GB750156A - Improvements in cyclohexyl-phenyl-amino-propanols - Google Patents

Improvements in cyclohexyl-phenyl-amino-propanols

Info

Publication number
GB750156A
GB750156A GB793653A GB793653A GB750156A GB 750156 A GB750156 A GB 750156A GB 793653 A GB793653 A GB 793653A GB 793653 A GB793653 A GB 793653A GB 750156 A GB750156 A GB 750156A
Authority
GB
United Kingdom
Prior art keywords
salts
cyclohexyl
phenyl
optically active
quaternary ammonium
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
GB793653A
Inventor
Donald Wallace Adamson
Walter Mark Duffin
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB793653A priority Critical patent/GB750156A/en
Publication of GB750156A publication Critical patent/GB750156A/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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain

Landscapes

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

Abstract

The invention comprises the laevo-rotatory forms of 1-cyclohexyl-1-phenyl-3-piperidino- and - 3 - pyrrolidino - propan - 1 - ol and their acid addition salts and lower (1-4 C) alkyl quaternary ammonium salts, and the preparation thereof by optical resolution of the racemic compounds, e.g. by fractional crystallization of their salts with an optically active acid, followed, if desired, by conversion of the isolated l-base to a salt of a non-optically active acid or to a lower alkyl quaternary ammonium salt thereof. The products are superior to the racemic forms in their atropine-like properties. In examples, resolution is effected by fractional crystallization of the D-tartrates from ethyl alcohol, and the l-bases are converted into their hydrochlorides, methiodides and ethiodides. A mixture of ethyl alcohol and ethyl acetate is also specified as a suitable solvent, and reference is made to propyl and butyl quaternary salts. Specifications 627,139, 646,198 and 708,805 are referred to.
GB793653A 1953-03-23 1953-03-23 Improvements in cyclohexyl-phenyl-amino-propanols Expired GB750156A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB793653A GB750156A (en) 1953-03-23 1953-03-23 Improvements in cyclohexyl-phenyl-amino-propanols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB793653A GB750156A (en) 1953-03-23 1953-03-23 Improvements in cyclohexyl-phenyl-amino-propanols

Publications (1)

Publication Number Publication Date
GB750156A true GB750156A (en) 1956-06-13

Family

ID=9842631

Family Applications (1)

Application Number Title Priority Date Filing Date
GB793653A Expired GB750156A (en) 1953-03-23 1953-03-23 Improvements in cyclohexyl-phenyl-amino-propanols

Country Status (1)

Country Link
GB (1) GB750156A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4111951A (en) * 1977-01-17 1978-09-05 Hoffmann-La Roche Inc. Process for L-3,4-dehydroproline
US5973182A (en) * 1998-10-22 1999-10-26 Sepracor Inc. Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters
US6140529A (en) * 1998-10-22 2000-10-31 Sepracor Inc. Synthesis of optically active cyclohexylphenylglycolate esters

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4111951A (en) * 1977-01-17 1978-09-05 Hoffmann-La Roche Inc. Process for L-3,4-dehydroproline
US5973182A (en) * 1998-10-22 1999-10-26 Sepracor Inc. Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters
US6090971A (en) * 1998-10-22 2000-07-18 Sepracor Inc. Resolution process for cyclohexylphenyl glycolic acid
US6140529A (en) * 1998-10-22 2000-10-31 Sepracor Inc. Synthesis of optically active cyclohexylphenylglycolate esters

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