HRP20020221A2 - Novel spiroheterocyclic compounds useful as reversible inhibitors of cysteine proteases - Google Patents
Novel spiroheterocyclic compounds useful as reversible inhibitors of cysteine proteases Download PDFInfo
- Publication number
- HRP20020221A2 HRP20020221A2 HR20020221A HRP20020221A HRP20020221A2 HR P20020221 A2 HRP20020221 A2 HR P20020221A2 HR 20020221 A HR20020221 A HR 20020221A HR P20020221 A HRP20020221 A HR P20020221A HR P20020221 A2 HRP20020221 A2 HR P20020221A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- phenyl
- piperidinyl
- methyl
- pyrrolidinyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 34
- 102000005927 Cysteine Proteases Human genes 0.000 title 1
- 108010005843 Cysteine Proteases Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 230000002441 reversible effect Effects 0.000 title 1
- -1 hexahydropyrimidinyl Chemical group 0.000 claims 780
- 125000003386 piperidinyl group Chemical group 0.000 claims 247
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 243
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 226
- 125000002757 morpholinyl group Chemical group 0.000 claims 225
- 125000004193 piperazinyl group Chemical group 0.000 claims 214
- 229910052757 nitrogen Inorganic materials 0.000 claims 212
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 208
- 125000004076 pyridyl group Chemical group 0.000 claims 193
- 125000002883 imidazolyl group Chemical group 0.000 claims 186
- 125000000335 thiazolyl group Chemical group 0.000 claims 182
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 181
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 180
- 125000002971 oxazolyl group Chemical group 0.000 claims 175
- 125000001544 thienyl group Chemical group 0.000 claims 172
- 229910052717 sulfur Inorganic materials 0.000 claims 166
- 125000004434 sulfur atom Chemical group 0.000 claims 160
- 150000003457 sulfones Chemical class 0.000 claims 159
- 150000003462 sulfoxides Chemical class 0.000 claims 159
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 149
- 125000004043 oxo group Chemical group O=* 0.000 claims 146
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 144
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 143
- 125000003118 aryl group Chemical group 0.000 claims 140
- 125000002541 furyl group Chemical group 0.000 claims 137
- 125000001424 substituent group Chemical group 0.000 claims 136
- 125000001041 indolyl group Chemical group 0.000 claims 119
- 125000003373 pyrazinyl group Chemical group 0.000 claims 112
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 110
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 105
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 97
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 89
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 86
- 125000001624 naphthyl group Chemical group 0.000 claims 85
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 83
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 82
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 80
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 79
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 77
- 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 76
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 75
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 73
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 72
- 229910052736 halogen Inorganic materials 0.000 claims 70
- 150000002367 halogens Chemical class 0.000 claims 70
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 68
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 68
- 125000000168 pyrrolyl group Chemical group 0.000 claims 65
- 125000003831 tetrazolyl group Chemical group 0.000 claims 59
- 150000003857 carboxamides Chemical class 0.000 claims 58
- 125000001153 fluoro group Chemical group F* 0.000 claims 57
- 125000001425 triazolyl group Chemical group 0.000 claims 57
- 229910052739 hydrogen Inorganic materials 0.000 claims 54
- 239000001257 hydrogen Substances 0.000 claims 54
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims 50
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 49
