GB1218135A - Substituted phenethylamine derivatives - Google Patents

Substituted phenethylamine derivatives

Info

Publication number
GB1218135A
GB1218135A GB3158768A GB3158768A GB1218135A GB 1218135 A GB1218135 A GB 1218135A GB 3158768 A GB3158768 A GB 3158768A GB 3158768 A GB3158768 A GB 3158768A GB 1218135 A GB1218135 A GB 1218135A
Authority
GB
United Kingdom
Prior art keywords
general formula
group
alkyl
cycloalkyl
hydrogen atom
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
Application number
GB3158768A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abbott Laboratories
Original Assignee
Abbott Laboratories
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Abbott Laboratories filed Critical Abbott Laboratories
Publication of GB1218135A publication Critical patent/GB1218135A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,218,135. Phenethylamine derivatives. ABBOTT LABORATORIES. 2 July, 1968 [28 July, 1967], No. 31587/68. Heading C2C. Novel phenethylamine derivatives of the general formula wherein R and R 1 are each a hydrogen or halogen atom or a trifluoromethyl, di-(C 1-7 alkyl)amino, C 1-7 alkoxy or C 1-7 alkyl group, or R and R 1 , taken together in the 2- and 3-positions, form a fused benzene ring, or R and R 1 , taken together in the 3- and 4- positions, form a methylenedioxy group; R2 is a hydrogen atom or a phenyl or C 1-7 alkyl group; R 3 is a hydrogen atom or a C 1-7 alkyl, aryl, aralkyl or trifluoromethyl group; and X is a cycloalkyl, cycloalkyl-C 1-7 alkyl or hydroxyalkyl group; and acid addition salts thereof are prepared (a) by reaction of an amine of the general formula NH 2 X with a phenylacetaldehyde derivative of the general formula followed by reduction of the resulting imine of the general formula with sodium borohydride or lithium aluminium hydride; or (b) when X is a cycloalkylmethyl group, reaction of a phenethylamine derivative of the first general formula above wherein X is a hydrogen atom with a carboxylic acid chloride of the general formula X<SP>1</SP>COCl, wherein X<SP>1</SP> is a cycloalkyl group, followed by reduction of the resulting amide with lithium aluminium hydride; optionally followed by salification of the product.
GB3158768A 1967-07-28 1968-07-02 Substituted phenethylamine derivatives Expired GB1218135A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US65665567A 1967-07-28 1967-07-28

Publications (1)

Publication Number Publication Date
GB1218135A true GB1218135A (en) 1971-01-06

Family

ID=24633982

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3158768A Expired GB1218135A (en) 1967-07-28 1968-07-02 Substituted phenethylamine derivatives

Country Status (3)

Country Link
CH (1) CH513109A (en)
DE (1) DE1793030A1 (en)
GB (1) GB1218135A (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2283673A1 (en) * 1974-09-06 1976-04-02 Synthelabo NEW M-TRIFLUOROMETHYLTHIO PHENETHYLAMINE DERIVATIVES, THEIR SALTS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING IT
EP0000036A1 (en) * 1977-06-01 1978-12-20 Merck & Co. Inc. Fluorinated alkylamines and process for preparing same
EP0000034A1 (en) * 1977-06-01 1978-12-20 Merck & Co. Inc. Fluorinated amines, compositions and process for preparing said compounds
FR2401905A1 (en) * 1977-09-01 1979-03-30 Merrell Toraude & Co NEW A-HALOGENOMETHYLAMINES USEFUL IN PARTICULAR AS MEDICINAL PRODUCTS AND PROCESS FOR THEIR PREPARATION
EP0002638A1 (en) * 1977-12-13 1979-06-27 LABORATOIRE L. LAFON Société anonyme dite: Addition salts of substituted aralkylamins and therapeutic composition containing them
EP0026298A1 (en) * 1979-08-16 1981-04-08 American Cyanamid Company Method for promoting growth and reducing fat in animals using phenylethanolamine derivatives
EP0049728A2 (en) * 1980-08-25 1982-04-21 American Cyanamid Company Method for enhancing the growth rate of meat-producing animals and for improving the lean meat to fat ratio thereof
EP0057870A1 (en) * 1978-10-05 1982-08-18 Hoechst Aktiengesellschaft N-optionelly substituted-2-amino-alpha-phenylphenethylamines and a method for their preparation
US4504680A (en) * 1978-10-05 1985-03-12 Hoechst-Roussel Pharmaceuticals Inc. 4-Phenyl-1,3-benzodiazepines
WO1988002254A1 (en) * 1986-09-25 1988-04-07 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. New psychostimulant agent
US4822914A (en) * 1978-10-05 1989-04-18 Hoechst-Roussel Pharmaceuticals, Inc. 2-amino-N-methyl-α-phenyl-phenethylamines
EP0318234A2 (en) * 1987-11-25 1989-05-31 Eli Lilly And Company Improvements in or relating to selective serotonin uptake inhibitors
US4933493A (en) * 1978-10-05 1990-06-12 Hoechst-Roussel Pharmaceuticals Inc. Intermediates for the preparation of 4-phenyl-1,3-benzodiazepines
US5185465A (en) * 1978-10-05 1993-02-09 Hoechst-Roussel Pharmaceuticals Inc. Carboxamides of 2-amino-alpha-phenlphenethylamines
US5220068A (en) * 1986-09-25 1993-06-15 Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. Psychostimulant agent
US5260339A (en) * 1978-10-05 1993-11-09 Hoechst-Roussel Pharmaceuticals Incorporated 4-phenyl-1,3-benzodiazepines and 2-amino-α-phenylphenethylamines for treating convulsions and protecting neurons
US9562001B2 (en) 2009-04-15 2017-02-07 Research Triangle Institute Monoamine reuptake inhibitors

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2283673A1 (en) * 1974-09-06 1976-04-02 Synthelabo NEW M-TRIFLUOROMETHYLTHIO PHENETHYLAMINE DERIVATIVES, THEIR SALTS, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING IT
EP0000036A1 (en) * 1977-06-01 1978-12-20 Merck & Co. Inc. Fluorinated alkylamines and process for preparing same
EP0000034A1 (en) * 1977-06-01 1978-12-20 Merck & Co. Inc. Fluorinated amines, compositions and process for preparing said compounds
FR2401905A1 (en) * 1977-09-01 1979-03-30 Merrell Toraude & Co NEW A-HALOGENOMETHYLAMINES USEFUL IN PARTICULAR AS MEDICINAL PRODUCTS AND PROCESS FOR THEIR PREPARATION
EP0002638A1 (en) * 1977-12-13 1979-06-27 LABORATOIRE L. LAFON Société anonyme dite: Addition salts of substituted aralkylamins and therapeutic composition containing them
US4372969A (en) 1977-12-13 1983-02-08 Societe Anonyme Dite: Laboratoire L. Lafon Addition salts of substituted aralkylamines, their method of preparation and their use as pharmaceuticals
US4822914A (en) * 1978-10-05 1989-04-18 Hoechst-Roussel Pharmaceuticals, Inc. 2-amino-N-methyl-α-phenyl-phenethylamines
US5260339A (en) * 1978-10-05 1993-11-09 Hoechst-Roussel Pharmaceuticals Incorporated 4-phenyl-1,3-benzodiazepines and 2-amino-α-phenylphenethylamines for treating convulsions and protecting neurons
US5185465A (en) * 1978-10-05 1993-02-09 Hoechst-Roussel Pharmaceuticals Inc. Carboxamides of 2-amino-alpha-phenlphenethylamines
EP0057870A1 (en) * 1978-10-05 1982-08-18 Hoechst Aktiengesellschaft N-optionelly substituted-2-amino-alpha-phenylphenethylamines and a method for their preparation
US4504680A (en) * 1978-10-05 1985-03-12 Hoechst-Roussel Pharmaceuticals Inc. 4-Phenyl-1,3-benzodiazepines
US4933493A (en) * 1978-10-05 1990-06-12 Hoechst-Roussel Pharmaceuticals Inc. Intermediates for the preparation of 4-phenyl-1,3-benzodiazepines
EP0026298A1 (en) * 1979-08-16 1981-04-08 American Cyanamid Company Method for promoting growth and reducing fat in animals using phenylethanolamine derivatives
EP0049728A3 (en) * 1980-08-25 1982-08-04 American Cyanamid Company Phenylethane derivatives and acid addition salts thereof for enhancing the growth rate of meat-producing animals, improving the efficiency of feed utilization thereby and/or improving the lean meat to fat ratio thereof
EP0049728A2 (en) * 1980-08-25 1982-04-21 American Cyanamid Company Method for enhancing the growth rate of meat-producing animals and for improving the lean meat to fat ratio thereof
WO1988002254A1 (en) * 1986-09-25 1988-04-07 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. New psychostimulant agent
US5220068A (en) * 1986-09-25 1993-06-15 Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. Psychostimulant agent
EP0318234A2 (en) * 1987-11-25 1989-05-31 Eli Lilly And Company Improvements in or relating to selective serotonin uptake inhibitors
EP0318234A3 (en) * 1987-11-25 1990-07-04 Eli Lilly And Company Improvements in or relating to selective serotonin uptake inhibitors
US9562001B2 (en) 2009-04-15 2017-02-07 Research Triangle Institute Monoamine reuptake inhibitors
US10919841B2 (en) 2009-04-15 2021-02-16 Research Triangle Institute Monoamine reuptake inhibitors

Also Published As

Publication number Publication date
DE1793030A1 (en) 1972-02-03
CH513109A (en) 1971-09-30

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