IE801453L - Compounds - Google Patents

Compounds

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Publication number
IE801453L
IE801453L IE801453A IE145380A IE801453L IE 801453 L IE801453 L IE 801453L IE 801453 A IE801453 A IE 801453A IE 145380 A IE145380 A IE 145380A IE 801453 L IE801453 L IE 801453L
Authority
IE
Ireland
Prior art keywords
group
carbon atoms
groups
alkyl
substituted
Prior art date
Application number
IE801453A
Other versions
IE50292B1 (en
Original Assignee
Thomae Gmbh Dr K
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Publication date
Priority claimed from DE19792928352 external-priority patent/DE2928352A1/en
Priority claimed from DE19792949259 external-priority patent/DE2949259A1/en
Priority claimed from DE19803016650 external-priority patent/DE3016650A1/en
Priority claimed from DE19803016651 external-priority patent/DE3016651A1/en
Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K
Publication of IE801453L publication Critical patent/IE801453L/en
Publication of IE50292B1 publication Critical patent/IE50292B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • C07D211/42—Oxygen atoms attached in position 3 or 5
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    • 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
    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals 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
    • C07D211/68—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
    • 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
    • C07D211/72—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 hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • 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
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE) Carboxylic acid amides of general formula I see diagramm : EP0023569,P97,F1 wherein R represents a hydrogen, chlorine or bromine atom or a cyclic alkyleneimino group with 4 to 7 carbon atoms in the imino ring ; R1 represents a hydrogen, fluorine, chlorine or bromine atom ; an alkyl or alkoxy group with 1 to 6 carbon atoms ; an alkoxy group with 1 to 3 carbon atoms substituted by a phenyl group ; a hydroxy, nitro, amino, cyano or carboxy group ; an alkanoylamino, alkoxycarbonyl or dialkylamidosulphonyl group, wherein the alkyl part may contain 1 to 3 carbon atoms ; R2 and R3 , which may be the same or different, represent alkyl groups with 1 to 7 carbon atoms, alkenyl groups with 3 to 7 carbon atoms, cycloalkyl groups with 3 to 7 carbon atoms, alkyl groups with 1 to 3 carbon atoms substituted by a phenyl group, or phenyl or adamantyl groups, or R2 and R3 together with the nitrogen atom between them represent an unbranched alkyleneimino group with 3 to 12 carbon atoms in the imino ring, an unbranched alkyleneimino group with 4 to 6 carbon atoms in the imino ring which may be substituted by one or two alkyl groups each with 1 to 4 carbon atoms, an alkoxy group with 1 to 3 carbon atoms, a hydroxy, phenyl, carboxy or alkoxycarbonyl group with a total of 2 to 4 carbon atoms and/or wherein a methylene group is replaced by an imino group (which may be substituted by an alkyl group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms, a phenyl, halophenyl, benzyl, pyridyl or furoyl group), by an oxygen or sulphur atom or by a carbonyl, sulphoxide or sulphonyl group ; a saturated or partially unsaturated azabicycloalkyl group with 7 to 10 carbon atoms, a piperidino group substituted in the 3- and 5-positions by a total of 3 or 4 alkyl groups each with 1 to 3 carbon atoms ; a 1,4-dioxa-8-aza-spiroalkyl group with 6 to 9 carbon atoms, or a pyrrolyl or tetrahydropyridino group ; R4 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms ; Y represents an oxygen atom, an imino group or a methylene group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, Z represents a hydrogen or halogen atom, a carboxy, cyano, formyl, hydroxymethyl, hydroxycarbonylethylene, nitro, amino, allyloxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl or phenylethoxycarbonyl group, an alkoxycarbonyl group with a total of 2 to 8 carbon atoms, a cycloalkoxycarbonyl group with a total of 4 to 8 carbon atoms, a methyl group optionally substituted by 2 or 3 alkoxy groups or by a carboxy, alkoxycarbonyl or ethylenedioxy group, wherein the alkoxy group may contain 1 to 3 carbon atoms ; an acetyl group, optionally