ZA200502222B - TriazaspiroÄ5.5Üundecane derivatives and drugs comprising the same as the active ingredient. - Google Patents
TriazaspiroÄ5.5Üundecane derivatives and drugs comprising the same as the active ingredient. Download PDFInfo
- Publication number
- ZA200502222B ZA200502222B ZA200502222A ZA200502222A ZA200502222B ZA 200502222 B ZA200502222 B ZA 200502222B ZA 200502222 A ZA200502222 A ZA 200502222A ZA 200502222 A ZA200502222 A ZA 200502222A ZA 200502222 B ZA200502222 B ZA 200502222B
- Authority
- ZA
- South Africa
- Prior art keywords
- triazaspiro
- hydroxy
- butyl
- dioxo
- phenylmethyl
- Prior art date
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- 239000004480 active ingredient Substances 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title description 11
- 229940079593 drug Drugs 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 207
- -1 4-(4- methylaminocarbonylphenoxy)phenyl Chemical group 0.000 claims description 66
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 150000001204 N-oxides Chemical class 0.000 claims description 29
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 28
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 28
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
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- 239000000126 substance Substances 0.000 claims description 10
- 239000005557 antagonist Substances 0.000 claims description 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 8
- 206010027476 Metastases Diseases 0.000 claims description 8
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 8
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- 206010063837 Reperfusion injury Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- AEWJBALBUWBZOP-LOYHVIPDSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxybenzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1OC AEWJBALBUWBZOP-LOYHVIPDSA-N 0.000 claims description 4
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- PNDVFZORZBQSBG-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclopentyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxybenzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1OC PNDVFZORZBQSBG-FQLXRVMXSA-N 0.000 claims description 3
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- IAMJMPDPPUCUSM-JWQCQUIFSA-N 4-[2-[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]ethoxy]-n-methylbenzamide Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CCOC1=CC=C(C(=O)NC)C=C1 IAMJMPDPPUCUSM-JWQCQUIFSA-N 0.000 claims description 2
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- YVOZVPPBHPQOQS-FIRIVFDPSA-N 4-[4-[[(3r)-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1-propyl-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxy-n,n-dimethylbenzamide Chemical compound N([C@@H](C(=O)N1CCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)N(C)C)C=C1OC YVOZVPPBHPQOQS-FIRIVFDPSA-N 0.000 claims 1
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- 238000004809 thin layer chromatography Methods 0.000 description 539
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 506
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- IVKMEQQABRPKMN-ZNBLAKOKSA-N 4-[4-[4-[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]butoxy]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CCCCOC(C=C1)=CC=C1OC1=CC=C(C(=O)NC)C=C1 IVKMEQQABRPKMN-ZNBLAKOKSA-N 0.000 description 1
- FJYRVRSRAMLEAY-PQQSRXGVSA-N 4-[4-[[(3r)-1-(2-cyanoethyl)-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1OC(C=C1)=CC=C1CN1CCC2(C(N[C@@H](C(=O)N2CCC#N)[C@H](O)C2CCCCC2)=O)CC1 FJYRVRSRAMLEAY-PQQSRXGVSA-N 0.000 description 1
- KJSINFRZIWZCFX-XBPPRYKJSA-N 4-[4-[[(3r)-1-(cyclobutylmethyl)-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1OC(C=C1)=CC=C1CN1CCC2(C(N[C@@H](C(=O)N2CC2CCC2)[C@H](O)C2CCCCC2)=O)CC1 KJSINFRZIWZCFX-XBPPRYKJSA-N 0.000 description 1
- YYZARCPGXOGDCG-GAQUOPITSA-N 4-[4-[[(3r)-1-but-3-enyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1OC(C=C1)=CC=C1CN1CCC2(C(N[C@@H](C(=O)N2CCC=C)[C@H](O)C2CCCCC2)=O)CC1 YYZARCPGXOGDCG-GAQUOPITSA-N 0.000 description 1
- CLWHVXNOWAYHAA-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-1-hydroxy-2-(oxan-4-yl)ethyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)CC2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 CLWHVXNOWAYHAA-PQQSRXGVSA-N 0.000 description 1
- YMFVEAGLUYIQDN-QMDRZIQZSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-1-hydroxy-2-methyl-2-phenylpropyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C(C)(C)C=2C=CC=CC=2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NC)C=C1 YMFVEAGLUYIQDN-QMDRZIQZSA-N 0.000 description 1
- MJCOVCCCHQXRDN-MFABWLECSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-1-hydroxy-2-methyl-2-phenylpropyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C(C)(C)C=2C=CC=CC=2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 MJCOVCCCHQXRDN-MFABWLECSA-N 0.000 description 1
- TWLMCFAUAUSXIT-CNZCJKERSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-1-hydroxy-3-methylbutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)CC(C)C)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC(=CC=3)C(O)=O)=CC=2)CC1 TWLMCFAUAUSXIT-CNZCJKERSA-N 0.000 description 1
- HOSIXNOOEQXNEM-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C=C(OC)C(C(O)=O)=CC=3)=CC=2)CC1 HOSIXNOOEQXNEM-PQQSRXGVSA-N 0.000 description 1
- IFJJSAVQXTXUEL-ROJLCIKYSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxy-n-(2-methoxyethyl)benzamide Chemical compound CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C(=CC(=CC=3)C(=O)NCCOC)OC)=CC=2)CC1 IFJJSAVQXTXUEL-ROJLCIKYSA-N 0.000 description 1
- YBFPDSSCNNUHEN-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxybenzoic acid;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C(=CC(=CC=3)C(O)=O)OC)=CC=2)CC1 YBFPDSSCNNUHEN-PQQSRXGVSA-N 0.000 description 1
- NWMOXSIFCGSFAA-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methylbenzoic acid;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C(=CC(=CC=3)C(O)=O)C)=CC=2)CC1 NWMOXSIFCGSFAA-PQQSRXGVSA-N 0.000 description 1
- BYPZVRVDQPXXFM-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC(=CC=3)C(=O)NC)=CC=2)CC1 BYPZVRVDQPXXFM-PQQSRXGVSA-N 0.000 description 1
- VOYSXHJRXVGQNV-LTRMXRMOSA-N 4-[4-[[(3r)-1-butyl-3-[(1r)-2-ethyl-1-hydroxybutyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzenesulfonamide;hydrochloride Chemical compound Cl.CCCCN1C(=O)[C@@H]([C@H](O)C(CC)CC)NC(=O)C11CCN(CC=2C=CC(OC=3C=CC(=CC=3)S(N)(=O)=O)=CC=2)CC1 VOYSXHJRXVGQNV-LTRMXRMOSA-N 0.000 description 1
- FRDOAIGJRCXLHX-XBPPRYKJSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-2,3-dihydro-1,4-benzodioxin-6-yl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C=2C=C3OCCOC3=CC=2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 FRDOAIGJRCXLHX-XBPPRYKJSA-N 0.000 description 1
- JWFVTUJGBKHFKD-LTRMXRMOSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclobutyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NC)C=C1 JWFVTUJGBKHFKD-LTRMXRMOSA-N 0.000 description 1
- IUWVDXJFXGAQBQ-CNZCJKERSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclobutyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 IUWVDXJFXGAQBQ-CNZCJKERSA-N 0.000 description 1
- IJROUCAXVJLKGO-GAQUOPITSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-2-(trifluoromethyl)phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1C(F)(F)F)=CC=C1OC1=CC=C(C(=O)NC)C=C1 IJROUCAXVJLKGO-GAQUOPITSA-N 0.000 description 1
- KJSXESQOSWXLLA-JOVGIXRXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]-3,5-dimethylphenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C(=C1)C)=C(C)C=C1OC1=CC=C(C(=O)NC)C=C1 KJSXESQOSWXLLA-JOVGIXRXSA-N 0.000 description 1
- ATYJUGKYKXRFBY-LOYHVIPDSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3,5-dimethylbenzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=C(C)C=C(C(O)=O)C=C1C ATYJUGKYKXRFBY-LOYHVIPDSA-N 0.000 description 1
- WTCZYXCAENPLPY-XBPPRYKJSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-ethoxybenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1OCC WTCZYXCAENPLPY-XBPPRYKJSA-N 0.000 description 1
- UMPCTYJCYDRVJC-GAQUOPITSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxybenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1OC UMPCTYJCYDRVJC-GAQUOPITSA-N 0.000 description 1
- RJHUQUNYIGWWRC-XBPPRYKJSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxybenzonitrile;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C#N)C=C1OC RJHUQUNYIGWWRC-XBPPRYKJSA-N 0.000 description 1
- UKPUOOMIFYZPSJ-GAQUOPITSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methylbenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1C UKPUOOMIFYZPSJ-GAQUOPITSA-N 0.000 description 1
