JP4478013B2 - オキソフェニルシクロヘキシルプロパノールアミン誘導体、それらの製造法、およびそれらの治療的適用 - Google Patents
オキソフェニルシクロヘキシルプロパノールアミン誘導体、それらの製造法、およびそれらの治療的適用 Download PDFInfo
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- JP4478013B2 JP4478013B2 JP2004507476A JP2004507476A JP4478013B2 JP 4478013 B2 JP4478013 B2 JP 4478013B2 JP 2004507476 A JP2004507476 A JP 2004507476A JP 2004507476 A JP2004507476 A JP 2004507476A JP 4478013 B2 JP4478013 B2 JP 4478013B2
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- phenyl
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- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 31
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- -1 cyano, phenyl Chemical group 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
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- 150000004677 hydrates Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
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- MJVWJMNBPKKIEJ-JOYXZSCHSA-N N1(CCC2(CC1)CC1=CC=CC=C1C2)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O Chemical compound N1(CCC2(CC1)CC1=CC=CC=C1C2)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O MJVWJMNBPKKIEJ-JOYXZSCHSA-N 0.000 claims description 2
- JSLXSDQUICOIKD-NAYUSWPISA-N N1(CCC2(CC1)CCCC1=CC=CC=C12)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O Chemical compound N1(CCC2(CC1)CCCC1=CC=CC=C12)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O JSLXSDQUICOIKD-NAYUSWPISA-N 0.000 claims description 2
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- UEESMNRENCAKTF-WMDTUVAQSA-N C1=C(O)C(S(=O)(=O)C)=CC(OC[C@@H](O)CN[C@@H]2CC[C@H](CC2)C=2C=CC(=CC=2)C(=O)N2CCC(CC2)C(O)C=2C=CC=CC=2)=C1 Chemical compound C1=C(O)C(S(=O)(=O)C)=CC(OC[C@@H](O)CN[C@@H]2CC[C@H](CC2)C=2C=CC(=CC=2)C(=O)N2CCC(CC2)C(O)C=2C=CC=CC=2)=C1 UEESMNRENCAKTF-WMDTUVAQSA-N 0.000 claims 1
- RPVOZYDEMJLEIE-ASVWTAOFSA-N CS(=O)(=O)Nc1cc(OC[C@@H](O)CN[C@H]2CC[C@@H](CC2)c2ccc(cc2)C(=O)N2CCC(Cc3ccccc3)CC2)ccc1O Chemical compound CS(=O)(=O)Nc1cc(OC[C@@H](O)CN[C@H]2CC[C@@H](CC2)c2ccc(cc2)C(=O)N2CCC(Cc3ccccc3)CC2)ccc1O RPVOZYDEMJLEIE-ASVWTAOFSA-N 0.000 claims 1
- XZJYOCQFJMSINF-NSGJQZOKSA-N N1(CCC2(CC1)CCC1=CC=CC=C12)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O Chemical compound N1(CCC2(CC1)CCC1=CC=CC=C12)C(=O)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)NC[C@@H](COC1=CC(=C(C=C1)O)S(=O)(=O)C)O XZJYOCQFJMSINF-NSGJQZOKSA-N 0.000 claims 1
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- 125000003545 alkoxy group Chemical group 0.000 claims 1
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- 230000003195 tocolytic effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- YJPRMAKYHDHWRV-YGGJGDQASA-N 4-[4-[benzyl-[(2s)-2-hydroxy-3-(3-methylsulfonyl-4-phenylmethoxyphenoxy)propyl]amino]cyclohexyl]benzoic acid Chemical compound C([C@H](O)COC=1C=C(C(=CC=1)OCC=1C=CC=CC=1)S(=O)(=O)C)N(C1CCC(CC1)C=1C=CC(=CC=1)C(O)=O)CC1=CC=CC=C1 YJPRMAKYHDHWRV-YGGJGDQASA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 239000003480 eluent Substances 0.000 description 3
- QAKHHCXRYVFFSY-UHFFFAOYSA-N ethyl 4-[4-(benzylamino)cyclohexyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1CCC(NCC=2C=CC=CC=2)CC1 QAKHHCXRYVFFSY-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- ZAQZWXVNTWEFPU-TUTQLFIHSA-N ethyl 4-[4-[benzyl-[(2s)-2-hydroxy-3-[3-(methanesulfonamido)-4-phenylmethoxyphenoxy]propyl]amino]cyclohexyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1CCC(N(C[C@H](O)COC=2C=C(NS(C)(=O)=O)C(OCC=3C=CC=CC=3)=CC=2)CC=2C=CC=CC=2)CC1 ZAQZWXVNTWEFPU-TUTQLFIHSA-N 0.000 description 1
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- 239000011630 iodine Chemical group 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- GWHOCCRKGBKUQO-QAAWUVONSA-N n-[5-[(2s)-3-[benzyl-[4-[4-(4-benzylpiperidine-1-carbonyl)phenyl]cyclohexyl]amino]-2-hydroxypropoxy]-2-phenylmethoxyphenyl]methanesulfonamide Chemical compound C([C@H](O)COC=1C=C(C(=CC=1)OCC=1C=CC=CC=1)NS(=O)(=O)C)N(C1CCC(CC1)C=1C=CC(=CC=1)C(=O)N1CCC(CC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 GWHOCCRKGBKUQO-QAAWUVONSA-N 0.000 description 1
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- DDRCHUGHUHZNKZ-UHFFFAOYSA-N phenyl(piperidin-4-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCNCC1 DDRCHUGHUHZNKZ-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- AJOICBZPOILCTP-UHFFFAOYSA-N spiro[1,3-dihydroindene-2,4'-piperidine] Chemical compound C1C2=CC=CC=C2CC11CCNCC1 AJOICBZPOILCTP-UHFFFAOYSA-N 0.000 description 1
