GB1410011A - Ethylene diamine derivatives - Google Patents

Ethylene diamine derivatives

Info

Publication number
GB1410011A
GB1410011A GB756771A GB756771A GB1410011A GB 1410011 A GB1410011 A GB 1410011A GB 756771 A GB756771 A GB 756771A GB 756771 A GB756771 A GB 756771A GB 1410011 A GB1410011 A GB 1410011A
Authority
GB
United Kingdom
Prior art keywords
alkyl
methyl
dihydrochloride
dimethylamino
methylpropylamine
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
GB756771A
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.)
Allen and Hanburys Ltd
Original Assignee
Allen and Hanburys 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
Priority to BE789025D priority Critical patent/BE789025A/en
Application filed by Allen and Hanburys Ltd filed Critical Allen and Hanburys Ltd
Priority to GB756771A priority patent/GB1410011A/en
Priority to ZA726282A priority patent/ZA726282B/en
Priority to CA152,009A priority patent/CA995220A/en
Priority to AU46798/72A priority patent/AU475627B2/en
Priority to IL40397A priority patent/IL40397A/en
Priority to JP47095039A priority patent/JPS4839409A/ja
Priority to CH1388472A priority patent/CH597153A5/xx
Priority to FR7233698A priority patent/FR2154559B1/fr
Priority to DE19722246728 priority patent/DE2246728A1/en
Priority to NL7212967A priority patent/NL7212967A/xx
Publication of GB1410011A publication Critical patent/GB1410011A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups

Abstract

1410011 Ethylenediamine derivatives ALLEN & HANBURYS Ltd 12 Sept 1972 [6 June 1972] 7567/71 and 26248/72 Heading C2C The invention comprises ethylenediamine derivatives of the formula and non-toxic acid addition salts thereof, wherein one of the groups R<SP>1</SP> and R<SP>2</SP> is acyl and the other is H or C 1-6 alkyl; R<SP>3</SP> and R<SP>4</SP> each are H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, cycloalkylalkyl or aralkyl, or R<SP>3</SP> and R<SP>4</SP> together form an alkylene group optionally interrupted by an -NH- or -N-alkyl-group; R<SP>5</SP> is H or alkyl; R<SP>6</SP> is H; and R<SP>7</SP> and R<SP>8</SP> are alkyl or together form a pentamethylene group except that when R<SP>2</SP>, R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> are H, R<SP>3</SP> is H or alkyl and R<SP>7</SP> and R<SP>8</SP> together form a pentamethylene group, R<SP>1</SP> cannot be alkoxycarbonyl and their preparation. The compounds are prepared by acylating the corresponding amines of the above formula in which one of R<SP>1</SP> and R<SP>2</SP> is H. Compounds in which R<SP>3</SP> or R<SP>4</SP> is H may be obtained by debenzylating the corresponding compounds in which R<SP>3</SP> or R<SP>4</SP> is benzyl, and those in which R<SP>3</SP> and/or R<SP>4</SP> are other than H by alkylating a compound of the above formula in which the group NR<SP>1</SP>R<SP>2</SP> is not capable of being alkylated. The following starting materials are also prepared:- 1 - (aminomethyl) - N,N - dimethylaminocyclohexylamine, 1 - cyano - N,N - dimethylcyclohexylamine, N,N-dimethyl- 1- (methylaminomethyl)cyclohexylamine dihydrochloride, 1 - (1 - aminoethyl) - N,N - dimethylcyclohexylamine, 1 - aminomethyl - N- methyl - N - benzylcyclohexylamine, 1 - cyano- N - methyl - N - benzylcyclohexylamine, 1 - [1- (aminomethyl)cyclohexyl]- piperidine dihydrochloride, 1-(1-cyanocyclohexyl)piperidine, 1 - [1 - methylaminomethyl)cyclohexyl] piperidine dihydrochloride, 1 - [1 - (aminomethyl)- cyclohexyl]-4-methyl piperazine dimethiodide, 1 - [1 - (methylaminomethyl)cyclohexyl]- 4- methylpiperazine, 2-dimethylamino-2-methylpropionamide 2-dimethylamino-2-methylpropylamine dihydrochloride, 2-dimethylamino- 1,2 - dimethylpropylamine dihydrochloride, N,N,1,1 - tetramethyl - 2 - iminopropylamine N - methyl - 2 - dimethylamino - 2 - methylpropylamine dihydrochloride, N-formyl-2- dimethylamino - 2 - methylpropylamine 2- benzylmethylamino - 2 - methylpropionitrile, 2 - benzylmethylamino - 2 - methylpropylamine, 2 - (benzylmethylamino) - 1,2 - dimethylpropylamine N - benzyl - N,1,1 - dimethyl - 2- iminopropylamine 2 - methylamino - 2 - methylpropionitrile, 2 - allylmethylamino - 2 - methylpropionitrile 2 - allylmethylamino - 2 - methylpropylamine, 2 - methyl - 2 - dimethylaminohexanenitrile, 2 - methyl - 2 - dimethylaminohexylamine and N,2-dimethyl-2-dimethylaminohexylamine. Pharmaceutical compositions, suitable for oral parenteral or rectal administration, contain the above compounds or acid addition salts thereof and suitable carriers. The compounds possess analgesic activity.
GB756771A 1971-09-23 1971-09-23 Ethylene diamine derivatives Expired GB1410011A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
BE789025D BE789025A (en) 1971-09-23 NEW ETHYLENE DIAMINES SUBSTITUTES
GB756771A GB1410011A (en) 1971-09-23 1971-09-23 Ethylene diamine derivatives
ZA726282A ZA726282B (en) 1971-09-23 1972-09-14 Ethylene diamine derivatives
CA152,009A CA995220A (en) 1971-09-23 1972-09-15 Ethylene diamine derivatives
AU46798/72A AU475627B2 (en) 1971-09-23 1972-09-18 Ethylene diamine derivatives
IL40397A IL40397A (en) 1971-09-23 1972-09-20 Ethylene diamine derivatives their production and pharmaceutical compositions containing them
JP47095039A JPS4839409A (en) 1971-09-23 1972-09-21
CH1388472A CH597153A5 (en) 1971-09-23 1972-09-22
FR7233698A FR2154559B1 (en) 1971-09-23 1972-09-22
DE19722246728 DE2246728A1 (en) 1971-09-23 1972-09-22 NEW SUBSTITUTED ETHYLENE DIAMINES, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING SUCH DIAMINES
NL7212967A NL7212967A (en) 1971-09-23 1972-09-25

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB756771A GB1410011A (en) 1971-09-23 1971-09-23 Ethylene diamine derivatives
GB2624872 1972-06-06

Publications (1)

Publication Number Publication Date
GB1410011A true GB1410011A (en) 1975-10-15

Family

ID=26241518

Family Applications (1)

Application Number Title Priority Date Filing Date
GB756771A Expired GB1410011A (en) 1971-09-23 1971-09-23 Ethylene diamine derivatives

Country Status (9)

Country Link
JP (1) JPS4839409A (en)
BE (1) BE789025A (en)
CA (1) CA995220A (en)
CH (1) CH597153A5 (en)
DE (1) DE2246728A1 (en)
FR (1) FR2154559B1 (en)
GB (1) GB1410011A (en)
IL (1) IL40397A (en)
NL (1) NL7212967A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006067414A2 (en) * 2004-12-23 2006-06-29 Glaxo Group Limited Glycine transport inhibitors
US7745642B2 (en) 2004-12-23 2010-06-29 Glaxo Group Limited Glycine transport inhibitors

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5319654B2 (en) 1974-03-14 1978-06-22
JPS5547977Y2 (en) * 1975-07-18 1980-11-10
JPS5253328A (en) * 1975-10-27 1977-04-28 Mazda Motor Corp Engine rotation control of car having power steering
JPH0723348B2 (en) * 1986-08-27 1995-03-15 花王株式会社 Novel acylated ethylenediamine derivative, production method and use thereof
PL341291A1 (en) * 1997-12-16 2001-04-09 Warner Lambert Co 1-substituted derivatives of 1-aminomethyl-ccycloalkanes (gabapentin analogues), their production and application of them in treating neurological disorders

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692265A (en) * 1951-01-23 1954-10-19 American Home Prod Substituted glycinamides
US2993068A (en) * 1958-07-01 1961-07-18 Ethicon Inc 1-aminomethyl-1-aminocyclohexanes
CH397684A (en) * 1961-05-02 1965-08-31 Kuhlmann Ets Process for the preparation of 3 ', 4', 5 'trimethoxy-benzoylaminoacetic acid pyrrolidide
US3258489A (en) * 1963-06-14 1966-06-28 Monsanto Co N-(1-aminocyclohexylmethyl)anilines and n-(1-nitrocyclohexylmethyl)an-ilines
GB1058002A (en) * 1964-07-07 1967-02-08 Farmochimica Cutolo Calosi S P Aryl-amino-acylamides
SE337810B (en) * 1966-05-13 1971-08-23 Tanabe Seiyaku Co
AT273969B (en) * 1966-08-01 1969-09-10 Miles Lab Process for the preparation of new N-aminoalkyl-N-benzylamides and their salts
US3510492A (en) * 1968-05-13 1970-05-05 Upjohn Co 2-anilino and 2-anilinomethyl cycloalkylamines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006067414A2 (en) * 2004-12-23 2006-06-29 Glaxo Group Limited Glycine transport inhibitors
WO2006067414A3 (en) * 2004-12-23 2006-09-08 Glaxo Group Ltd Glycine transport inhibitors
US7745642B2 (en) 2004-12-23 2010-06-29 Glaxo Group Limited Glycine transport inhibitors

Also Published As

Publication number Publication date
NL7212967A (en) 1973-03-27
CH597153A5 (en) 1978-03-31
FR2154559A1 (en) 1973-05-11
FR2154559B1 (en) 1976-08-20
BE789025A (en) 1973-03-20
IL40397A (en) 1977-06-30
IL40397A0 (en) 1972-11-28
DE2246728A1 (en) 1973-05-03
CA995220A (en) 1976-08-17
JPS4839409A (en) 1973-06-09

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee