DK1876169T3 - Phenyl-indeholdende n-acyl-amin- og aminosyrederivater, fremgangsmåder til fremstilling deraf, farmaceutisk sammensætning og anvendelse deraf - Google Patents

Phenyl-indeholdende n-acyl-amin- og aminosyrederivater, fremgangsmåder til fremstilling deraf, farmaceutisk sammensætning og anvendelse deraf Download PDF

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DK1876169T3
DK1876169T3 DK06733250.2T DK06733250T DK1876169T3 DK 1876169 T3 DK1876169 T3 DK 1876169T3 DK 06733250 T DK06733250 T DK 06733250T DK 1876169 T3 DK1876169 T3 DK 1876169T3
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derivative
pharmaceutically acceptable
ester
methyl ester
compounds
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Tatyana Alexandrovna Kromova
Galina Alexandrovna Zheltukhina
Violetta Leonidovna Kovaleva
Vladimir Evgenievich Nebolsin
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Obschestvo S Ogranichennoi Otvetstennostiyu Pharmentpr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated

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Claims (14)

1. Phenyl-N-acylderivat af en biogen amin, hvilket derivat er en forbindelse med den almene formel (I):
udvalgt fra: 1) Ri er
R2 er H, R3 er COOH, R4 er OH; 2) Ri er
R2 er H, R3 er COOH, R4 er H; 3) Ri er
R2 er H, R3 er COOCH3, R4 er OH; 4) Ri er
R2 er H, R3 er COOCH3, R4 er H; 5) Ri er
R2 er H, R3 er
R4 er OH; 6) Ri er
Ro fir H.
Ro fir R4 er H ; 7Ί Ri er
R2 er
R3 er H, R4 er H; 8) Ri er
R2 er
R3 er H, R4 er OH; 9) Ri er
R2 er H, R3 er H, R4 er OH; 10) R-ι er
R2 er H, R3 er H, R4 er H; 11) Ri er
R2 er H, R3 er
R4 er H; 12) R-ι er
R2 er H, R3 er
R4 er H; eller et farmaceutisk acceptabelt salt deraf til anvendelse som et analgetikum eller anti-inflammatorisk middel.
2. Phenyl-N-acylderivat af en biogen amin, hvor derivatet er som defineret i krav 1, eller et farmaceutisk acceptabelt salt deraf, forudsat at derivatet ikke er p-hydroxyphenylacetyltyrosinmethylester eller p- hydroxyphenylacetylphenylalaninmethylester.
3. Derivat ifølge krav 2, udvalgt fra p-hydroxyphenylacetyltyrosin, p-hydroxyphenylacetylphenylalanin, p-hydroxyphenylacetyltyrosinbenzylester, p-hydroxyphenylacetylphenylalaninbenzylester, N-acetyltyrosylphenylethylamin, N-acetyltyrosylty ram i n, p-hydroxyphenylacetyltyramin, p-hydroxyphenylacetylphenylethylamin, 3-(p-hydroxyphenyl)propionylphenylalaninbenzylester, 3-phenylpropionylphenylalaninbenzylester og farmaceutisk acceptable salte deraf.
4. Fremgangsmåde til fremstilling af et derivat ifølge krav 1, forudsat at derivatet ikke er p-hydroxyphenylacetyltyrosinmethylester eller p-hydroxyphenylacetylphenylalaninmethylester, hvilken fremgangsmåde omfatter aktivering af en carboxylgruppe af en forbindelse med den almene formel
ved omsætning med diphenylphosphorylazid og triethylamin i et organisk opløsningsmiddel ved afkøling, efterfulgt af omsætning med en aminoforbin-delse med den almene formel,
hvor R1-R4 er som defineret i krav 1.
5. Fremgangsmåde ifølge krav 4, hvorved 1-1.2 ækvivalenter af diphenylphosphorylazid og triethylamin anvendes, og/eller som et aminoderivat en tyrosin- eller phenylalaninester anvendes, og/eller som et organisk opløsningsmiddel Ν,Ν-dimethylformamid eller ethylacetat anvendes, og/eller fremgangsmåden gennemføres ved en temperatur fra -25° C til 0° C.
6. Fremgangsmåde til fremstilling af et derivat ifølge krav 1, forudsat at derivatet ikke er p-hydroxyphenylacetyltyrosinmethylester eller p-hydroxyphenylacetylphenylalaninmethylester, hvilken fremgangsmåde omfatter omdannelsen af p-hydroxyphenyleddikesyre, phenyleddikesyre eller N-substitueret tyrosin med den almene formel
til aktiveret N-oxvsuccinimidester med den almene formel
ved anvendelse af Ν,Ν'-dicyclohexylcarbodiimid-fremgangsmåden, efterfulgt af omsætning af den aktiverede N-oxysuccinimidester med et aminoderivat med den almene formel
hvor R1-R4 er som defineret i krav 1.
7. Fremgangsmåde ifølge krav 6, hvorved der som et aminoderivat anvendes en tyrosin- eller phenylalaninester.
8. Farmaceutisk sammensætning, der som aktivt middel omfatter en virksom mængde af et derivat ifølge krav 1 eller et farmaceutisk acceptabelt salt deraf, forudsat at derivatet ikke er p-hydroxyphenylacetyltyrosinmethylester eller p-hydroxyphenylacetylphenylalaninmethylester, og en farmaceutisk acceptabel bærer.
9. Farmaceutisk sammensætning ifølge krav 8 til anvendelse som et analge-tikum, anti-inflammatorisk middel, spasmolytikum, anti-hypoksisk middel, antidepressivt middel eller antiparkinsonmiddel eller til at forstærke virkningen af andre analgetika.
10. Derivat ifølge krav 1 eller et farmaceutisk acceptabelt salt deraf til anvendelse for at opnå en spasmolytisk, anti-hypoksisk, antidepressiv eller antipar-kinson-virkning.
11. Derivat ifølge krav 1 eller et farmaceutisk acceptabelt salt deraf til anvendelse for at forstærke virkningen af andre analgetika.
12. Anvendelse af et derivat ifølge krav 1 eller et farmaceutisk acceptabelt salt deraf ved fremstilling af et medikament til anvendelse ved behandling af smertesyndromer af forskellig oprindelse, inflammatoriske og inflammatoriskdegenerative led- og konnektive vævssygdomme samt skelet-muskelsystem, andre sygdomme med inflammation, spasmer, depression, hypoksi eller tegn på parkinsonisme.
13. Anvendelse af et derivat ifølge krav 1 eller et farmaceutisk acceptabelt salt deraf ved fremstilling af et medikament til anvendelse ved behandling af postoperative smerter, posttraumatiske smerter samt smertesyndromer af gynækologisk, neurologisk, kræftagtig eller dental oprindelse, reumatoid artri-tis, artropati, Bekhterevs sygdom, ikke-specifik spondylartrit, gigtartritis, oste-oartrose, ekstraartikulær gigtfeber eller thrombophlebitis eller tilstande med emotionel stress og lidelser forårsaget af spasmer, hypoksi og medfølgende Parkinsons sygdom.
14. Anvendelse ifølge krav 12 eller 13, hvor medikamentet er til indgivelse i kombination med andre analgetika.
DK06733250.2T 2005-03-25 2006-03-24 Phenyl-indeholdende n-acyl-amin- og aminosyrederivater, fremgangsmåder til fremstilling deraf, farmaceutisk sammensætning og anvendelse deraf DK1876169T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2005108492/04A RU2309144C2 (ru) 2005-03-25 2005-03-25 Фенилсодержащие n-ацильные производные аминов, способ их получения, фармацевтическая композиция и их применение в качестве противовоспалительных и анальгетических средств
PCT/RU2006/000139 WO2006101422A1 (fr) 2005-03-25 2006-03-24 Derives n-acyles d'amines et d'acides amines amines contenant des phenyles, procede de fabrication, composition pharmaceutique et son utilisation

