JP2004519484A5 - - Google Patents

Info

Publication number

JP2004519484A5

JP2004519484A5 JP2002569121A JP2002569121A JP2004519484A5 JP 2004519484 A5 JP2004519484 A5 JP 2004519484A5 JP 2002569121 A JP2002569121 A JP 2002569121A JP 2002569121 A JP2002569121 A JP 2002569121A JP 2004519484 A5 JP2004519484 A5 JP 2004519484A5

Authority

JP

Japan

Prior art keywords

phenyl

alkyl

methyl

hydroxy

pharmaceutical composition

Prior art date

2002-02-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 125000000217 alkyl group Chemical group 0.000 claims 12
• 239000000203 mixture Substances 0.000 claims 12
• 239000008194 pharmaceutical composition Substances 0.000 claims 12
• -1 YM-49244 Chemical compound 0.000 claims 7
• 239000013543 active substance Substances 0.000 claims 7
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 4
• 238000009472 formulation Methods 0.000 claims 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• XPNMCDYOYIKVGB-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 XPNMCDYOYIKVGB-CONSDPRKSA-N 0.000 claims 3
• ATALOFNDEOCMKK-OITMNORJSA-N aprepitant Chemical compound O([C@@H]([C@@H]1C=2C=CC(F)=CC=2)O[C@H](C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCN1CC1=NNC(=O)N1 ATALOFNDEOCMKK-OITMNORJSA-N 0.000 claims 3
• 239000000843 powder Substances 0.000 claims 3
• 239000003380 propellant Substances 0.000 claims 3
• HUTHJVYJUPXHDF-DEOSSOPVSA-N (2s)-n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(cyclopropylmethyl)piperazin-1-yl]-n-methyl-2-phenylacetamide Chemical compound O=C([C@@H](N1CCN(CC2CC2)CC1)C=1C=CC=CC=1)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HUTHJVYJUPXHDF-DEOSSOPVSA-N 0.000 claims 2
• XILNRORTJVDYRH-HKUYNNGSSA-N (2s,3s)-n-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)N2C(=NN=N2)C(F)(F)F)=CC=CC=C1 XILNRORTJVDYRH-HKUYNNGSSA-N 0.000 claims 2
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 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 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
• 108010092101 MEN 11420 Proteins 0.000 claims 2
• 239000000443 aerosol Substances 0.000 claims 2
• 125000004429 atom Chemical group 0.000 claims 2
• NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 2
• NGCNKEZHGRXHNL-WVWQGFTISA-N n-[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[(1s,4s,7s,10s,13s,16s)-13-benzyl-16-(1h-indol-3-ylmethyl)-7-(2-methylpropyl)-3,6,9,12,15,18,20-heptaoxo-2,5,8,11,14,17,21-heptazabicyclo[8.8.4]docosan-4-yl]acetamide Chemical compound C([C@H]1C(=O)N[C@H]2CC(=O)NC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC2=O)C(=O)N[C@H](C(N1)=O)CC(C)C)C(=O)N[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O NGCNKEZHGRXHNL-WVWQGFTISA-N 0.000 claims 2
• XMAVVCOSFCHLNQ-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-[2-hydroxyethyl(3-hydroxypropyl)amino]piperidin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CC(N(CCO)CCCO)CCN1C(C=1C=CC=CC=1)C(=O)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XMAVVCOSFCHLNQ-UHFFFAOYSA-N 0.000 claims 2
• NJGRIQCLLOJEHU-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-[3-hydroxypropyl(methyl)amino]piperidin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CC(N(CCCO)C)CCN1C(C=1C=CC=CC=1)C(=O)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NJGRIQCLLOJEHU-UHFFFAOYSA-N 0.000 claims 2
• ASBGMDZIWCEVNG-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-[cyclopropylmethyl(methyl)amino]piperidin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CN(C(C(=O)N(C)CCC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=CC=CC=2)CCC1N(C)CC1CC1 ASBGMDZIWCEVNG-UHFFFAOYSA-N 0.000 claims 2
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
• PGKXDIMONUAMFR-AREMUKBSSA-N saredutant Chemical compound C([C@H](CN(C)C(=O)C=1C=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1(NC(C)=O)C1=CC=CC=C1 PGKXDIMONUAMFR-AREMUKBSSA-N 0.000 claims 2
• 239000000725 suspension Substances 0.000 claims 2
• LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
• LDXQLWNPGRANTO-GOSISDBHSA-N (9r)-7-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-methyl-5-(4-methylphenyl)-8,9,10,11-tetrahydro-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione Chemical compound C([C@H](CN(CC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=O)C)CN(C(C2=NC=CC=C22)=O)C1=C2C1=CC=C(C)C=C1 LDXQLWNPGRANTO-GOSISDBHSA-N 0.000 claims 1
• NQHFSECYQAQZBN-LSYPWIJNSA-M 1-[(3s)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]octan-1-yl)ethyl]piperidin-1-yl]-2-(3-propan-2-yloxyphenyl)ethanone;chloride Chemical compound [Cl-].CC(C)OC1=CC=CC(CC(=O)N2C[C@](CC[N+]34CCC(CC3)(CC4)C=3C=CC=CC=3)(CCC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 NQHFSECYQAQZBN-LSYPWIJNSA-M 0.000 claims 1
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical class C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
• PQRLQZNKDQQMBC-LSYPWIJNSA-M benzenesulfonate;1-[(3s)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]octan-1-yl)ethyl]piperidin-1-yl]-2-(3-propan-2-yloxyphenyl)ethanone Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1.CC(C)OC1=CC=CC(CC(=O)N2C[C@](CC[N+]34CCC(CC3)(CC4)C=3C=CC=CC=3)(CCC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 PQRLQZNKDQQMBC-LSYPWIJNSA-M 0.000 claims 1
• 239000001273 butane Chemical class 0.000 claims 1
• 239000000812 cholinergic antagonist Substances 0.000 claims 1
• 150000002016 disaccharides Chemical class 0.000 claims 1
• 201000010099 disease Diseases 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 150000004676 glycans Chemical class 0.000 claims 1
• 150000005826 halohydrocarbons Chemical class 0.000 claims 1
• 150000004677 hydrates Chemical class 0.000 claims 1
• 229930195733 hydrocarbon Natural products 0.000 claims 1
• 150000002430 hydrocarbons Chemical class 0.000 claims 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
• 230000002757 inflammatory effect Effects 0.000 claims 1
• OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims 1
• 239000001282 iso-butane Substances 0.000 claims 1
• 229950005286 lanepitant Drugs 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
• 150000002772 monosaccharides Chemical group 0.000 claims 1
• JXDKAWGCUBTYFX-BMPTZRATSA-N n-[(1s,2r)-2-[[(2r)-2-[methyl-[2-(4-methylphenyl)acetyl]amino]-3-naphthalen-2-ylpropanoyl]amino]cyclohexyl]-1h-indole-3-carboxamide Chemical compound CN([C@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@H]1[C@H](CCCC1)NC(=O)C=1C2=CC=CC=C2NC=1)C(=O)CC1=CC=C(C)C=C1 JXDKAWGCUBTYFX-BMPTZRATSA-N 0.000 claims 1
• CVXJAPZTZWLRBP-MUUNZHRXSA-N n-[(2r)-1-[acetyl-[(2-methoxyphenyl)methyl]amino]-3-(1h-indol-3-yl)propan-2-yl]-2-(4-piperidin-1-ylpiperidin-1-yl)acetamide Chemical compound COC1=CC=CC=C1CN(C(C)=O)C[C@H](NC(=O)CN1CCC(CC1)N1CCCCC1)CC1=CNC2=CC=CC=C12 CVXJAPZTZWLRBP-MUUNZHRXSA-N 0.000 claims 1
• IGAXDMFXJYIUIV-XIFFEERXSA-N n-[1-[[(2s)-1-[benzyl(methyl)amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]carbamoyl]cyclohexyl]-1h-indole-3-carboxamide Chemical compound O=C([C@H](CC=1C=C2C=CC=CC2=CC=1)NC(=O)C1(CCCCC1)NC(=O)C=1C2=CC=CC=C2NC=1)N(C)CC1=CC=CC=C1 IGAXDMFXJYIUIV-XIFFEERXSA-N 0.000 claims 1
• VSKQRMHRWDXZPR-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(1,3-dihydroxypropan-2-ylamino)piperidin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CC(NC(CO)CO)CCN1C(C=1C=CC=CC=1)C(=O)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VSKQRMHRWDXZPR-UHFFFAOYSA-N 0.000 claims 1
• GIALVDJQVZLCEJ-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-[cyclopropylmethyl(3-hydroxypropyl)amino]piperidin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CC(N(CCCO)CC2CC2)CCN1C(C=1C=CC=CC=1)C(=O)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GIALVDJQVZLCEJ-UHFFFAOYSA-N 0.000 claims 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
• 229950000640 nepadutant Drugs 0.000 claims 1
• 108010066363 neuronorm Proteins 0.000 claims 1
• 229950011147 nolpitantium besilate Drugs 0.000 claims 1
• 230000000414 obstructive effect Effects 0.000 claims 1
• 150000002482 oligosaccharides Polymers 0.000 claims 1
• NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical class CC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1 NVOYVOBDTVTBDX-PMEUIYRNSA-N 0.000 claims 1
• 229920001282 polysaccharide Polymers 0.000 claims 1
• 239000005017 polysaccharide Substances 0.000 claims 1
• 239000001294 propane Chemical class 0.000 claims 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
• 125000003373 pyrazinyl group Chemical group 0.000 claims 1
• 125000002098 pyridazinyl group Chemical group 0.000 claims 1
• 125000004076 pyridyl group Chemical group 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 239000002464 receptor antagonist Substances 0.000 claims 1
• 229940044551 receptor antagonist Drugs 0.000 claims 1
• 210000002345 respiratory system Anatomy 0.000 claims 1
• 150000003839 salts Chemical class 0.000 claims 1
• 229950004387 saredutant Drugs 0.000 claims 1
• 239000012453 solvate Substances 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• 150000005846 sugar alcohols Polymers 0.000 claims 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1