GB973887A - Phenyl-cycloalkane-methylamines and processes of preparing them - Google Patents

Phenyl-cycloalkane-methylamines and processes of preparing them

Info

Publication number
GB973887A
GB973887A GB5345/61A GB534561A GB973887A GB 973887 A GB973887 A GB 973887A GB 5345/61 A GB5345/61 A GB 5345/61A GB 534561 A GB534561 A GB 534561A GB 973887 A GB973887 A GB 973887A
Authority
GB
United Kingdom
Prior art keywords
amine
phenyl
reducing
hydrogen
reacting
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
GB5345/61A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB973887A publication Critical patent/GB973887A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0973887/C1/1> and acid addition salts thereof, wherein R1 and R2 are H, OH, CH3 or OCH3 or together form a methylenedioxy group, X together with the CH2 and CHR3 groups and the central carbon atom forms a cycloalkane ring of 3-5 carbon atoms i.e. cyclopropane cyclobutane and cyclopentane, R3 is hydrogen or a C1-3 alkyl group, and R4 and R5 represent hydrogen or saturated or unsaturated aliphatic hydrocarbon groups of 1-4 carbon atoms or cycloalkyl groups of 4-6 carbon atoms or together with the nitrogen atom form a saturated ring which may be interrupted by a further hetero-atom e.g. azetidine, methyl azetidine, pyrrolidine dimethylpyrrolidene, piperidine, hexamethylene-imine, morpholine, thiamorpholine and piperazine. The compounds are prepared by (a) reacting an amine of the formula <FORM:0973887/C1/2> with an ester R4Y, wherein Y is the residue of an organic or inorganic acid; (b) reducing the amine II in the presence of an aldehyde or ketone R6.CO.R7 wherein R6 and R7 are each hydrogen or a saturated or unsaturated aliphatic hydrocarbon of 1-3 carbon atoms; (c) heating II in the presence of an alcohol R4OH; (d) reacting the amine II with a dihalide Hal.(CH2)n.Hal wherein n is 3, 4 or 5, preferably in the presence of an agent splitting off hydrogen halide; (e) reacting II with benzaldehyde, adding an ester R4Y to the resulting benzylidene compound and splitting off the acid radical from the resulting addition product by hydrolysis; (f) treating an appropriate secondary amine (wherein R5 is hydrogen) with an ester R5Y to give a tertiary amine product; (g) reducing a corresponding 1-phenyl-cycloalkyl-carboxylic amide with lithium aluminium hydride; (h) reducing a corresponding N-acyl-1-phenyl-1-aminomethyl-cycloalkane with lithium aluminium hydride; (i) reducing a 1-phenyl-cycloalkyl-(1)-aldehyde in the presence of an amine R4(R5)NH or (j) reacting a 1-halo-methyl-1-phenyl-cycloalkane with an amine R4(R5)NH. Amines of the Formula II used as starting materials are made by reducing the corresponding nitriles, which themselves are obtained by reaction of the appropriate benzyl cyanides with twice the molar amount of sodamide and an equimolar amount of a diahlo-alkane. Pharmaceutical preparations having central-analeptic properties comprise the above compounds of the invention, including their salts with organic or inorganic acids, in admixture or conjunction with a carrier. The preparations suitably are in a form adapted for parenteral or, more preferably, oral administration such as tablets, dragees, capsules, solutions, suspensions or emulsions.
GB5345/61A 1960-02-12 1961-02-13 Phenyl-cycloalkane-methylamines and processes of preparing them Expired GB973887A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF30529A DE1124485B (en) 1960-02-12 1960-02-12 Process for the preparation of analeptically active phenylcycloalkylmethylamines

Publications (1)

Publication Number Publication Date
GB973887A true GB973887A (en) 1964-10-28

Family

ID=7093800

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5345/61A Expired GB973887A (en) 1960-02-12 1961-02-13 Phenyl-cycloalkane-methylamines and processes of preparing them

Country Status (4)

Country Link
CH (4) CH443274A (en)
DE (1) DE1124485B (en)
FR (1) FR1133M (en)
GB (1) GB973887A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2504920A1 (en) * 1981-04-06 1982-11-05 Boots Co Ltd PHENYLCYCLOBUTYL DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
US4443449A (en) * 1981-04-06 1984-04-17 The Boots Company Limited Arylcyclobutylalkylamines and anti-depression composition and methods using same
EP0108488A1 (en) * 1982-09-30 1984-05-16 The Boots Company PLC (1-Arylcyclobutyl) (heterocyclyl) methylamine compounds, their preparation and their use as therapeutic agents
EP0111994A1 (en) * 1982-09-30 1984-06-27 The Boots Company PLC (1-Arylcyclobutyl) alkylamine derivatives, their preparation and their use as therapeutic agents
US4522828A (en) * 1981-04-06 1985-06-11 The Boots Company Plc Therapeutic agents
US4925879A (en) * 1985-01-17 1990-05-15 Boots Company, Plc Arylcyclobutylmethylamines
US4929629A (en) * 1985-12-17 1990-05-29 Boots Company, Plc Therapeutic compound
EP1595873A1 (en) * 2004-05-13 2005-11-16 Boehringer Ingelheim Pharma GmbH & Co.KG Substituted cycloalkyl derivatives for the treatment of respiratory diseases
US7423035B2 (en) 2004-05-13 2008-09-09 Boehringer Ingelheim International Gmbh Substituted cycloalkyl derivatives, process for the manufacture thereof and use thereof as medicament

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL128184C (en) * 1963-06-27
US4535186A (en) * 1983-04-19 1985-08-13 American Home Products Corporation 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives
IE56324B1 (en) * 1982-12-13 1991-06-19 American Home Prod Phenethylamine derivatives and intermediates therefor
US4552982A (en) * 1983-08-01 1985-11-12 Eli Lilly And Company Synthesis of 9-carbamoyl-9-(3-aminopropyl)fluorenes
US4611078A (en) * 1983-10-26 1986-09-09 American Home Products Corporation Substituted phenylacetonitriles
RU2361862C2 (en) 2003-12-29 2009-07-20 Сепракор Инк. Pyrrole and pyrazole daao inhibitors
CA2614282A1 (en) 2005-07-06 2007-01-11 Sepracor Inc. Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders
KR101294014B1 (en) * 2006-01-06 2013-08-09 선오비온 파마슈티컬스 인코포레이티드 Cycloalkylamines as monoamine reuptake inhibitors
US8053603B2 (en) 2006-01-06 2011-11-08 Sunovion Pharmaceuticals Inc. Tetralone-based monoamine reuptake inhibitors
PT2816024T (en) 2006-03-31 2017-10-20 Sunovion Pharmaceuticals Inc Chiral amines
US7884124B2 (en) 2006-06-30 2011-02-08 Sepracor Inc. Fluoro-substituted inhibitors of D-amino acid oxidase
US7902252B2 (en) 2007-01-18 2011-03-08 Sepracor, Inc. Inhibitors of D-amino acid oxidase
RU2470011C2 (en) 2007-05-31 2012-12-20 Сепракор Инк. Cycloalkylamines, containing phenyl as substituent, as inhibitors of monoamine reuptake

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE483205C (en) * 1925-11-20 1929-10-05 I G Farbenindustrie Akt Ges Process for the preparation of cyclohexylamines
DE970480C (en) * 1940-05-15 1958-09-25 Knoll Ag Process for the preparation of ª-cyclohexylisopropylmethylamine
DE937952C (en) * 1953-10-21 1956-01-19 Schering Ag Process for the preparation of 2-aminoindan compounds with analeptic activity

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2504920A1 (en) * 1981-04-06 1982-11-05 Boots Co Ltd PHENYLCYCLOBUTYL DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
US4443449A (en) * 1981-04-06 1984-04-17 The Boots Company Limited Arylcyclobutylalkylamines and anti-depression composition and methods using same
US4522828A (en) * 1981-04-06 1985-06-11 The Boots Company Plc Therapeutic agents
AT382612B (en) * 1981-04-06 1987-03-25 Boots Co Plc METHOD FOR PRODUCING NEW ARYLCYCLOBUTYLALKYLAMINES
US4746680A (en) * 1981-04-06 1988-05-24 The Boots Company P.L.C. Therapeutic agents
EP0108488A1 (en) * 1982-09-30 1984-05-16 The Boots Company PLC (1-Arylcyclobutyl) (heterocyclyl) methylamine compounds, their preparation and their use as therapeutic agents
EP0111994A1 (en) * 1982-09-30 1984-06-27 The Boots Company PLC (1-Arylcyclobutyl) alkylamine derivatives, their preparation and their use as therapeutic agents
US4629727A (en) * 1982-09-30 1986-12-16 The Boots Company Plc Therapeutic agents
US4925879A (en) * 1985-01-17 1990-05-15 Boots Company, Plc Arylcyclobutylmethylamines
US5047432A (en) * 1985-01-17 1991-09-10 The Boots Company Plc Arylcyclobutylmethylamine therapeutic agents
US4929629A (en) * 1985-12-17 1990-05-29 Boots Company, Plc Therapeutic compound
US5068440A (en) * 1985-12-17 1991-11-26 Boots Company, Plc Process for the manufacture of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate
EP1595873A1 (en) * 2004-05-13 2005-11-16 Boehringer Ingelheim Pharma GmbH & Co.KG Substituted cycloalkyl derivatives for the treatment of respiratory diseases
WO2005111002A2 (en) * 2004-05-13 2005-11-24 Boehringer Ingelheim International Gmbh Substituted cycloalkyl derivatives for use in the treatment of respiratory diseases
WO2005111002A3 (en) * 2004-05-13 2006-03-16 Boehringer Ingelheim Int Substituted cycloalkyl derivatives for use in the treatment of respiratory diseases
JP2007537185A (en) * 2004-05-13 2007-12-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Substituted cycloalkyl derivatives, methods for their preparation and their use as drugs
US7423035B2 (en) 2004-05-13 2008-09-09 Boehringer Ingelheim International Gmbh Substituted cycloalkyl derivatives, process for the manufacture thereof and use thereof as medicament
US7563806B2 (en) 2004-05-13 2009-07-21 Boehringer Ingelheim International Gmbh Substituted cycloalkyl derivatives, process for the manufacture thereof and use thereof as medicament

Also Published As

Publication number Publication date
DE1124485B (en) 1962-03-01
CH443274A (en) 1967-09-15
CH430702A (en) 1967-02-28
CH430703A (en) 1967-02-28
FR1133M (en) 1962-02-19
CH443279A (en) 1967-09-15

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