Patent
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Substituted Methyl Aryl or Heteroaryl Amide Compounds

التفاصيل البيبلوغرافية
العنوان: Substituted Methyl Aryl or Heteroaryl Amide Compounds
Document Number: 20090163558
تاريخ النشر: June 25, 2009
Appl. No: 12/368778
Application Filed: February 10, 2009
مستخلص: This invention provides a compound of the formula (I): [chemical expression included] wherein X represents a carbon atom or the like: Y represents imino, or the like: R1 represents an alkyl group having from 1 to 6 carbon atoms or the like: R2 and R3 independently represents a hydrogen atom or the like. These compounds are useful for the treatment of disease conditions mediated by prostaglandin such as pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.
Inventors: Koike, Hiroki (Aichi-ken, JP); Kon-i, Kana (Aichi-ken, JP); Matsumoto, Yukari (Aichi-ken, JP); Nakao, Kazunari (Aichi-ken, JP); Okumura, Yoshiyuki (Aichi-ken, JP); Yamagishi, Tatsuya (Aichi-ken, JP)
Assignees: RaQualia Pharma Inc. (Aichi-ken, JP)
Claim: 1. A compound of the formula (I): [chemical expression included] wherein X represents a nitrogen atom; Y represents —NR4, an oxygen atom or a sulfur atom; R4 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; Z represents a hydrogen atom or a halogen atom; R1 represents an alkyl group having from 1 to 6 carbon atoms optionally substituted with an alkoxy group having from 1 to 6 carbon atoms or a cycloalkyl group having from 3 to 7 carbon atoms; a cycloalkyl group having from 3 to 7 carbon atoms optionally substituted by an alkyl group having from 1 to 3 carbon atoms; or a phenyl group optionally substituted with one or more substituents α; or a group Het1 optionally substituted with one or more substituents α; Het1 represents a heterocyclic group having from 4 to 7 ring atoms which contains either from 1 to 4 ring nitrogen heteroatoms or from 0 to 2 nitrogen ring heteroatoms and 1 oxygen or 1 sulfur ring heteroatom; R2 and R3 independently represent a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; or R2 and R3 groups together from an alkylene chain having from 3 to 6 carbon atoms; and said substituent α is selected from the group consisting of halogen atoms, alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, hydroxy groups, alkoxy groups having from 1 to 4 carbon atoms, haloalkoxy groups having from 1 to 4 carbon atoms, cyano groups, hydroxy alkyl groups having from 1 to 4 carbon atoms, alkoxyalkyl groups having from 1 to 4 carbon atoms in alkoxy and alkyl groups, alkylsulfonyl groups having from 1 to 4 carbon atoms, alkanoyl groups having from 2 to 5 carbon atoms, alkenyl groups having from 2 to 4 carbon atoms, alkynyl groups having from 2 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms, nitro groups, amino groups, mono- or di-alkylamino groups having from 1 to 4 carbon atoms, aminosulfonyl groups, alkoxycarbonyl groups having from 1 to 4 carbon atoms, alkylsulfonylamino groups having from 1 to 4 carbon atoms, cycloalkyl groups having from 3 to 7 carbon atoms and a mono- or di-alkylaminocarbonyl groups having from 1 to 6 carbon atoms; or a pharmaceutically acceptable ester of such compound; or a pharmaceutically acceptable salt thereof.
Claim: 2.-3. (canceled)
Claim: 4. A compound according to claim 1, wherein Y represents NR4 or an oxygen atom; and R4 represents an alkyl group having from 1 to 3 carbon atoms.
Claim: 5. A compound according to claim 1, wherein Y represents an oxygen atom.
Claim: 6. A compound according to claim 1, wherein Z represents a halogen atom.