- PLWMBYBVKVUTBR-UHFFFAOYSA-N spiro[2,3-dihydro-1h-naphthalene-4,4'-piperidine] Chemical compound C1CCC2=CC=CC=C2C21CCNCC2 PLWMBYBVKVUTBR-UHFFFAOYSA-N 0.000 description 1
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- VMKJKEINOOXOCH-GOSISDBHSA-N tert-butyl n-methylsulfonyl-n-[5-[[(2s)-oxiran-2-yl]methoxy]-2-phenylmethoxyphenyl]carbamate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(N(C(=O)OC(C)(C)C)S(C)(=O)=O)=CC=1OC[C@@H]1CO1 VMKJKEINOOXOCH-GOSISDBHSA-N 0.000 description 1
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Classifications
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0206560A FR2840304B1 (fr) | 2002-05-29 | 2002-05-29 | Derives d'oxophenyl-cyclohexyl-propanolamine, leur preparation et leur application en therapeutique |
| PCT/FR2003/001579 WO2003099819A2 (fr) | 2002-05-29 | 2003-05-26 | Derives d'oxophenyl-cyclohexyl-propanolamine, leur preparation et leur application en therapeutique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005535599A JP2005535599A (ja) | 2005-11-24 |
| JP2005535599A5 JP2005535599A5 (enExample) | 2006-07-13 |
| JP4478013B2 true JP4478013B2 (ja) | 2010-06-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2004507476A Expired - Lifetime JP4478013B2 (ja) | 2002-05-29 | 2003-05-26 | オキソフェニルシクロヘキシルプロパノールアミン誘導体、それらの製造法、およびそれらの治療的適用 |
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| US (2) | US7625929B2 (enExample) |
| EP (1) | EP1511728B1 (enExample) |
| JP (1) | JP4478013B2 (enExample) |
| AT (1) | ATE356805T1 (enExample) |
| AU (1) | AU2003260569A1 (enExample) |
| DE (1) | DE60312511T2 (enExample) |
| FR (1) | FR2840304B1 (enExample) |
| WO (1) | WO2003099819A2 (enExample) |
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| FR2817257B1 (fr) * | 2000-11-30 | 2009-03-20 | Sanofi Synthelabo | Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant |
| EP2011490A1 (en) * | 2007-07-05 | 2009-01-07 | Sanofi-Aventis | Beta adrenergic receptor ligand derivatives for modulating apoptosis |
| FR2935141B1 (fr) * | 2008-08-21 | 2010-10-08 | Sanofi Aventis | Procede de preparation de l'ester ethylique de l'acide 4-[trans-4-[(phenylmethyl)-amino]cyclohexyl]benzoique et de son sel hemifumarate |
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| US6130217A (en) * | 1995-09-20 | 2000-10-10 | Pfizer Inc | Compounds enhancing antitumor activity of other cytotoxic agents |
| AU6050000A (en) * | 1999-07-22 | 2001-02-13 | Eli Lilly And Company | Improved method of treating type ii diabetes and obesity |
| CN1423637A (zh) * | 1999-12-16 | 2003-06-11 | 旭化成株式会社 | 新的取代的三环化合物 |
| FR2817257B1 (fr) * | 2000-11-30 | 2009-03-20 | Sanofi Synthelabo | Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant |
| US6770645B2 (en) * | 2001-03-16 | 2004-08-03 | Pfizer Inc. | Pharmaceutically active compounds |
-
2002
- 2002-05-29 FR FR0206560A patent/FR2840304B1/fr not_active Expired - Fee Related
-
2003
- 2003-05-26 WO PCT/FR2003/001579 patent/WO2003099819A2/fr not_active Ceased
- 2003-05-26 JP JP2004507476A patent/JP4478013B2/ja not_active Expired - Lifetime
- 2003-05-26 AT AT03755201T patent/ATE356805T1/de not_active IP Right Cessation
- 2003-05-26 US US10/515,093 patent/US7625929B2/en not_active Expired - Fee Related
- 2003-05-26 EP EP03755201A patent/EP1511728B1/fr not_active Expired - Lifetime
- 2003-05-26 AU AU2003260569A patent/AU2003260569A1/en not_active Abandoned
- 2003-05-26 DE DE60312511T patent/DE60312511T2/de not_active Expired - Lifetime
-
2009
- 2009-11-30 US US12/627,536 patent/US20100075986A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003260569A1 (en) | 2003-12-12 |
| US20050176731A1 (en) | 2005-08-11 |
| ATE356805T1 (de) | 2007-04-15 |
| WO2003099819A2 (fr) | 2003-12-04 |
| EP1511728B1 (fr) | 2007-03-14 |
| US20100075986A1 (en) | 2010-03-25 |
| FR2840304A1 (fr) | 2003-12-05 |
| DE60312511D1 (de) | 2007-04-26 |
| WO2003099819A3 (fr) | 2004-04-01 |
| US7625929B2 (en) | 2009-12-01 |
| EP1511728A2 (fr) | 2005-03-09 |
| AU2003260569A8 (en) | 2003-12-12 |
| FR2840304B1 (fr) | 2007-05-18 |
| DE60312511T2 (de) | 2007-11-29 |
| JP2005535599A (ja) | 2005-11-24 |
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