EP1389185A2 - Derives d'amino-alcool - Google Patents

Derives d'amino-alcool

Info

Publication number
EP1389185A2
EP1389185A2 EP02728093A EP02728093A EP1389185A2 EP 1389185 A2 EP1389185 A2 EP 1389185A2 EP 02728093 A EP02728093 A EP 02728093A EP 02728093 A EP02728093 A EP 02728093A EP 1389185 A2 EP1389185 A2 EP 1389185A2
Authority
EP
European Patent Office
Prior art keywords
phenyl
ethyl
amino
sulfonyl
alkoxycarbonyl
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.)
Withdrawn
Application number
EP02728093A
Other languages
German (de)
English (en)
Inventor
Minoru Fujisawa Pharmaceutical Co. Ltd. SAKURAI
K. Fujisawa Pharmaceutical Co. Ltd. WASHIZUKA
H. Fujisawa Pharmaceutical Co. Ltd HAMASHIMA
Y. Fujisawa Pharmaceutical Co. Ltd TOMISHIMA
M. Fujisawa Pharmaceutical Co. Ltd. IMANISHI
H. Fujisawa Pharmaceutical Co. Ltd. KAYAKIRI
K. Fujisawa Pharmaceutical Co. Ltd. TANIGUCHI
F. Fujisawa Pharmaceutical Co. Ltd. TAKAMURA
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.)
Astellas Pharma Inc
Original Assignee
Fujisawa Pharmaceutical Co 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
Priority claimed from AUPR5232A external-priority patent/AUPR523201A0/en
Priority claimed from AUPR9780A external-priority patent/AUPR978001A0/en
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of EP1389185A2 publication Critical patent/EP1389185A2/fr
Withdrawn legal-status Critical Current

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    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • 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
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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    • 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
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • This invention relates to new aminoalcohol derivatives and salts thereof which are beta-3 3) adrenergic receptor agonists and useful as a medicament.
  • This invention relates to new aminoalcohol derivatives which are ⁇ adrenergic receptor agonists and salts thereof.
  • new aminoalcohol derivatives and salts thereof which have gut sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence, anti-pollakiuria activities, anti-diabetes and anti-obesity, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method of using the same therapeutically in the treatment and/or prevention of gastro-intestinal disorders caused by smooth muscle contractions in a human being or an animal.
  • One object of this invention is to provide new and useful aminoalcohol derivatives and salts thereof which have gut sympathomimetic, anti-ulcerous, lipolytic, anti-urinary incontinence, anti-pollakiuria activities, anti-diabetes and anti-obesity.
  • Another object of this invention is to provide processes for the preparation of said aminoalcohol derivatives and salts thereof.
  • a further object of this invention is to provide a pharmaceutical composition comprising, as an active ingredient, said aminoacohol derivatives and salts thereof.
  • Still further object of this invention is to provide a therapeutical method for the treatment and/or prevention of aforesaid diseases in a human being or an animal, using said aminoalcohol derivatives and salts thereof.
  • the object aminoalcohol derivatives of this invention are new and can be represented by compound of the following formula [I] :
  • ?- is phenyl, pyridyl, indolyl or carbazolyl, each of which may be substituted with one or two same or different substituent (s) selected from a group consisting of halogen; hydroxy; benzyloxy; nitro; cyano; mono (or di or tri) halo (lower) alkyl; and (lower alkylsulfonyl) amino
  • R ⁇ is hydrogen, [5- (lower alkyl) -2-oxo-l, 3-dioxol-4- yl] (lower) alkoxycarbony or an amino protective group
  • R ⁇ and R ⁇ are each independently hydrogen, lower alkyl or hydroxy (lower) alkyl,
  • R 5 is aryl, ar (lower) alkyl, a heterocyclic group or lower alkyl, each of which may be substituted with one, two or three same or different substituent (s) selected from a group consisting of halogen; hydroxy; cyano; amino (hydroxyimino)methyl; phenyl optionally substituted with carboxy or lower alkoxycarbonyl; phenoxy optionally substituted with halogen; lower alkoxy optionally substituted with hydroxy, amino, cyano, carboxy, carbamoyl, mono (or di) (lower) alkylcarbamoyl, lower alkoxycarbonyl, cyclo (lower) alkyloxycarbonyl, hydroxy (lower) alkoxycarbonyl, di [ (lower) alkoxy] (lower) alkoxycarbonyl, pyridyl (lower) alkoxycarbonyl, phenyl or tetrazolyl; mono (or di or tri) halo (low
  • R° and R 7 are each independently hydrogen, carboxy or lower alkoxycarbonyl, hydrogen or halogen, X is a single bond or -0-CH2-/ and n is 0, 1 or 2, or a salt thereof.
