GB1299172A - Heterocyclic anti-inflammatory agents - Google Patents

Heterocyclic anti-inflammatory agents

Info

Publication number
GB1299172A
GB1299172A GB4878368A GB4878368A GB1299172A GB 1299172 A GB1299172 A GB 1299172A GB 4878368 A GB4878368 A GB 4878368A GB 4878368 A GB4878368 A GB 4878368A GB 1299172 A GB1299172 A GB 1299172A
Authority
GB
United Kingdom
Prior art keywords
group
ethyl
methyl
atom
formula
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
GB4878368A
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.)
Lilly Industries Ltd
Original Assignee
Lilly Industries Ltd
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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Priority to GB4878368A priority Critical patent/GB1299172A/en
Publication of GB1299172A publication Critical patent/GB1299172A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D211/34—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Abstract

1299172 Heterocyclicphenylalkanoic acids and derivatives LILLY INDUSTRIES Ltd . 15 Jan 1970 [15 Oct 1968] 48783/68 Heading C2C Novel compounds of Formula L wherein n is an integer from 1 to 4 inclusive, R<SP>2</SP> is a hydroxyl group, in which case R<SP>1</SP> is oxygen; or R<SP>2</SP> is an -NH 2 or -NH 2 group where R is a methyl, ethyl or n-propyl group or the two groups R taken together with the nitrogen atom to which they are attached represent a morpholino radical in which case R<SP>1</SP> is oxygen or sulphur; R<SP>3</SP> is preferably hydrogen, or may be a chlorine, bromine, fluorine or iodine atom or a methyl, ethyl, methoxy, hydroxy, acetyl, trifluoromethyl, -SO 2 CH 3 , -SOCH 3 , nitro, amino, dimethylamino, benzylmercapto or methylthio group; R<SP>4</SP> is hydrogen, and in no more than one instance where it occurs on the alkylene chain it may also be a methyl, ethyl, n-propyl or -CH(OH)CCl 3 group; and A is 1-adamantylamino or a heterocyclic group of formula wherein Y is >CH- and C is >N.CH 3 , or Y is a nitrogen atom and X is >N.CH 3 , a methylene group, an oxygen atom or a sulphur atom; and x and y are selected from zero or integers from 1 to 6 such that the sum of x and y is 3, 4, 5 or 6; and the pharmaceutically acceptable salts and esters thereof with the exception of compounds of formula wherein R<SP>2</SP> is a hydroxyl group, or on -NH 2 or -NR 2 group where R is methyl, ethyl or n-propyl; or the two groups R taken together with the nitrogen atom to which they are attached represent a morpholino radical; R<SP>3</SP> is a chlorine, bromine, fluorine or iodine atom or a methyl, ethyl, methoxy, hydroxy, acetyl, trifluoromethyl, -SO 2 CH 3 , -SOCH 3 , nitro, amino, dimethylamino or methylthio group; R<SP>4</SP> is a hydrogen atom or a methyl, ethyl or n-propyl group; and A is a heterocyclic radical of the formula wherein X is -CH 2 -, O or S and the sum of x and y is 3-6 and salts and esters are prepared by one of the following reaction schemes wherein the symbols have the above meaning and B is a, niorile, ester or carboxylate group. Starting materials wherein A is piperidine are prepared either by reacting the compound wherein A is NH 2 with 1,5-dihalopentane or the compound wherein A is F with piperidine. 4 - (1 - Adamantylamino) - 3 - nitroacetophenone is prepared by reaction of 1-aminoadamantane and 4-bromo-3-nitroacetophenone and reduced to the 3-amino compound. Pharmaceutical compositions in conventional forms for oral, rectal, parenteral and topical administration having anti-inflammatory activity comprise an above novel compound and a diluent or carrier.
GB4878368A 1968-10-15 1968-10-15 Heterocyclic anti-inflammatory agents Expired GB1299172A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4878368A GB1299172A (en) 1968-10-15 1968-10-15 Heterocyclic anti-inflammatory agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4878368A GB1299172A (en) 1968-10-15 1968-10-15 Heterocyclic anti-inflammatory agents

Publications (1)

Publication Number Publication Date
GB1299172A true GB1299172A (en) 1972-12-06

Family

ID=10449898

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4878368A Expired GB1299172A (en) 1968-10-15 1968-10-15 Heterocyclic anti-inflammatory agents

Country Status (1)

Country Link
GB (1) GB1299172A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190665A (en) 1976-11-30 1980-02-26 Lipha, Lyonnaise Industrielle Pharmaceutique Substituted arylaliphatic acids
EP0076996A1 (en) * 1981-10-08 1983-04-20 Roche Diagnostics GmbH Carboxylic-acid derivatives, process for their preparation and medicines containing them
FR2552760A1 (en) * 1980-10-31 1985-04-05 Otsuka Pharma Co Ltd Process for obtaining carbostyril derivatives and synthesis intermediates.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190665A (en) 1976-11-30 1980-02-26 Lipha, Lyonnaise Industrielle Pharmaceutique Substituted arylaliphatic acids
FR2552760A1 (en) * 1980-10-31 1985-04-05 Otsuka Pharma Co Ltd Process for obtaining carbostyril derivatives and synthesis intermediates.
EP0076996A1 (en) * 1981-10-08 1983-04-20 Roche Diagnostics GmbH Carboxylic-acid derivatives, process for their preparation and medicines containing them

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Legal Events

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