KR937000532A - N-phenylglycineamide derivatives, their preparation and drugs containing them - Google Patents

Abstract

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Description

N-phenylglycineamide derivatives, their preparation and drugs containing them

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Claims (14)

Racemates and enantiomers thereof when containing a compound of the general formula and at least one subsidiary center: Wherein -R ₁ represents a hydrogen atom, an alkyl or alkoxycarbonyl radical or a phenyl radical (optionally substituted with a halogen atom and one or more substituents selected from alkyl, alkoxy, alkylthio, nitro and amino radicals), -R ₂ represents an alkoxy, cycloalkyloxy (optionally substituted with at least one alkyl radical), cycloalkylalkyloxy, phenylalkyloxy, polyfluoroalkyloxy or cinnamiloxy radicals or radicals -NR ₅ R ₆ ,- R ₃ is phenylamino wherein the phenyl ring is a halogen atom and alkyl, alkoxy, alkylthio, carboxy, hydroxy, mono- or polyhydroxyalkyl, nitro, amino, acyl, cyano, sulfamoyl, carbamoyl, Benzoyl, trifluoromethylsulfonamido, alkoxycarbonyl, phenylhydroxymethyl, piperidino, hydroxyaminoalkyl, alkoxyaminoalkyl, alkylsulfinyl, hydroxy Minocarbonyl, alkoxyaminocarbonyl, 5-tetaryl, 5-tetrazolylalkyl, sulfo, -alk-O-CO-alk, -alk-O-alk, alk-COOX, -O-alk-COOX, from the -alk′-COOX, —CH═CH—COOX, —CO—COOX, —alk—SO ₃ H, —CH═CH—alk ′, —C (═NOH) —COOX and —S-alk-COOX radicals Optionally substituted with one or more substituents selected), phenyl (optionally substituted with halogen atoms and one or more substituents selected from alkyl, alkoxy and alkylthio radicals), naphthyl, indolyl or quinolyl radicals, and -R ₄ Is a halogen atom, alkyl, alkoxy, hydroxy, polyfluoroalkyl, nitro, alkylthio, alkoxycarbonyl, carboxy, acylamino, methylenedioxy, polyfluoroalkoxy, trifluoromethylthio, phenoxy, phenyl, One or more substituents selected from benzyl and phenyl amino radicals represent the phenyl radical and the radical-CO-NR ₅ R ₆ , wherein -R ₅ and R ₆ are the same or May be different and represent a hydrogen atom or an alkyl, phenyl, optionally substituted with halogen atom and one or more substituents selected from alkyl, alkoxy and alkylthio radicals, indanyl, cycloalkylalkyl, cycloalkyl or phenylalkyl radicals Or alternatively R ₅ and R ₆ together with their attached nitrogen atoms contain 4 to 9 carbon atoms and at least one hetero atom (O, N, S) and at least one alkyl, alkoxy, alkoxycarbonyl Optionally, one or more heteroatoms (O, S, N) together with carbon atoms of a saturated or unsaturated mono- or polycyclic heterocycle or an optionally substituted heterocycle optionally substituted with a dialkyl carbamoyl or phenyl radical To form a 4- or 5-membered spiromonocyclic ring system, wherein -alk represents an alkyl or alkylene radical, -alk 'represents a hydroxyalkylene or Hydroxyalkyl radicals, -X represents a hydrogen atom or an alkyl radical, wherein the alkyl, alkylene and alkoxy radicals and the alkyl, alkylene and alkoxy moieties represent 1 to 4 carbon atoms in a straight or branched chain. Wherein the cycloalkyl radical and moiety contain 3 to 6 carbon atoms and the acyl radical contains 2 to 4 carbon atoms. The compound of claim 1, wherein R ₅ and R ₆ , together with the nitrogen atom to which they are attached, are optionally substituted with at least one alkyl, phenyl, alkoxycarbonyl or dialkyl carbamoyl radical; or Pohydro-1-azinyl, 1-indolinyl 1,2,3,6-tetrahydro-1-pyridyl, 1,2,3,4-tetrahydro-1-quinolyl, 1-pyrrolidinyl -3,4-dihydro-2H-1,4-benzoxazin-4-yl, 3,4-dihydro-2H-1,4-benzothiazin-4-yl, N-alkyl-1,2, 3,4-tetrahydro-1-quinoxalinyl, perhydro-1-quinolyl, 1,2,3,4-tetrahydro-2-isoquinolyl, 8-azaspiro [4,5] decane-8 -Yl, 8-aza-1,4-dioxaspiro [4,5] decane-8-yl, 2- or 3-phenyl-1-pyrrolidinyl or thiomorpholino (optionally at least one alkyl radical) Compound of formula (I) to form a ring system. The compound of formula (I) according to claim 1 or 2, wherein the halogen atoms are chlorine, bromine and fluorine atoms. 4. The compound of claim 1, wherein R ₁ represents a hydrogen atom, R ₂ represents an alkoxy radical or a radical —NR ₅ R ₆ , and R ₃ represents a phenylamino radical, wherein the phenyl ring is alkyl, monohydroxy Substituted with one or more substituents selected from alkyl, carboxy and -alk-COOH radicals, and R ₄ is a halogen atom and a phenyl radical and radical -CO substituted with one or more substituents selected from alkoxy, hydroxy and alkoxycarbonyl radicals. A compound of formula (I) representing -NR ₅ R ₆ . Isocyanates of the general formula: [Wherein R ₉ is phenyl radical (halogen atom and alkyl, alkoxy, alkylthio, nitro, amino, acyl, cyano, sulfamoyl, benzoyl, alkoxycarbonyl, -alk-O-alk, 5-tetrazolyl and 5 -Optionally substituted with one or more substituents selected from tetrazolylalkyl radicals. (Wherein, R _1, R ₂ is R ₄ is having the same meaning as in claim 1) and the reaction was then isolating the product, the phenyl R ₃ amino radical (wherein the phenyl ring is a halogen atom and an alkyl, alkoxy, Optionally substituted with one or more substituents selected from alkylthio, nitro, acyl, cyano, sulfanoyl, benzoyl, alkoxycarbonyl, -alk-O-alk, 5-tetrazolyl and 5-tetrazolylalkyl radicals) The method for producing a compound of formula (I) according to claim 1. Amines of the general formula: (Wherein R ₁ , R ₂ and R ₄ have the same meaning as in claim 1), the acid of the general formula (Wherein R ₃ has the same meaning), or R ₃ reacting with a reactive derivative of the acid and then isolating the product is a phenylamino radical, wherein the phenyl ring is a halogen atom and alkyl, alkoxy, alkylthio, Optionally with one or more substituents selected from nitro, acyl, cyano, sulfamoyl, benzoyl, alkoxycarbonyl, 5-tetrazolyl, 5-tetrazolylalkyl, trifluoromethylsunponamido and -alk-O-alk radicals To a compound of formula (I) according to claim 1. Derivatives of the general formula: A (wherein R _1, R ₂ is R ₄ is having the same meaning as in claim 1), to the amine of the general formula: [Wherein R ₁₁ is a phenyl radical (halogen atom and alkyl, alkoxy, alkoxyo, carboxy, hydroxy, mono- or polyhydroxyalkyl, nitro, amino, acyl, cyano, sulfamoyl, carbamoyl, benzoyl, Alkoxycarbonyl, phenylhydroxymethyl, piperidino, hydroxyaminoalkyl, alkoxyiminoalkyl, alkylsulfinyl, trifluoromethylsulfonamido, hydroxyaminocarbonyl, alkoxyaminocarbonyl, 5-tetrazolyl, 5-tetrazolylalkyl, sulfo, -alk-O-CO-alk, alk-COOX, -alk-O-alk, -alk′-COOX, -O-alk-COOX, -CH = CH-COOX, -CO Optionally substituted with one or more substituents selected from -COOX, -alk-SO ₃ H, -CH = CH-alk ', -C (= NOH) -COOX and -S-alk-COOX radicals. The process for preparing a compound of formula (I) according to claim 1, wherein R ₃ represents a phenylamino radical optionally substituted with a phenyl ring. Amines of the general formula: Wherein R ₁₁ has the same meaning as in claim 7 (Wherein R ₁ , R ₂ and R ₄ have the same meaning as in claim 1), and then R ₃ represents phenylaminoradical, wherein the phenyl ring is optionally substituted, isolating the product, A process for preparing the compound of formula (I) according to claim 1. R ₃ , which hydrolyzes the rising ester and then isolates the product, has a phenyl ring having at least one carboxy, -alk-COOH, -O-alk-COOH, -alk'-COOH, -CH = CH-COOH, An alkoxycarbonyl radical, which represents a phenylamino radical substituted with a -CO-COOH, -C (= NOH) or -S-alk-COOH radical and / or R ₄ represents a phenyl radical substituted with a carboxyl radical A method for producing a compound of formula (I) according to claim 1, except for containing the compound. Alkoxy, alkoxycarbonyl, alkylthio, wherein R ₄ represents a phenyl radical substituted with a hydroxy radical, after hydrolysis of the corresponding compound, where R ₄ represents a phenyl radical substituted with an alkoxy radical, and then the product is isolated. A process for preparing a compound of formula (I) according to claim 1, except for compounds containing cycloalkyloxy, cycloalkylalkyloxy, phenylalkyloxy, polyfluoroalkyloxy or cinnamil oxy radicals. Amines of the general formula: Wherein R ₁ , R ₂ and R ₄ have the same meaning as in claim 1. (Wherein R ₃ is jinim the same meaning as described hereinbefore.) And the reaction was then isolating the product, R ₃ is an optionally substituted phenyl radical or a naphthyl, indolyl or quinolyl represents the radical, a general according to claim 1, wherein Process for preparing a compound of formula (I). A drug containing at least one compound of formula (I) according to claim 1 as an active ingredient. A drug containing at least one compound according to any one of claims 2, 3 and 4 as an active ingredient. A drug according to claims 12 and 13 for the treatment and prevention of disorders associated with cck gastrin at the neurological and gastrointestinal level. ※ Note: The disclosure is based on the initial application.