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 47
- 125000004104 aryloxy group Chemical group 0.000 claims 45
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 41
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 41
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 41
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 38
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 37
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 36
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 36
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 34
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 32
- 150000002431 hydrogen Chemical group 0.000 claims 32
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 31
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 31
- 125000005239 aroylamino group Chemical group 0.000 claims 30
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 27
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 26
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 26
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 26
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 25
- 125000003435 aroyl group Chemical group 0.000 claims 25
- 229910052801 chlorine Inorganic materials 0.000 claims 25
- 239000000460 chlorine Substances 0.000 claims 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims 25
- 229910052731 fluorine Inorganic materials 0.000 claims 25
- 239000011737 fluorine Chemical group 0.000 claims 25
- 125000005110 aryl thio group Chemical group 0.000 claims 24
- JWJRTTQZJDDBBU-UHFFFAOYSA-N cyano(nitrocarbonyl)carbamic acid Chemical compound OC(=O)N(C#N)C(=O)[N+]([O-])=O JWJRTTQZJDDBBU-UHFFFAOYSA-N 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 22
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 21
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 21
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 20
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 20
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 19
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 19
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 18
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 18
- 125000005333 aroyloxy group Chemical group 0.000 claims 18
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 18
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 17
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 16
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 16
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 16
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims 15
- DXNQLZJOTVNBOZ-UHFFFAOYSA-N [O]C(=O)Nc1ccccc1 Chemical group [O]C(=O)Nc1ccccc1 DXNQLZJOTVNBOZ-UHFFFAOYSA-N 0.000 claims 15
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims 15
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 15
- 125000002393 azetidinyl group Chemical group 0.000 claims 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 14
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 13
- 229910020008 S(O) Inorganic materials 0.000 claims 13
- 125000003725 azepanyl group Chemical group 0.000 claims 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims 13
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 12
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 11
- 125000003551 oxepanyl group Chemical group 0.000 claims 11
- 125000003566 oxetanyl group Chemical group 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 10
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 9
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 9
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 8
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 8
- 150000002825 nitriles Chemical group 0.000 claims 8
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 7
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 7
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 5
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 4
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 125000006301 indolyl methyl group Chemical group 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 4
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 3
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N CH2-hydantoin Natural products O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 3
- SXSDVAQMOJWYEM-UHFFFAOYSA-N [(3-ethoxy-4-methoxy-2-propoxyphenyl)-phenoxy-propan-2-yloxymethyl] hypofluorite Chemical group CCCOC1=C(OCC)C(OC)=CC=C1C(OF)(OC(C)C)OC1=CC=CC=C1 SXSDVAQMOJWYEM-UHFFFAOYSA-N 0.000 claims 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 2
- JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 claims 2
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 claims 2
- LTQBUWVDIKUNHJ-UHFFFAOYSA-N 2-thia-5-azabicyclo[2.2.1]heptane Chemical compound C1SC2CNC1C2 LTQBUWVDIKUNHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 2
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 2
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 2
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims 2
- 125000000532 dioxanyl group Chemical group 0.000 claims 2
- 125000005883 dithianyl group Chemical group 0.000 claims 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 2
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
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- CXJWXUVSYCVHFS-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-4-methyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CC1(C#N)NC(=O)C(CC(C)C)NC(=O)N1CCOCC1 CXJWXUVSYCVHFS-UHFFFAOYSA-N 0.000 claims 2
- LCBHDVOQNVEVBL-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4-methyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)C)NC(=O)N1CCOCC1 LCBHDVOQNVEVBL-UHFFFAOYSA-N 0.000 claims 2
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- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 2
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- PEHDFSFYZKSKGH-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound NC1=NCCCN1 PEHDFSFYZKSKGH-UHFFFAOYSA-N 0.000 claims 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
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- VIRVFGOUFHKKPU-UHFFFAOYSA-N N-[1-[(4-cyanopiperidin-4-yl)-(1-phenylethyl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=CC=CC=1C(C)N(C1(CCNCC1)C#N)C(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 VIRVFGOUFHKKPU-UHFFFAOYSA-N 0.000 claims 1
- 229910019567 Re Re Inorganic materials 0.000 claims 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
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- UPBFWQFPFIRKQA-UHFFFAOYSA-N benzyl n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)carbamoyl]cyclohexyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1(C(=O)NC2(CN(CC=3C=CC=CC=3)CC2)C#N)CCCCC1 UPBFWQFPFIRKQA-UHFFFAOYSA-N 0.000 claims 1
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- 125000001246 bromo group Chemical group Br* 0.000 claims 1
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- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
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- QTLDISYMDFRRBU-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-4-(methanesulfonamido)benzamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)NC(C(=O)NC1(CN(CC=2C=CC=CC=2)CC1)C#N)CC1CCCCC1 QTLDISYMDFRRBU-UHFFFAOYSA-N 0.000 claims 1
- OHVQFYYBGNOGJV-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1CC1=CC=CC=C1 OHVQFYYBGNOGJV-UHFFFAOYSA-N 0.000 claims 1
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- HOMNVODSRLKSIX-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]pyrrolidine-1-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCCC1)C(=O)NC(C1)(C#N)CCN1CC1=CC=CC=C1 HOMNVODSRLKSIX-UHFFFAOYSA-N 0.000 claims 1
- LKUZESSPIVOPMW-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1CC1=CC=CC=C1 LKUZESSPIVOPMW-UHFFFAOYSA-N 0.000 claims 1
- NQVVTIMSWZDUPL-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-4-(methanesulfonamido)benzamide Chemical compound C1CN(CC=2C=CC=CC=2)CC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 NQVVTIMSWZDUPL-UHFFFAOYSA-N 0.000 claims 1
- XUGFAKBIVNIOGI-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 XUGFAKBIVNIOGI-UHFFFAOYSA-N 0.000 claims 1
