GB1280699A - 0-substituted-4-phenoxypiperidines - Google Patents

0-substituted-4-phenoxypiperidines

Info

Publication number
GB1280699A
GB1280699A GB6196969A GB6196969A GB1280699A GB 1280699 A GB1280699 A GB 1280699A GB 6196969 A GB6196969 A GB 6196969A GB 6196969 A GB6196969 A GB 6196969A GB 1280699 A GB1280699 A GB 1280699A
Authority
GB
United Kingdom
Prior art keywords
piperidine
benzyl
acetyl
reacting
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
GB6196969A
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.)
AH Robins Co Inc
Original Assignee
AH Robins Co 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 AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of GB1280699A publication Critical patent/GB1280699A/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
    • C07D211/44—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

Abstract

1280699 Piperidine derivatives A H ROBINS CO Inc 19 Dec 1969 [23 Dec 1968 7 Nov 1969] 61969/69 Heading C2C Novel piperidine derivatives of the Formula I wherein R is CONH 2 , C 1-8 alkylcarbamoyl, di- (C 1-8 alkyl)carbamoyl, unsubstituted or monosubstituted phenylcarbamoyl monosubstituted benzoylalkyl, mono- or disubstituted phenoxyalkyl, CH 3 CH 2 OCO, or HOCH 2 CHOHCH 2 -, R<SP>1</SP> is H, C 1-8 alkyl, C 1-8 alkoxy, CF 3 , F, Cl or Br, and R<SP>2</SP> is H or CH 3 CO, and the acid addition salts of those compounds posessing a basic nitrogen atom are prepared by reacting the corresponding piperidine compounds unsubstituted in the 1-position with compounds selected from nitrourea, metal cyanates, C 1-8 alkyl isocyanates, N,N-di-(C 1-8 alkyl)-carbamoyl halides, unsubstituted or monosubstituted phenyl isocyanates, monosubstituted benzoylalkyl halides, mono- or di-substituted phenoxyalkyl halides ethyl chloroformate and 3-halo-1,2-dihydroxypropanes. 4 - (2 - Methoxyphenoxy)piperidine is obtained by hydrolysing 1-acetyl-4-(2-methoxyphenoxy)piperidine, obtained by reacting the tosylate ester of 1-acetyl-4-hydroxypiperidine with 2-methoxyphenol. By a similar process 4 - (4 - methoxyphenoxy) -, 4 - 4(p - chlorophenoxy) - and 4 - (4 - acetyl - 2 - methoxy) - piperidine and their corresponding 1-acetyl derivatives are prepared. 4 - (3 - Trifluoromethylphenoxy)piperidine hydrochloride is made by hydrolysing the corresponding 1-acetyl compound and converting the resulting base into the hydrochloride. 1 - Benzyl - 4 - (p - bromophenoxy)piperidine hydrochloride and 1 - benzyl - 4 - phenoxypiperidine hydrochloride are obtained by reacting 1- benzyl-4-piperidinol with p-bromofluorobenzene and fluorobenzene respectively and converting the resulting free bases into the hydrochlorides. 4 - (p - Trifluoromethylphenoxy)piperidine is prepared by the hydrogenolysis of 1-benzyl-4-(ptrifluoromethylphenoxy)piperidine obtained by reacting 1-benzyl-4-piperidinol with p-fluorotrifluorobenzene. Pharmaceutical compositions, suitable for oral or parenteral administration contain the above novel piperidine derivatives or acid addition salts thereof and pharmaceutically acceptable carriers or excipients - The compounds have mucsle relaxant and/or anticonvulsive and/or tranquilizing activities. Reference has been directed by the Comptroller to Specification 1,031,749.
GB6196969A 1968-12-23 1969-12-19 0-substituted-4-phenoxypiperidines Expired GB1280699A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US78639268A 1968-12-23 1968-12-23
US87498769A 1969-11-07 1969-11-07

Publications (1)

Publication Number Publication Date
GB1280699A true GB1280699A (en) 1972-07-05

Family

ID=27120533

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6196969A Expired GB1280699A (en) 1968-12-23 1969-12-19 0-substituted-4-phenoxypiperidines

Country Status (5)

Country Link
JP (1) JPS4931990B1 (en)
CH (1) CH537387A (en)
DE (1) DE1964515A1 (en)
FR (1) FR2026922B1 (en)
GB (1) GB1280699A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0333028A1 (en) * 1988-03-14 1989-09-20 Hoechst-Roussel Pharmaceuticals Incorporated 1-Substituted 4-pentafluorophenoxypiperidines, a process for their preparation and their use as medicaments
EP0333025A1 (en) * 1988-03-14 1989-09-20 Hoechst-Roussel Pharmaceuticals Incorporated 1-Carbonylderivatives of 4-aryl-4-aryloxypiperidines, a process for their preparation and their use as medicaments
US5192776A (en) * 1988-03-14 1993-03-09 Hoechst-Roussel Pharmaceuticals Incorporated 1-subsituted-4-pentafluorophenoxypiperidines
US5212184A (en) * 1988-03-14 1993-05-18 Hoechst-Roussel Pharmaceuticals Inc. 1-substituted-4-pentafluorophenoxypiperidines

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE45511B1 (en) * 1976-09-01 1982-09-08 Ciba Geigy Ag New derivatives of perhydro-aza-heterocycles and processesfor the production thereof
FR2481278A1 (en) * 1980-04-28 1981-10-30 Synthelabo Antidepressant 4:benzyloxy piperidine(s) - are prepd. from 4:hydroxy piperidine and benzyl halide
FR2514353A2 (en) * 1980-04-28 1983-04-15 Synthelabo Antidepressant 4-benzyloxy-piperidine derivs. - prepd. by react-ng piperidine deriv. with benzyl deriv.
EP0077427B1 (en) * 1981-10-15 1985-05-22 Synthelabo Piperidine derivatives, their preparation and use in medicine
US4954511A (en) * 1988-03-14 1990-09-04 Hoechst-Roussell Pharmaceuticals Inc. 4-pentafluorophenoxypiperidines
US4914204A (en) * 1988-03-14 1990-04-03 Hoechst-Roussel Pharmaceuticals Incorporated 4-Pentafluorophenoxypiperidines
FR2667317B1 (en) * 1990-10-02 1992-12-04 Synthelabo 2-AMINOPYRIMIDINE-4-CARBOXAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0333028A1 (en) * 1988-03-14 1989-09-20 Hoechst-Roussel Pharmaceuticals Incorporated 1-Substituted 4-pentafluorophenoxypiperidines, a process for their preparation and their use as medicaments
EP0333025A1 (en) * 1988-03-14 1989-09-20 Hoechst-Roussel Pharmaceuticals Incorporated 1-Carbonylderivatives of 4-aryl-4-aryloxypiperidines, a process for their preparation and their use as medicaments
US5192776A (en) * 1988-03-14 1993-03-09 Hoechst-Roussel Pharmaceuticals Incorporated 1-subsituted-4-pentafluorophenoxypiperidines
US5212184A (en) * 1988-03-14 1993-05-18 Hoechst-Roussel Pharmaceuticals Inc. 1-substituted-4-pentafluorophenoxypiperidines

Also Published As

Publication number Publication date
JPS4931990B1 (en) 1974-08-27
FR2026922B1 (en) 1973-08-10
DE1964515A1 (en) 1970-07-23
FR2026922A1 (en) 1970-09-25
CH537387A (en) 1973-05-31

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee