ZA200401882B - Novel compounds and compositions as cathepsin inhibitors. - Google Patents

Novel compounds and compositions as cathepsin inhibitors. Download PDF

Info

Publication number: ZA200401882B
Authority: ZA; South Africa
Prior art keywords: alkyl; hetero; aryl; cycloalkyl; cos
Prior art date: 2001-09-14

Application number

ZA200401882A

Other languages

English (en)

Inventor

Michael Graupe

David J Aldous

Jame T Palmer

Sukanthini Thurairatnam

Original Assignee

Aventis Pharma Inc

Axys Pharm Inc

Priority date (The priority date 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 date listed.)

2001-09-14

Filing date

2004-03-08

Publication date

2005-04-18

2004-03-08 Application filed by Aventis Pharma Inc, Axys Pharm Inc filed Critical Aventis Pharma Inc

2005-04-18 Publication of ZA200401882B publication Critical patent/ZA200401882B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 79
239000000203 mixture Substances 0.000 title claims description 34
108010084457 Cathepsins Proteins 0.000 title description 2
102000005600 Cathepsins Human genes 0.000 title description 2
239000003112 inhibitor Substances 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims description 361
-1 oyridine3-yl Chemical group 0.000 claims description 273
125000005842 heteroatom Chemical group 0.000 claims description 153
125000003118 aryl group Chemical group 0.000 claims description 131
125000000753 cycloalkyl group Chemical group 0.000 claims description 85
239000001257 hydrogen Substances 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 65
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
125000005843 halogen group Chemical group 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
201000010099 disease Diseases 0.000 claims description 24
150000001204 N-oxides Chemical class 0.000 claims description 21
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
229940002612 prodrug Drugs 0.000 claims description 18
239000000651 prodrug Substances 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 14
125000002723 alicyclic group Chemical group 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 12
STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 11
230000007170 pathology Effects 0.000 claims description 11
125000001118 alkylidene group Chemical group 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
108090000613 Cathepsin S Proteins 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
102100035654 Cathepsin S Human genes 0.000 claims description 7
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
239000005977 Ethylene Substances 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
UFHXXKMVPZBVTM-UHFFFAOYSA-N 2-(4-amino-3-oxoazepan-1-yl)sulfonylbenzonitrile Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC=C1C#N UFHXXKMVPZBVTM-UHFFFAOYSA-N 0.000 claims description 2
UDQSDFPIODEIDH-UHFFFAOYSA-N 2-methylpropyl 4-amino-3-oxoazepane-1-carboxylate Chemical compound CC(C)COC(=O)N1CCCC(N)C(=O)C1 UDQSDFPIODEIDH-UHFFFAOYSA-N 0.000 claims description 2
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 2
ROVXRNQOGCLZEF-UHFFFAOYSA-N 4-amino-1-(3,4-dimethoxyphenyl)sulfonylazepan-3-one Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1CC(=O)C(N)CCC1 ROVXRNQOGCLZEF-UHFFFAOYSA-N 0.000 claims description 2
VBRZTRVCXPRKHF-UHFFFAOYSA-N 4-amino-1-(benzenesulfonyl)azepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC=C1 VBRZTRVCXPRKHF-UHFFFAOYSA-N 0.000 claims description 2
CFYNKSMQENUXBD-UHFFFAOYSA-N 4-amino-1-benzoylpiperidin-3-one Chemical compound C1C(=O)C(N)CCN1C(=O)C1=CC=CC=C1 CFYNKSMQENUXBD-UHFFFAOYSA-N 0.000 claims description 2
HITZBUYSEUYPAX-UHFFFAOYSA-N 4-amino-1-benzoylpyrrolidin-3-one Chemical compound C1C(=O)C(N)CN1C(=O)C1=CC=CC=C1 HITZBUYSEUYPAX-UHFFFAOYSA-N 0.000 claims description 2
RPAUJFPZVNMLGH-UHFFFAOYSA-N 4-amino-1-benzylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1CC1=CC=CC=C1 RPAUJFPZVNMLGH-UHFFFAOYSA-N 0.000 claims description 2
FPHKMPZHZFUZPH-UHFFFAOYSA-N 4-amino-1-benzylpiperidin-3-one Chemical compound C1C(=O)C(N)CCN1CC1=CC=CC=C1 FPHKMPZHZFUZPH-UHFFFAOYSA-N 0.000 claims description 2
YDZTXVJDWKNZPG-UHFFFAOYSA-N 4-amino-1-benzylpyrrolidin-3-one Chemical compound C1C(=O)C(N)CN1CC1=CC=CC=C1 YDZTXVJDWKNZPG-UHFFFAOYSA-N 0.000 claims description 2
LDSRSNPGCKDESN-UHFFFAOYSA-N 4-amino-1-naphthalen-1-ylsulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC2=CC=CC=C12 LDSRSNPGCKDESN-UHFFFAOYSA-N 0.000 claims description 2
ZMAILSBNDKAJFT-UHFFFAOYSA-N 4-amino-1-pyridin-2-ylsulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CC=N1 ZMAILSBNDKAJFT-UHFFFAOYSA-N 0.000 claims description 2
RUBLFSUOLZEFIO-UHFFFAOYSA-N 4-amino-1-pyrrolidin-1-ylsulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)N1CCCC1 RUBLFSUOLZEFIO-UHFFFAOYSA-N 0.000 claims description 2
LSPBQXJZUFXYNN-UHFFFAOYSA-N 4-amino-1-thiophen-2-ylsulfonylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1S(=O)(=O)C1=CC=CS1 LSPBQXJZUFXYNN-UHFFFAOYSA-N 0.000 claims description 2
ICHUXGCWAYUATC-UHFFFAOYSA-N 4-amino-n,n-dimethyl-3-oxoazepane-1-carboxamide Chemical compound CN(C)C(=O)N1CCCC(N)C(=O)C1 ICHUXGCWAYUATC-UHFFFAOYSA-N 0.000 claims description 2
OAMWDDNZMBZCOS-UHFFFAOYSA-N 4-amino-n-benzyl-3-oxoazepane-1-carboxamide Chemical compound C1C(=O)C(N)CCCN1C(=O)NCC1=CC=CC=C1 OAMWDDNZMBZCOS-UHFFFAOYSA-N 0.000 claims description 2
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 3
QICCAKGBTMTXSU-UHFFFAOYSA-N n-[1-[[1-(benzenesulfonyl)-4-oxopyrrolidin-3-yl]amino]-3-benzylsulfonyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(NC(=O)N1CCOCC1)C(=O)NC(C(C1)=O)CN1S(=O)(=O)C1=CC=CC=C1 QICCAKGBTMTXSU-UHFFFAOYSA-N 0.000 claims 2
KPZHSRPORHPODY-UHFFFAOYSA-N 2-amino-1-methylsulfonylazepan-3-one Chemical compound CS(=O)(=O)N1CCCCC(=O)C1N KPZHSRPORHPODY-UHFFFAOYSA-N 0.000 claims 1
FGTABFMYEAECLU-UHFFFAOYSA-N 4-amino-1-(5-methylhexyl)pyrrolidin-3-one Chemical compound CC(C)CCCCN1CC(N)C(=O)C1 FGTABFMYEAECLU-UHFFFAOYSA-N 0.000 claims 1
YZHNULGGDXVGON-UHFFFAOYSA-N 4-amino-1-(pyrrolidine-1-carbonyl)azepan-3-one Chemical compound C1C(=O)C(N)CCCN1C(=O)N1CCCC1 YZHNULGGDXVGON-UHFFFAOYSA-N 0.000 claims 1
DEGURJZGSQVFSW-UHFFFAOYSA-N 4-amino-1-benzoylazepan-3-one Chemical compound C1C(=O)C(N)CCCN1C(=O)C1=CC=CC=C1 DEGURJZGSQVFSW-UHFFFAOYSA-N 0.000 claims 1
125000000815 N-oxide group Chemical group 0.000 claims 1
BRENAYZEMJPHQA-UHFFFAOYSA-N [3-[[3-benzylsulfonyl-2-(morpholine-4-carbonylamino)propanoyl]amino]-4-oxoazetidin-2-yl] acetate Chemical compound CC(=O)OC1NC(=O)C1NC(=O)C(NC(=O)N1CCOCC1)CS(=O)(=O)CC1=CC=CC=C1 BRENAYZEMJPHQA-UHFFFAOYSA-N 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
VXYRWYVHSLFFOR-UHFFFAOYSA-N benzyl 4-[[3-benzylsulfonyl-2-(morpholine-4-carbonylamino)propanoyl]amino]-3-oxoazepane-1-carboxylate Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(NC(=O)N1CCOCC1)C(=O)NC(C(C1)=O)CCCN1C(=O)OCC1=CC=CC=C1 VXYRWYVHSLFFOR-UHFFFAOYSA-N 0.000 claims 1