substituted by a carboxy group or alkoxycarbonyl group with a total of 2 to 4 carbon atoms ; an ethyl or ethylene group substituted by one or two alkoxycarbonyl groups each having a total of 2 to 4 carbon atoms, or by two carboxy groups ; an aminocarbonyl group optionally mono- or di-substituted by an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms and/or an alkenyl group with 3 to 7 carbon atoms ; a piperidinocarbonyl, morpholinocarbonyl, thiomorpholinocarbonyl or N-alkyl-piperazinocarbonyl group wherein the alkyl group may contain 1 to 3 carbon atoms ; or an ethyl group substituted by a carboxy group if the groups R2 and R3 together with the nitrogen atom between them represent one of the above-mentioned cyclic imino groups, and the physiologically acceptable salts thereof with inorganic or organic acids and also bases if Z represents or contains a carboxy group. 1. Claims (for the Contracting State AT) Process for the preparation of new carboxylic acid amides of general formula I see diagramm : EP0023569,P104,F1 wherein R represents a hydrogen, chlorine or bromine atom or a cyclic alkyleneimino group with 4 to 7 carbon atoms in the imino ring ; R1 represents a hydrogen, fluorine, chlorine or bromine atom ; an alkyl or alkoxy group with 1 to 6 carbon atoms ; an alkoxy group with 1 to 3 carbon atoms substituted by a phenyl group ; a hydroxy, nitro, amino, cyano or carboxy group ; an alkanoylamino, alkoxycarbonyl or dialkylamido-sulphonyl group, wherein the alkyl part may contain 1 to 3 carbon atoms ; R2 and R3 , which may be the same or different, represent alkyl groups with 1 to carbon atoms, alkenyl groups with 3 to 7 carbon atoms, cycloalkyl groups with 3 to 7 carbon atoms, alkyl groups with 1 to 3 carbon atoms substituted by a phenyl group, or phenyl or adamantyl groups, or R2 and R3 together with the nitrogen atom between them represent an unbranched alkyleneimino group with 3 to 12 carbon atoms in the imino ring, an unbranched alkyleneimino group with 4 to 6 carbon atoms in the imino ring which may be substituted by one or two alkyl groups each with 1 to 4 carbon atoms, an alkoxy group with 1 to 3 carbon atoms, a hydroxy, phenyl, carboxy or alkoxycarbonyl group with a total of 2 to 4 carbon atoms and/or wherein a methylene group is replaced by an imino group (which may be substituted by an alkyl group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms, a phenyl, halophenyl, benzyl, pyridyl or furoyl group), by an oxygen or sulphur atom or by a carbonyl, sulphoxide or sulphonyl group ; with 7 to 10 carbon atoms, a piperidino group substituted in the 3- and 5-positions by a total of 3 or 4-alkyl groups each with 1 to 3 carbon atoms ; a 1,4-dioxa-8-aza-spiroalkyl group with 6 to 9 carbon atoms, or a pyrrolyl or tetrahydropyridino group ; R4 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms ; Y represents an oxygen atom, an imino group or a methylene group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, Z represents a hydrogen or halogen atom, a carboxy, cyano, formyl, hydroxymethyl, hydroxycarbonylethylene, nitro, amino, allyloxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl or phenylethoxycarbonyl group, an alkoxycarbonyl group with a total of 2 to 8 carbon atoms, a cycloalkoxycarbonyl group with a total of 4 to 8 carbon atoms, a methyl group optionally substituted by 2 or 3 alkoxy groups or by a carboxy, alkoxycarbonyl or ethylene-dioxy group, wherein the alkoxy group may contain 1 to 3 carbon atoms ; an acetyl group, optionally substituted by a carboxy group or alkoxycarbonyl group with a total of 2 to 4 carbon atoms ; an ethyl or ethylene group substituted by 1 or two alkoxycarbonyl groups each having a total of 2 to 4 carbon atoms, or by two carboxy groups ; an aminocarbonyl group optionally mono- or di-substituted by an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms and/or an alkenyl group with 3 to 7 carbon atoms ; a piperidinocarbonyl, morpholinocarbonyl, thiomorpholinocarbonyl or N-alkyl-piperazinocarbonyl group wherein the alkyl group may contain 1 to 3 carbon atoms ; or an ethyl group substituted by a carboxy group if the groups R2 and R3 together with the nitrogen atom between them represent one of the above-mentioned cyclic imino groups, and the physiologically acceptable salts thereof with inorganic or organic acids and also bases if Z represents or contains a carboxy group, characterised in that a) an aminobenzoic acid of general formula II see diagramm : EP0023569,P105,F1 wherein R, R1 , R2 and R3 are as hereinbefore defined, or a reactive derivative thereof, optionally prepared in the reaction mixture, is reacted with an amine of general formula III see diagramm : EP0023569,P105,F2 wherein R4 , Y and Z are as hereinbefore defined, or with an N-activated amine of general formula III optionally formed in the reaction mixture, if an aminobenzoic acid of general formula II is used and if Z in an N-activated amine of general formula III does not contain any carboxy or amino groups, or b) in order to prepare compounds of general formula I wherein R1 has the definitions given hereinbefore, with the exception of the hydroxy and amino group, and Y represents a methylene group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, a compound of general formula IV see diagramm : EP0023569,P105,F3 wherein R, R4 and Z are as hereinbefore defined, R1 and Y are defined as above and E represents a halogen atom, is reacted with an amine of general formula V see diagramm : EP0023569,P105,F4 wherein R2 and R3 are as hereinbefore defined, or c) in order to prepare compounds of general formula I wherein Z represents a carboxy group and Y does not represent an NH group a compound of general formula VI see diagramm : EP0023569,P105,F5 wherein R and R1 to R4 are as hereinbefore defined, Y has the meanings given hereinbefore with the exception of the NH group and A represents a group which can be converted into a carboxy group by oxidation, is oxidised or d) in order to prepare compounds of general formula I wherein Z represents a carboxy group, a compound of general formula VII see diagramm : EP0023569,P106,F1 wherein R, R1 to R4 and Y are as hereinbefore defined and B represents a group which can be converted into a carboxy group by hydrolysis, is hydrolysed, or e) in order to prepare compounds of general formula I wherein R2 represents an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an alkyl group with 1 to 3 carbon atoms substituted by a phenyl group, or an alkenyl group with 3 to 7 carbon atoms, R3 represents an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an alkenyl group with 3 to 7 carbon atoms, an alkyl group with 1 to 3 carbon atoms substituted by a phenyl group, or an adamantyl group, or R2 and R3 together with the nitrogen atom between them represent a 5- to 7-membered alkyleneimino ring, a piperidino group [EP0023569A1]
IE1453/80A 1979-07-13 1980-07-11 Chemical compounds IE50292B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19792928352 DE2928352A1 (en) 1979-07-13 1979-07-13 Hypoglycaemic 2-amino-benzamido-ethyl-benzoic acid derivs. - prepd. e.g. by reaction of 2-amino-benzoic acid derivs. with 4-aminoethyl-benzoic acid derivs.
DE19792949259 DE2949259A1 (en) 1979-07-13 1979-12-07 Amino-pyridine or benzene carboxylic acid derivs. - with metabolic, esp. hypoglycaemic and hypolipaemic, activity
DE19803016650 DE3016650A1 (en) 1979-07-13 1980-04-30 Amino-pyridine or benzene carboxylic acid derivs. - with metabolic, esp. hypoglycaemic and hypolipaemic, activity
DE19803016651 DE3016651A1 (en) 1980-04-30 1980-04-30 Amino-pyridine or benzene carboxylic acid derivs. - with metabolic, esp. hypoglycaemic and hypolipaemic, activity

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DE3139970A1 (en) * 1981-10-08 1983-04-28 Boehringer Mannheim Gmbh, 6800 Mannheim NEW CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
DE3211934A1 (en) * 1982-03-31 1983-10-13 Hoechst Ag, 6230 Frankfurt SALICYL ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS BASED ON THESE COMPOUNDS AND THEIR USE
EP0210574B1 (en) * 1985-07-31 1991-10-23 Hoechst Aktiengesellschaft N-substituted 5-nitro anthranilic acids, process for their preparation, their use and pharmaceutical compositions based on these compounds
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AU6036280A (en) 1981-01-15
EP0023569A1 (en) 1981-02-11
AU535924B2 (en) 1984-04-12
PT71551A (en) 1980-08-01
NO152005C (en) 1985-07-17
DE3063878D1 (en) 1983-07-28
EP0023569B1 (en) 1983-06-22
DD200152A5 (en) 1983-03-23
NO802087L (en) 1981-01-14
DD153207A5 (en) 1981-12-30
NO152005B (en) 1985-04-09
DK294180A (en) 1981-01-14
IE50292B1 (en) 1986-03-19
PT71551B (en) 1982-01-13

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