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- JHRQJCZRRGFQNT-UHFFFAOYSA-N n-[1-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-4-methyl-1-oxopentan-2-yl]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(CC(C)C)C(=O)NC(C1)(C#N)CCN1CC1=CC=CC=C1 JHRQJCZRRGFQNT-UHFFFAOYSA-N 0.000 claims 1
- RFMAMOXGFSKWPV-UHFFFAOYSA-N n-[1-[(1-benzyl-4-cyanopiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(CC1)(C#N)CCN1CC1=CC=CC=C1 RFMAMOXGFSKWPV-UHFFFAOYSA-N 0.000 claims 1
- UXTLPZQSDLKIPA-UHFFFAOYSA-N n-[1-[(1-benzyl-4-cyanopiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 UXTLPZQSDLKIPA-UHFFFAOYSA-N 0.000 claims 1
- XPOASTKUDYQHHQ-UHFFFAOYSA-N n-[1-[(3-cyano-1-cyclohexylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1C1CCCCC1 XPOASTKUDYQHHQ-UHFFFAOYSA-N 0.000 claims 1
- ZTCCMNLMEXARLR-UHFFFAOYSA-N n-[1-[(3-cyano-1-cyclopentylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1C1CCCC1 ZTCCMNLMEXARLR-UHFFFAOYSA-N 0.000 claims 1
- ANUKOPFIGVJEJB-UHFFFAOYSA-N n-[1-[(3-cyano-1-cyclopentylpyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C2CCCC2)CC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 ANUKOPFIGVJEJB-UHFFFAOYSA-N 0.000 claims 1
- DCFJKIMLNMPXKH-UHFFFAOYSA-N n-[1-[(3-cyano-1-ethylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 DCFJKIMLNMPXKH-UHFFFAOYSA-N 0.000 claims 1
- UIVPCIQLAQMYPY-UHFFFAOYSA-N n-[1-[(3-cyano-1-methylpiperidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C)CCCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 UIVPCIQLAQMYPY-UHFFFAOYSA-N 0.000 claims 1
- DYUZEXVBQPHQAP-UHFFFAOYSA-N n-[1-[(3-cyano-1-methylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 DYUZEXVBQPHQAP-UHFFFAOYSA-N 0.000 claims 1
- RZSBXJKMGDSJEG-UHFFFAOYSA-N n-[1-[(3-cyano-1-pentan-3-ylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C(CC)CC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 RZSBXJKMGDSJEG-UHFFFAOYSA-N 0.000 claims 1
- IQCKXZJSZFWFQH-UHFFFAOYSA-N n-[1-[(3-cyano-1-pentan-3-ylpyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C(CC)CC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 IQCKXZJSZFWFQH-UHFFFAOYSA-N 0.000 claims 1
- UPWAMSGYOSTFTI-UHFFFAOYSA-N n-[1-[(3-cyano-1-propan-2-ylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C(C)C)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 UPWAMSGYOSTFTI-UHFFFAOYSA-N 0.000 claims 1
- PNHZYLSDSNJAPM-UHFFFAOYSA-N n-[1-[(3-cyano-1-propan-2-ylpyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1N(C(C)C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 PNHZYLSDSNJAPM-UHFFFAOYSA-N 0.000 claims 1
- JAPXLQWMLFIZPP-UHFFFAOYSA-N n-[1-[(3-cyano-1-propylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 JAPXLQWMLFIZPP-UHFFFAOYSA-N 0.000 claims 1
- BKJJSIQISAJXJT-UHFFFAOYSA-N n-[1-[(3-cyano-1-propylpyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 BKJJSIQISAJXJT-UHFFFAOYSA-N 0.000 claims 1
- GRWCWNBGKIZOGM-UHFFFAOYSA-N n-[1-[(4-cyano-1,2-dimethylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C)C(C)CC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 GRWCWNBGKIZOGM-UHFFFAOYSA-N 0.000 claims 1
- JFPTUVMZLFCYRE-UHFFFAOYSA-N n-[1-[(4-cyano-1-cyclohexylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C2CCCCC2)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 JFPTUVMZLFCYRE-UHFFFAOYSA-N 0.000 claims 1
- WZCKLWAWMUSUQM-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-3-phenoxybenzamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)C=1C=C(OC=2C=CC=CC=2)C=CC=1)CC1CCCCC1 WZCKLWAWMUSUQM-UHFFFAOYSA-N 0.000 claims 1
- RUEHEILPOVCPHQ-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-4-fluorobenzamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)C=1C=CC(F)=CC=1)CC1CCCCC1 RUEHEILPOVCPHQ-UHFFFAOYSA-N 0.000 claims 1
- LRKULUVEMGTGCS-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]benzamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)C=1C=CC=CC=1)CC1CCCCC1 LRKULUVEMGTGCS-UHFFFAOYSA-N 0.000 claims 1
- IRSOCWQJNYLTDD-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 IRSOCWQJNYLTDD-UHFFFAOYSA-N 0.000 claims 1
- FUXCYUAWCXUFIH-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]pyrazine-2-carboxamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)C=1N=CC=NC=1)CC1CCCCC1 FUXCYUAWCXUFIH-UHFFFAOYSA-N 0.000 claims 1
- DGYGBWIDUMDEBY-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]pyridine-4-carboxamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=O)C=1C=CN=CC=1)CC1CCCCC1 DGYGBWIDUMDEBY-UHFFFAOYSA-N 0.000 claims 1
- QHNKYMQZPQHTKX-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-4-(methanesulfonamido)benzamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 QHNKYMQZPQHTKX-UHFFFAOYSA-N 0.000 claims 1
- HEOCTASVMGAOMR-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]benzamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)C1=CC=CC=C1 HEOCTASVMGAOMR-UHFFFAOYSA-N 0.000 claims 1
- WUJUEWKPELOTCU-UHFFFAOYSA-N n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 WUJUEWKPELOTCU-UHFFFAOYSA-N 0.000 claims 1
- VLDULZMRDHLQIY-UHFFFAOYSA-N n-[1-[(4-cyano-1-propan-2-ylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 VLDULZMRDHLQIY-UHFFFAOYSA-N 0.000 claims 1
- QFYLALQVSSZTGX-UHFFFAOYSA-N n-[1-[(4-cyano-1-propan-2-ylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 QFYLALQVSSZTGX-UHFFFAOYSA-N 0.000 claims 1
- KFLRFXOJSWLCPS-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-(3,4-dichlorophenyl)-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1=CC=C(Cl)C(Cl)=C1 KFLRFXOJSWLCPS-UHFFFAOYSA-N 0.000 claims 1
- QKDPOLJIBGOWFA-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 QKDPOLJIBGOWFA-UHFFFAOYSA-N 0.000 claims 1
- SZHFBLNVHHHCRB-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1=CC=C(C=CC=C2)C2=C1 SZHFBLNVHHHCRB-UHFFFAOYSA-N 0.000 claims 1
- MLJLTOGPAKLYJE-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 MLJLTOGPAKLYJE-UHFFFAOYSA-N 0.000 claims 1
- NNGVKWVSMDQNSR-UHFFFAOYSA-N n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]pyrazine-2-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)C1=CN=CC=N1 NNGVKWVSMDQNSR-UHFFFAOYSA-N 0.000 claims 1
- SSXLTZKUWRTROD-UHFFFAOYSA-N n-[1-[(4-cyanopiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide;hydrochloride Chemical compound Cl.C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC1(C#N)CCNCC1 SSXLTZKUWRTROD-UHFFFAOYSA-N 0.000 claims 1
- RCTOBPRCGHONCY-UHFFFAOYSA-N n-[1-[[3-cyano-1-(1h-indol-3-ylmethyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CC=2C3=CC=CC=C3NC=2)CC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 RCTOBPRCGHONCY-UHFFFAOYSA-N 0.000 claims 1
- WXNYFYULNSKWQR-UHFFFAOYSA-N n-[1-[[3-cyano-1-(2-methylpent-2-enyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CC(C)=CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 WXNYFYULNSKWQR-UHFFFAOYSA-N 0.000 claims 1
- XYGHCJFBSRZPQF-UHFFFAOYSA-N n-[1-[[3-cyano-1-(2-methylpropyl)piperidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CC(C)C)CCCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 XYGHCJFBSRZPQF-UHFFFAOYSA-N 0.000 claims 1
- BKPDUNCXYWFCER-UHFFFAOYSA-N n-[1-[[3-cyano-1-(2-methylpropyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CC(C)C)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1CCCCC1 BKPDUNCXYWFCER-UHFFFAOYSA-N 0.000 claims 1
- RCBRTQUQNFHXBS-UHFFFAOYSA-N n-[1-[[3-cyano-1-(2-methylpropyl)pyrrolidin-3-yl]amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1N(CC(C)C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 RCBRTQUQNFHXBS-UHFFFAOYSA-N 0.000 claims 1
- RDVFWLFNAPLGJG-UHFFFAOYSA-N n-[1-[[3-cyano-1-(cyclohexylmethyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1CC1CCCCC1 RDVFWLFNAPLGJG-UHFFFAOYSA-N 0.000 claims 1
- XSKPZPRUGOTUTE-UHFFFAOYSA-N n-[1-[[3-cyano-1-(cyclohexylmethyl)pyrrolidin-3-yl]amino]-4,4-dimethyl-1-oxopentan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CC2CCCCC2)CC1(C#N)NC(=O)C(CC(C)(C)C)NC(=O)N1CCOCC1 XSKPZPRUGOTUTE-UHFFFAOYSA-N 0.000 claims 1
- PVFCNFIPCCTUOG-UHFFFAOYSA-N n-[1-[[3-cyano-1-(cyclohexylmethyl)pyrrolidin-3-yl]amino]-4-methyl-1-oxopentan-2-yl]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(CC(C)C)C(=O)NC(C1)(C#N)CCN1CC1CCCCC1 PVFCNFIPCCTUOG-UHFFFAOYSA-N 0.000 claims 1
- JTGYDYGFAIKGIG-UHFFFAOYSA-N n-[1-[[3-cyano-1-(cyclopentylmethyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1CC1CCCC1 JTGYDYGFAIKGIG-UHFFFAOYSA-N 0.000 claims 1