MZYVYLDADHXZSQ-UHFFFAOYSA-N benzyl n-[5-[[3-benzylsulfonyl-2-(morpholine-4-carbonylamino)propanoyl]amino]-6-[(4-methoxyphenyl)sulfamoyl]hexyl]carbamate Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)CC(NC(=O)C(CS(=O)(=O)CC=1C=CC=CC=1)NC(=O)N1CCOCC1)CCCCNC(=O)OCC1=CC=CC=C1 MZYVYLDADHXZSQ-UHFFFAOYSA-N 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
HQAXXYUOHOUKNB-INIZCTEOSA-N n-[(2r)-3-benzylsulfonyl-1-[(3,4-dioxocyclopentyl)amino]-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound O=C([C@H](CS(=O)(=O)CC=1C=CC=CC=1)NC(=O)N1CCOCC1)NC1CC(=O)C(=O)C1 HQAXXYUOHOUKNB-INIZCTEOSA-N 0.000 claims 1
LJLWUYTUSBYOEI-SFHVURJKSA-N n-[(2r)-3-benzylsulfonyl-1-oxo-1-[(6-oxocyclohexen-1-yl)amino]propan-2-yl]morpholine-4-carboxamide Chemical compound O=C([C@H](CS(=O)(=O)CC=1C=CC=CC=1)NC(=O)N1CCOCC1)NC1=CCCCC1=O LJLWUYTUSBYOEI-SFHVURJKSA-N 0.000 claims 1
HJOVLRHETNMCSH-UHFFFAOYSA-N n-[1-[(1-benzoyl-4-oxopyrrolidin-3-yl)amino]-3-benzylsulfonyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(NC(=O)N1CCOCC1)C(=O)NC(C(C1)=O)CN1C(=O)C1=CC=CC=C1 HJOVLRHETNMCSH-UHFFFAOYSA-N 0.000 claims 1
KOWFSLUMPQTFAR-UHFFFAOYSA-N n-[1-[[3-(benzenesulfonamido)-2-oxopropyl]amino]-3-benzylsulfonyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCC(=O)CNC(=O)C(NC(=O)N1CCOCC1)CS(=O)(=O)CC1=CC=CC=C1 KOWFSLUMPQTFAR-UHFFFAOYSA-N 0.000 claims 1
VYPMJWFQAGNGBH-UHFFFAOYSA-N n-[1-[[3-(benzylamino)-2,3-dioxopropyl]amino]-3-benzylsulfonyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1CNC(=O)C(=O)CNC(=O)C(NC(=O)N1CCOCC1)CS(=O)(=O)CC1=CC=CC=C1 VYPMJWFQAGNGBH-UHFFFAOYSA-N 0.000 claims 1
HJTHDOZBXZPTFK-UHFFFAOYSA-N n-[1-[[6-amino-1-[(4-methoxyphenyl)sulfamoyl]hexan-2-yl]amino]-3-benzylsulfonyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)CC(CCCCN)NC(=O)C(NC(=O)N1CCOCC1)CS(=O)(=O)CC1=CC=CC=C1 HJTHDOZBXZPTFK-UHFFFAOYSA-N 0.000 claims 1
OAILKWAAFDSGSQ-UHFFFAOYSA-N n-[3-benzylsulfonyl-1-[(3-hydroxy-2-methyl-4-oxo-4-phenylbutan-2-yl)amino]-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1C(=O)C(O)C(C)(C)NC(=O)C(NC(=O)N1CCOCC1)CS(=O)(=O)CC1=CC=CC=C1 OAILKWAAFDSGSQ-UHFFFAOYSA-N 0.000 claims 1
PZDZOTFHGOXZHL-UHFFFAOYSA-N n-[3-benzylsulfonyl-1-[[1-[(4-methoxyphenyl)sulfamoyl]-4-phenylbutan-2-yl]amino]-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)CC(NC(=O)C(CS(=O)(=O)CC=1C=CC=CC=1)NC(=O)N1CCOCC1)CCC1=CC=CC=C1 PZDZOTFHGOXZHL-UHFFFAOYSA-N 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
125000006239 protecting group Chemical group 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 6
SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 6
108010005843 Cysteine Proteases Proteins 0.000 description 5
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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125000002993 cycloalkylene group Chemical group 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
101150065749 Churc1 gene Proteins 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102100038239 Protein Churchill Human genes 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
239000012634 fragment Substances 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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230000003000 nontoxic effect Effects 0.000 description 1
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OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
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235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000005188 oxoalkyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
201000001976 pemphigus vulgaris Diseases 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
208000028169 periodontal disease Diseases 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1

