GB666778A - Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues - Google Patents

Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues

Info

Publication number
GB666778A
GB666778A GB25947/48A GB2594748A GB666778A GB 666778 A GB666778 A GB 666778A GB 25947/48 A GB25947/48 A GB 25947/48A GB 2594748 A GB2594748 A GB 2594748A GB 666778 A GB666778 A GB 666778A
Authority
GB
United Kingdom
Prior art keywords
dimethylaminoethyl
pyridyl
pyridylacetonitrile
halide
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
GB25947/48A
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.)
Merck Sharp and Dohme Corp
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Publication of GB666778A publication Critical patent/GB666778A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Pyridyl aminonitriles of formula <FORM:0666778/IV (b)/1> where R1 is aralkyl, aryl, cycloaliphatic, or heterocyclic, all of which may be substituted by chlorine, bromine, lower alkyl or alkoxy groups, R2 is lower alkyl or hydrogen, R3 is a di-(lower alkyl) amino group, piperidino or morpholino, and R is an alkylene group of 2-4 carbon atoms, are prepared by condensing a substituted acetonitrile with a pyridyl or alkylpyridyl halide, and with a di-(lower-alkyl) aminoalkyl, piperidinoalkyl or morpholinoalkyl halide all together or successively in either order. The pyridylaminonitriles when heated with acids lose the cyano group to give pyridylamines. In the examples, 2 - pyridylphenylacetonitrile, prepared from a 2-pyridyl halide and phenylacetonitrile, is condensed in presence of sodamide with (1) b -dimethylaminoethyl chloride; (2) b -diethylaminoethyl chloride to give the corresponding a -phenyl-a -(b 1-dialkylaminoethyl)-2-pyridylacetonitrile. Ten other examples are given illustrating the preparation of, for example, a - (2 - thienyl) - a - (b 1 - dimethylaminoethyl) - 2 - pyridylacetonitrile, a - (p - methoxyphenyl) - a - b (1-dimethylaminoethyl)-2 - pyridylacetonitrile, a - (p - bromophenyl) - a - (b 1 - dimethylaminoethyl) - 2 - pyridylaceto-nitrile, and b -cyclohexyl-a -(b 1-dimethylaminoethyl)-a -(2-pyridyl) propionitrile. The Specification as open to inspection under Sect. 91 comprises the additional compound a - (2 - furyl) - a - (b - dimethylaminoethyl) - 2 - pyridylacetonitrile, a ,a - bis - (2 - pyridyl) - a - (N,N - dimethylaminoethyl) octonitrile and other aminonitriles in which the group R1 is 2-thiazyl, 2-pyrimidyl, and 5-chloro-2-thienyl. It is also stated that R1 may be alkyl, and additional solvents and catalysts are specified as suitable for the reaction. This subject-matter does not appear in the Specification as accepted.
GB25947/48A 1947-10-13 1948-10-05 Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues Expired GB666778A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US666778XA 1947-10-13 1947-10-13

Publications (1)

Publication Number Publication Date
GB666778A true GB666778A (en) 1952-02-20

Family

ID=22070999

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25947/48A Expired GB666778A (en) 1947-10-13 1948-10-05 Pyridyldialkylaminoalkyl acetonitriles and their piperidino and morpholino-analogues

Country Status (3)

Country Link
FR (1) FR1013690A (en)
GB (1) GB666778A (en)
NL (1) NL70757C (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3029189A (en) * 1962-04-10 S-aryl-z-mno-x-qxazolibinones
EP0027412A1 (en) * 1979-10-11 1981-04-22 Sanofi S.A. Pyridine derivatives, process for their preparation and medicaments containing them
EP0105458A2 (en) * 1982-09-30 1984-04-18 Fujisawa Pharmaceutical Co., Ltd. Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same
US4783537A (en) * 1985-11-13 1988-11-08 Pennwalt Corporation α-(aminoalkyl)-arylacetic acid derivatives
US4847301A (en) * 1985-11-13 1989-07-11 Pennwalt Corporation Methods of use of α-(aminoalkyl)-arylacetic acid derivatives

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3029189A (en) * 1962-04-10 S-aryl-z-mno-x-qxazolibinones
EP0027412A1 (en) * 1979-10-11 1981-04-22 Sanofi S.A. Pyridine derivatives, process for their preparation and medicaments containing them
EP0105458A2 (en) * 1982-09-30 1984-04-18 Fujisawa Pharmaceutical Co., Ltd. Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same
EP0105458A3 (en) * 1982-09-30 1985-11-27 Fujisawa Pharmaceutical Co., Ltd. Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same
US4564621A (en) * 1982-09-30 1986-01-14 Fujisawa Pharmaceutical Co., Ltd. α-Aryl-α-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same
US4783537A (en) * 1985-11-13 1988-11-08 Pennwalt Corporation α-(aminoalkyl)-arylacetic acid derivatives
US4847301A (en) * 1985-11-13 1989-07-11 Pennwalt Corporation Methods of use of α-(aminoalkyl)-arylacetic acid derivatives
AU596805B2 (en) * 1985-11-13 1990-05-17 Fisons Corporation Alpha-(aminoalkyl)-arylacetic acid derivatives

Also Published As

Publication number Publication date
NL70757C (en)
FR1013690A (en) 1952-08-01

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