GB1037014A - Derivatives of 1-aminoindane - Google Patents

Derivatives of 1-aminoindane

Info

Publication number
GB1037014A
GB1037014A GB30832/63A GB3083263A GB1037014A GB 1037014 A GB1037014 A GB 1037014A GB 30832/63 A GB30832/63 A GB 30832/63A GB 3083263 A GB3083263 A GB 3083263A GB 1037014 A GB1037014 A GB 1037014A
Authority
GB
United Kingdom
Prior art keywords
aminoindane
formamide
reacting
indanone
alkyl
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
GB30832/63A
Inventor
Maurice Ward Gittos
John William James
Leslie Frederick Wiggins
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.)
Aspro Nicholas Ltd
Original Assignee
Aspro Nicholas Ltd
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 Aspro Nicholas Ltd filed Critical Aspro Nicholas Ltd
Priority to GB30832/63A priority Critical patent/GB1037014A/en
Priority to CH289467A priority patent/CH509967A/en
Priority to CH985664A priority patent/CH451124A/en
Priority to CH1261367A priority patent/CH460750A/en
Priority to FI162864A priority patent/FI41394C/en
Priority to DE19641443403 priority patent/DE1443403C/en
Priority to FR983761A priority patent/FR4230M/fr
Priority to DK378764A priority patent/DK126585B/en
Priority to NL646408887A priority patent/NL147036B/en
Priority to SE938564A priority patent/SE334348B/xx
Priority to DK306266A priority patent/DK125701B/en
Publication of GB1037014A publication Critical patent/GB1037014A/en
Priority to SE02714/69A priority patent/SE338039B/xx
Priority to US00882730A priority patent/US3709996A/en
Priority to US00057391A priority patent/US3758690A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton

Abstract

Novel 1-aminoindanes of formula <FORM:1037014/C2/1> and pharmaceutically acceptable acid addition salts thereof, wherein R1 is hydrogen or alkyl, and R2 is cyclopropyl or -CN2C­C-R3, R3\t being hydrogen or alkyl, are prepared (A) when R1 is hydrogen, (1) by reacting 1-indanone with a formamide of formula HCONHR2 and submitting the resulting 1-indane formamide to acid or alkaline hydrolysis, and (2) by condensing a 1-haloindane with an amine R2NH2, and (B) when R1 is alkyl, (1) by reacting 1-indanone with a formamide HCONHR1, hydrolysing the 1-indane formamide with acid or alkali, and reacting the N - mono - substituted 1 - amino indane formed with a compound R2X, where X is halogen, (2) by condensing a 1-haloindane with an amine R1NH2 and reacting the N-monosubstituted 1-aminoindane with a halogen compound R2X, and (3) alkylating, using an appropriate alkylating agent, an R2-substituted-1-aminoindane, and, in each case, if desired, converting the aminoindane formed into a pharmaceutically acceptable acid addition salt. Therapeutic compositions having monoamine oxidase-inhibiting and adrenolytic activity, which may be useful as antidepressant or psychostimulant agents and in the treatment of cardiovascular diseases, and which may be administered orally, parenterally or rectally, contain as active ingredients the 1-aminoindane derivatives of formula I above. N,N - Di - (1 - indanyl) - propargylamine hydrochloride is obtained as by-product in the reaction of 1-chloroindane and propargylamine. 1-Indanone may be prepared by catalytically reducing cinnamic acid, and cyclizing the hydrocinnamic acid obtained with thionyl chloride and aluminium chloride.
GB30832/63A 1963-08-02 1963-08-02 Derivatives of 1-aminoindane Expired GB1037014A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
GB30832/63A GB1037014A (en) 1963-08-02 1963-08-02 Derivatives of 1-aminoindane
CH289467A CH509967A (en) 1963-08-02 1964-07-28 N-substd 1-aminoindane derivs
CH985664A CH451124A (en) 1963-08-02 1964-07-28 Process for preparing an aminoindane derivative or an acid addition salt thereof
CH1261367A CH460750A (en) 1963-08-02 1964-07-28 Process for the preparation of aminoidane derivatives
FI162864A FI41394C (en) 1963-08-02 1964-07-29 Process for the preparation of therapeutically active N-substituted I-aminoindan derivatives
DE19641443403 DE1443403C (en) 1963-08-02 1964-07-29 N Cyclopropyl 1 aminoindan derivatives and process for their preparation
DK378764A DK126585B (en) 1963-08-02 1964-07-31 Analogous process for the preparation of N-disubstituted 1-aminoindane derivatives or acid addition salts thereof.
FR983761A FR4230M (en) 1963-08-02 1964-07-31
NL646408887A NL147036B (en) 1963-08-02 1964-08-03 METHOD OF PREPARING A MEDICINAL PRODUCT WITH AN ANTI-DEPRESSION OR PSYCHOSTIMULATING ACTION, AND ANY SUITABLE INDEX DERIVATIVES.
SE938564A SE334348B (en) 1963-08-02 1964-08-03
DK306266A DK125701B (en) 1963-08-02 1966-06-15 Analogous process for the preparation of N-monosubstituted 1-aminoindanes or acid addition salts thereof.
SE02714/69A SE338039B (en) 1963-08-02 1969-02-27
US00882730A US3709996A (en) 1963-08-02 1969-12-05 Pharmaceutical compositions containing n-cyclopropyl-1-aminoindane compounds and adapted for administration to obtain inhibition of monoamine oxidase enzyme and process
US00057391A US3758690A (en) 1963-08-02 1970-06-05 And use of such n-cyclopropyl compounds as hypotensives pharmaceutical compositions containing n-cyclopropyl-1-amino indanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB30832/63A GB1037014A (en) 1963-08-02 1963-08-02 Derivatives of 1-aminoindane

