic or inorganic bases or acids, are prepared by condensing a substituted α-halo carbonyl compound of the formula R<SP>3</SP>-CHXCO-R<SP>2</SP> where X represents a halogen atom, with an appropriately substituted 3,4-dihydro isoquinoline derivative, if desired subjecting the cyclization product so obtained to appropriate transformations of the substituent groups to obtain the desired compound of Formula I and, if desired, subjecting the compound to catalytic hydrogenation to obtain the corresponding pyrrolidene compound. Pharmaceutical compositions comprising a compound of Formula I as active ingredient are administered orally, parenterally or rectally and have hypotensive, sympathicolytic and psychotropic activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE690792 | 1966-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1153670A true GB1153670A (en) | 1969-05-29 |
Family
ID=3849828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5537167A Expired GB1153670A (en) | 1966-12-07 | 1967-12-05 | Isoquinoline Derivatives and preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE690792A (en) |
| GB (1) | GB1153670A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0130069A3 (en) * | 1983-06-23 | 1985-09-11 | Mcneilab, Inc. | Hexahydropyrrolo (2,1-a) isoquinoline derivatives |
| EP0150474A3 (en) * | 1984-01-13 | 1985-09-25 | Boehringer Ingelheim Kg | 5,6-dihydro-pyrrolo-û2,1-a¨isoquinolines and process for their preparation |
| EP0172692A1 (en) * | 1984-08-02 | 1986-02-26 | McNeilab, Inc. | Hexahydroindolizine compounds, pharmaceutical compositions and methods and intermediates |
| US4595688A (en) * | 1983-06-23 | 1986-06-17 | Mcneilab, Inc. | Hexahydropyrrolo[2,1-a]isoquinoline derivatives and antidepressant use thereof |
| US4719216A (en) * | 1983-06-23 | 1988-01-12 | Mcneilab, Inc. | Hexahydropyrrolo(2,1-A)isoquinoline derivatives as antidepressants |
| EP0303446A1 (en) * | 1987-08-11 | 1989-02-15 | May & Baker Limited | Pyrroloisoquinolines |
| WO2002048144A1 (en) * | 2000-12-13 | 2002-06-20 | Bayer Aktiengesellschaft | Pyrrolo (2.1-a) dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
| WO2003014117A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Corporation | 3-substituted pyrrolo[2.1-a]isoquinoline derivatives |
| JP2009513494A (en) * | 2003-06-30 | 2009-04-02 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Pyrrodihydroisoquinoline as a PDE10 inhibitor |
-
1966
- 1966-12-07 BE BE690792D patent/BE690792A/xx unknown
-
1967
- 1967-12-05 GB GB5537167A patent/GB1153670A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0130069A3 (en) * | 1983-06-23 | 1985-09-11 | Mcneilab, Inc. | Hexahydropyrrolo (2,1-a) isoquinoline derivatives |
| US4595688A (en) * | 1983-06-23 | 1986-06-17 | Mcneilab, Inc. | Hexahydropyrrolo[2,1-a]isoquinoline derivatives and antidepressant use thereof |
| US4719216A (en) * | 1983-06-23 | 1988-01-12 | Mcneilab, Inc. | Hexahydropyrrolo(2,1-A)isoquinoline derivatives as antidepressants |
| EP0150474A3 (en) * | 1984-01-13 | 1985-09-25 | Boehringer Ingelheim Kg | 5,6-dihydro-pyrrolo-û2,1-a¨isoquinolines and process for their preparation |
| EP0172692A1 (en) * | 1984-08-02 | 1986-02-26 | McNeilab, Inc. | Hexahydroindolizine compounds, pharmaceutical compositions and methods and intermediates |
| EP0303446A1 (en) * | 1987-08-11 | 1989-02-15 | May & Baker Limited | Pyrroloisoquinolines |
| US4933350A (en) * | 1987-08-11 | 1990-06-12 | May & Baker Limited | Pyrroloisoquinolines useful as hypercholesterolemic and hyperlipoprotienimic agents |
| WO2002048144A1 (en) * | 2000-12-13 | 2002-06-20 | Bayer Aktiengesellschaft | Pyrrolo (2.1-a) dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
| US6930114B2 (en) | 2000-12-13 | 2005-08-16 | Bayer Pharmaceuticals Corporation | Pyrrolo (2.1a)dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
| WO2003014117A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Corporation | 3-substituted pyrrolo[2.1-a]isoquinoline derivatives |
| WO2003014115A1 (en) * | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | 3-substituted pyrrolo (2.1-a) isoquinoline derivatives |
| JP2009513494A (en) * | 2003-06-30 | 2009-04-02 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Pyrrodihydroisoquinoline as a PDE10 inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| BE690792A (en) | 1967-05-16 |
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