GB948874A - 4-aryl-4-propionyl-piperidine derivatives - Google Patents

4-aryl-4-propionyl-piperidine derivatives

Info

Publication number
GB948874A
GB948874A GB7443/62A GB744362A GB948874A GB 948874 A GB948874 A GB 948874A GB 7443/62 A GB7443/62 A GB 7443/62A GB 744362 A GB744362 A GB 744362A GB 948874 A GB948874 A GB 948874A
Authority
GB
United Kingdom
Prior art keywords
reacting
alkyl
phenyl
compound
substituted
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
GB7443/62A
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
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
Priority claimed from DEB61540A external-priority patent/DE1294381B/en
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of GB948874A publication Critical patent/GB948874A/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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached 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
    • C07D211/06—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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

The invention comprises (1) compounds of the general formula: <FORM:0948874/C2/1> wherein R represents an alkyl or alkenyl group of 3 to 4 carbon atoms which is substituted in the 3 or 4 position by a monocyclic aromatic group (e.g phenyl, alkyl-substituted phenyl, 2-furyl or 4-pyridyl), and their acid addition salts, and pharmaceutical compositions containing them (see Division A5); (2) the preparation of compounds (1) (a) reacting 4-(3-hydroxyphenyl)-4-propionyl-peridine with an R halide, or (b) (when R represents a phenyl-or alkyl-substituted-phenyl-alkyl or -alkenyl group) hydrolysing with an acid a ketimine of the general formula: <FORM:0948874/C2/2> (wherein R1 has the meaning given immediately above for R, and Alk represents an alkyl group) or (c) reacting a 3-(3-hydroxyphenyl)-3-propionyl-1, 5-dihalopentane with an amine R-NH2 or (d)(when R represents a phenyl- or alkyl-substituted-phenyl-alkyl group) by hydrolysing with an ethersplitting agent a compound of the general formula <FORM:0948874/C2/3> (wherein R111 has the meaning given immediately above for R and Alk represents an alkyl group), and in cases (a), (b) and (c) if desired, converting the product into an acid addition salt; (3) the combination of process (a) with the preparation of the starting material by reacting a m-alkoxylbenzyl cyanide with a di-(b -haloethyl)-tosylamine in the presence of a basic condensation agent to form a 1-tosyl - 4 - (3 - alkoxyphenyl) - 4 - cyanopiperidine, reacting this with an ethyl Grignard reagent and decomposing the magnesium complex to form a 1-tosyl- 4 -(3-alkoxyphenyl-piperidyl-(4) ethyl ketimine and hydrolysing the latter; (4) the combination of process (b) with the preparation of the starting material by reacting a m-alkoxybenzyl cyanide with a tertiary amine of the formula (Hal-CH2CH2)2NR1 (wherein Hal represents a halogen atom) in the presence of a basic condensation agent to form a 4-cyanopiperidine derivative, reacting this with an ethyl Grignard reagent and decomposing the magnesium complex; (5) the combination of process (d) with the preparation of the starting material by reacting an m-alkoxybenzyl cyanide with a compound of the formula Hal-CH2CH2-NR11R111(where R11 represents a benzyl group), reacting the product with a compound of the formula X-CH2CH2-X (wherein X represents a halogen atom or a sulphonic ester group) to form a 4-(3-alkoxyphenyl)-4-cyanopiperidinium compound, reacting this with an ethyl Grignard reagent and decomposing the magnesium complex to form a ketimide, which is then hydrolysed to a 4-(3-alkoxyphenyl)-4-propionyl-piperidinium compound and the latter reduced.ALSO:Pharmaceutical compositions comprise a compound (having analgesic and morphineantagonistic properties) of the general formula <FORM:0948874/A5-A6/1> (wherein R represents an alkyl or alkenyl group or 3 or 4 carbon atoms which is substituted in the 3 or 4 position by a monocyclic aromatic group, e.g. phenyl, alkyl-substituted phenyl, 2-furyl or 4-pyridyl), or an acid addition salt thereof, together with a pharmaceutical carrier or excipient and, if desired, a morphinic analgesic. In examples, 1-cinnamyl-4-(3-hydroxyphenyl) - 4 - propionylpiperidine methanesulphonate or 1 - (3 - phenylpropyl) - 4 - (3 - hydroxyphenyl) - 4 - propionylpiperidine hydrochloride is made up into ampoules of injectable solution also containing hydroxyethyltheophylline, suppositories and tablets. Reference is also made to pills, capsules, dragees, suspensions, emulsions, syrups, linctuses and elixirs.
GB7443/62A 1961-03-06 1962-02-26 4-aryl-4-propionyl-piperidine derivatives Expired GB948874A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEB61540A DE1294381B (en) 1961-03-06 1961-03-06 1-cinnamyl-4- (3'-hydroxyphenyl) -4-propionylpiperidine, its acid addition salts and processes for their preparation
DEB0065960 1962-02-15

Publications (1)

Publication Number Publication Date
GB948874A true GB948874A (en) 1964-02-05

Family

ID=25965884

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7443/62A Expired GB948874A (en) 1961-03-06 1962-02-26 4-aryl-4-propionyl-piperidine derivatives

Country Status (3)

Country Link
BE (1) BE614689A (en)
CH (1) CH407120A (en)
GB (1) GB948874A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005037269A1 (en) * 2003-10-21 2005-04-28 Dainippon Sumitomo Pharma Co., Ltd. Novel piperidine derivative
EP1224188B1 (en) * 1999-10-20 2007-01-17 Archimedes Development Limited Nasal delivery composition comprising the methane sulphonate salt of morphine and chitosan

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1224188B1 (en) * 1999-10-20 2007-01-17 Archimedes Development Limited Nasal delivery composition comprising the methane sulphonate salt of morphine and chitosan
WO2005037269A1 (en) * 2003-10-21 2005-04-28 Dainippon Sumitomo Pharma Co., Ltd. Novel piperidine derivative

Also Published As

Publication number Publication date
CH407120A (en) 1966-02-15
BE614689A (en) 1962-09-05

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