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NL7004461A - New heterocyclic antiphlogistic compounds - Google Patents

New heterocyclic antiphlogistic compounds

Info

Publication number
NL7004461A
NL7004461A NL7004461A NL7004461A NL7004461A NL 7004461 A NL7004461 A NL 7004461A NL 7004461 A NL7004461 A NL 7004461A NL 7004461 A NL7004461 A NL 7004461A NL 7004461 A NL7004461 A NL 7004461A
Authority
NL
Netherlands
Prior art keywords
lower alkyl
4ars
9brs
alkenyl
formula
Prior art date
Application number
NL7004461A
Other versions
NL166019B (en
NL166019C (en
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 CH525869A external-priority patent/CH513864A/en
Priority claimed from CH691169A external-priority patent/CH517744A/en
Application filed filed Critical
Publication of NL7004461A publication Critical patent/NL7004461A/en
Publication of NL166019B publication Critical patent/NL166019B/en
Application granted granted Critical
Publication of NL166019C publication Critical patent/NL166019C/en

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
    • C07D211/08—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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)

Abstract

Preparation of new (4aRS,5SR,9bSR)- and (4aRS,5SR,9bRS)-1,3,4,4a,5,9b-hexahydro-5-phenyl-2H-indeno 1,2,c - pyridines of formula (I) is effected by the following schemes: (R1=R11=lower alkyl, alkenyl or alkynyl) X = acid residue of a reactive ester cyclising to I cyclising with polyphosphoric acid to I (R1II=R1=H, lower alkyl or alkenyl; R3=R2) reduction with lithium aluminium hydride right arrow I (R1=H or lower alkyl) aluminium hydride or diborane Ie (R1 = H, lower alkyl or alkoxy) (hydrogenolytic) right arrow I (R1 = H) splitting (R4 = methyl or benzyl) or heating a cpd. (4aRS,5SR,9bRS) of formula (I) in alkaline medium to obtain a cpd. (4aRS,5RS,9bRS) of formula (I) and desirably separating the mixture of (4aRS,5SR,9bSR) and (4aRS,5SR,9bRS) cpds. into their isomers. In the formulae either R1, R2 and R3 stand for H or R1 is H, lower alkyl, alkenyl or alkynyl or has a limited meaning as given in brackets uner specific formulae, R2 is Cl, Br, F or lower alkyl and R3 is H, Cl, Br, F or a lower alkyl, alkylthio- or alkoxy gp. or trifluoromethyl.
NL7004461.A 1969-04-08 1970-03-26 METHOD FOR THE PREPARATION OF A MEDICINAL PRODUCT CONTAINING A HYDROGENATED 5-PHENYL-2H-INDENO-1,2-C-PYRIDINE DERIVATIVE AND/OR AN ACID ADDITION SALT THEREOF AND THE FORMED MEDICINAL PRODUCTS OBTAINED BY THIS METHOD, AND METHOD FOR PREPARING THESE PYRIDINE DERIVATIVES. NL166019C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH525869A CH513864A (en) 1969-04-08 1969-04-08 New heterocyclic antiphlogistic compounds
CH691169A CH517744A (en) 1969-05-06 1969-05-06 New heterocyclic antiphlogistic compounds
CH889169 1969-06-11
CH914569 1969-06-16
CH1361069 1969-09-09
CH1837969 1969-12-10
CH1842269 1969-12-11

Publications (3)

Publication Number Publication Date
NL7004461A true NL7004461A (en) 1970-10-12
NL166019B NL166019B (en) 1981-01-15
NL166019C NL166019C (en) 1981-06-15

Family

ID=27561104

Family Applications (1)

Application Number Title Priority Date Filing Date
NL7004461.A NL166019C (en) 1969-04-08 1970-03-26 METHOD FOR THE PREPARATION OF A MEDICINAL PRODUCT CONTAINING A HYDROGENATED 5-PHENYL-2H-INDENO-1,2-C-PYRIDINE DERIVATIVE AND/OR AN ACID ADDITION SALT THEREOF AND THE FORMED MEDICINAL PRODUCTS OBTAINED BY THIS METHOD, AND METHOD FOR PREPARING THESE PYRIDINE DERIVATIVES.

Country Status (9)

Country Link
JP (1) JPS4815943B1 (en)
CA (1) CA955260A (en)
DK (1) DK130292B (en)
FI (1) FI52976C (en)
IE (1) IE34654B1 (en)
IL (1) IL34246A (en)
NL (1) NL166019C (en)
NO (1) NO133401C (en)
RO (1) RO58032A (en)

Also Published As

Publication number Publication date
IL34246A (en) 1973-02-28
FI52976B (en) 1977-09-30
IL34246A0 (en) 1970-06-17
JPS4815943B1 (en) 1973-05-18
RO58032A (en) 1975-06-15
NL166019B (en) 1981-01-15
DK130292B (en) 1975-02-03
NL166019C (en) 1981-06-15
IE34654B1 (en) 1975-07-09
DK130292C (en) 1975-06-30
IE34654L (en) 1970-10-08
NO133401C (en) 1976-04-28
FI52976C (en) 1978-01-10
NO133401B (en) 1976-01-19
CA955260A (en) 1974-09-24

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Legal Events

Date Code Title Description
V1 Lapsed because of non-payment of the annual fee