- QNNBMSGFNQRUEH-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 QNNBMSGFNQRUEH-PQQSRXGVSA-N 0.000 description 1
- KFEAARJNKQNWQS-LTRMXRMOSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclopent-3-en-1-yl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-2-hydroxybenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CC=CC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(O)=C1 KFEAARJNKQNWQS-LTRMXRMOSA-N 0.000 description 1
- QLJPPRKFYFOSFN-GAQUOPITSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclopent-3-en-1-yl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-ethoxybenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CC=CC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1OCC QLJPPRKFYFOSFN-GAQUOPITSA-N 0.000 description 1
- FXXGAKSPPYYLDT-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclopent-3-en-1-yl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methylbenzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CC=CC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1C FXXGAKSPPYYLDT-FQLXRVMXSA-N 0.000 description 1
- YPWNXJNRPXRAKH-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclopentyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3,5-dimethylbenzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=C(C)C=C(C(O)=O)C=C1C YPWNXJNRPXRAKH-PQQSRXGVSA-N 0.000 description 1
- HNHOQLFRHJPFPB-LTRMXRMOSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-furan-3-yl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2=COC=C2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NC)C=C1 HNHOQLFRHJPFPB-LTRMXRMOSA-N 0.000 description 1
- DXACXHGTPHJLOC-JOVGIXRXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxy-n-(2-methoxyethyl)benzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NCCOC)C=C1OC DXACXHGTPHJLOC-JOVGIXRXSA-N 0.000 description 1
- TXRLYCBIFLNQMR-CZNDPXEESA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxy-n-(2-methylpropyl)benzamide Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NCC(C)C)C=C1OC TXRLYCBIFLNQMR-CZNDPXEESA-N 0.000 description 1
- HBVZHVGFNXORCU-JOVGIXRXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-3-methoxy-n-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NC(C)C)C=C1OC HBVZHVGFNXORCU-JOVGIXRXSA-N 0.000 description 1
- IMPMVRWIADSZNZ-CZNDPXEESA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-(2,2-dimethylpropyl)-3-methoxybenzamide Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NCC(C)(C)C)C=C1OC IMPMVRWIADSZNZ-CZNDPXEESA-N 0.000 description 1
- TYDQLBFSQKGMLI-JOVGIXRXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-(2-methylpropyl)benzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NCC(C)C)C=C1 TYDQLBFSQKGMLI-JOVGIXRXSA-N 0.000 description 1
- DYPKKYSRQIQTBB-PQQSRXGVSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-hydroxy(oxan-4-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzonitrile;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCOCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C#N)C=C1 DYPKKYSRQIQTBB-PQQSRXGVSA-N 0.000 description 1
- SLFNTGSEFIXGPG-RCZDCTQYSA-N 4-[4-[[(3r)-3-[(r)-cyclohexyl(hydroxy)methyl]-1-(3-hydroxybutyl)-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCC(O)C)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 SLFNTGSEFIXGPG-RCZDCTQYSA-N 0.000 description 1
- HCXPQOZBGQWUBN-JOVGIXRXSA-N 4-[4-[[(3r)-3-[(r)-cyclohexyl(hydroxy)methyl]-1-[(1-oxidopyridin-1-ium-3-yl)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1OC(C=C1)=CC=C1CN1CCC2(C(N[C@@H](C(=O)N2CC=2C=[N+]([O-])C=CC=2)[C@H](O)C2CCCCC2)=O)CC1 HCXPQOZBGQWUBN-JOVGIXRXSA-N 0.000 description 1
- PMLIEEMDSACCFK-ZNBLAKOKSA-N 4-[4-[[(3r)-3-[(r)-cyclohexyl(hydroxy)methyl]-1-heptyl-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]-n-methylbenzamide;hydrochloride Chemical compound Cl.N([C@@H](C(=O)N1CCCCCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(=O)NC)C=C1 PMLIEEMDSACCFK-ZNBLAKOKSA-N 0.000 description 1
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- QKRLRVIWZXQILD-XBPPRYKJSA-N prop-2-enyl n-[2-[(3r)-3-[(r)-cyclohexyl(hydroxy)methyl]-9-[[4-[4-(methylcarbamoyl)phenoxy]phenyl]methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-1-yl]ethyl]carbamate;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1OC(C=C1)=CC=C1CN1CCC2(C(N[C@@H](C(=O)N2CCNC(=O)OCC=C)[C@H](O)C2CCCCC2)=O)CC1 QKRLRVIWZXQILD-XBPPRYKJSA-N 0.000 description 1