  • the object compounds can be prepared by processes which are illustrated in the following schemes.
  • R 1 , R 2 , R 3 , R 4 , , R 5 , R 8 , X and n are each as defined above, R is [5- (lower alkyl) -2-oxo-l, 3-dioxol-4- yl] (lower) alkoxycarbonyl or an amino protective group,
  • R ⁇ is lower alkyl optionally substituted with hydroxy, amino, cyano, carboxy, carbamoyl, mono (or di) (lower) alkylcarbamoyl, lower alkoxycarbonyl , cyclo (lower) alkyloxycarbonyl , hydroxy (lower) alkoxycarbonyl, di [ (lower) alkoxy] (lower) alkoxycarbonyl, pyridyl (lower) alkoxycarbonyl, phenyl or tetrazolyl, and Y is halogen.
  • lower is intended to mean a group having 1 to 6, preferably 1 to 4, carbon atom(s) , unless otherwise indicated.
  • Suitable "lower alkyl” and “lower alkyl” moiety in the terms of "(lower alkylsulfonyl) amino", “di (lower) alkyl- carbamoyl”, etc. may include straight or branched one having 1 to 6 carbon atom(s) , such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylpentyl, tert-pentyl, neo-pentyl, hexyl, isohexyl and the like, in which more preferable one is C ⁇ -C ⁇ alkyl, and the most preferable one is methyl.
  • Suitable "lower alkenyl” may include vinyl, l-(or 2-)- propenyl, l-(or 2- or 3-)butenyl, l-(or 2- or 3- or 4-)- pentenyl, l-(or 2- or 3- or 4- or 5-)hexenyl, methyl inyl, ethylvinyl, l-(or 2- or 3-)methyl-l- (or 2-) propenyl, l-(or 2- or 3-) ethyl-1- (or 2-) propenyl, l-(or 2- or 3- or 4-)methyl-l- (or 2- or 3-)butenyl and the like, in which more preferable one may be C 2 -C4 alkenyl.
  • Suitable "cyclo (lower) alkyl” moiety in the term of "cyclo (lower) alkyloxycarbonyl” may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, in which more preferable one is cyclo (C3 ⁇ Cg) alkyl, and the most preferable one is cyclohexyl.
  • Suitable "lower alkoxy” and “lower alkoxy” moiety in the terms of “mono (or di or tri) (lower) alkoxy” and “lower alkoxycarbonyl” may include methoxy, ethoxy, propoxy, isopropoxy, butoxy, iso-butoxy, t-butoxy, pentyloxy, t- pentyloxy, hexyloxy and the like, in which preferable one is C ] _-C 4 alkoxy, and the most preferable one is methoxy or ethoxy.
  • Suitable “lower alkanoyl” may include for yl, acetyl, propanoyl, butanoyl, 2-methylpropanoyl, pentanoyl, 2,2- dimethylpropanoyl, hexanoyl and the like, in which preferable one is C2-C4 alkanoyl, and the most preferable one is formyl.
  • Suitable "halogen” may be fluoro, chloro, bromo and iodo, in which preferable one is chloro.
  • aromatic (lower) alkyl may include phenyl, naphthyl, anthryl and the like, in which the preferred one may be phenyl.
  • heterocyclic group may include unsaturated 3 to 8-membered (more preferably 5 or 6- membered) heteromonocyclic group containing 1 to 4 nitrogen atom(s), for example, pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, dihydropyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazolyl (e.g., 1H-1, 2, -triazolyl, 4H-1,2,4- triazolyl, 1H-1, 2, 3-triazolyl or 2H-1, 2, 3-triazolyl) , tetrazolyl (e.g.
  • Suitable "mono (or di or tri) halo (lower) alkoxy” may include chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, dibromomethoxy, tribromomethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 or 2-chloroethoxy, 1 or 2-bromoethoxy, 1 or 2-fluoroethoxy, 1, 1-difluoroethoxy, 2,2- difluoroethoxy and the like, in which more preferable one is mono (or di or tri) halo (C- j _-C 4 ) alkoxy, and the most preferable one is difluoromethoxy.
