WO2001036375A1 - Aminoalcohol derivatives useful for the treatment of gastrointestinal disorders - Google Patents
Aminoalcohol derivatives useful for the treatment of gastrointestinal disorders Download PDFInfo
- Publication number
- WO2001036375A1 WO2001036375A1 PCT/JP2000/008007 JP0008007W WO0136375A1 WO 2001036375 A1 WO2001036375 A1 WO 2001036375A1 JP 0008007 W JP0008007 W JP 0008007W WO 0136375 A1 WO0136375 A1 WO 0136375A1
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- amino
- alkyl
- phenyl
- alkylsulfonylamino
- hydroxy
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- 0 CC=C([C@@](*)(C*)c1ccccc1)C=CC=C Chemical compound CC=C([C@@](*)(C*)c1ccccc1)C=CC=C 0.000 description 3
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- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
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- A61P13/00—Drugs for disorders of the urinary system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/70—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
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- C07C233/34—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 amino groups
- C07C233/42—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 amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—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 amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C07C307/04—Diamides of sulfuric acids
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/135—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Definitions
- This invention relates to new aminoalcohol derivatives and salts thereof which are ⁇ 3 adrenergic receptor agonists and useful as a medicament.
- This invention relates to new aminoalcohol derivatives which are ⁇ 3 adrenergic receptor agonists and salts thereof.
- new aminoalcohol derivatives and salts thereof which have gut selective sympathomimetic, anti-ulcerous, anti- pancreatitis, lipolytic, anti-urinary incontinence and anti-pollakiuria activities, 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 human beings or animals.
- A is phenyl, pyridyl, indolyl, benzimidazolyl or 2,3-dihydro-2- oxobenzimidazolyl, each of which may have 1 to 3 same or different substituent(s) selected from the group consisting of hydroxy, lower alkylcarbonyloxy, lower alkoxycarbonyloxy, amino, halogen atom, lower alkylsulfonylamino, carboxy(lower)alkylsulfonylamino, N-lower alkyl-N- (lower) alkylsulfonylamino, mono(or di or tri) halo (lower) alkylsulfonylamino , phenyl(lower)alkylsulfonylamino, thienylsulfonylamino, phenyl(lower)alkoxy, lower alkyl, hydroxy (lower) alkyl, amino(lower)alkyl,
- R 2 is hydrogen atom, lower alkyl, hydroxy (lower) alkyl or carboxy (lower) alkyl
- R 3 is hydrogen atom or hydroxy
- R 4 , R 5 , R 6 and R 7 are each independently hydrogen atom, hydroxy, lower alkyl, lower alkoxy, amino, lower alkylsulfonylamino, lower alkoxycarbonylamino, carboxy(lower)alkylamino, lower alkoxycarbonyl(lower)alk lamino, formylamino, lower alkylcarbonylamino, ureido, halogen atom, phenyl(lower)alkoxy, lower alkoxycarbonyloxy, lower alkylcarbonyloxy, lower alkoxycarbonyl(lower) alkoxy, carboxy (lower) alkoxy, carbamoyl, lower alkylcarbamoyl, lower alkylsulfonylcarbamoyl, morpholinyl, isothiazolidinyl wherein isothiazolidinyl may be substituted by 1 or 2 oxo(s), pyrrolidinyl or imidazo
- R : a is amino-protective group
- R 8 is lower alkyl
- Y is halogen atom
- R 4 a is R 4 or R 6
- R 5 a is R 5 or R 7 , wherein R 4 , R 5 , R 6 , and R 7 are each as defined above.
- lower is intended to mean a group having 1 to 6 carbon atom(s), unless otherwise provided.
- lower alkyl and “lower alkyl” moiety may include a 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.
- Suitable "lower alkoxy” and “lower alkoxy” moiety may be a straight or branched one such as methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, neopentyloxy, tert- pentyloxy, hexyloxy, and the like, in which the preferred one may be C_-C4 alkoxy, and the more preferred one may be methoxy, ethoxy and butoxy, and the most preferred one may be methoxy.
- halogen may be fluoro, chloro, bromo and iodo, and the preferred one may be fluoro and chloro.
- Suitable example of "aryl”, “aryl” moiety, “arene” and “aryl” moiety in aralkyl may include phenyl, naphthyl, anthryl, and the like, in which the preferred one may be phenyl.
- amino-protective group may be common amino-protective group such as aryl(lower) alkyl [e.g. trityl, benzyl, etc.] or acyl, for example, 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.
- aryl(lower) alkyl e.g. trityl, benzyl, etc.
- acyl for example, substituted or unsubstituted lower alkanoyl [e.g. formyl, acetyl, propionyl, trifluoroacetyl, etc.], phthaloy
- benzyloxycarbonyl p-nitrobenzyloxycarbonyl, etc.
- substituted or unsubstituted arenesulfonyl e.g. benzenesulfonyl, tosyl, etc.
- nitrophenylsulfenyl and the like, in which preferable one is phenyl(lower)alkyl such as benzyl.
- Suitable example of "lower alkylsulfonylamino" and “ lower alkylsulfonylamino” moiety may include methylsulfonylamino, ethylsulfonyl- amino, propylsulfonylamino, butylsulfonylamino, pentylsulfonylamino, hexylsulfonylamino, and the like, in which the preferred one may be (C_- C4)alkylsulfonylamino, and the more preferred one may be methylsulfonylamino, ethylsulfonylamino and butylsulfonylamino, and the most preferred one may be methylsulfonylamino.