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- PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical compound C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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WO1998031364A1 (en) * | 1997-01-21 | 1998-07-23 | Merck & Co., Inc. | 3,3-disubstituted piperidines as modulators of chemokine receptor activity |
US6288083B1 (en) * | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
JP4721087B2 (ja) * | 1999-12-03 | 2011-07-13 | 小野薬品工業株式会社 | トリアザスピロ[5.5]ウンデカン誘導体およびそれらを有効成分とする薬剤 |
WO2002074769A1 (fr) * | 2001-03-19 | 2002-09-26 | Ono Pharmaceutical Co., Ltd. | Medicaments contenant comme principe actif des derives du triazaspiro [5.5] undecane |
ES2266452T3 (es) * | 2001-03-19 | 2007-03-01 | Ono Pharmaceutical Co., Ltd. | Derivados de triazaespiro (5.5) undecano y composiciones farmaceuticas que los contienen como ingrediente activo. |
JP2002348288A (ja) * | 2001-05-28 | 2002-12-04 | Ono Pharmaceut Co Ltd | スピロ複素環誘導体およびそれらを有効成分とする薬剤 |
CN1571671A (zh) * | 2001-10-23 | 2005-01-26 | 小野药品工业株式会社 | 含三氮杂螺[5.5]十一烷衍生物与细胞色素p450同工酶3a4抑制剂和/或p-糖蛋白抑制剂组合的药剂 |
WO2003104233A1 (en) * | 2002-06-07 | 2003-12-18 | Altana Pharma Ag | 4,5-dihydro-imidazo (4,5,1-ij) quinolin-6-ones derivatives and their use as poly (adp-ribosyl) transferase (parp) inhibitors |
AU2003266152A1 (en) * | 2002-09-13 | 2004-04-30 | University Of Maryland Biotechnology | COMPOSITIONS FOR INDUCING INCREASED LEVELS OF Beta-CHEMOKINES AND METHODS OF USE THEREFOR |
EP1541573A4 (en) * | 2002-09-18 | 2007-05-02 | Ono Pharmaceutical Co | NEW CRYSTALS OF DERIVATIVE TRIAZASPIRO 5.5 | UNDECANES |
US7556806B2 (en) * | 2002-10-11 | 2009-07-07 | University Of Maryland Biotechnology Institute | Carbohydrate-based synthetic vaccines for HIV |
US20060019977A1 (en) * | 2002-10-18 | 2006-01-26 | Ono Pharmaceutical Co., Ltd. | Spiroheterocyclic derivative compounds and drugs comprising the compound as the active ingredient |
US7498323B2 (en) * | 2003-04-18 | 2009-03-03 | Ono Pharmaceuticals Co., Ltd. | Spiro-piperidine compounds and medicinal use thereof |
JPWO2004098638A1 (ja) * | 2003-05-06 | 2006-07-13 | 小野薬品工業株式会社 | エフェクター細胞機能阻害剤 |
WO2005001027A2 (en) * | 2003-05-16 | 2005-01-06 | University Of Maryland Biotechnology Institute | Compositions for down-regulation of ccr5 expression and methods of use therefor |
CA2573951A1 (en) * | 2003-07-18 | 2005-01-27 | Virochem Pharma Inc. | Spiro compounds and methods for the modulation of chemokine receptor activity |
IL157398A0 (en) * | 2003-08-14 | 2004-02-19 | Hadasit Med Res Service | Pharmaceutical compositions comprising ccr5 antagonists |
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- 2003-09-17 WO PCT/JP2003/011834 patent/WO2004026873A1/ja not_active Application Discontinuation
- 2003-09-17 RU RU2005111225/04A patent/RU2005111225A/ru not_active Application Discontinuation
- 2003-09-17 KR KR1020057004600A patent/KR20050057408A/ko not_active Application Discontinuation
- 2003-09-17 JP JP2004537582A patent/JPWO2004026873A1/ja not_active Withdrawn
- 2003-09-17 AU AU2003272879A patent/AU2003272879A1/en not_active Abandoned
- 2003-09-17 PL PL03376154A patent/PL376154A1/xx not_active Application Discontinuation
- 2003-09-17 CA CA002497903A patent/CA2497903A1/en not_active Abandoned
- 2003-09-17 US US10/527,435 patent/US20050267114A1/en not_active Abandoned
- 2003-09-17 EP EP03753933A patent/EP1541574A4/en not_active Withdrawn
- 2003-09-17 MX MXPA05002771A patent/MXPA05002771A/es unknown
- 2003-09-17 TW TW092125573A patent/TW200413372A/zh unknown
- 2003-09-17 BR BR0314304-0A patent/BR0314304A/pt not_active IP Right Cessation
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2005
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EP1541574A4 (en) | 2007-06-20 |
TW200413372A (en) | 2004-08-01 |
BR0314304A (pt) | 2005-07-26 |
CA2497903A1 (en) | 2004-04-01 |
CN1688577A (zh) | 2005-10-26 |
NO20051379L (no) | 2005-06-17 |
WO2004026873A1 (ja) | 2004-04-01 |
EP1541574A1 (en) | 2005-06-15 |
KR20050057408A (ko) | 2005-06-16 |
AU2003272879A1 (en) | 2004-04-08 |
MXPA05002771A (es) | 2005-06-06 |
PL376154A1 (en) | 2005-12-27 |
US20050267114A1 (en) | 2005-12-01 |
RU2005111225A (ru) | 2005-08-27 |
JPWO2004026873A1 (ja) | 2006-01-19 |
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