- CPYHYXKPTZDWMU-UHFFFAOYSA-N n-[1-[[3-cyano-1-(cyclopropylmethyl)pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CCCCC1CC(NC(=O)N1CCOCC1)C(=O)NC(C1)(C#N)CCN1CC1CC1 CPYHYXKPTZDWMU-UHFFFAOYSA-N 0.000 claims 1
- AKWRDYPNFXZINM-UHFFFAOYSA-N n-[1-[[3-cyano-1-[(3-methylphenyl)methyl]pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound CC1=CC=CC(CN2CC(CC2)(NC(=O)C(CC2CCCCC2)NC(=O)N2CCOCC2)C#N)=C1 AKWRDYPNFXZINM-UHFFFAOYSA-N 0.000 claims 1
- WIOAKLGGTTXIQC-UHFFFAOYSA-N n-[1-[[3-cyano-1-[(5-methylthiophen-2-yl)methyl]pyrrolidin-3-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound S1C(C)=CC=C1CN1CC(C#N)(NC(=O)C(CC2CCCCC2)NC(=O)N2CCOCC2)CC1 WIOAKLGGTTXIQC-UHFFFAOYSA-N 0.000 claims 1
- RZAAJFYVDRDTGC-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-1-[(4-cyano-1-propylpiperidin-4-yl)amino]-1-oxopropan-2-yl]morpholine-4-carboxamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=O)N1CCOCC1)CC1=CC=C(Cl)C=C1 RZAAJFYVDRDTGC-UHFFFAOYSA-N 0.000 claims 1
- PKBNJGGAEDJQMV-UHFFFAOYSA-N n-[4-[(1-benzyl-3-cyanopyrrolidin-3-yl)amino]-3-(cyclohexylmethyl)-4-oxobutan-2-yl]pyridine-4-carboxamide Chemical compound C1CCCCC1CC(C(=O)NC1(CN(CC=2C=CC=CC=2)CC1)C#N)C(C)NC(=O)C1=CC=NC=C1 PKBNJGGAEDJQMV-UHFFFAOYSA-N 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000004886 thiomorpholines Chemical class 0.000 claims 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims 1
- 125000005289 uranyl group Chemical group 0.000 claims 1
Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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- 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
- 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
- C07D211/66—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 having a hetero atom as the second substituent in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
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- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
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- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15373899P | 1999-09-13 | 1999-09-13 | |
| US22290000P | 2000-08-03 | 2000-08-03 | |
| PCT/US2000/023584 WO2001019816A1 (fr) | 1999-09-13 | 2000-08-28 | Composes spiroheterocycliques utiles comme inhibiteurs reversibles de cysteine protease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20020221A2 true HRP20020221A2 (en) | 2005-10-31 |
| HRP20020221B1 HRP20020221B1 (fr) | 2007-01-31 |
Family
ID=26850810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020221A HRP20020221A2 (en) | 1999-09-13 | 2002-03-12 | Novel spiroheterocyclic compounds useful as reversible inhibitors of cysteine proteases |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1218372B1 (fr) |
| JP (1) | JP2003529546A (fr) |
| KR (1) | KR20030024651A (fr) |
| CN (1) | CN100410250C (fr) |
| AR (1) | AR032136A1 (fr) |
| AT (1) | ATE244235T1 (fr) |
| AU (1) | AU782246B2 (fr) |
| BG (1) | BG106483A (fr) |
| BR (1) | BR0013966A (fr) |
| CA (1) | CA2385130C (fr) |
| CZ (1) | CZ2002844A3 (fr) |
| DE (1) | DE60003702T2 (fr) |
| DK (1) | DK1218372T3 (fr) |
| EE (1) | EE200200132A (fr) |
| ES (1) | ES2199856T3 (fr) |
| HK (1) | HK1048807A1 (fr) |
| HR (1) | HRP20020221A2 (fr) |
| HU (1) | HUP0302380A2 (fr) |
| IL (2) | IL148184A0 (fr) |
| MY (1) | MY122696A (fr) |
| NO (1) | NO323354B1 (fr) |
| NZ (1) | NZ518255A (fr) |
| PL (1) | PL364045A1 (fr) |
| PT (1) | PT1218372E (fr) |
| RU (1) | RU2255937C2 (fr) |
| SA (1) | SA00210456B1 (fr) |
| SK (1) | SK286463B6 (fr) |
| TW (1) | TWI230159B (fr) |
| WO (1) | WO2001019816A1 (fr) |
| YU (1) | YU17402A (fr) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR200103390T2 (tr) | 1999-03-15 | 2002-05-21 | Axys Pharmaceuticals, Inc. | Proteaz inhibitörleri olan yeni bileşikler ve terkipler. |
| US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| US7030116B2 (en) | 2000-12-22 | 2006-04-18 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
| AR036375A1 (es) * | 2001-08-30 | 2004-09-01 | Novartis Ag | Compuestos pirrolo [2,3-d] pirimidina -2- carbonitrilo, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos compuestos para la preparacion de medicamentos |