- ⁇ carboxy(lower)alkylsulfonylamino may be carboxymethylsulfonylamino, carboxyethylsulfonylamino, carboxypropyl- sulfonylamino, carboxybutylsulfonylamino, carboxypentylsulfonylamino, carboxyhexylsulfonylamino, and the like, in which the preferred one may be carboxyJCi-C ⁇ Jalkylsulfonylamino, and the most preferred one may be carboxymethylsulfonylamino .
- N-lower alkyl-N-(lower)alkylsulfonylamino is the above-mentioned lower alkylsulfonylamino wherein amino is substituted by the above-mentioned lower alkyl.
- the lower alkyl moiety of "N-lower alkyl-N-(lower)alkylsulfonylamino" may be those as described above, and the suitable example of "N-lower alkyl-N-
- (lower) alkylsulfonylamino may be N-methyl-N-methylsulfonylamino, N-methyl- N-ethylsulfonylamino, N-methyl-N-propylsulfonylamino, N-methyl-N- butylsulfonylamino, N-methyl-N-pentylsulfonylamino, N-methyl-N- hexylsulfonylamino, N-ethyl-N-methylsulfonylamino, N-propyl-N- methylsulfonylamino, N-butyl-N-methylsulfonylamino, N-pentyl-N- methylsulfonylamino, N-hexyl-N-methylsulfonylamino, N-ethyl-N- ethylsulfonylamino, N-ethyl-N-
- “Lower alkylsulfonylamino wherein amino is protected by amino- protective group” is the above-mentioned lower alkylsulfonylamino wherein amino is protected by the above-mentioned amino-protective group.
- the suitable amino-protecting group may be substituted or unsubstituted aralkyloxycarbonyl, in which the preferred one may be benzyloxycarbonyl.
- lower alkylsulfonylamino wherein amino is protected by amino-protective group may be N-benzyloxycarbonyl-N-memylsulfonylamino, N- benzyloxycarbonyl-N-ethylsulfonylamino, N-benzyloxycarbonyl-N- propylsulfonylamino, N-benzyloxycarbonyl-N-butylsulfonylamino, N- benzyloxycarbonyl-N-pentylsulfonylamino, N-benzyloxycarbonyl-N- hexylsulfonylamino, and the like, in which the preferred one may be N- benzyloxycarbonyl-N-(C_-C4)alkylsulfonylamino, and the most preferred one may be N-benzyloxycarbonyl-N-methylsulfonylamino.
- “Mono(or di or tri)halo(lower)a_kyl” moiety is the above-mentioned lower alkyl which is mono(or di or tri)-substituted by halogen atom(s).
- the suitable example may be lower alkyl which is mono(or di or tri)-substituted by fluorine atom(s), in which the preferred one may be alkyl which is mono(or di or tri) -substituted by fluorine atom(s), such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,2-difluoroethyl, 2,2,2-trifluoroethyl, and the like, and the most preferred one may be trifluoromethyl.
- Suitable example of "mono(or di or tri)halo(lower)alkylsulfonylamino” may be mono(or di or tri)fluoromethylsulfonylamino, mono(or di or tri)fluoroethyl- sulfonylamino, mono(or di or trijfluoropropylsulfonylamino, mono(or di or trijfluorobutylsulfonylamino, mono(or di or tri)fluoropentylsulfonylamino, mono(or di or tri)fluorohexylsulfonylamino, and the like, in which the preferred one may be mono(or di or tri)fluoro(C ⁇ -C4)alkylsulfonylamino, and the more preferred one may be triiluoromethylsulfonylamino and 2,2,2- trifluoroethylsulfonylamino, and the most preferred one may
- the lower alkylsulfonylamino moiety of "phenyl(lower)al_kylsulfonylamino” may be those as described above, and the suitable example of “phenyl(lower)- alkylsulfonylamino” may be benzylsulfonylamino, phenethylsulfonylamino, phenylpropylsulfonylamino, phenylbutylsulfonylamino, phenylpentylsulfonyl- amino, phenylhexylsulfonylamino, and the like, in which the preferred one may be phenyl(C ⁇ -C4)alkylsulfonylamino, and the most preferred one may be benzylsulfonylamino .
- Thienylsulfonylamino includes 2-thienylsulfonylamino and 3- thienylsulfonylamino.
- the lower alkyl moieties of "[N,N-di(lower)alkylsulfamoyl] amino may be the same or different and the suitable example of lower alkyl moiety may be those as described above.
- the suitable example of "[N,N-di(lower)alkylsulfamoyl]amino" may be (N,N-dimethylsulfamoyl)amino, (N,N-diethylsulfamoyl)amino, (N,N- dipropylsulfamoyl)amino, (N,N-dibutylsulfamoyl)amino, (N,N-dipentylsulfamoyl)- amino, (N,N-dihexylsulfamoyl)amino, and the like.
- [N,N-di(lower)alkylsulfamoyl]amino may be [N,N-di(C 1 -C4)all ⁇ lsulfamoyl]amino, and the most preferred one may be (N,N-dimethylsulfamoyl)amino.
- Phenyl(lower)alkoxy is the above-mentioned lower alkoxy substituted by phenyl, such as benzyloxy, phenethyloxy, phenylpropoxy, phenylbutoxy, phenylpentyloxy, phenylhexyloxy, and the like, in which the preferred one maybe phenylfC.-C ⁇ Jalkoxy, and the most preferred one may be benzyloxy.
- Carboxy(lower)alkoxy is the above-mentioned lower alkoxy substituted by carboxy, such as carboxymethoxy, carboxyethoxy, carboxypropoxy, carboxybutoxy, carboxypentyloxy, carboxyhexyloxy, and the like, in which the preferred one may be carboxy(C ⁇ -C4)alkoxy, and the most preferred one may be carboxymethoxy.
- lower alkoxycarbonyl and “lower alkoxycarbonyl” moiety may be methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, and the like, in which the preferred one may be (C_-C4)alkoxycarbonyl, and the more preferred one may be methoxycarbonyl, ethoxycarbonyl and butoxycarbonyl.
- “Lower alkoxycarbonyl(lower) alkoxy” is the above-mentioned (lower)alkoxy substituted by the above-mentioned lower alkoxycarbonyl, such as, methoxycarbonylmethoxy, methoxycarbonylethoxy, methoxycarbonylpropoxy, methoxycarbonylbutoxy, methoxycarbonylpentyloxy, methoxycarbonylhexyloxy, ethoxycarbonylmethoxy, propoxycarbonylmethoxy, butoxycarbonylmethoxy, pentyloxycarbonylmethoxy, hexyloxycarbonylmethoxy, ethoxycarbonylethoxy, ethoxycarbonylpropoxy, and the like, in which the preferred one may be (d- C4)alkoxycarbonyl(C 1 -C4)alkoxy, and the most preferred one may be ethoxycarbonylmethoxy.
- “Lower alkoxycarbonylamino” is amino substituted by the above- mentioned lower alkoxycarbonyl, such as, methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, butoxycarbonylamino, pentyloxycarbonylamino, hexyloxycarbonylamino, and the like, in which the preferred one may be and the more preferred one may be methoxycarbonylamino, ethoxycarbonylamino and
- the lower alkoxycarbonylamino moiety of "lower alkoxycarbonylamino- sulfonylamino" may be those as described above, and the suitable example of "lower alkoxycarbonylaminosulfonylamino" may be methoxycarbonylamino- sulfonylamino, ethoxycarbonylaminosulfonylamino, propoxycarbonylamino- sulfonylamino, butoxy
- lower alkoxycarbonyl moiety and lower alkyl moiety of "lower alkoxycarbonyl(lower)alkylamino” may be those as described above respectively, and the suitable example of “lower alkoxycarbonyl(lower)alkylamino” may be methoxycarbonylmethylamino, ethoxycarbonylmethylamino, propoxycarbonyl- methylamino, butoxycarbonylmethylamino, pentyloxycarbonylmethylamino, hexyloxycarbonylmethylamino, methoxycarbonylethylamino, methoxycarbonyl- propylamino, methoxycarbonylbutylamino, methoxycarbonylpentylamino, methoxycarbonylhexylamino, ethoxycarbonylethylamino, propoxycarbonyl- ethylamino, butoxycarbonylethylamino, and the like, in which the preferred one may be
- the lower alkyl moiety of "hydroxy (lower) alkyl” may be the above- mentioned lower alkyl and the suitable example of “hydroxy (lower) alkyl” may be hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, and the like, in which the preferred one may be hydroxy(C ⁇ - C4)alkyl, and the more preferred one may be hydroxymethyl and hydroxyethyl.
- Carboxy(lower)alkyl is the above-mentioned lower alkyl substituted by carboxy, and the suitable example may be carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl, carboxypentyl, carboxyhexyl, and the like, in which the preferred one may be carboxy(C ⁇ -C4)alkyl, and the most preferred one maybe carboxymethyl.
- Carboxy (lower) alkylamino is amino substituted by the above-mentioned carboxy(lower)alkyl, and the suitable example may be carboxymethylamino, carboxyethylamino, carboxypropylamino, carboxybutylamino, carboxypentyl- amino, carboxyhexylamino, and the like, in which the preferred one may be carboxy(Ci-C4)alkylamino, and the most preferred one may be carboxymethylamino .
- amino(lower)alkyF may be aminomethyl, aminoethyl, aminopropyl, aminobutyl, aminopentyl, aminohexyl, and the like, in which the preferred one may be amino(C 1 -C4)alkyl, and the most preferred one may be aminomethyl.
- “Lower alkylsulfonylamino (lower) alkyl” is the above-mentioned lower alkyl substituted by the above-mentioned lower alkylsulfonylamino, and the suitable example may be methylsulfonylaminomethyl, ethylsulfonylaminomethyl, propylsulfonylaminomethyl, butylsulfonylaminomethyl, pentylsulfonylamino- methyl, hexylsulfonylaminomethyl, methylsulfonylaminoethyl, methylsulfonyl- aminopropyl, methylsulfonylaminobutyl, methylsulfonylaminopentyl, methylsulfonylaminohexyl, ethylsulfonylaminoethyl, propylsulfonylaminoethyl,
- “Lower alkylcarbonyF moiety is carbonyl substituted by above-mentioned lower alkyl, and the suitable example may be methylcarbonyl, ethylcarbonyl, propylcarbonyl, butylcarbonyl, pentylcarbonyl, hexylcarbonyl, and the like, in which the preferred one may be (C.-C ⁇ alkylcarbonyl, and the most preferred one may be methylcarbonyl.
- “Lower alkylcarbonylamino” is amino substituted by the above-mentioned lower alkylcarbonyl, and the suitable example may be methylcarbonylamino, ethylcarbonylamino, propylcarbonylamino, butylcarbonylamino, pentylcarbonylamino, hexylcarbonylamino, and the like, in which the preferred one may be (C ⁇ -C4)alkylcarbonylamino, and the more preferred one may be . methylcarbonylamino and ethylcarbonylamino, and the most preferred one may be methylcarbonylamino.
- lower alkyl moiety of "lower alkylaminocarbonylamino” may be those as described above, and the suitable example of “lower alkylaminocarbonylamino” may be methylaminocarbonylamino, ethylaminocarbonylamino, propylaminocarbonylamino, butylaminocarbonylamino, pentylaminocarbonyl- amino, hexylaminocarbonylamino, and the like, in which the preferred one may be (Ci-C )alkylaminocarbonylamino, and the most preferred one may be methylaminocarbonylamino .
- lower alkoxycarbonyl moiety of "lower alkoxycarbonyloxy” may be those as described above, and the suitable example of “lower alkoxycarbonyloxy” may be methoxycarbonyloxy, ethoxycarbonyloxy, propoxycarbonyloxy, butoxycarbonyloxy, pentyloxycarbonyloxy, hexyloxycarbonyloxy, and the like, in which the preferred one may be (d-C ⁇ alkoxycarbonyoxy, and the more preferred one may be methoxycarbonyloxy and propoxycarbonyloxy, and the most preferred one may be methoxycarbonyloxy.
- lower alkyl moiety of "lower alkylcarbonyloxy” may be those as described above, and the suitable example of “lower alkylcarbonyloxy” may be methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, butylcarbonyloxy, pentylcarbonyloxy, hexylcarbonyloxy, and the like, in which the preferred one may be (Ci-djalkylcarbonyloxy, and the more preferred one may be methylcarbonyloxy and butylcarbonyloxy, and the most preferred one may be methylcarbonyloxy.
- “Lower alkylcarbamoyl” is carbamoyl substituted by the above-mentioned lower alkyl, and the suitable example may be methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, butylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, and the like, in which the preferred one may be (C1-C4) alkylcarbamoyl, and the most preferred one may be methylcarbamoyl.
- lower alkylsulfonylcarbamoyl may be methylsulfonylcarbamoyl, ethylsulfonylcarbamoyl, propylsulfonylcarbamoyl, butylsulfonylcarbamoyl, pentylsulfonylcarbamoyl, hexylsulfonylcarbamoyl, and the like, in which the preferred one may be (C ⁇ -d)alkylsulfonylcarbamoyl, and the most preferred one may be methylsulfonylcarbamoyl.
- halogen, lower alkyl and lower alkoxy moieties of "phenylsulfonylamino wherein phenyl may be substituted by halogen atom, lower alkyl or lower alkoxy" may be those as described above respectively, and the positions of halogen atom, lower alkyl and lower alkoxy are not limited as long as each position is chemically acceptable.
- phenylsulfonylamino wherein phenyl may be substituted by halogen atom, lower alkyl or lower alkoxy may be phenylsulfonylamino and chlorophenylsulfonylamino, and the more preferred one may be phenylsulfonylamino and p-chlorophenylsulfonyl- amino.
- the morpholinyl includes 1-morpholinyl, 2-morpholinyl, 3-morpholinyl and mo ⁇ holino, and the preferred one is morpholino.
- the isothiazolidinyl includes 2-isothiazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl and 5-isothiazolidinyl, and the preferred one is 2-isothiazolidinyl.
- the pyrrolidinyl includes 1-pyrrolidinyl, 2-pyrrolidinyl and 3-pyrrolidinyl, and the preferred one is 1-pyrrolidinyl.
- the imidazolidinyl includes 1-imidazolidinyl, 2-imidazolidinyl, 4- imidazolidinyl and the preferred one is 1-imidazolidinyl.
- the isothiazolidinyl may be substituted by 1 or 2 oxo(s) and the position(s) of oxo(s) is(are) not limited as long as the position is chemically acceptable.
- the preferred one is 1, 1 -dioxoisothiazolidin-2-yl.
- the pyrrolidinyl and imidazolidinyl may be substituted by oxo and the position of oxo is not limited as long as the position is chemically acceptable.
- the preferred ones are respectively 2-oxopyrrolidinyl and 2-oxoimidazolidinyl.
- the substituents represented by R 4 , R 5 , R 6 and R 7 may bind at any position of ortho-, meta- and para-positions in each phenyl group in the general formula [I], with preference given to the meta- and/or para-position(s).
- the phenyl, pyridyl, indolyl, benzimidazolyl and 2,3-dihydro-2- oxobenzimidazolyl represented by A may have 1 to 3 same or different substituent(s) and the position of the substituent(s) is not limited as long as the position is chemically acceptable.
- said phenyl may have substituent(s) at any position of ortho-, meta- and para-positions, preferably at the meta- and/or para-position(s).
- the pyridyl represented by A includes pyridin- 1-yl, pyridin-2-yl, pyridin- 3-yl and pyridin-4-yl, and the preferred one is pyridin-3-yl.
- the substituent(s) may be at any position of the pyridine ring.
- the indolyl represented by A includes indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl and indol-7-yl, and the preferred one is indol-4-yl.
- the substituent(s) may be at any position of the indole ring.
- the benzimidazolyl represented by A includes benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, and the preferred one is benzimidazol-7-yl.
- the substituent(s) may be at any position of the benzimidazole ring.
- the 2,3-dihydro-2-oxobenzimidazolyl represented by A includes 2,3- dihydro-2-oxobenzimidazol- 1-yl, 2,3-dihydro-2-oxobenzimidazol-3-yl, 2,3- dihydro-2-oxobenzimidazol-4-yl and 2,3-dihydro-2-oxobenzimidazol-5-yl, and the preferred one is 2,3-dihydro-2-oxobenzimidazol-4-yl.
- the substituent(s) may be at any position of the 2,3-dihydro-2-oxobenzimidazole ring.
- A is phenyl, pyridyl, indolyl, benzimidazolyl or 2,3-dihydro-2- oxobenzimidazolyl, each of which may have 1 to 3 same or different substituent(s) selected from the group consisting of hydroxy, lower alkylcarbonyloxy, lower alkoxycarbonyloxy, amino, halogen atom, lower alkylsulfonylamino, carboxy(lower)alkylsulfonylamino, N-lower alkyl-N- (lower) alkylsulfonylamino, mono(or di or tri) halo(lower) alkylsulfonylamino , phenyl(lower)alkylsulfonylamino, thienylsulfonylamino, phenyl(lower)alkoxy, hydroxy(lower)alkyl,
- X is single bond or -O-CH2-
- R 1 is hydrogen atom or amino-protective group
- R 2 is hydrogen atom, lower alkyl, hydroxy (lower) alkyl or carboxy(lower)alkyl
- R 3 is hydrogen atom or hydroxy
- R 4 , R 5 , R 6 and R 7 are each independently hydrogen atom, hydroxy, lower alkyl, lower alkoxy, amino, lower alkylsulfonylamino, lower alkoxycarbonylamino, carboxy (lower) alky lamino, lower alkoxycarbonyl(lower)alkylamino, halogen atom, phenyl(lower)alkoxy, lower alkoxycarbonyloxy, lower alkylcarbonyloxy, lower alkoxycarbonyl(lower)alkoxy, carboxy (lower) alkoxy, carbamoyl, lower alkylcarbamoyl, lower alkylsulfonylcarbamoyl, morpholinyl, pyrrolidinyl or imidazolidinyl wherein pyrrolidinyl and imidazolidinyl may be substituted by oxo, and n is 0 or 1; provided that A should be phenyl, pyridy
- A is phenyl which may have 1 to 3 same or different substituent(s) selected from the group consisting of hydroxy, amino, lower alkylsulfonylamino, phenyl(lower) alkoxy, hydroxy(lower)alkyl, amino(lower)alkyl, lower alkylsulfonylamino(lower) alkyl, formylamino, lower alkylcarbonylamino, [N,N-di(lower)alkylsulfamoyl]amino, lower alkoxycarbonylamino, ureido, lower alkoxycarbonyl, formyl, nitro and phenylsulfonylamino wherein phenyl may be substituted by halogen atom, X is single bond or -O-CH2-,
- R 1 is hydrogen atom or amino-protective group
- R 2 is hydrogen atom, lower alkyl or hydroxy(lower)alkyl
- R 3 is hydrogen atom or hydroxy
- R 4 , R 5 , R 6 and R 7 are each independently hydrogen atom, hydroxy, lower alkoxy, amino, lower alkoxycarbonylamino, halogen atom, phenyl(lower) alkoxy, lower alkoxycarbonyl(lower) alkoxy or carboxy(lower)alkoxy, and n is O or 1; provided that A should be phenyl which has at least one substituent selected from the group consisting of hydroxy(lower)alkyl, amino(lower) alkyl, lower alkylsulfonylamino(lower) alkyl, formylamino, lower alkylcarbonylamino, [N,N-di(lower)alkylsulfamoyl]amino, lower alkoxycarbonylamino, ureido, lower alkoxycarbonyl, formyl, nitro and phenylsulfonylamino wherein phenyl may be substituted by halogen atom
- A is phenyl which has 1 or 2 same or different substituent(s) selected from the group consisting of hydroxy, lower alkylsulfonylamino, hydroxy(lower) alkyl, formylamino, [N,N- di(lower)alkylsulfamoyl] amino and phenylsulfonylamino wherein phenyl may be substituted by halogen atom, X is single bond or -O-CH 2 -,
- R 1 , R 2 and R 3 are each hydrogen atom
- R 4 , R 5 , R 6 and R 7 are each independently hydrogen atom, lower alkoxy or lower alkoxycarbonylamino, and n is 0 or 1, provided that A should be phenyl which has at least one substituent selected from the group consisting of hydroxy(lower)alkyl, formylamino, [N,N- di(lower)alkylsulfamoyl] amino and phenylsulfonylamino wherein phenyl may be substituted by halogen atom, when n is 1, or a pharmaceutically acceptable salt thereof.
- A is phenyl which has 1 or 2 same or different substituent(s) selected from the group consisting of hydroxy, lower alkylsulfonylamino, hydroxy(lower) alkyl, formylamino,
- R 1 , R 2 and R 3 are each hydrogen atom
- R 4 , R 5 , R 6 and R 7 are each independently hydrogen atom or hydroxy
- n is 0, or a pharmaceutically acceptable salt thereof.
- Preferred objective compounds [I] are as follows. (R)-l-(4-hydroxy-3-benzenesulfonylaminophenyl)-2-[[2,2-bis(4- methoxyphenyl) ethyl] amino] ethanol
- Suitable salts of the object aminoalcohol derivatives [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, 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, methanesulfonate, benzen
- 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.
- 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.
- 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.
- 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].
- This reaction is carried out in accordance with a conventional method such as hydrolysis, reduction or the like.
- Suitable base may include an inorganic base and an organic base such as an alkali metal [e.g. sodium, potassium, etc.], an alkaline earth metal [e.g. magnesium, calcium, etc.], the hydroxide or carbonate or bicarbonate thereof, hydrazine, trialkylamine [e.g. trimethylamine, triethylamine, etc.], picoline, 1,5- diazabicyclo[4.3.0]non-5-ene, l,4-diazabicyclo[2.2.2]octane, 1,8- diazabicyclo[5.4.0]undec-7-ene, or the like.
- an alkali metal e.g. sodium, potassium, etc.
- an alkaline earth metal e.g. magnesium, calcium, etc.
- the hydroxide or carbonate or bicarbonate thereof hydrazine
- trialkylamine e.g. trimethylamine, triethylamine, etc.
- picoline 1,5- diazabicyclo[
- Suitable acid may include an organic acid [e.g. formic acid, acetic acid, propionic acid, trichloroacetic acid, trifluoroacetic acid, etc.], an inorganic acid [e.g. hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc.] and an acid addition salt compound [e.g. pyridine hydrochloride, etc.].
- organic acid e.g. formic acid, acetic acid, propionic acid, trichloroacetic acid, trifluoroacetic acid, etc.
- an inorganic acid e.g. hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc.
- an acid addition salt compound e.g. pyridine hydrochloride, etc.
- trihaloacetic acid e.g. trichloroacetic acid, trifluoroacetic acid, etc.
- cation trapping agents e.g. anisole, phenol, etc.
- the reaction is usually carried out in a solvent such as water, an alcohol [e.g. methanol, ethanol, etc.], methylene chloride, chloroform, tetrachloromethane, tetrahydrofuran, a mixture thereof or any other solvent which does not adversely influence the reaction.
- a liquid base or acid can be also used as the solvent.
- the reaction temperature is not critical and the reaction is usually carried out under cooling to heating.
- the reduction method applicable for the elimination reaction may include chemical reduction and catalytic reduction.
- Suitable reducing agents to be used in chemical reduction are a combination of metal [e.g. tin, zinc, iron, etc.] or metallic compound [e.g. chromium chloride, chromium acetate, etc.] and an organic or inorganic acid [e.g. formic acid, acetic acid, propionic acid, trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid, hydrobromic acid, etc.].
- metal e.g. tin, zinc, iron, etc.
- metallic compound e.g. chromium chloride, chromium acetate, etc.
- organic or inorganic acid e.g. formic acid, acetic acid, propionic acid, trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid, hydrobromic acid, etc.
- Suitable catalysts to be used in catalytic reduction are conventional ones such as platinum catalysts [e.g. platinum plate, spongy platinum, platinum black, colloidal platinum, platinum oxide, platinum wire, etc.], palladium catalysts [e.g. spongy palladium, palladium black, palladium oxide, palladium on carbon, colloidal palladium, palladium on barium sulfate, palladium on barium carbonate, etc.], nickel catalysts [e.g. reduced nickel, nickel oxide, Raney nickel, etc.], cobalt catalysts [e.g. reduced cobalt, Raney cobalt, etc.], iron catalysts [e.g. reduced iron, Raney iron, etc.], copper catalysts [e.g. reduced copper, Raney copper, Ullman copper, etc.] and the like.
- platinum catalysts e.g. platinum plate, spongy platinum, platinum black, colloidal platinum, platinum oxide, platinum wire, etc.
- palladium catalysts e.g. spongy
- the reduction is preferably carried out in the presence of a combination of palladium catalysts [e.g. palladium black, palladium on carbon, etc.] and formic acid or its salt [e.g. ammonium formate, etc.].
- palladium catalysts e.g. palladium black, palladium on carbon, etc.
- formic acid or its salt e.g. ammonium formate, etc.
- the reduction is usually carried out in a conventional solvent which does not adversely influence the reaction such as water, an alcohol [e.g. methanol, ethanol, propanol, etc.], chlorobenzene, N,N-dimethylformamide, or a mixture thereof.
- a suitable solvent to be used in catalytic reduction may be the above-mentioned solvent, and other conventional solvent such as diethyl ether, dioxane, tetrahydrofuran, etc. or a mixture thereof.
- the reaction temperature of this reduction is not critical and the reaction is usually carried out under cooling to heating. Process 3
- the object compound [Ic] or a salt thereof can be prepared by reacting a compound [IV] or a salt thereof with a compound [V] or a salt thereof.
- Suitable salt of the compounds [Ic], [IN] and [V] may be the same as those exemplified for the compound [I].
- reaction is carried out in the manner disclosed in Preparation 3 to be described later or similar manners thereto.
- the object compound [I] or a salt thereof can be obtained by modification of substituent(s) of A and R 4 , R 5 , R 6 and R 7 , by a known method or according to the methods as described in Preparations or Examples or to the similar manners thereto.
- 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. It is further to be noted that isomerization or rearrangement of the compound [I] and the other compounds 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 is also included within the scope of the present invention. It is also to be noted that the solvating form of the compound [I] and the other compounds (e.g. hydrate, etc.) and any form of the crystal of the compound [I] and the other compounds are included within the scope of the present invention.
- the object compound [I] or a salt thereof possesses gut selective 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 particularly for the treatment and /or prevention of spasm or hyperanakinesia in case of irritable bowel syndrome, gastritis, gastric ulcer, duodenal ulcer, enteritis, cholecystopathy, cholangitis, urinary calculus and the like; for the treatment and/or prevention of ulcer such as gastric ulcer, duodenal ulcer, peptic ulcer, ulcer caused by non steroidal anti-inflammatory drugs, 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, cyst
- the pharmaceutical composition of the present invention can be used in the form of a pharmaceutical preparation, for example, in solid, semisolid or liquid form, which contains an aminoalcohol derivative in the present application or a pharmaceutically acceptable salt thereof, as an active ingredient in admixture with an organic or inorganic pharmaceutically acceptable carrier or excipient suitable for rectal, pulmonary (nasal or buccal inhalation), nasal, ocular, external (topical), oral or parenteral (including subcutaneous, intravenous and intramuscular) administrations or insufflation.
- a pharmaceutical preparation for example, in solid, semisolid or liquid form, which contains an aminoalcohol derivative in the present application or a pharmaceutically acceptable salt thereof, as an active ingredient in admixture with an organic or inorganic pharmaceutically acceptable carrier or excipient suitable for rectal, pulmonary (nasal or buccal inhalation), nasal, ocular, external (topical), oral or parenteral (including subcutaneous, intravenous and intramuscular) administrations or insufflation.
- the active ingredient may be compounded, for example, with the usual non-toxic, pharmaceutically acceptable carriers for tablets, pellets, troches, capsules, suppositories, creams, ointments, aerosols, powders for insufflation, solutions, emulsions, suspensions, and any other forms suitable for use. And, if necessary, in addition, auxiliary, stabilizing, thickening and coloring agents and perfumes may be used.
- aminoalcohol derivative in the present invention or a pharmaceutically acceptable salt thereof is included in the pharmaceutical composition in: an amount sufficient to produce the desired effect upon the process or condition of the diseases.
- the pharmaceutical composition of the present invention can be manufactured by the conventional method in this field of the art. If necessary, the technique generally used in this field of the art for improving the bioavailability of a drug can be applied to the pharmaceutical composition of the present invention.
- composition for applying the composition to a human being or an animal, it is preferable to apply it by intravenous (including i.v. infusion), intramuscular, pulmonary, or oral administration, or insufflation.
- intravenous including i.v. infusion
- intramuscular including i.v. infusion
- pulmonary including pulmonary pulmonary
- oral administration or insufflation.
- While the dosage of therapeutically effective amount of the aminoalcohol derivative in the present invention varies from and also depends upon the age and condition of each individual patient to be treated, in the case of intravenous administration, a daily dose of 0.01- 100 mg of the aminoalcohol derivative in the present invention per kg weight of a human being or an animal, in case of intramuscular administration, a daily dose of 0.01- 100 mg of the aminoalcohol derivative in the present invention per kg weight of a human being or an animal, in case of oral administration, a daily dose of 0.01-200 mg of the aminoalcohol derivative in the present invention per kg weight of a human being or an animal is generally given for the prophylactic and/or therapeutic treatment of above- mentioned diseases in a human being or an animal.
- a 12F Foley catheter was lubricated with water soluble jelly, inserted into the urethral orifice and advanced approximately 10 cm until the balloon tip was placed well inside the bladder. The balloon was then inflated with 5 ml of room air and the catheter was slowly withdrawn to just the point where the first resistance was felt at the bladder neck. Urine was completely drained out through the catheter, and 30 ml of biological saline was infused. The catheter was connected to pressure transducer, and intravesical pressure was continuously recorded. The test compound was injected intravenously at 5 minutes before the administration of carbachol (1.8 ⁇ g/kg).
- Test Compound (1) 1.7 ⁇ 0.4* (0.001 mg/kg)
- Test Compound (2) 0.8 ⁇ 0.3** (0.001 mg/kg)
- Test Compound (3) 2.2 ⁇ 0.5*** (0.00032 mg/kg)
- test results show that the test compounds (1), (2) and (3) possess a relaxation effect on the smooth muscle in the urinary bladder and these compounds are useful for the treatment of pollakiuria and urinary incontinence in human beings or animals.
- the test compounds (2) and (3) have been known as described in the above-mentioned publications. It has not been known, however, that these compounds are useful for the treatment of pollakiuria and urinary incontinence in human beings or animals.
- N-Ben2yl-2,2-bis(4-methoxyphenyl)ethylamine was obtained from methyl dibenzylaminoacetate and 4-bromoanisole by a similar manner to that of Preparation 3 to be described later, followed by catalytic hydrogenation on palladium on charcoal in a usual manner.
- Example 4 The following compound was obtained according to a similar manner to that of Preparation 7 to be described later.
- Example 6 The following compound was obtained according to a similar manner to that of Example 25 to be described later.
- reaction mixture was worked up by the usual manner to give (2 S) - 1 -(3-acetylamino-4-ben2yloxyphenoxy) -3 - [N-benzyl- [(3 RS)- 1 , 1 -bis(4- methoxyphenyl)-3-butyl]amino]-2-propanol.
- Example 37 The following compound was obtained according to a similar manner to that of Example 39 to be described later.
- reaction mixture was worked up in the usual manner and purified by silica gel column chromatography to give 3-(dibenzylamino)- 1 , l-bis(4-bromophenyl)- 1- propanol (8.43 g).
- (2S)- l-Phenoxy-3-[[(3RS)- 1 , l-bis(4-fluorophenyl)- l-hydroxy-3- butyl]amino]-2-propanol was obtained from (3RS)-3-[((2S)-2-hydroxy-3- phenoxypropyl) amino] butyric acid methyl ester and 4-fluorobromobenzene by a similar manner to that of Preparation 3.
- Example 44 (2S)-l-Phenoxy-3-[[(lS)-3,3-bis(4-methoxyphenyl)-l-(hydroxymethyl)- propyl]amino]-2-propanol was obtained from (S)-2-amino-4,4-bis(4- methoxyphenyl)-l-butanol and (S)-(phenoxymethyl)oxirane by a similar manner to that of Example 9.
- Example 63 (S)- l-[4-Benzyloxy-3-(benzenesulfonylamino)phenoxy]-3-[N-benzyl-[2,2- bis[4 - (methoxycarbonylamino) phenyl] ethyl] amino] -2 -propanol was obtained according to a similar manner to that of Example 50.
- Example 74 The following compounds were obtained according to a similar manner to that of Example 9.
- Example 80 To a mixture of (R)- l-(4-benzyloxy-3-nitrophenyl)-2-[N-benzyl-[2,2-bis(4- hydroxyphenyl) ethyl] amino] ethanol (422 mg), N,N-dimethylformamide (1 ml) and potassium carbonate (128 mg), isopropyl chloroformate (80 ⁇ l) was added.
- Example 81 The following compound was obtained according to a similar manner to that of Example 78.
- Example 83 A mixture of tert-butyl N-benzyl-N-[2,2-bis(3-chloro-4-hydroxyphenyl)- ethyl]carbamate (112 mg) and 4N hydrogen chloride solution in 1,4-dioxane (1 ml) was stood at room temperature for 3 hours, diluted with ethyl acetate (40 ml), washed by saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated to afford a free amine. A mixture of the amine, (S)-[(3-formyl-4- benzyloxyphenoxy)methyl]oxirane (73 mg) and isopropanol (2 ml) was refluxed for 16 hours.
- Example 88 The following compounds were obtained according to a similar manner to that of Example 50.
- the mixture was partitioned between ethyl acetate and water.
- the organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered.
- the filtrate was concentrated and the residual oil was dissolved in tetrahydrofuran (2.5 ml).
- To the solution was added 6N hydrochloric acid, and the mixture was stirred at room temperature for 3 hours.
- the mixture was partitioned between ethyl acetate and water.
- the water layer was neutralized with saturated sodium bicarbonate solution and extracted twice with ethyl acetate.
- the combined extract was washed with brine, dried over magnesium sulfate, and filtered.
- Example 99 0.5 ml of a mixture of acetic anhydride (1.25 ml) and formic acid ( 1.00 ml) was added to a solution of (S)-l-(3-amino-4-benzyloxyphenoxy)-3-[N-benzyl-[2,2- bis(4-benzyloxyphenyl) ethyl] amino] -2 -propanol (314 mg) and pyridine (0.1 ml) in dichloromethane (6 ml) under ice water cooling over 10 minutes and the mixture was stirred at room temperature for a further 1 hour. To this reaction mixture was added aqueous saturated solution of sodium bicarbonate (5.0 ml). The mixture was stirred at the same temperature for 18 hours, and which was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo.
- Example 100 The following compounds were obtained according to a similar manner to that of Example 100.
- Example 102 The following compound was obtained according to a similar manner to that of Example 99.
- the compound of the formula [I] and a salt thereof possesses gut selective sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence and anti-pollakiuria activities.
- These compounds are useful for the treatment and/or prevention of gastro-intestinal disorders caused by smooth muscle contractions in human beings or animals, and more particularly for the treatment and/or prevention of spasm or hyperanakinesia in case of irritable bowel syndrome, gastritis, gastric ulcer, duodenal ulcer, enteritis, cholecystopathy, cholangitis, urinary calculus and the like; for the treatment and/or prevention of ulcer such as gastric ulcer, duodenal ulcer, peptic ulcer, ulcer caused by non steroidal anti-inflammatory drugs, 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, cystospasm, chronic cystitis, chronic prostatitis, prostatic hypertrophy or the like; for the treatment and/ or prevention of pancreatitis, obesity, diabetes, glycosuria, hyperlipidemia, hypertension, atherosclerosis
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00974972A EP1230210A1 (en) | 1999-11-16 | 2000-11-13 | Aminoalcohol derivatives useful for the treatment of gastrointestinal disorders |
JP2001538867A JP2003514793A (en) | 1999-11-16 | 2000-11-13 | Amino alcohol derivatives useful for the treatment of gastrointestinal disorders |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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AUPQ4076 | 1999-11-16 | ||
AUPQ4076A AUPQ407699A0 (en) | 1999-11-16 | 1999-11-16 | Aminoalcohol derivatives |
Publications (1)
Publication Number | Publication Date |
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WO2001036375A1 true WO2001036375A1 (en) | 2001-05-25 |
Family
ID=3818221
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PCT/JP2000/008007 WO2001036375A1 (en) | 1999-11-16 | 2000-11-13 | Aminoalcohol derivatives useful for the treatment of gastrointestinal disorders |
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EP (1) | EP1230210A1 (en) |
JP (1) | JP2003514793A (en) |
AU (1) | AUPQ407699A0 (en) |
WO (1) | WO2001036375A1 (en) |
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AUPQ407699A0 (en) | 1999-12-09 |
JP2003514793A (en) | 2003-04-22 |
EP1230210A1 (en) | 2002-08-14 |
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