  • amino protective group may be common amino protective group such as substituted or unsubstituted lower alkanoyl [e.g. formyl, acetyl, propionyl, trifluoroacetyl, etc.], phthaloyl, lower alkoxycarbonyl [e.g. tert-butoxycarbonyl, tert-amyloxycarbonyl, etc.], substituted or unsubstituted aralkyloxycarbonyl [e.g. benzyloxycarbonyl, p-nitrobenzyloxycarbonyl, etc.], substituted or unsubstituted arenesulfonyl [e.g.
  • benzenesulfonyl, tosyl, etc.] nitrophenylsulfenyl, ar (lower) alkyl [e.g. trityl, benzyl, etc.], and the like, in which preferable one is benzyl.
  • Suitable salts of the object aminoalcohol derivative [I] are pharmaceutically acceptable salts and include conventional non-toxic salts such as an inorganic acid addition salt [e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.], an organic acid addition salt [e.g. formate, acetate, trifluoroacetate, oxalate, maleate, fumarate, tartrate, citrate, methanesulfonate, benzenesulfonate, toluenesulfonate, etc., an alkali metal salt [e.g. sodium salt, potassium salt, etc.] or the like.
  • an inorganic acid addition salt e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.
  • an organic acid addition salt e.g. formate, acetate, trifluoroacetate, oxalate, maleate, fumarate, tartrate, citrate, methanesulfon
  • the object compound [I] or a salt thereof can be prepared by reacting a compound [II] or a salt thereof with a compound [III] or a salt thereof.
  • Suitable salt of the compounds [II] and [III] may be the same as those exemplified for the compound [I] .
  • the reaction is preferably carried out in the presence of a base such as an alkali metal carbonate [e.g. sodium carbonate, potassium carbonate, etc.], an alkaline earth metal carbonate [e.g. magnesium carbonate, calcium carbonate, etc.], an alkali metal bicarbonate [e.g. sodium bicarbonate, potassium bicarbonate, etc.], tri (lower) alkylamine [e.g. trimethylamine, triethylamine, etc.], picoline or the like.
  • the reaction is usually carried out in a conventional solvent, such as an alcohol [e.g. methanol, ethanol, propanol, isopropanol, etc.], diethyl ether, tetrahydrofuran, dioxane, or any other organic solvent which does not adversely influence the reaction.
  • the reaction temperature is not critical, and the reaction can be carried out under cooling to heating.
  • the object compound [lb] or a salt thereof can be prepared by subjecting a compound [la] or a salt thereof to elimination reaction of the amino protective group.
  • Suitable salts of the compounds [la] and [lb] may be the same as those exemplified for the compound [I] .
  • the object compound [Id] or a salt thereof can be prepared by reacting a compound [Ic] or a salt thereof with a compound [IV] or a salt thereof.
  • Suitable salts of the compounds [Ic] and [IV] may be the same as those exemplified for the compound [I] . This reaction can be carried out in a similar manner to that of Example 19 or 21.
  • the compounds obtained by the above processes can be isolated and purified by a conventional method such as pulverization, recrystallization, column chromatography, reprecipitation, or the like, and converted to the desired salt in conventional manners, if necessary.
  • the compound [I] and the other compounds may include one or more stereoisomers due to asymmetric carbon atoms, and all of such isomers and mixture thereof are included within the scope of this invention.
  • isomerization or rearrangement of the object compound [I] may occur due to the effect of the light, acid base or the like, and the compound obtained as the result of said isomerization or rearrangement if also included within the scope of the present invention.
  • the object compound [I] or a salt thereof • possesses gut sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence and anti-pollakiuria activities, and are useful for the treatment and/or prevention of gastro-intestinal disorders caused by smooth muscle contractions in human beings or animals, and more parcitularly for the treatment and/or prevention of spasm or hyperanakinesia in case of irritable bowel syndrome, gastritis, gastric ulcer, duodenal ulcer, enteritis, cholecystopathy, cholantitis, urinary calculus and the like; for the treatment and/or prevention of ulcer such as gastric ulcer, duodenal ulcer, peptic ulcer, ulcer causes by non steroidal anti-inflammatory drags, or the like; for the treatment and/or prevention of dysuria such as pollakiuria, urinary incontinence or the like in case of nervous pollakiuria, neurogenic bladder dysfunction, nocturia, unstable bladder
  • ⁇ 3 adrenergic receptor agonists are known to lower triglyceride and cholesterol levels and to raise high density lipoprotein levels in mammals (US Patent No. 5,451,677). Accordingly, the object compound [I] in useful in the treatment and/or prevention of conditions such as hyper-triglyceridaemia, hypercholesterolaemia and in lowering high density lipoprotein levels as well as in the treatment of atherosclerotic and cardiovascular diseases and relates conditions.