Classifications

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- 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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Rheumatology (AREA)
Tropical Medicine & Parasitology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Peptides Or Proteins (AREA)
Pyrrole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

ZA200401882A 2001-09-14 2004-03-08 Novel compounds and compositions as cathepsin inhibitors. ZA200401882B (en)

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US32231801P	2001-09-14	2001-09-14

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ZA200401882B true ZA200401882B (en)	2005-04-18

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ZA200401882A ZA200401882B (en)	2001-09-14	2004-03-08	Novel compounds and compositions as cathepsin inhibitors.

Country Status (18)

Country	Link
US (2)	US7196099B2 (fr)
EP (1)	EP1436255A1 (fr)
JP (1)	JP2005504078A (fr)
KR (1)	KR20040044920A (fr)
CN (1)	CN1324008C (fr)
BR (1)	BR0212535A (fr)
CA (1)	CA2460125A1 (fr)
CO (1)	CO5560538A2 (fr)
HR (1)	HRP20040249A2 (fr)
IL (1)	IL160819A0 (fr)
MX (1)	MXPA04002282A (fr)
NO (1)	NO20040996L (fr)
NZ (1)	NZ531352A (fr)
PL (1)	PL369312A1 (fr)
RS (1)	RS19504A (fr)
RU (1)	RU2316546C2 (fr)
WO (1)	WO2003024924A1 (fr)
ZA (1)	ZA200401882B (fr)

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US20040147503A1 (en) *	2002-06-04	2004-07-29	Sheila Zipfeil	Novel compounds and compositions as cathepsin inhibitors
MXPA04004450A (es) *	2001-11-14	2004-08-11	Aventis Pharma Inc	Nuevos compuestos y composiciones como inhibidores de catepsina s.
EP1575576A2 (fr)	2002-09-24	2005-09-21	Novartis AG	Composes organiques
EP1664003A1 (fr) *	2003-09-18	2006-06-07	Axys Pharmaceuticals, Inc.	Composes contenant un haloalkyle utilise comme inhibiteurs de cysteine protease
PE20060213A1 (es)	2004-04-30	2006-04-24	Irm Llc	Compuestos y composiciones como inhibidores de catepsinas
EP1819667B1 (fr)	2004-12-02	2012-10-17	ViroBay, Inc.	Composes de sulfonamide utilises comme inhibiteurs des cysteine proteases
WO2006064286A1 (fr) *	2004-12-13	2006-06-22	Medivir Uk Ltd	Inhibiteurs de cathepsine s
US7488848B2 (en) *	2005-03-21	2009-02-10	Virobay, Inc.	Alpha ketoamide compounds as cysteine protease inhibitors
UA90138C2 (uk) *	2005-03-21	2010-04-12	Вайробей, Инк.	Альфа-кетоамідні сполуки як інгібітори цистеїнових протеаз
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EP2079683B1 (fr)	2006-10-04	2015-01-21	Virobay, Inc.	Composés contenant un di-fluoro en tant qu'inhibiteurs de cystéine-protéase
EP2240491B1 (fr)	2008-01-09	2015-07-15	Amura Therapeutics Limited	DÉRIVÉS DE TÉTRAHYDROFURO(2,3-b)PYRROL-3-ONE COMME INHIBITEURS DE CYSTÉINE PROTÉINASES
JP2011525189A (ja)	2008-06-20	2011-09-15	ノバルティスアーゲー	多発性硬化症を治療するための小児科の組成物
BRPI0922283A2 (pt) *	2008-12-19	2015-12-29	Medivir Uk Ltd	inibidores da cistéina protease
US8324417B2 (en)	2009-08-19	2012-12-04	Virobay, Inc.	Process for the preparation of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid and alkyl esters and acid salts thereof
JP2013513597A (ja) *	2009-12-10	2013-04-22	メディヴィル・ユーケイ・リミテッド	システインプロテアーゼ阻害薬

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2002
- 2002-09-16 JP JP2003528772A patent/JP2005504078A/ja active Pending
- 2002-09-16 IL IL16081902A patent/IL160819A0/xx unknown
- 2002-09-16 RU RU2004111291/04A patent/RU2316546C2/ru not_active IP Right Cessation
- 2002-09-16 BR BR0212535-8A patent/BR0212535A/pt not_active IP Right Cessation
- 2002-09-16 KR KR10-2004-7003765A patent/KR20040044920A/ko not_active Ceased
- 2002-09-16 RS YUP-195/04A patent/RS19504A/sr unknown
- 2002-09-16 EP EP02798975A patent/EP1436255A1/fr not_active Withdrawn
- 2002-09-16 HR HR20040249A patent/HRP20040249A2/hr not_active Application Discontinuation
- 2002-09-16 CN CNB028178904A patent/CN1324008C/zh not_active Expired - Fee Related
- 2002-09-16 WO PCT/US2002/029323 patent/WO2003024924A1/fr not_active Ceased
- 2002-09-16 MX MXPA04002282A patent/MXPA04002282A/es unknown
- 2002-09-16 NZ NZ531352A patent/NZ531352A/en unknown
- 2002-09-16 PL PL02369312A patent/PL369312A1/xx not_active Application Discontinuation
- 2002-09-16 CA CA002460125A patent/CA2460125A1/fr not_active Abandoned
2004
- 2004-02-26 US US10/787,367 patent/US7196099B2/en not_active Expired - Lifetime
- 2004-03-08 ZA ZA200401882A patent/ZA200401882B/en unknown
- 2004-03-09 NO NO20040996A patent/NO20040996L/no not_active Application Discontinuation
- 2004-03-12 CO CO04022770A patent/CO5560538A2/es unknown
2007
- 2007-01-22 US US11/625,369 patent/US20070135386A1/en not_active Abandoned

Also Published As

Publication number	Publication date
RU2004111291A (ru)	2005-09-10
US20040192742A1 (en)	2004-09-30
CA2460125A1 (fr)	2003-03-27
US20070135386A1 (en)	2007-06-14
EP1436255A1 (fr)	2004-07-14
HRP20040249A2 (en)	2005-04-30
PL369312A1 (en)	2005-04-18
JP2005504078A (ja)	2005-02-10
CN1553892A (zh)	2004-12-08
WO2003024924A1 (fr)	2003-03-27
IL160819A0 (en)	2004-08-31
HK1071886A1 (en)	2005-08-05
NZ531352A (en)	2006-01-27
BR0212535A (pt)	2004-10-19
RS19504A (sr)	2007-02-05
CN1324008C (zh)	2007-07-04
MXPA04002282A (es)	2005-03-07
CO5560538A2 (es)	2005-09-30
RU2316546C2 (ru)	2008-02-10
US7196099B2 (en)	2007-03-27
NO20040996L (no)	2004-05-12
KR20040044920A (ko)	2004-05-31

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