Claim: 7. A compound according to claim 1, wherein R1 represents an alkyl group having from 1 to 6 carbon atoms; a cycloalkyl group having from 3 to 7 carbon atoms, or a phenyl group optionally substituted with one or more substituents a; or a group Het1 optionally substituted with one or more substituents Het1 represents a heterocyclic group having from 5 to 6 ring atoms which contains either from 1 to 2 ring nitrogen heteroatoms or from 0 to 2 nitrogen ring heteroatoms and 1 oxygen or 1 sulfur ring heteroatom; said substituents α are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, hydroxy groups, alkoxy groups having from 1 to 4 carbon atoms, haloalkoxy groups having from 1 to 4 carbon atoms, cyano groups, hydroxy alkyl groups having from 1 to 4 carbon atoms, alkoxyalkyl groups having from 1 to 4 carbon atoms in alkoxy and alkyl groups, alkylsulfonyl groups having from 1 to 4 carbon atoms and alkanoyl groups having from 2 to 5 carbon atoms.
Claim: 8. A compound according to claim 1, wherein R1 represents an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 4 to 6 carbon atoms, or a phenyl group, a pyridyl group, an oxazolyl group, a pyrazolyl group, a thiazolyl group, a tetrahydrofuranyl group or a tetrahydropyranyl group; said phenyl group, pyridyl group, oxazolyl group, pyrazolyl group, thiazolyl group, tetrahydrofuranyl group and tetrahydropyranyl group referred to in the definitions of R1 are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents α; and said α substituents are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 2 carbon atoms and cyano groups.
Claim: 9. A compound according to claim 1, wherein R1 represents a phenyl group, optionally substituted by 1 to 2 groups independently selected from a fluorine atom, a chlorine atom and a methyl group.
Claim: 10. A compound according to claim 1, wherein R2 and R3 independently represent a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms.
Claim: 11. A compound according to claim 1, wherein R2 represents a hydrogen atom; and R3 represents a methyl group.
Claim: 12. A compound according to claim 1 selected from: 4-[(1S)-1-({5-Chloro-2-[(4-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(4-methylphenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(4-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,3-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3,4-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,4-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-{(1S)-1-[({5-Chloro-2-[(3-chlorophenoxy)methyl]pyridine-3-yl}carbonyl)amino]ethyl}benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3,5-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-{(1S)-1-[({5-chloro-2-[(4-chlorophenoxy)methyl]pyridine-3-yl}carbonyl)amino]ethyl}benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,6-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,5-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; and 4-{(1S)-1-[({2-[(4-chlorophenoxy)methyl]-5-fluoropyridin-3-yl}carbonyl)amino]ethyl}benzoic acid; or a pharmaceutically acceptable ester of such compound; or a pharmaceutically acceptable salt thereof.
Claim: 13. A pharmaceutical composition, which comprises a compound according to claim 1, or a pharmaceutically acceptable ester or such compound, or a pharmaceutically acceptable salt thereof, and a suitable pharmaceutically acceptable carrier.
Claim: 14. A pharmaceutical for the treatment of disease conditions mediated by prostaglandin, in a mammalian subject, which comprises a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, and a suitable pharmaceutically acceptable carrier.
Claim: 15. (canceled)
Claim: 16. A combination of a compound of the formula (I), as defined in claim 1, and another pharmacologically active agent.
Current U.S. Class: 514/355
Current International Class: 61; 07
رقم الانضمام: edspap.20090163558
قاعدة البيانات: USPTO Patent Applications
ResultId 1
Header edspap
USPTO Patent Applications
edspap.20090163558
719
3
Patent
patent
719.021850585938
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&scope=site&db=edspap&AN=edspap.20090163558&custid=s6537998&authtype=sso
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Items Array ( [Name] => Title [Label] => Title [Group] => Ti [Data] => Substituted Methyl Aryl or Heteroaryl Amide Compounds )
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Array ( [Name] => DateEntry [Label] => Publication Date [Group] => Patent [Data] => June 25, 2009 )
Array ( [Name] => DocumentID [Label] => Appl. No [Group] => Patent [Data] => 12/368778 )
Array ( [Name] => DateFiled [Label] => Application Filed [Group] => Patent [Data] => February 10, 2009 )
Array ( [Name] => Abstract [Label] => Abstract [Group] => Ab [Data] => This invention provides a compound of the formula (I): [chemical expression included] wherein X represents a carbon atom or the like: Y represents imino, or the like: R1 represents an alkyl group having from 1 to 6 carbon atoms or the like: R2 and R3 independently represents a hydrogen atom or the like. These compounds are useful for the treatment of disease conditions mediated by prostaglandin such as pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound. )
Array ( [Name] => Author [Label] => Inventors [Group] => Patent [Data] => <searchLink fieldCode="ZA" term="%22Koike%2C+Hiroki%22">Koike, Hiroki</searchLink> (Aichi-ken, JP); <searchLink fieldCode="ZA" term="%22Kon-i%2C+Kana%22">Kon-i, Kana</searchLink> (Aichi-ken, JP); <searchLink fieldCode="ZA" term="%22Matsumoto%2C+Yukari%22">Matsumoto, Yukari</searchLink> (Aichi-ken, JP); <searchLink fieldCode="ZA" term="%22Nakao%2C+Kazunari%22">Nakao, Kazunari</searchLink> (Aichi-ken, JP); <searchLink fieldCode="ZA" term="%22Okumura%2C+Yoshiyuki%22">Okumura, Yoshiyuki</searchLink> (Aichi-ken, JP); <searchLink fieldCode="ZA" term="%22Yamagishi%2C+Tatsuya%22">Yamagishi, Tatsuya</searchLink> (Aichi-ken, JP) )
Array ( [Name] => OtherAuthors [Label] => Assignees [Group] => Patent [Data] => <searchLink fieldCode="ZS" term="%22RaQualia+Pharma+Inc%2E%22">RaQualia Pharma Inc.</searchLink> (Aichi-ken, JP) )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 1. A compound of the formula (I): [chemical expression included] wherein X represents a nitrogen atom; Y represents —NR4, an oxygen atom or a sulfur atom; R4 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; Z represents a hydrogen atom or a halogen atom; R1 represents an alkyl group having from 1 to 6 carbon atoms optionally substituted with an alkoxy group having from 1 to 6 carbon atoms or a cycloalkyl group having from 3 to 7 carbon atoms; a cycloalkyl group having from 3 to 7 carbon atoms optionally substituted by an alkyl group having from 1 to 3 carbon atoms; or a phenyl group optionally substituted with one or more substituents α; or a group Het1 optionally substituted with one or more substituents α; Het1 represents a heterocyclic group having from 4 to 7 ring atoms which contains either from 1 to 4 ring nitrogen heteroatoms or from 0 to 2 nitrogen ring heteroatoms and 1 oxygen or 1 sulfur ring heteroatom; R2 and R3 independently represent a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; or R2 and R3 groups together from an alkylene chain having from 3 to 6 carbon atoms; and said substituent α is selected from the group consisting of halogen atoms, alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, hydroxy groups, alkoxy groups having from 1 to 4 carbon atoms, haloalkoxy groups having from 1 to 4 carbon atoms, cyano groups, hydroxy alkyl groups having from 1 to 4 carbon atoms, alkoxyalkyl groups having from 1 to 4 carbon atoms in alkoxy and alkyl groups, alkylsulfonyl groups having from 1 to 4 carbon atoms, alkanoyl groups having from 2 to 5 carbon atoms, alkenyl groups having from 2 to 4 carbon atoms, alkynyl groups having from 2 to 4 carbon atoms, alkylthio groups having from 1 to 4 carbon atoms, nitro groups, amino groups, mono- or di-alkylamino groups having from 1 to 4 carbon atoms, aminosulfonyl groups, alkoxycarbonyl groups having from 1 to 4 carbon atoms, alkylsulfonylamino groups having from 1 to 4 carbon atoms, cycloalkyl groups having from 3 to 7 carbon atoms and a mono- or di-alkylaminocarbonyl groups having from 1 to 6 carbon atoms; or a pharmaceutically acceptable ester of such compound; or a pharmaceutically acceptable salt thereof. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 2.-3. (canceled) )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 4. A compound according to claim 1, wherein Y represents NR4 or an oxygen atom; and R4 represents an alkyl group having from 1 to 3 carbon atoms. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 5. A compound according to claim 1, wherein Y represents an oxygen atom. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 6. A compound according to claim 1, wherein Z represents a halogen atom. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 7. A compound according to claim 1, wherein R1 represents an alkyl group having from 1 to 6 carbon atoms; a cycloalkyl group having from 3 to 7 carbon atoms, or a phenyl group optionally substituted with one or more substituents a; or a group Het1 optionally substituted with one or more substituents Het1 represents a heterocyclic group having from 5 to 6 ring atoms which contains either from 1 to 2 ring nitrogen heteroatoms or from 0 to 2 nitrogen ring heteroatoms and 1 oxygen or 1 sulfur ring heteroatom; said substituents α are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, hydroxy groups, alkoxy groups having from 1 to 4 carbon atoms, haloalkoxy groups having from 1 to 4 carbon atoms, cyano groups, hydroxy alkyl groups having from 1 to 4 carbon atoms, alkoxyalkyl groups having from 1 to 4 carbon atoms in alkoxy and alkyl groups, alkylsulfonyl groups having from 1 to 4 carbon atoms and alkanoyl groups having from 2 to 5 carbon atoms. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 8. A compound according to claim 1, wherein R1 represents an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 4 to 6 carbon atoms, or a phenyl group, a pyridyl group, an oxazolyl group, a pyrazolyl group, a thiazolyl group, a tetrahydrofuranyl group or a tetrahydropyranyl group; said phenyl group, pyridyl group, oxazolyl group, pyrazolyl group, thiazolyl group, tetrahydrofuranyl group and tetrahydropyranyl group referred to in the definitions of R1 are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents α; and said α substituents are selected from the group consisting of halogen atoms, alkyl groups having from 1 to 2 carbon atoms and cyano groups. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 9. A compound according to claim 1, wherein R1 represents a phenyl group, optionally substituted by 1 to 2 groups independently selected from a fluorine atom, a chlorine atom and a methyl group. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 10. A compound according to claim 1, wherein R2 and R3 independently represent a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 11. A compound according to claim 1, wherein R2 represents a hydrogen atom; and R3 represents a methyl group. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 12. A compound according to claim 1 selected from: 4-[(1S)-1-({5-Chloro-2-[(4-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(4-methylphenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(4-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,3-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3,4-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,4-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-{(1S)-1-[({5-Chloro-2-[(3-chlorophenoxy)methyl]pyridine-3-yl}carbonyl)amino]ethyl}benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2-chlorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3,5-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-{(1S)-1-[({5-chloro-2-[(4-chlorophenoxy)methyl]pyridine-3-yl}carbonyl)amino]ethyl}benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(3-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,6-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2-fluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; 4-[(1S)-1-({5-Chloro-2-[(2,5-difluorophenoxy)methyl]benzoyl}amino)ethyl]benzoic acid; and 4-{(1S)-1-[({2-[(4-chlorophenoxy)methyl]-5-fluoropyridin-3-yl}carbonyl)amino]ethyl}benzoic acid; or a pharmaceutically acceptable ester of such compound; or a pharmaceutically acceptable salt thereof. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 13. A pharmaceutical composition, which comprises a compound according to claim 1, or a pharmaceutically acceptable ester or such compound, or a pharmaceutically acceptable salt thereof, and a suitable pharmaceutically acceptable carrier. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 14. A pharmaceutical for the treatment of disease conditions mediated by prostaglandin, in a mammalian subject, which comprises a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, and a suitable pharmaceutically acceptable carrier. )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 15. (canceled) )
Array ( [Name] => Comment [Label] => Claim [Group] => Patent [Data] => 16. A combination of a compound of the formula (I), as defined in claim 1, and another pharmacologically active agent. )
Array ( [Name] => CodeClass [Label] => Current U.S. Class [Group] => Patent [Data] => 514/355 )
Array ( [Name] => CodeClass [Label] => Current International Class [Group] => Patent [Data] => 61; 07 )
Array ( [Name] => AN [Label] => Accession Number [Group] => ID [Data] => edspap.20090163558 )
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