  • the object compound [I] is useful for inhibiting uterine contractions, preventing premature labor, and treating and preventing dysmenorrhea.
  • Preferred embodiments of the object compound [I] are as follows :
  • R-- is phenyl, pyridyl, indolyl or carbazolyl, each of which may be substituted with one or two same or different substituent (s) selected from a group consisting of halogen (more preferably fluoro or chloro) ; hydroxy; benzyloxy; nitro; cyano; mono (or di or tri) halo (lower) alkyl (more preferably mono (or di or tri) halo (C- ] _-C 4 ) alkyl, most preferably trifluoromethyl) and (lower alkylsulfonyl) amino (more preferably (C ⁇ -C ⁇ alkylsulfonyl) amino, most preferably (methanesulfonyl) mino) , R2 is hydrogen, [5- (lower alkyl) -2-oxo-l, 3-dioxol-4- yl] (lower) alkoxycarbonyl (more preferably [5- (C
  • More preferred embodiments of the object compound [I] are as follows:
  • R-*- is phenyl which may be substituted with one or two same or different substituent (s) selected from a group consisting of halogen (more preferably fluoro or chloro) ; hydroxy; benzyloxy; nitro and (lower alkylsulfonyl) amino (more preferably (C ] _-C 4 alkylsulfonyl) amino, most preferably (methanesulfonyl) amino)
  • R 2 is hydrogen or [5- (lower alkyl) -2-oxo-l, 3-dioxol-4- yl] (lower) alkoxycarbonyl (more preferably [5-(C ] _-C alkyl) -2-oxo-l, 3-dioxol-4-yl] (C- ] _-C ) alkoxycarbonyl, most preferably (5-methyl-2-oxo-l, 3-dioxol-4- yl)methoxy
  • R ⁇ is phenyl, benzyl, triazolyl (more preferably 1H-1,2,4- triazolyl), tetrazolyl (more preferably 1H-1, 2,3,4- tetrazolyl), quinolyl, thiazolyl, thienyl or lower alkyl (more preferably C ] _-C 4 alkyl, most preferably propyl) , each of which may be substituted with one, two or three same or different substituent (s) selected from a group consisting of halogen (more preferably fluoro or chloro); hydroxy; cyano; amino (hydroxyimino) methyl; phenyl optionally substituted with carboxy or lower alkoxycarbonyl (more preferably C- ] _-C 4 alkoxycarbonyl, most preferably ethoxycarbonyl); phenoxy optionally substituted with halogen (more preferably fluoro) ; lower alkoxy (more preferably C_-C 4 alkoxy,
  • More preferred embodiments of the object compound [I] are as follows:
  • R1 is phenyl which may be substituted with halogen
  • R 2 is hydrogen
  • R 5 is phenyl which may be substituted with one, two or three same or different substituent (s) selected from a group consisting of halogen; hydroxy; cyano; amino (hydroxyimino) methyl; phenyl optionally substituted with carboxy or lower alkoxycarbonyl; phenoxy optionally substituted with halogen; lower alkoxy optionally substituted with hydroxy, amino, cyano, carboxy, carbamoyl, mono (or di) (lower) alkoxycarbamoyl, lower alkoxycarbonyl, cyclo (lower) alkyloxycarbonyl, hydroxy (lower) alkoxycarbonyl, di [ (lower) alkoxy] (lower) alkoxycarbonyl, pyridyl (lower) alkoxycarbonyl, phenyl or tetrazolyl; mono (or di or tri) halo (lower) alkoxy; lower alkyl optionally substituted with carboxy, lower alkoxy
  • More preferred embodiments of the object compound [I] are as follows:
  • R-"- is phenyl which may be substituted with halogen
  • R 2 is hydrogen
  • R and R 4 are each hydrogen
  • R 5 is phenyl substituted with lower alkoxy optionally substituted with a substituent selected from a group consisting of hydroxy, amino, cyano, carboxy, carbamoyl, mono (or di) (lower) alkoxycarbamoyl, lower alkoxycarbonyl, cyclo (lower) alkyloxycarbonyl, hydroxy (lower) alkoxycarbonyl, di [ (lower) alkoxy] (lower) alkoxycarbonyl, pyridyl (lower) alkoxycarbonyl, phenyl and tetrazolyl, R° is hydrogen,
  • X is a single bond, and n is 1.
  • the precipitate was removed by filtration, and the filter cake was washed with a mixture of ethyl acetate and ethanol (95:5).
