GB1458537A - - Google Patents

Info

Publication number
GB1458537A
GB1458537A GB5820273A GB5820273A GB1458537A GB 1458537 A GB1458537 A GB 1458537A GB 5820273 A GB5820273 A GB 5820273A GB 5820273 A GB5820273 A GB 5820273A GB 1458537 A GB1458537 A GB 1458537A
Authority
GB
United Kingdom
Prior art keywords
alkyl
acid
reaction
amino
cyano
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
GB5820273A
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 filed Critical
Priority to GB5820273A priority Critical patent/GB1458537A/en
Priority to IE2440/74A priority patent/IE40251B1/en
Priority to ZA00747769A priority patent/ZA747769B/en
Priority to AU76155/74A priority patent/AU7615574A/en
Priority to US05/531,556 priority patent/US3998965A/en
Priority to BE151436A priority patent/BE823272A/en
Priority to NL7416161A priority patent/NL7416161A/en
Priority to DE19742459077 priority patent/DE2459077A1/en
Priority to DK652274A priority patent/DK652274A/da
Priority to JP49144360A priority patent/JPS5089343A/ja
Priority to FR7441315A priority patent/FR2254329A1/fr
Priority to US05/679,165 priority patent/US4035497A/en
Publication of GB1458537A publication Critical patent/GB1458537A/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
    • C07D295/04—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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1458537 Butanoic and butenoic acid derivatives ASPRO-NICHOLAS Ltd 3 Dec 1974 [15 Dec 1973] 58202/73 Heading C2C Novel "alkyl" (including unsaturated hydrocarbon radicals) esters, di-"alkyl"-amides and saturated heterocyclic amides of 4-amino- "alkyl" - 4 - phenyl - 4 - cyano - butanoic and but-2-enoic acids which are substituted in at least one of the two and three positions by an "alkyl" group of 1-4 C or by a divalent "alkylene" (including unsaturated hydrocarbon radicals) radical which together with at least one of the carbon atoms at said two and three positions forms a stable carbocyclic ring of 3-8 C and which are optionally substituted, except in the said "alkyl" or "alkylene" groups in the two and/or three positions, by therapeutically compatible substituents and acid addition salts thereof are prepared by reaction of a corresponding 4 - aminoalkyl - 4 - cyano - 4 - phenyl -1- alkoxy or alkylthio-1-dialkylamino or saturated heterocyclic amino-but-1-ene or buta-1,2-diene with a strong non-nucleophilic acid in the presence of a primary alcohol and an orthoester and hydrolysing the resultant product; reaction of an alkali metal alpha-aminoalkylbenzyl cyanide with an alkyl ester of a corresponding prop-1-enoic acid having a suitable leaving group in the 3-position; reaction of an alkali metal alpha-aminoalkylbenzyl cyanide with a dialkyl ester of a corresponding ethylene-1,1- dicarboxylic acid or reaction of a corresponding 4 - amino - alkyl - 4 - cyano - 4 - phenyl - 1- alkoxy or alkylthio-1-dialkylamino or heterocyclic amino-but-1-ene or buta-1,2-diene with NaI and a strong acid. Pharmaceutical compositions in the form of tablets, capsules, suppositories, solutions and suspensions comprise one of the above novel compounds together with a suitable carrier and are useful as CNS- or cardiovascular-active agents.
GB5820273A 1972-12-28 1973-12-15 Expired GB1458537A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB5820273A GB1458537A (en) 1973-12-15 1973-12-15
IE2440/74A IE40251B1 (en) 1973-12-15 1974-11-27 Derivatives of butanoic and butenoic acids
ZA00747769A ZA747769B (en) 1973-12-15 1974-12-06 Derivatives of butanoic and butenoic acids
AU76155/74A AU7615574A (en) 1973-12-15 1974-12-06 Derivatives of butanoic and butenoic acids
US05/531,556 US3998965A (en) 1973-12-15 1974-12-11 4-Aminoalkyl-4-cyano-4-phenyl-butanoic acid esters
BE151436A BE823272A (en) 1973-12-15 1974-12-12 BUTANOIC ACID AND BUTENOIC ACID DERIVATIVES
NL7416161A NL7416161A (en) 1973-12-15 1974-12-12 PROCESS FOR THE PREPARATION OF MEDICINAL PRODUCTS WITH ACTION ON THE CENTRAL NERVOUS SYSTEM OR WITH CARDIOVASCULAR ACTION, FORMATED MEDICINAL PRODUCTS WITH SUCH ACTION AND PROCESS FOR PREPARING THE MEDICINAL COMPOUNDS.
DE19742459077 DE2459077A1 (en) 1973-12-15 1974-12-13 ALKYLESTERS, DIALKYLAMIDES AND SATURATED HETEROCYCLIC AMIDES OF 4-AMINOALKYL-4-CYANO-4-PHENYL-BUTANE- AND -BUT-2-ENACIDS
DK652274A DK652274A (en) 1973-12-15 1974-12-13
JP49144360A JPS5089343A (en) 1973-12-15 1974-12-16
FR7441315A FR2254329A1 (en) 1973-12-15 1974-12-16
US05/679,165 US4035497A (en) 1972-12-28 1976-04-22 Butanoic and butenoic acid morpholides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5820273A GB1458537A (en) 1973-12-15 1973-12-15

Publications (1)

Publication Number Publication Date
GB1458537A true GB1458537A (en) 1976-12-15

Family

ID=10481022

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5820273A Expired GB1458537A (en) 1972-12-28 1973-12-15

Country Status (10)

Country Link
JP (1) JPS5089343A (en)
AU (1) AU7615574A (en)
BE (1) BE823272A (en)
DE (1) DE2459077A1 (en)
DK (1) DK652274A (en)
FR (1) FR2254329A1 (en)
GB (1) GB1458537A (en)
IE (1) IE40251B1 (en)
NL (1) NL7416161A (en)
ZA (1) ZA747769B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007031737A1 (en) * 2005-09-14 2007-03-22 Prestwick Pharmaceuticals, Inc. 4,4-dimethylpiperidine-2,6-dione derivatives for use in the treatment of hypertension

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639524A (en) * 1984-07-09 1987-01-27 G. D. Searle & Co. Monobasic disobutamide derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007031737A1 (en) * 2005-09-14 2007-03-22 Prestwick Pharmaceuticals, Inc. 4,4-dimethylpiperidine-2,6-dione derivatives for use in the treatment of hypertension
GB2445888A (en) * 2005-09-14 2008-07-23 Prestwick Pharmaceuticals Inc 4,4-dimethylpiperidine-2, 6-dione derivatives for use in the treatment of hypertension
GB2445888B (en) * 2005-09-14 2010-01-06 Prestwick Pharmaceuticals Inc Treatment of hypertension

Also Published As

Publication number Publication date
ZA747769B (en) 1976-08-25
NL7416161A (en) 1975-06-17
BE823272A (en) 1975-06-12
IE40251L (en) 1975-06-15
DK652274A (en) 1975-08-25
JPS5089343A (en) 1975-07-17
FR2254329A1 (en) 1975-07-11
AU7615574A (en) 1976-06-10
DE2459077A1 (en) 1975-07-03
IE40251B1 (en) 1979-04-11

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee