RU2005111975A - Производные фенэтаноламина для лечения респираторных заболеваний - Google Patents
Производные фенэтаноламина для лечения респираторных заболеваний Download PDFInfo
- Publication number
- RU2005111975A RU2005111975A RU2005111975/04A RU2005111975A RU2005111975A RU 2005111975 A RU2005111975 A RU 2005111975A RU 2005111975/04 A RU2005111975/04 A RU 2005111975/04A RU 2005111975 A RU2005111975 A RU 2005111975A RU 2005111975 A RU2005111975 A RU 2005111975A
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- Prior art keywords
- compound
- formula
- phenyl
- hydroxyethyl
- amino
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- 238000011282 treatment Methods 0.000 title claims 4
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title 1
- 230000000241 respiratory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 39
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- CMKZQSHWRVZOOY-PMERELPUSA-N 4-[(1r)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CCCC2)=C1 CMKZQSHWRVZOOY-PMERELPUSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- IPMLTYNMMWXXGZ-RFPXNCDYSA-N 4-[(1r)-2-[6-[4-(3-cyclopentylsulfinylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)C2CCCC2)=C1 IPMLTYNMMWXXGZ-RFPXNCDYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- -1 {3- [3- (Cyclopentylsulfonyl) phenyl] propyl} oxy Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 229940124225 Adrenoreceptor agonist Drugs 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- AHBQEXAYASMAHF-HKBQPEDESA-N 4-[(1r)-2-[6-[4-(3-cyclohexylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CCCCC2)=C1 AHBQEXAYASMAHF-HKBQPEDESA-N 0.000 claims 1
- NHCKCBLLRKMQRA-PMERELPUSA-N 4-[(1r)-2-[6-[4-(3-cyclopent-3-en-1-ylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CC=CC2)=C1 NHCKCBLLRKMQRA-PMERELPUSA-N 0.000 claims 1
- QZWUZHTUCRGGJA-HKBQPEDESA-N 4-[(1r)-2-[6-[4-(3-cyclopentylsulfonyl-5-methylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=C(C=2)S(=O)(=O)C2CCCC2)C)=CC=C(O)C(CO)=C1 QZWUZHTUCRGGJA-HKBQPEDESA-N 0.000 claims 1
- RDCHCGRUXILZCM-LJAQVGFWSA-N 4-[(1r)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-fluorophenol Chemical compound C([C@H](O)C=1C=C(F)C(O)=CC=1)NCCCCCCOCCCCC(C=1)=CC=CC=1S(=O)(=O)C1CCCC1 RDCHCGRUXILZCM-LJAQVGFWSA-N 0.000 claims 1
- XGHCBYFGZZQETE-PMERELPUSA-N 4-[(1r)-2-[6-[4-(4-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=CC(=CC=2)S(=O)(=O)C2CCCC2)=C1 XGHCBYFGZZQETE-PMERELPUSA-N 0.000 claims 1
- DXDPRGIAAPVRTR-HKBQPEDESA-N 4-[(1r)-2-[6-[5-(3-cyclopentylsulfonylphenyl)pentoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CCCC2)=C1 DXDPRGIAAPVRTR-HKBQPEDESA-N 0.000 claims 1
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims 1
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 claims 1
- LVQFHDAKZHGEAJ-UHFFFAOYSA-M 4-methylbenzenesulfonate Chemical compound [CH2]C1=CC=C(S([O-])(=O)=O)C=C1 LVQFHDAKZHGEAJ-UHFFFAOYSA-M 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- CDAKJSRRZUGPEG-UHFFFAOYSA-N 6-[2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol Chemical compound C1=C(O)C(CO)=NC(C(O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CCCC2)=C1 CDAKJSRRZUGPEG-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- OAQRLDKPZZCJKS-BHVANESWSA-N [4-[(1R)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl] 3-methylbenzenesulfonate Chemical compound Cc1cccc(c1)S(=O)(=O)Oc1ccc(cc1CO)[C@@H](O)CNCCCCCCOCCCCc1cccc(c1)S(=O)(=O)C1CCCC1 OAQRLDKPZZCJKS-BHVANESWSA-N 0.000 claims 1
- ZZGJVOZYVRSHNK-RWYGWLOXSA-N [4-[(1R)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl] 4-phenylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)OC1=C(C=C(C=C1)[C@H](CNCCCCCCOCCCCC1=CC(=CC=C1)S(=O)(=O)C1CCCC1)O)CO)C1=CC=CC=C1 ZZGJVOZYVRSHNK-RWYGWLOXSA-N 0.000 claims 1
- XDJHIJVTHJOXDP-KDXMTYKHSA-N [4-[(1R)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl] naphthalene-2-sulfonate Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)OC1=C(C=C(C=C1)[C@H](CNCCCCCCOCCCCC1=CC(=CC=C1)S(=O)(=O)C1CCCC1)O)CO XDJHIJVTHJOXDP-KDXMTYKHSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- UGNBYGPBCLYWCL-PMERELPUSA-N n-[5-[(1r)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-hydroxyphenyl]formamide Chemical compound C([C@H](O)C=1C=C(NC=O)C(O)=CC=1)NCCCCCCOCCCCC(C=1)=CC=CC=1S(=O)(=O)C1CCCC1 UGNBYGPBCLYWCL-PMERELPUSA-N 0.000 claims 1
- GDRIEPJFIXGEBM-PMERELPUSA-N n-[5-[(1r)-2-[6-[4-(3-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=C(C=CC=2)S(=O)(=O)C2CCCC2)=C1 GDRIEPJFIXGEBM-PMERELPUSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
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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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
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- A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
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- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms 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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- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
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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
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- 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
- C07D215/20—Oxygen atoms
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
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- 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
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- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
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Claims (21)
1. Соединение формулы (I)
или его соль, сольват или физиологически функциональное производное, где
m представляет собой целое число от 2 до 8; и
n представляет собой целое число от 3 до 11;
при условии, что m+n составляет число от 5 до 19;
R1 представляет собой SR6, SOR6 или SO2R6,
где R6 представляет собой С3-7циклоалкильную или С3-7циклоалкенильную группу;
R2 и R3 независимо выбраны из водорода, С1-6алкила, С1-6алкокси, галогено, фенила и С1-6галогеноалкила;
R4 и R5 независимо выбраны из водорода и С1-4алкила, при условии, что общее количество атомов углерода в R4 и R5 не превышает 4;
Ar представляет собой группу, выбранную из
где R8 представляет собой водород, галоген, -(CH2)qOR11, -NR11C(O)R12, -NR11SO2R12, -SO2NR11R12, -NR11R12, -OC(O)R13 или OC(O)NR11R12, и R7 представляет собой водород, галоген или С1-4алкил;
или R8 представляет собой -NHR14, и R7 и -NHR14 вместе образуют 5- или 6-членное гетероциклическое кольцо;
R9 представляет собой водород, галоген, -OR11 или -NR11R12;
R10 представляет собой водород, галоген, галогеноС1-4алкил, -OR11, -NR11R12, -OC(O)R13 или OC(O)NR11R12;
каждый из R11 и R12 независимо представляет собой водород или С1-4алкил, или в группах -NR11R12, -SO2NR11R12 и -OC(O)NR11R12 радикалы R11 и R12 независимо представляют собой водород или С1-4алкил или вместе с атомом азота, к которому они присоединены, образуют 5-, 6- или 7-членное азотсодержащее кольцо,
R13 представляет собой арильную (например фенильную или нафтильную) группу, которая может быть незамещенной или замещенной одним или более чем одним заместителем, выбранным из галогена, С1-4алкила, гидрокси, С1-4алкокси или галогеноС1-4алкила; и
q представляет собой ноль или целое число от 1 до 4.
2. Соединение формулы (I) или его соль, сольват или физиологически функциональное производное, где формула (I) является такой, как определено в формуле изобретения, за исключением того, что R8 не представляет собой водород.
3. Соединение по п.1 или 2, где R1 представляет собой -SO2R6.
4. Соединение по любому из п.1 или 2, где R6 представляет собой С3-7циклоалкильную группу.
5. Соединение по любому из п.1 или 2, где каждый из R2 и R3 представляет собой водород.
6. Соединение по любому из п.1 или 2, где R4 и R5 независимо выбраны из водорода и метила.
8. Соединение формулы (Ia)
или его соль, сольват или физиологически функциональное производное, где
m представляет собой целое число от 2 до 8; и
n представляет собой целое число от 3 до 11;
при условии, что m+n составляет число от 5 до 19;
R1 представляет собой SR6, SOR6 или SO2R6,
где R6 представляет собой С3-7циклоалкильную или С3-7циклоалкенильную группу;
R2 и R3 независимо выбраны из водорода, С1-6алкила, С1-6алкокси, галогено, фенила и С1-6галогеноалкила; и
R4 и R5 независимо выбраны из водорода и С1-4алкила, при условии, что общее количество атомов углерода в R4 и R5 не превышает 4.
