GB905993A - Benzyl pyridine derivatives and methods of making same - Google Patents

Benzyl pyridine derivatives and methods of making same

Info

Publication number
GB905993A
GB905993A GB2566460A GB2566460A GB905993A GB 905993 A GB905993 A GB 905993A GB 2566460 A GB2566460 A GB 2566460A GB 2566460 A GB2566460 A GB 2566460A GB 905993 A GB905993 A GB 905993A
Authority
GB
United Kingdom
Prior art keywords
benzyl
salts
dimethylaminoethoxy
pyridine
chloro
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
GB2566460A
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.)
Janssen Pharmaceuticals Inc
Original Assignee
McNeilab Inc
McNeil Laboratories Inc
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 McNeilab Inc, McNeil Laboratories Inc filed Critical McNeilab Inc
Publication of GB905993A publication Critical patent/GB905993A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (-)-2-[p-chloro-a -(2-dimethylaminoethoxy)benzyl]pyridine, ((-)-carbinoxamine) and its salts, substantially free from the corresponding diastereoisomeric compounds, and their preparation by separating the salts formed from (\sB)-2-[p-chloro-a -(2-dimethylaminoethoxy)benzyl]pyridine with a optically active acid, e.g. d-tartaric acid, liberating (-)-2-[p-chloro-a -(2-dimethylaminoethoxy)benzyl] pyridine from the corresponding salt, and if desired forming another salt by treating the (-)-base with an acid. The separation of the diastereoisomeric salts may be achieved by treatment with a selective solvent, e.g. hot acetone, or by fractional crystallisation. Specified salts are the d-tartrate, maleate, fumarate, meso-tartrate, and other salt-forming acids are listed. Examples detail the preparation of racemic 2-[p-chloro-a -(2-dimethylaminoethoxy)benzyl]pyridine, its resolution as the d-tartrate, and formation of the (-)-base and its salts.
GB2566460A 1959-07-23 1960-07-22 Benzyl pyridine derivatives and methods of making same Expired GB905993A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82895459A 1959-07-23 1959-07-23

Publications (1)

Publication Number Publication Date
GB905993A true GB905993A (en) 1962-09-19

Family

ID=25253154

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2566460A Expired GB905993A (en) 1959-07-23 1960-07-22 Benzyl pyridine derivatives and methods of making same

Country Status (1)

Country Link
GB (1) GB905993A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2229401A1 (en) * 1973-05-17 1974-12-13 Medimac Sa Optical resolution of rotoxamine - using dextro-maleic acid and direct pptn. of the laevo-rotoxamine-dextro-maleate salt useful as an antihistamine
EP0385491A1 (en) * 1989-03-03 1990-09-05 MAGIS FARMACEUTICI S.p.A. Optically active isomer of cloperastine possessing antitussive activity, a process for its preparation and pharmaceutical compositions which contain it

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2229401A1 (en) * 1973-05-17 1974-12-13 Medimac Sa Optical resolution of rotoxamine - using dextro-maleic acid and direct pptn. of the laevo-rotoxamine-dextro-maleate salt useful as an antihistamine
EP0385491A1 (en) * 1989-03-03 1990-09-05 MAGIS FARMACEUTICI S.p.A. Optically active isomer of cloperastine possessing antitussive activity, a process for its preparation and pharmaceutical compositions which contain it

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