| WO2003024924A1 (fr) | 2001-09-14 | 2003-03-27 | Aventis Pharmaceuticals Inc. | Nouveaux composes et nouvelles compositions utiles comme inhibiteurs de la cathepsine |
| US6936606B2 (en) | 2001-10-02 | 2005-08-30 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cyanoamido-containing heterocyclic compounds useful as reversible inhibitors of cysteine proteases |
| WO2003037892A1 (fr) * | 2001-10-29 | 2003-05-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Composes convenant comme inhibiteurs reversibles de proteases de la cysteine |
| IL161950A0 (en) | 2001-11-14 | 2005-11-20 | Axys Pharm Inc | Oligopeptides and compositions containing them as cathepsin s inhibitors |
| WO2003075853A2 (fr) | 2002-03-08 | 2003-09-18 | Bristol-Myers Squibb Company | Derives cycliques servant de modulateurs de l'activite du recepteur de la chimiokine |
| AU2003256305A1 (en) | 2002-06-24 | 2004-01-06 | Axys Pharmaceuticals, Inc. | Peptidic compounds as cysteine protease inhibitors |
| WO2004050024A2 (fr) | 2002-11-27 | 2004-06-17 | Incyte Corporation | Derives de la 3-aminopyrrolidine modulateurs des recepteurs de la chemoquine |
| WO2004052921A1 (fr) * | 2002-12-05 | 2004-06-24 | Axys Pharmaceuticals, Inc. | Derives de cyanomethyle en tant qu'inhibiteurs de la protease a cysteine |
| US7384970B2 (en) | 2003-03-24 | 2008-06-10 | Irm Llc | Inhibitors of cathepsin S |
| US7109243B2 (en) | 2003-03-24 | 2006-09-19 | Irm Llc | Inhibitors of cathepsin S |
| WO2004108661A1 (fr) * | 2003-06-04 | 2004-12-16 | Axys Pharmaceuticals | Composes amidino servant d'inhibiteurs de proteases a cysteine |
| US7173051B2 (en) | 2003-06-13 | 2007-02-06 | Irm, Llc | Inhibitors of cathepsin S |
| US7256207B2 (en) | 2003-08-20 | 2007-08-14 | Irm Llc | Inhibitors of cathepsin S |
| BRPI0410979A (pt) * | 2003-09-18 | 2006-07-04 | Axys Pharm Inc | composto, composição farmacêutica, e, métodos para tratar uma doença em um animal mediada pela catepsina s e para tratar um paciente submetido a uma terapia |
| US7297714B2 (en) * | 2003-10-21 | 2007-11-20 | Irm Llc | Inhibitors of cathepsin S |
| EP1819667B1 (fr) | 2004-12-02 | 2012-10-17 | ViroBay, Inc. | Composes de sulfonamide utilises comme inhibiteurs des cysteine proteases |
| NZ561681A (en) | 2005-03-21 | 2011-01-28 | Virobay Inc | Alpha ketoamide compounds as cysteine protease inhibitors |
| JP5215167B2 (ja) | 2005-03-22 | 2013-06-19 | ビロベイ，インコーポレイティド | システインプロテアーゼ阻害剤としてのスルホニル基含有化合物 |
| WO2006138265A2 (fr) * | 2005-06-14 | 2006-12-28 | Schering Corporation | Preparation et utilisation de composes en tant qu'inhibiteurs de proteases |
| WO2007053498A1 (fr) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Composés pouvant être employés en tant qu'antagonistes de ccr2 |
| WO2007053499A2 (fr) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Composés pouvant être employés en tant qu'antagonistes de ccr2 |
| AR059035A1 (es) * | 2006-01-16 | 2008-03-12 | Syngenta Participations Ag | Insecticidas derivados de antranilamida |
| CA2653662C (fr) * | 2006-06-01 | 2015-02-10 | Sanofi-Aventis | Nitriles spirocycliques en tant qu'inhibiteurs de protease |
| US7893112B2 (en) | 2006-10-04 | 2011-02-22 | Virobay, Inc. | Di-fluoro containing compounds as cysteine protease inhibitors |
| DK2079683T3 (en) | 2006-10-04 | 2015-04-27 | Virobay Inc | Difluoro-containing compounds as cysteine protease inhibitors |
| DE102006057036A1 (de) * | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
| EP2719700A1 (fr) | 2008-01-09 | 2014-04-16 | Amura Therapeutics Limited | Derives de tetrhydrofur(3,2-b)pyrrol-3-one comme inhibiteurs des proteases de cysteine |
| EP2198879A1 (fr) | 2008-12-11 | 2010-06-23 | Institut Curie | Agent modulateur de CD74 pour la régulation de la migration de cellules dendritiques et dispositif pour l'étude de la capacité de motilité d'une cellule |
| 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 |
| US8680152B2 (en) | 2011-05-02 | 2014-03-25 | Virobay, Inc. | Cathepsin inhibitors for the treatment of bone cancer and bone cancer pain |