  • the filtrate was evaporated under reduced pressure.
  • the residue was dissolved in ethyl acetate (40 ml) and cooled to 5°C.
  • To this one was added 4N hydrogen chloride in 1,4-dioxane (8.4 ml) and the mixture was stirred at room temperature for 30 minutes to deposit the corresponding salt followed by collection by filtration.
  • the filter cake was washed with ethyl acetate and dissolved in a mixture of ethyl acetate and IN sodium hydroxide.
  • Example 7 The following compounds were obtained according to a similar manner to that of Example 6.
  • Example 8 A mixture of (2S) -2- [N-benzyl-N- ( (2S) -2-hydroxy-3- phenoxypropyl) amino] -3- [4- (phenylsulfonyl) phenyl] -1-propanol (96 mg) and 10% palladium on activated carbon (50% wet, 30 ' mg) in methanol (5 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 7.5 hours.
  • Example 11 The following compounds were obtained according to a ' similar manner to that of Example 10.
  • Example 16 A mixture of (S) -1- [N-benzyl-N- [2- [4- [ (4- methoxyphenyl) sulfonyl] phenyl] ethyl] amino] -3- (lH-indol-4- yloxy) -2-propanol (140 mg) and 10% palladium on activated carbon (50% wet, 70 mg) in methanol (3 ml) and chlorobenzene (3 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 1 hour.
  • Example 30 The following compound was obtained according to a similar manner to that of Example 29.
  • Example 36 A mixture of (R) -4- [ [4- [2- [N-benzyl-N- [2- (3- chlorophenyl) -2-hydroxyethyl] amino] ethyl]phenyl] sulfonyl] - phenol (1.31 g) , triethylamine (3.3 ml) and 10% pallasium on activated carbon (50% wet, 0.65 g) in a mixture of methanol (13 ml) and chlorobenzene (13 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 5 hours. After filtration, the filtrate was evaporated under reduced pressure.
  • the resulting mixture was poured into saturated aqueous sodium hydrogen carbonate and the aqueous mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure.
  • Example 39 At room temperature, to a solution of isopropyl (R)-[4- [ [4- [2- [N- (tert-butoxycarbonyl) -N- [2- (3-chlorophenyl) -2- hydroxyethyl] amino] ethyl] phenyl] sulfonyl] phenoxy] acetate (103 mg) in ethyl acetate (1 ml) was added 4N hydrogen chloride in 1,4-dioxane (1 ml), and the mixture was stirred at the same temperature for 1.5 hours to give a precipitate.
  • Example 42 Under nitrogen at room temperature, to a solution of tert-butyl (R) -N- [2- [3-chlorophenyl] -2-hydroxyethyl] -N- [2- [4- [ (4-hydroxyphenyl) sulfonyl] phenyl] ethyl] carbamate (900 mg) in N,N-dimethylformamide (10 ml) was added powdered potassium carbonate (257 mg) and ethyl bromoacetate (0.21 ml), and the mixture was stirred at 60°C for 1.5 hours. The resulting mixture was poured into water and the aqueous mixture was extracted with ethyl acetate.
  • Example 47 The following compound was obtained according to a similar manner to that of Example 44.
  • Example 50 At room temperature, to a solution of tert-butyl (R)-N- [2- (3-chlorophenyl) -2-hydroxyethyl] -N- [2- [4- [ [4- (2- hydroxyethoxy) phenyl] sulfonyl] phenyl] ethyl] carbamate (67 mg) in ethyl acetate (1 ml) was added 4N hydrogen chloride in 1,4-dioxane (1 ml), and the mixture was stirred at the same temperature for 1.5 hours. The resulting mixture was poured into saturated aqueous sodium hydrogen carbonate and the aqueous mixture was extracted with ethyl acetate.
  • Example 65 The following compound was obtained according to a similar manner to that of Example 57.
  • Example 68 Ethyl [2-chloro-4-[ [4- [2- [[ (2R) -2- (3-chlorophenyl) -2- hydroxyethyl) amino] ethyl] phenyl] sulfonyl] phenoxy] acetate (64.0 mg) was suspended in 4N hydrogen chloride in ethanol (500 ⁇ l) and the mixture was stirred at room temperature for 1 hour.
  • Example 70 To a suspension of 4- [ [4- (2-aminoethyl) phenyl] - sulfonyl] -2-chlorophenol (579 mg) in dimethyl sulfoxide (2.9 ml) was added (2R) -2- (3-chlorohenyl) oxirane (287 mg) and the mixture was stirred at 80 °C for 48 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (30 ml) and washed with water (30 ml x 1) . The aqueous layer was extracted with ethyl acetate (15 ml x 2) .