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US (2) US8309766B2 (da)
EP (1) EP1876169B1 (da)
JP (1) JP5384096B2 (da)
KR (1) KR101383580B1 (da)
CN (1) CN101180267B (da)
CA (1) CA2602545C (da)
CY (1) CY1117449T1 (da)
DK (1) DK1876169T3 (da)
EA (1) EA013644B1 (da)
ES (1) ES2564238T3 (da)
HU (1) HUE027009T2 (da)
MX (1) MX2007011852A (da)
PL (1) PL1876169T3 (da)
PT (1) PT1876169E (da)
RU (1) RU2309144C2 (da)
SI (1) SI1876169T1 (da)
UA (1) UA88688C2 (da)
WO (1) WO2006101422A1 (da)

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RU2309144C2 (ru) 2007-10-27
HUE027009T2 (en) 2016-10-28
WO2006101422A1 (fr) 2006-09-28
ES2564238T3 (es) 2016-03-21
US20130109880A1 (en) 2013-05-02
KR20080008345A (ko) 2008-01-23
PT1876169E (pt) 2016-03-21
US20090111874A1 (en) 2009-04-30
PL1876169T3 (pl) 2016-06-30
JP2008534495A (ja) 2008-08-28
CN101180267A (zh) 2008-05-14
HK1118798A1 (en) 2009-02-20
CA2602545A1 (en) 2006-09-28
CA2602545C (en) 2014-08-19
MX2007011852A (es) 2008-02-21
EP1876169B1 (en) 2015-12-30
EP1876169A4 (en) 2009-11-04
CN101180267B (zh) 2015-06-17
EP1876169A1 (en) 2008-01-09
CY1117449T1 (el) 2017-04-26
RU2005108492A (ru) 2006-10-10
EA200702072A1 (ru) 2008-02-28
EA013644B1 (ru) 2010-06-30
US8309766B2 (en) 2012-11-13
JP5384096B2 (ja) 2014-01-08
US8546612B2 (en) 2013-10-01
UA88688C2 (ru) 2009-11-10
KR101383580B1 (ko) 2014-04-09

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