| US9278966B2 (en) | 2011-06-07 | 2016-03-08 | Kureha Corporation | Method for manufacturing oxetane compound, method for manufacturing azolylmethylcyclopentanol compound, and intermediate compound |
| EP2537532A1 (fr) | 2011-06-22 | 2012-12-26 | J. Stefan Institute | Composés capables de se lier à une cathepsine, liés à un nanodispositif et leur utilisation thérapeutique et diagnostique |
| PL2780015T3 (pl) | 2011-11-18 | 2017-06-30 | Heptares Therapeutics Limited | Agonisty receptora muskarynowego M1 |
| GB201617454D0 (en) * | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| US11124497B1 (en) | 2020-04-17 | 2021-09-21 | Pardes Biosciences, Inc. | Inhibitors of cysteine proteases and methods of use thereof |
| US11174231B1 (en) | 2020-06-09 | 2021-11-16 | Pardes Biosciences, Inc. | Inhibitors of cysteine proteases and methods of use thereof |
| IL298529A (en) * | 2020-06-09 | 2023-01-01 | Pardes Biosciences Inc | Cysteine protease inhibitors and methods of using them |
| KR20230169977A (ko) * | 2021-03-10 | 2023-12-18 | 빈시어 바이오사이언시스, 인크. | Usp30 억제제 및 이의 용도 |
| WO2023044171A1 (fr) * | 2021-09-20 | 2023-03-23 | Pardes Biosciences, Inc. | Inhibiteurs de cystéine protéases et leurs méthodes d'utilisation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2216151A1 (fr) * | 1995-03-24 | 1996-10-03 | Arris Pharmaceutical Corporation | Inhibiteurs de protease reversibles |
| US5776718A (en) * | 1995-03-24 | 1998-07-07 | Arris Pharmaceutical Corporation | Reversible protease inhibitors |
| TW438591B (en) * | 1995-06-07 | 2001-06-07 | Arris Pharm Corp | Reversible cysteine protease inhibitors |
| TR200103390T2 (tr) * | 1999-03-15 | 2002-05-21 | Axys Pharmaceuticals, Inc. | Proteaz inhibitörleri olan yeni bileşikler ve terkipler. |
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2000
- 2000-08-28 DE DE60003702T patent/DE60003702T2/de not_active Expired - Lifetime
- 2000-08-28 NZ NZ518255A patent/NZ518255A/en unknown
- 2000-08-28 CN CNB008146772A patent/CN100410250C/zh not_active Expired - Fee Related
- 2000-08-28 IL IL14818400A patent/IL148184A0/xx active IP Right Grant
- 2000-08-28 YU YU17402A patent/YU17402A/sh unknown
- 2000-08-28 CA CA002385130A patent/CA2385130C/fr not_active Expired - Fee Related
- 2000-08-28 PL PL00364045A patent/PL364045A1/xx unknown
- 2000-08-28 SK SK490-2002A patent/SK286463B6/sk not_active IP Right Cessation
- 2000-08-28 BR BR0013966-1A patent/BR0013966A/pt not_active Expired - Fee Related
- 2000-08-28 AT AT00959506T patent/ATE244235T1/de not_active IP Right Cessation
- 2000-08-28 WO PCT/US2000/023584 patent/WO2001019816A1/fr not_active Application Discontinuation
- 2000-08-28 CZ CZ2002844A patent/CZ2002844A3/cs unknown
- 2000-08-28 JP JP2001523393A patent/JP2003529546A/ja active Pending
- 2000-08-28 EP EP00959506A patent/EP1218372B1/fr not_active Expired - Lifetime
- 2000-08-28 HU HU0302380A patent/HUP0302380A2/hu unknown
- 2000-08-28 PT PT00959506T patent/PT1218372E/pt unknown
- 2000-08-28 AU AU70818/00A patent/AU782246B2/en not_active Ceased
- 2000-08-28 EE EEP200200132A patent/EE200200132A/xx unknown
- 2000-08-28 ES ES00959506T patent/ES2199856T3/es not_active Expired - Lifetime
- 2000-08-28 RU RU2002107433/04A patent/RU2255937C2/ru not_active IP Right Cessation
- 2000-08-28 DK DK00959506T patent/DK1218372T3/da active
- 2000-08-28 KR KR1020027003368A patent/KR20030024651A/ko not_active Application Discontinuation
- 2000-09-11 MY MYPI20004216A patent/MY122696A/en unknown
- 2000-09-11 TW TW089118587A patent/TWI230159B/zh not_active IP Right Cessation
- 2000-09-13 AR ARP000104795A patent/AR032136A1/es not_active Suspension/Interruption
- 2000-10-17 SA SA00210456A patent/SA00210456B1/ar unknown
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2002
- 2002-02-14 IL IL148184A patent/IL148184A/en not_active IP Right Cessation
- 2002-03-05 BG BG106483A patent/BG106483A/bg active Pending
- 2002-03-12 NO NO20021207A patent/NO323354B1/no unknown
- 2002-03-12 HR HR20020221A patent/HRP20020221A2/hr not_active IP Right Cessation
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2003
- 2003-02-06 HK HK03100843.6A patent/HK1048807A1/zh unknown
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