IE41352B1 - 5-aryl-1,2,3,4-tetrahydro- -carbolines - Google Patents
5-aryl-1,2,3,4-tetrahydro- -carbolinesInfo
- Publication number
- IE41352B1 IE41352B1 IE589/75A IE58975A IE41352B1 IE 41352 B1 IE41352 B1 IE 41352B1 IE 589/75 A IE589/75 A IE 589/75A IE 58975 A IE58975 A IE 58975A IE 41352 B1 IE41352 B1 IE 41352B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- general formula
- reacting
- tetrahydro
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/20—Hypnotics; Sedatives
Abstract
1476087 5 - Phenyl - 1,2,3,4 - tetrahydro- γ-carbolines PFIZER Inc 26 March 1975 [1 April 1974] 12773/75 Heading C2C Novel 5 - phenyl - 1,2,3,4 - tetrahydro - γ- carbolines of the general Formula I wherein X is a hydrogen, fluorine, chlorine or bromine atom or a methyl group, Z is a hydrogen, fluorine or chlorine atom or a methoxy or trifluoromethyl group and R is a hydrogen atom, a C 1-6 alkyl or benzyl group, or a group of the Formula X in which A is a C 1-5 alkylene group, M is -CH = CH-, -CH 2 -, -CO-, -CH(OR 1 )- or -C(CH 3 )(OR 1 )-, where R 1 is a hydrogen atom or C 2-6 alkanoyl group, and K is a hydrogen, fluorine or chlorine atom or a methyl or trifluoromethyl group, with the proviso that when Z is a hydrogen atom, X is a fluorine, chlorine or bromine atom or a methyl group, and pharmaceutically acceptable acid addition salts thereof are prepared (a) when R is a hydrogen atom, by heating the corresponding ester of the general Formula III with ethanolic KOH; (b) when R is a C 1-6 alkyl or benzyl group or a group of the Formula X in which M is -CH 2 - or -CO-, by reacting the product of (a) with R-hal, wherein hal is a halogen atom or a sulphonate ester group; (c) when R is a C 1-6 alkyl group, by reacting a 1,2,3,4-tetrahydro-γ-carboline of the general formula with a Z-substituted bromobenzene in the presence of Cu 2 Br 2 and Na 2 CO 3 ; (d) when R is a C 2-6 alkyl group, by reducing the corresponding compound in which R is a C 2-6 alkanoyl group with a metal hydride; (e) when R is a methyl group, by reducing the ester of the general Formula III with LiAlH 4 or aluminium hydride; (f) when R is a group of the Formula X, by reacting a nitrile of the general formula with a Y-substituted phenyl magnesium halide; (g) when R is a group of the Formula X and M is -CH(OH)-, by reducing the corresponding compound in which M is -CO- with NaBH 4 ; (h) when R is a group of the Formula X and M is -C(OH)(CH 3 )-, by reacting the corresponding compound in which M is -CO- with CH 3 MgI; (i) when R is a group of the Formula X and M is -CH(OR 1 )- or -C(CH 3 )(OR 1 )-, in which R 1 is a C 2-6 alkanoyl group, by esterifying the corresponding compound in which M is -CH(OH)- or -C(CH 3 )(OH)-; and (j) when R is a group of the Formula X in which M is -CH = CH-, by dehydrating the corresponding compound M is -CH(OH)- and A is an alkylene group containing one more C atom than in the desired product, followed optionally by salification. Esters of the general Formula III are prepared by reacting a p-X-phenylhydrazine with N- ethoxycarbonyl-4-piperidone and reacting the resulting 2 - ethoxycarhonyl - 8 - W - 1,2,3,4- tetrahydro - γ - carboline with a Z - substituted bromobenzene in the presence of Cu 2 Br 2 and Na 2 CO 3 . Ketones of the general Formula I wherein R is a C 2-6 alkanoyl group are prepared by acylation of the corresponding compound in which R is a hydrogen atom. 1,2,3,4 - Tetrahydro - γ - carbolines of the general Formula IV are prepared by reacting a p-X-phenylhydrazine with a N-R-4-piperidone. Nitriles of the general Formula VI are prepared by reacting the corresponding compound I wherein R is a hydrogen atom with halogen- A-CN. Pharmaceutical compositions having tranquillizing activity comprise, as active ingredient, a novel 5-phenyl-1,2,3,4-tetrahydro-γ-carboline (I), wherein R is other than a hydrogen atom, or a pharmaceutically acceptable acid addition salt thereof, in admixture with a pharmacologically acceptable carrier.
[GB1476087A]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45664074A | 1974-04-01 | 1974-04-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE41352L IE41352L (en) | 1975-10-01 |
IE41352B1 true IE41352B1 (en) | 1979-12-19 |
Family
ID=23813560
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE589/75A IE41352B1 (en) | 1974-04-01 | 1975-03-19 | 5-aryl-1,2,3,4-tetrahydro- -carbolines |
Country Status (6)
Country | Link |
---|---|
JP (3) | JPS5874682A (en) |
BE (1) | BE827451A (en) |
CA (1) | CA1056381A (en) |
GB (1) | GB1476087A (en) |
IE (1) | IE41352B1 (en) |
ZA (1) | ZA751990B (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004063818A (en) | 2002-07-30 | 2004-02-26 | Oki Electric Ind Co Ltd | Method for manufacturing semiconductor device using flexible tube |
US8993572B2 (en) | 2010-04-22 | 2015-03-31 | Intra-Cellular Therapies, Inc. | Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines derivatives and [1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole derivatives |
US11053245B2 (en) | 2012-04-14 | 2021-07-06 | Intra-Cellular Therapies, Inc. | Methods |
PT2968320T (en) | 2013-03-15 | 2021-01-28 | Intra Cellular Therapies Inc | Organic compounds |
EP3666271A1 (en) | 2013-12-03 | 2020-06-17 | Intra-Cellular Therapies, Inc. | Miscrospheres comprising a plga matrix for medical use |
EP3125893B1 (en) | 2014-04-04 | 2023-09-20 | Intra-Cellular Therapies, Inc. | Deuterated heterocycle fused gamma-carbolines as antagonists of 5-ht2a receptors |
EP3125892A4 (en) | 2014-04-04 | 2017-12-27 | Intra-Cellular Therapies, Inc. | Organic compounds |
EP3407888B1 (en) | 2016-01-26 | 2020-12-30 | Intra-Cellular Therapies, Inc. | Pyridopyrroloquinoxaline compounds, their compositions and uses |
EP3888656A1 (en) | 2016-03-25 | 2021-10-06 | Intra-Cellular Therapies, Inc. | Deuterated heterocyclic gamma-carboline compounds and their use in the treatment or prophylaxis of a central nervous system disorder |
JP2019510039A (en) | 2016-03-28 | 2019-04-11 | イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. | Novel compositions and methods |
JP7013454B2 (en) | 2016-10-12 | 2022-02-15 | イントラ-セルラー・セラピーズ・インコーポレイテッド | Amorphous solid dispersion |
WO2018126143A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
MX2021013640A (en) | 2017-03-24 | 2022-08-31 | Intra Cellular Therapies Inc | Novel compositions and methods. |
JP7224333B2 (en) | 2017-07-26 | 2023-02-17 | イントラ-セルラー・セラピーズ・インコーポレイテッド | organic compound |
CA3071119A1 (en) | 2017-07-26 | 2019-01-31 | Intra-Cellular Therapies, Inc. | Organic compounds |
WO2019241278A1 (en) | 2018-06-11 | 2019-12-19 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
CA3108558A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
BR112021003655A2 (en) | 2018-08-31 | 2021-05-18 | Intra-Cellular Therapies, Inc. | new methods |
-
1975
- 1975-03-19 IE IE589/75A patent/IE41352B1/en unknown
- 1975-03-26 GB GB1277375A patent/GB1476087A/en not_active Expired
- 1975-03-27 CA CA223,250A patent/CA1056381A/en not_active Expired
- 1975-04-01 BE BE1006567A patent/BE827451A/en not_active IP Right Cessation
- 1975-04-01 ZA ZA00751990A patent/ZA751990B/en unknown
-
1982
- 1982-09-14 JP JP57160718A patent/JPS5874682A/en active Pending
- 1982-09-14 JP JP57160719A patent/JPS5874683A/en active Pending
- 1982-09-14 JP JP57160717A patent/JPS5915911B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IE41352L (en) | 1975-10-01 |
GB1476087A (en) | 1977-06-10 |
JPS5874683A (en) | 1983-05-06 |
ZA751990B (en) | 1976-02-25 |
JPS5874682A (en) | 1983-05-06 |
JPS5915911B2 (en) | 1984-04-12 |
CA1056381A (en) | 1979-06-12 |
BE827451A (en) | 1975-10-01 |
JPS5874681A (en) | 1983-05-06 |
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