  • Example 71 The following compounds were obtained according to a similar manner to that of Example 67.
  • Example 77 The following compounds were obtained according to a similar manner to that of Example 76.

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Abstract

La presente invention concerne une formule (I) de composé où R1 représente phényle, pyridyle, etc., qui peuvent chacun être substitués par un ou deux substituant(s); R2 est de l' hydrogène, un groupe aminé protecteur, etc.; R3 et R4 sont chacun indépendamment hydrogène, un alkyle inférieur ou hydroxyalkyl (inférieur); R5 représente aryle, aralkyl(inférieur), etc., qui peuvent chacun être substitués par un, deux ou trois substituant(s); R8 représente hydrogène ou halogène, X est une liaison simple ou O-CH¿2?-, et n représente 0, 1 ou 2, ou un sel de ces derniers. Le composé [I] selon la présente invention et des sels pharmaceutiquement acceptables de ces derniers présentent une grande utilité pour le traitement prophylatique et/ou thérapeutique de la pollakiurie ou de l'incontinence urinaire.
EP02728093A 2001-05-24 2002-05-20 Derives d'amino-alcool Withdrawn EP1389185A2 (fr)

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AUPR523201 2001-05-24
AUPR5232A AUPR523201A0 (en) 2001-05-24 2001-05-24 Aminoalcohol derivatives
AUPR978001 2001-12-28
AUPR9780A AUPR978001A0 (en) 2001-12-28 2001-12-28 Aminoalcohol derivatives
AUPR079902 2002-02-28
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MXPA05003080A (es) 2002-09-19 2005-06-15 Kyorin Seiyaku Kk Derivado de amino alcohol, sales de los mismos y agentes inmunosupresores.
AU2002952839A0 (en) * 2002-11-21 2002-12-05 Fujisawa Pharmaceutical Co., Ltd. Aminoalcohol derivatives
KR20050100681A (ko) * 2003-02-14 2005-10-19 깃세이 야쿠힌 고교 가부시키가이샤 아미노알코올 유도체, 그것을 함유하는 의약조성물 및그들의 용도
CN100418944C (zh) * 2003-02-14 2008-09-17 橘生药品工业株式会社 氨基醇衍生物、含有所述氨基醇衍生物的药物组合物及其应用
SA04250253B1 (ar) 2003-08-21 2009-11-10 استرازينيكا ايه بي احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن
US7417169B2 (en) 2003-10-24 2008-08-26 Kissei Pharmaceutical Co., Ltd. Amino alcohol derivatives, medicinal composition containing the same, and use of these
WO2005110981A1 (fr) * 2004-05-17 2005-11-24 Astellas Pharma Inc. Dérivés d'aminoalcools
AU2005285812B2 (en) * 2004-09-21 2011-02-24 Astellas Pharma Inc. Aminoalcohol derivatives
DE602005018503D1 (de) * 2004-09-21 2010-02-04 Astellas Pharma Inc Aminoalkoholderivate
WO2006041015A1 (fr) * 2004-10-12 2006-04-20 Kyorin Pharmaceutical Co., Ltd. Dérivé d’aminoalcool, sel d’addition dudit dérivé, et agent immunosuppresseur
TW200740779A (en) 2005-07-22 2007-11-01 Mitsubishi Pharma Corp Intermediate compound for synthesizing pharmaceutical agent and production method thereof
EP1945612A2 (fr) 2005-10-13 2008-07-23 Orchid Research Laboratories Limited Nouveaux composes heterocycliques en tant qu'inhibiteurs de pstat3/il6
TW200732313A (en) * 2005-12-15 2007-09-01 Astrazeneca Ab Oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators

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EP0089154A3 (fr) * 1982-03-12 1984-08-08 Beecham Group Plc Dérivés d'éthanolamine, leur fabrication et leur utilisation en compositions pharmaceutiques
EP0091749A3 (fr) * 1982-04-08 1984-12-05 Beecham Group Plc Dérivés de l'éthanolamine, procédé pour leur préparation et compositions pharmaceutiques les contenant
US5541204A (en) * 1994-12-02 1996-07-30 Bristol-Myers Squibb Company Aryloxypropanolamine β 3 adrenergic agonists
US6451814B1 (en) * 2000-07-17 2002-09-17 Wyeth Heterocyclic β-3 adrenergic receptor agonists

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