9. Соединение по любому из пп.1, 2 или 8, где m представляет собой 5 или 6, и n представляет собой 3 или 4.
10. Соединение формулы (I) или (Ia), выбранное из
4-{(1R)-2-[(6-{4-[3-(Циклопентилсульфинил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола;
4-{(1R)-2-[(6-{4-[3-(Циклопентилсульфинил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола (Изомер 1);
4-{(1R)-2-[(6-{4-[3-(Циклопентилсульфинил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола (Изомер 2);
4-{(1R)-2-[(6-{4-[3-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола;
4-{(R)-2-[(6-{4-[4-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола;
4-((1R)-2-{[6-({4-[3-(Циклогексилсульфонил)фенил]бутил}окси)гексил]-амино}-1-гидроксиэтил)-2-(гидроксиметил)фенола;
4-((1R)-2-{[6-({4-[3-(3-Циклопентен-1-илсульфонил)фенил]бутил}окси)-гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенола;
4-((1R)-2-{[6-({5-[3-(Циклопентилсульфонил)фенил]пентил}окси)гексил]-амино}-1-гидроксиэтил)-2-(гидроксиметил)-фенола;
4-((1R)-2-{(7-({3-[3-(Циклопентилсульфонил)фенил]пропил}окси)гептил]-амино}-1-гидроксиэтил)-2-(гидроксиметил)-фенола;
4-((1R)-2-{[6-({4-[3-(Циклопентилсульфонил)-5-метилфенил]бутил}окси)-гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)-фенола;
N-[5-((1R)-2-{[6-({4-[3-(Циклопентилсульфонил)фенил]бутил}окси)гексил]-амино}-1-гидроксиэтил)-2-гидроксифенил]метансульфонамида;
4-((1R)-2{[6-({4-[3-(Циклопентилсульфонил)фенил]бутил}окси)гексил]-амино}-1-гидроксиэтил)-2-фторфенола;
6-{2-[(6-{4-[3-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)пиридин-3-ола;
5-{(1R)-2-[(6-{4-[3-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-8-гидрокси-3,4-дигидрохинолин-2(1H)-она;
5-{(1R)-2-[(6-{4-[3-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-гидроксифенилформамида;
и их солей, сольватов и физиологически функциональных производных.
11. Соединение формулы (I) или (Ia), которое представляет собой
4-{(1R)-2-[(6-{4-[3-(Циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенол;
или его соль, сольват или физиологически функциональное производное.
12. Соединение по любому из пп.1, 2, 8, 10 или 11 в форме соли, образованной с арилсульфоновой кислотой.
13. Соединение по п.8, которое выбрано из
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола4-метилбензолсульфоната;
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола4-бромбензолсульфоната;
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола 4-хлорбензолсульфоната;
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола 3-толуолсульфоната;
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)фенола 4-бифенилсульфоната и
4-{(1R)-2-[(6-{4-[3-(циклопентилсульфонил)фенил]бутокси}гексил)амино]-1-гидроксиэтил}-2-(гидроксиметил)-фенола нафталин-2-сульфоната.
14. Соединение по п.13, где соль находится в кристаллической форме.
15. Способ профилактики или лечения клинического состояния, при котором показан селективный агонист β2-адренорецептора, у млекопитающего, такого как человек, включающий введение терапевтически эффективного количества соединения формулы (I) или (Ia) по любому из пп.1-14 или его фармацевтически приемлемой соли, сольвата или физиологически функционального производного.
16. Соединение формулы (I) или (Ia) по любому из пп.1, 2, 8, 10 или 11 или его фармацевтически приемлемая соль, сольват или физиологически функциональное производное для применения в терапевтическом лечении.
17. Фармацевтический препарат, содержащий соединение формулы (I) или (Ia) по любому из пп.1-14 или его фармацевтически приемлемую соль, сольват или физиологически функциональное производное и фармацевтически приемлемый носитель или эксципиент, и возможно один или более чем один другой терапевтический ингредиент.
18. Комбинация, включающая соединение формулы (I) или (Ia) по любому из пп.1-14 или его фармацевтически приемлемую соль, сольват или физиологически функциональное производное и один или более чем один другой терапевтический ингредиент.
19. Применение соединения формулы (I) или (Ia) по любому из пп.1-14 или его фармацевтически приемлемой соли, сольвата или физиологически функционального производного в производстве лекарства для профилактики или лечения клинического состояния, для которого показан селективный агонист β2-адренорецептора.
20. Способ получения соединения формулы (I) или (Ia) по любому из пп.1-14 или его соли, сольвата или физиологически функционального производного, включающий
(а) снятие защиты с защищенного промежуточного соединения, например формулы (II):
или его соли или сольвата, где R1, R2, R3, R4, R5, m и n являются такими, как определено для соединения формулы (I), R19 представляет собой возможно защищенную форму Ar, и каждый из R20 и R21 независимо представляет собой водород или защитную группу, при условии, что соединение формулы (II) содержит по меньшей мере одну защитную группу;
(б) взаимодействие соединения формулы (X)
где R2, R3, R4, R5, R19, R20, R21, m и n являются такими, как определено для формулы (II), каждый R26 независимо представляет собой водород или С1-4алкил, и каждый из х и у представляют собой 0, 1 или 2, для осуществления замыкания цикла;
(в) алкилирование амина формулы (XIII)
где каждый из R22, R23, R20 и R21 представляет собой независимо водород или защитную группу, соединением формулы (XVII)
где R1, R2, R3, R4, R5, m и n являются такими, как определено для соединения формулы (I), и L1 представляет собой уходящую группу;
(г) восстановление соединения формулы (XIX)
где R1, R2, R3, R4, R5, m и n являются такими, как определено для формулы (I), R19 представляет собой возможно защищенную форму Ar, и каждый из R20 и R21 представляет собой независимо водород или защитную группу как определено выше;
(д) взаимодействие соединения формулы (XXIII)
где R19 является таким, как определено выше, и L3 представляет собой уходящую группу, как определено выше для L1 или L2;
или соединения формулы (XXIV)
где R19 является таким, как определено выше,
с амином формулы (XXV)
где R1, R2, R3, R4, R5, R20, тип являются такими, как определено для формулы (II); или
(е) удаление хиральной вспомогательной группы из соединения формулы (IIa)
где R1-R5, m и n являются такими, как определено для формулы (I), R19 представляет собой возможно защищенную форму Ar, R21 представляет собой водород или защитную группу, и R27 представляет собой хиральную вспомогательную группу;
с последующими стадиями, осуществляемыми в любой порядке:
(1) возможное удаление любых защитных групп;
(2) возможное выделение энантиомера из смеси энантиомеров;
(3) возможное превращение одного соединения формулы (I) в другое соединение формулы (I), например превращение соединения, где R1 представляет собой SR6, в соединение, где R1 представляет собой SOR6 или SO2R6, или превращение соединения, где R1 представляет собой SOR6, в соединение, где R1 представляет собой SO2R6;
(4) возможное превращение соединения, где R6 представляет собой циклоалкенил, в соединение, где R6 представляет собой циклоалкил, например гидрированием;
(5) возможное превращение продукта в его соответствующую соль, сольват или физиологически функциональное производное.
21. Промежуточное соединение, выбранное из соединения формулы (II), (III), (IV), (X) и (XIX), как определено выше.
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PT1556342E (pt) | 2008-04-28 |
WO2004037773A8 (en) | 2004-07-22 |
AU2003286143A1 (en) | 2004-05-13 |
EP1556342B1 (en) | 2008-03-26 |
MXPA05004527A (es) | 2005-07-26 |
SI1556342T1 (sl) | 2008-08-31 |
DK1556342T3 (da) | 2008-07-21 |
ES2302956T3 (es) | 2008-08-01 |
IS7814A (is) | 2005-04-20 |
BR0315720A (pt) | 2005-09-06 |
JP2006503888A (ja) | 2006-02-02 |
DE60320007D1 (de) | 2008-05-08 |
NO20051962L (no) | 2005-05-19 |
EP1556342A1 (en) | 2005-07-27 |
NZ539676A (en) | 2006-10-27 |
CA2503588A1 (en) | 2004-05-06 |
KR20050057681A (ko) | 2005-06-16 |
RU2332400C2 (ru) | 2008-08-27 |
MA27697A1 (fr) | 2006-01-02 |
ATE390407T1 (de) | 2008-04-15 |
US20060205794A1 (en) | 2006-09-14 |
HK1081173A1 (en) | 2006-05-12 |
TWI285195B (en) | 2007-08-11 |
WO2004037773A1 (en) | 2004-05-06 |
PL377122A1 (pl) | 2006-01-23 |
DE60320007T2 (de) | 2009-06-18 |
TW200418772A (en) | 2004-10-01 |
US7442839B2 (en) | 2008-10-28 |
AR041724A1 (es) | 2005-05-26 |
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