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GB1304589A - - Google Patents

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Publication number
GB1304589A
GB1304589A GB1707970A GB1707970A GB1304589A GB 1304589 A GB1304589 A GB 1304589A GB 1707970 A GB1707970 A GB 1707970A GB 1707970 A GB1707970 A GB 1707970A GB 1304589 A GB1304589 A GB 1304589A
Authority
GB
United Kingdom
Prior art keywords
formula
prepared
compound
reaction
intermediates
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
GB1707970A
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 CH691369A external-priority patent/CH513865A/en
Application filed filed Critical
Publication of GB1304589A publication Critical patent/GB1304589A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • 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
    • C07D211/20—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 singly bound oxygen or sulphur atoms
    • C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
    • 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
    • C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • 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

Landscapes

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

Abstract

1304589 1 - Phenacetyl -1,3,4,4a,5,9bhexahydro - 5 - phenyl - 2H - indeno [1,2c]- pyridines SANDOZ Ltd 10 April 1970 [6 May 1969 9 June 1969 11 Dec 1969 5 Feb 1970] 17079/70 Heading C2C Novel compounds of formula and acid addition salts thereof wherein R 1 is H, C 1-4 alkyl, F, Br or Cl and each of R 2 , R 3 , and R 4 are H, C 1-4 alkyl, F, Br, Cl, CF 3 , C 1-4 alkoxy or C 1-4 alkylthio are prepared by reaction of a compound of Formula III where X is the acid radical of a reactive ester and a compound of Formula II Intermediates of Formula II above are prepared by reaction of a compound of Formula IIa wherein R 5 is CH 2 or benzyl with a chloroformic ester and hydrolysis in situ of the urethane so formed. Intermediates of Formula IIa above are prepared by one of the following methods, (a) a compound of Formula V or Va is cyclized or (b) a compound of Formula VI is reduced or (c) one isomer is converted into another by heating with an alkali. Intermediates of Formula VI above are prepared by dehydration of the corresponding 5-hydroxy compounds which are prepared by reaction of a substituted phenyl lithium and the 5-keto compound. Intermediates of Formula Va above are prepared by NaBH 4 reduction of the corresponding ketones which are prepared by reaction of at least 2 moles of a Grignard reagent of formula R 1 C 6 H 4 MgBr and a compound of Formula X 4 - Benzyl - 4 - hydroxy - 3 - phenyl - 1 - methylpiperidine is prepared by reaction of phenyl magnesium bromide and 1-methyl-3-phenylpiperidin-4-one. Pharmaceutical compositions in conventional forms for oral administration which have a serotonin antagonistic effect and which exhibit an inhibition of hematoblast aggregation, comprise an above novel compound or salt and an adjuvant.
GB1707970A 1969-05-06 1970-04-10 Expired GB1304589A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH691369A CH513865A (en) 1969-05-06 1969-05-06 Indeno-pyridine derivs
CH874769 1969-06-09
CH1842369 1969-12-11
CH165070 1970-02-05

Publications (1)

Publication Number Publication Date
GB1304589A true GB1304589A (en) 1973-01-24

Family

ID=27428251

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1707970A Expired GB1304589A (en) 1969-05-06 1970-04-10

Country Status (5)

Country Link
CA (1) CA945560A (en)
DE (1) DE2021690A1 (en)
FR (1) FR2051500B1 (en)
GB (1) GB1304589A (en)
SE (1) SE357364B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005110987A1 (en) * 2004-05-12 2005-11-24 Pfizer Products Inc. Piperidine derivatives as nk1 and nk3 antagonists

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4387229A (en) 1977-09-13 1983-06-07 Pfizer Inc. 3-[2-Hydroxy-4-(substituted)phenyl]azacycloalkanols and derivatives thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005110987A1 (en) * 2004-05-12 2005-11-24 Pfizer Products Inc. Piperidine derivatives as nk1 and nk3 antagonists

Also Published As

Publication number Publication date
SE357364B (en) 1973-06-25
FR2051500B1 (en) 1973-07-13
FR2051500A1 (en) 1971-04-09
DE2021690A1 (en) 1970-11-19
CA945560A (en) 1974-04-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees