GB836083A - Heterocyclic amine compounds - Google Patents

Heterocyclic amine compounds

Info

Publication number
GB836083A
GB836083A GB641558A GB641558A GB836083A GB 836083 A GB836083 A GB 836083A GB 641558 A GB641558 A GB 641558A GB 641558 A GB641558 A GB 641558A GB 836083 A GB836083 A GB 836083A
Authority
GB
United Kingdom
Prior art keywords
phenyl
magnesium bromide
product
methyl
cyclohexane
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
GB641558A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB836083A publication Critical patent/GB836083A/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
    • C07D295/027—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 containing only one hetero ring
    • C07D295/033—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 containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • 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
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—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 no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0836083/IV (b)/1> (wherein R is pyrrolidino, piperidino or hexa methyleneimino which may be substituted by alkyl groups containing at most 4 carbon atoms, and their acid-addition salts. They may be prepared by reacting a 1-R-1-cyano-cyclohexane with a phenyl alkali metal compound in the presence of Lewis acids such as magnesium halides, BF3, FeCl3, AlCl3 or ZnCl2 or wit a phenyl magnesium halide and hydrolysing the product; by reacting a quaternary ammonium compound of the formula <FORM:0836083/IV (b)/2> (wherein Y is an alkylene radical of 4 to 6 carbon atoms and Z is an anion) with a phenyl magnesium halide; or by reacting a compound R-CO-C6H5 with a compound Me-(CH2)5-Me (wherein Me is an alkali metal or a magnesium halide) and hydrolysing the product. In examples: (1) 1-piperidinocyclohexanecarbonitrile and phenyl magnesium bromide yield 1-(1-phenylcyclohexyl)-piperidine; (2) magnesium bromide etherate and phenyl lithium replace the phenyl magnesium bromide of (1), the product being the same; (3) cyclohexanone cyanohydrin and pyrrolidine in benzene yield, on azeotropic distillation, 1-(1-pyrrolidino) cyclohexane carbonitrile and this with phenyl magnesium bromide yields 1-(1-phenylcyclohexyl)-pyrrolidine; (4) cyclohexanone cyanohydrin and 3 - ethyl - 3 - methyl - pyrrolidine (prepared by lithium aluminium hydride reduction of x - methyl - x - ethylsuccinimide) yield 1 - (3-ethyl - 3 - methyl - pyrrolidino) - cyclohexane carbonitrile and this with phenyl magnesium bromide yields 1-(1-phenylcyclohexyl)-3-ethyl3 - methyl - pyrrolidine; (5) cyclohexanone cyanohydrin and hexamethyleneimine yield 1-(1 - hexamethyleneimino) - cyclohexane carbonitrile and this with phenyl magnesium bromide yields 1 - (1 - phenylcyclohexyl) - hexamethyl leneimine; (6) 1 - (3 - and 4 - methyl - 1 piperidino) - cyclohexane carbonitriles and 1 - (1-phenyl - cyclohexyl) - 3 - and 4 - methylpiperidines are similarly prepared; (7) pentamethylene-bis-magnesium bromide and Nbenzoyl-piperidine are heated together and the product hydrolysed to give the product of (1); and (8) piperidine and cyclohexane in benzene yield, on azeotropic distillation, N-(1-cyclohexenyl)-piperidine, this is mixed with a toluene solution of p-toluenesulphonic acid and this mixture with phenyl magnesium bromide in ether yields, on hydrolysis, the product of (1). Hydrochlorides, hydrobromides, p-toluenesulphonates and sulphates of some of the products are described and other salt-forming acids are also referred to.ALSO:Pharmaceutical compositions comprise compounds of the formula <FORM:0836083/VI/1> (wherein R is pyrrolidino, piperidino or hexamethyleneimino which may be substituted by alkyl groups containing at most 4 carbon atoms) or their acid-addition salts made up as tablets, dragees, capsules, syrups, suppositories or parenteral solutions. Typical salts are the hydrochloride, succinate, benzoate, p-toluene, sulphonate and sulphamate.
GB641558A 1957-09-19 1958-02-27 Heterocyclic amine compounds Expired GB836083A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68484857A 1957-09-19 1957-09-19
US71039158A 1958-01-22 1958-01-22

Publications (1)

Publication Number Publication Date
GB836083A true GB836083A (en) 1960-06-01

Family

ID=27103445

Family Applications (1)

Application Number Title Priority Date Filing Date
GB641558A Expired GB836083A (en) 1957-09-19 1958-02-27 Heterocyclic amine compounds

Country Status (3)

Country Link
BE (1) BE565262A (en)
DE (2) DE1470152A1 (en)
GB (1) GB836083A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989009209A1 (en) * 1988-03-25 1989-10-05 Marion Laboratories, Inc. Piperidine ring modified phencyclidine analogs as anticonvulsants
WO2017093354A1 (en) 2015-11-30 2017-06-08 INSERM (Institut National de la Santé et de la Recherche Médicale) Nmdar antagonists for the treatment of diseases associated with angiogenesis

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989009209A1 (en) * 1988-03-25 1989-10-05 Marion Laboratories, Inc. Piperidine ring modified phencyclidine analogs as anticonvulsants
WO2017093354A1 (en) 2015-11-30 2017-06-08 INSERM (Institut National de la Santé et de la Recherche Médicale) Nmdar antagonists for the treatment of diseases associated with angiogenesis

Also Published As

Publication number Publication date
DE1470152A1 (en) 1969-04-30
BE565262A (en)
DE1470151A1 (en) 1969-04-30

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