Publications (1)

Publication Number Publication Date
GB1037014A true GB1037014A (en) 1966-07-20

Family

ID=10313839

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30832/63A Expired GB1037014A (en) 1963-08-02 1963-08-02 Derivatives of 1-aminoindane

Country Status (7)

Country Link
CH (2) CH451124A (en)
DK (2) DK126585B (en)
FI (1) FI41394C (en)
FR (1) FR4230M (en)
GB (1) GB1037014A (en)
NL (1) NL147036B (en)
SE (2) SE334348B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4833169A (en) * 1985-08-27 1989-05-23 Ciba-Geigy Corporation Hydropyridine derivatives
EP0436492A2 (en) * 1990-01-03 1991-07-10 Teva Pharmaceutical Industries Limited R-Enantiomer of N-propargyl-1-aminoindan, its preparation and pharmaceutical compositions containing it
US5637624A (en) * 1989-02-27 1997-06-10 Eli Lilly And Company Ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes and 3-aminochromanes
LT4455B (en) 1995-05-22 1999-01-25 Teva Pharmaceutical Industries, Ltd. Use of r-enantiomer of n-propargyl-1-aminoindan, salts, and compositions thereof
WO2011012140A2 (en) 2008-07-11 2011-02-03 Synthon Bv Polymorphs of rasagiline hydrochloride
US8334390B2 (en) 2007-07-31 2012-12-18 Bayer Cropscience Ag Fungicide N-cycloalkyl-N-bicyclic-carboxamide derivatives
US8461388B2 (en) 2007-12-24 2013-06-11 Cipla Limited Process for the synthesis of propargylated aminoindan derivatives

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4833169A (en) * 1985-08-27 1989-05-23 Ciba-Geigy Corporation Hydropyridine derivatives
US4939160A (en) * 1985-08-27 1990-07-03 Ciba-Geigy Corporation Hydropyridine derivatives
US5637624A (en) * 1989-02-27 1997-06-10 Eli Lilly And Company Ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes and 3-aminochromanes
EP0436492A2 (en) * 1990-01-03 1991-07-10 Teva Pharmaceutical Industries Limited R-Enantiomer of N-propargyl-1-aminoindan, its preparation and pharmaceutical compositions containing it
EP0436492A3 (en) * 1990-01-03 1991-11-13 Teva Pharmaceutical Industries Limited R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them
AU630772B2 (en) * 1990-01-03 1992-11-05 Technion Research & Development Foundation Ltd. R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them
US6956060B2 (en) 1990-01-03 2005-10-18 Teva Pharmaceutical Industries, Ltd. Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof
LT4455B (en) 1995-05-22 1999-01-25 Teva Pharmaceutical Industries, Ltd. Use of r-enantiomer of n-propargyl-1-aminoindan, salts, and compositions thereof
US8334390B2 (en) 2007-07-31 2012-12-18 Bayer Cropscience Ag Fungicide N-cycloalkyl-N-bicyclic-carboxamide derivatives
US9102588B2 (en) 2007-07-31 2015-08-11 Philippe Desbordes Fungicide N-cycloalkyl-N-bicyclic-carboxamide derivatives
US8461388B2 (en) 2007-12-24 2013-06-11 Cipla Limited Process for the synthesis of propargylated aminoindan derivatives
WO2011012140A2 (en) 2008-07-11 2011-02-03 Synthon Bv Polymorphs of rasagiline hydrochloride

Also Published As

Publication number Publication date
DK125701B (en) 1973-03-26
CH460750A (en) 1968-08-15
SE338039B (en) 1971-08-30
FR4230M (en) 1966-06-20
CH451124A (en) 1968-05-15
DK126585B (en) 1973-07-30
DE1443403A1 (en) 1968-10-31
NL6408887A (en) 1965-02-03
SE334348B (en) 1971-04-26
NL147036B (en) 1975-09-15
FI41394C (en) 1969-11-10
FI41394B (en) 1969-07-31

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