GB780027A - 3-piperidyl ethers and thioethers - Google Patents

3-piperidyl ethers and thioethers

Info

Publication number
GB780027A
GB780027A GB1586/56A GB158656A GB780027A GB 780027 A GB780027 A GB 780027A GB 1586/56 A GB1586/56 A GB 1586/56A GB 158656 A GB158656 A GB 158656A GB 780027 A GB780027 A GB 780027A
Authority
GB
United Kingdom
Prior art keywords
benzhydryl
piperidyl
ethers
halide
appropriate
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
GB1586/56A
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 GB780027A publication Critical patent/GB780027A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • 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
    • C07D211/54—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

The invention comprises 3-piperidyl ethers of the formula: <FORM:0780027/IV (a)/1> and acid addition and quaternary salts thereof, wherein R1 is a lower alkyl or monocyclic aralkyl group, R2 is an unsubstituted or halogen lower alkyl or lower alkoxy substituted 1 : 1-diphenylethyl, benzhydryl, fluorenyl or xanthyl radical and X is oxygen or sulphur, the lower alkyl and alkoxy groups having less than seven carbon atoms. The compounds are made by heating the appropriate N - substituted 3-hydroxy or 3-mercapto piperidine with a halide R2Hal, for example with a benzhydryl halide, preferably in an inert solvent such as a hydrocarbon or a high boiling ether and in the presence of an acid acceptor such as pyridine, a dialkylaniline, sodium or potassium carbonate, or an excess of the piperidine alcohol or thiol itself. Alternatively the appropriate piperidinol may be treated with a benzhydryl halide in liquid ammonia using sodamide as a catalyst, or the sodium salt of the amino alcohol is reacted with the appropriate halide. Conversely the sodium compound of the appropriate, e.g. benzhydryl, alcohol is reacted with a N-substituted 3-halo piperidine. Acid addition and quaternary salts of the compounds are made by known methods. Examples describe the preparation of N-substituted 3-piperidyl benzhydryl ethers in which the N-substituents are methyl -, ethyl -, isopropyl -, hexyl - and benzyl-groups; N-ethyl-3-piperidyl, p : p1-dimethylbenzhydryl -, p - chlorobenzhydryl -, p-methoxybenzhydryl -, m - bromobenzhydryl-, and 91 - fluorenyl - ethers; N - methyl - 3-piperidyl, p - methylbenzhydryl -, a - p - tolyl-a - phenylethyl -, and 91 - xanthyl - ethers; N - ethyl - 3 - piperidyl benzhydryl thioether and corresponding quaternary and acid addition salts of some of these compounds.
GB1586/56A 1955-01-20 1956-01-17 3-piperidyl ethers and thioethers Expired GB780027A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US780027XA 1955-01-20 1955-01-20

Publications (1)

Publication Number Publication Date
GB780027A true GB780027A (en) 1957-07-31

Family

ID=22141321

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1586/56A Expired GB780027A (en) 1955-01-20 1956-01-17 3-piperidyl ethers and thioethers

Country Status (1)

Country Link
GB (1) GB780027A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU602453B2 (en) * 1988-07-08 1990-10-11 Pfizer Inc. Piperidine derivatives
EP0433167A1 (en) * 1989-12-12 1991-06-19 Adir Et Compagnie Piperidine derivates, process for their preparation and pharmaceutical compositions containing them
WO1991010651A1 (en) * 1990-01-06 1991-07-25 Pfizer Limited Anticholinergic agents
WO1991010650A1 (en) * 1990-01-06 1991-07-25 Pfizer Limited Piperidine and pyrrolidine derivatives
US5231104A (en) * 1988-07-08 1993-07-27 Pfizer Inc. 1-arylethyl-3-substituted piperidines
US20130324507A1 (en) * 2012-06-05 2013-12-05 Bioprojet Novel (aza)Benzhydryl Ether Derivatives, Their Process of Preparation and Their Use as H4-Receptor Ligands for Therapeutical Applications
US10906904B2 (en) 2015-07-02 2021-02-02 Horizon Orphan Llc ADO-resistant cysteamine analogs and uses thereof

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5410046A (en) * 1988-07-08 1995-04-25 Pfizer Inc. 1-arylethyl-3-substituted piperidines
US5534626A (en) * 1988-07-08 1996-07-09 Pfizer Inc. 1-arylethyl-3-substituted piperidines
US5231104A (en) * 1988-07-08 1993-07-27 Pfizer Inc. 1-arylethyl-3-substituted piperidines
AU602453B2 (en) * 1988-07-08 1990-10-11 Pfizer Inc. Piperidine derivatives
US5089505A (en) * 1988-07-08 1992-02-18 Pfizer Inc. 1-arylethyl-3-substituted piperidines
EP0350309B1 (en) * 1988-07-08 1992-11-11 Pfizer Limited Piperidine derivatives
EP0433167A1 (en) * 1989-12-12 1991-06-19 Adir Et Compagnie Piperidine derivates, process for their preparation and pharmaceutical compositions containing them
AU629076B2 (en) * 1989-12-12 1992-09-24 Adir Et Compagnie New piperidine derivatives the process for the preparation thereof and the pharmaceutical compositions containing them
US5344835A (en) * 1990-01-06 1994-09-06 Pfizer Inc. Piperidine and pyrrolidine derivatives
WO1991010650A1 (en) * 1990-01-06 1991-07-25 Pfizer Limited Piperidine and pyrrolidine derivatives
WO1991010651A1 (en) * 1990-01-06 1991-07-25 Pfizer Limited Anticholinergic agents
US20130324507A1 (en) * 2012-06-05 2013-12-05 Bioprojet Novel (aza)Benzhydryl Ether Derivatives, Their Process of Preparation and Their Use as H4-Receptor Ligands for Therapeutical Applications
US9242959B2 (en) * 2012-06-05 2016-01-26 Bioprojet (Aza)benzhydryl ether derivatives, their process of preparation and their use as H4-receptor ligands for therapeutical applications
US10906904B2 (en) 2015-07-02 2021-02-02 Horizon Orphan Llc ADO-resistant cysteamine analogs and uses thereof
US11505550B2 (en) 2015-07-02 2022-11-22 Horizon Orphan Llc ADO-resistant cysteamine analogs and uses thereof

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