ES342860A1 - Novel piperidino-butyrophenones and a process for the manufacture thereof - Google Patents

Novel piperidino-butyrophenones and a process for the manufacture thereof

Info

Publication number
ES342860A1
ES342860A1 ES342860A ES342860A ES342860A1 ES 342860 A1 ES342860 A1 ES 342860A1 ES 342860 A ES342860 A ES 342860A ES 342860 A ES342860 A ES 342860A ES 342860 A1 ES342860 A1 ES 342860A1
Authority
ES
Spain
Prior art keywords
alkyl
hydroxypiperidine
give
formula
benzyl
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
ES342860A
Other languages
Spanish (es)
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of ES342860A1 publication Critical patent/ES342860A1/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
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom 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
    • C07D211/36—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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Novel compounds of the formula and their acid addition and quaternary salts where R 1 is C 1-7 alkyl, C 3-6 cycloalkyl, (C 3-6 cycloalkyl) - (C 1-7 alkyl), C 1-7 hydroxyalkyl or (C 1-7 alkoxy)C 1-7 alkyl, R 2 is acyl and X is halogen are prepared by reacting a 4-hydroxy piperidine of the formula with a compound of the formula where Y is a leaving group and then optionally subjecting the (C 1-7 alkoxy) C 1-7 alkyl group, if present, to ether cleavage to give a C 1-7 hydroxyalkyl group and optionally acylating the hydroxy group. The 4-hydroxypiperidines are made (a) by hydrogenating 4-hydroxy-4-phenylpiperidine in the presence of platinum oxide to give 4- cyclohexyl - 4 - hydroxypiperidine, (b) by reacting an alkyl lithium or cyclopropyl lithium with 1-benzyl-4-piperidone to give a 4-alkyl-1- benzyl - 4 - hydrorypiperidine or 1 - benzyl - 4 - cyclopropyl-4-hydroxypiperidine and then hydrogenating these compounds in the presence of palladium on charcoal to give 4-alkyl-4-hydroxypiperidine or 4 - cyclopropyl - 4 - hydroxypiperidine and (c) 1-benzy]-4-[3-(1,1-dimethylpropoxy)-propyl]-4-hydroxypiperidine is hydrogenated in the presence of palladium on charcoal to give 4-[3-(1,1-dimethylpropory)-propyl]- 4-hydroxypiperidine. Pharmaceutical compositions effective as analgesics, sedatives, antipyretics and anti-inflammatory agents comprise one of the novel compounds of the above formula or an acid addition or quaternary salt as the active ingredient and a carrier and are administered as tablets, dragÚes, capsules, solutions, suspensions or emulsions.
ES342860A 1966-07-11 1967-07-10 Novel piperidino-butyrophenones and a process for the manufacture thereof Expired ES342860A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US56396266A 1966-07-11 1966-07-11

Publications (1)

Publication Number Publication Date
ES342860A1 true ES342860A1 (en) 1968-09-01

Family

ID=24252613

Family Applications (1)

Application Number Title Priority Date Filing Date
ES342860A Expired ES342860A1 (en) 1966-07-11 1967-07-10 Novel piperidino-butyrophenones and a process for the manufacture thereof

Country Status (7)

Country Link
BE (1) BE701114A (en)
DE (1) DE1695194A1 (en)
ES (1) ES342860A1 (en)
FR (1) FR7229M (en)
GB (1) GB1131534A (en)
GR (1) GR36824B (en)
NL (1) NL6709605A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI52216C (en) * 1969-07-16 1977-07-11 Sumitomo Chemical Co Process for the preparation of gamma-piperidinobutyrophenone derivatives.
JPS568318A (en) * 1979-06-28 1981-01-28 Janssen Pharmaceutica Nv Non oral long acting composition of haloperidol and bromperidol derivative
GB8621892D0 (en) * 1986-09-11 1986-10-15 Lundbeck & Co As H Organic compound

Also Published As

Publication number Publication date
BE701114A (en) 1968-01-10
DE1695194A1 (en) 1971-03-18
NL6709605A (en) 1968-01-12
GR36824B (en) 1969-03-12
GB1131534A (en) 1968-10-23
FR7229M (en) 1969-09-01

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