JP2005533803A5 - - Google Patents
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- JP2005533803A5 JP2005533803A5 JP2004515328A JP2004515328A JP2005533803A5 JP 2005533803 A5 JP2005533803 A5 JP 2005533803A5 JP 2004515328 A JP2004515328 A JP 2004515328A JP 2004515328 A JP2004515328 A JP 2004515328A JP 2005533803 A5 JP2005533803 A5 JP 2005533803A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- carbonitrile
- alkyl
- chlorophenyl
- morpholin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 38
- -1 amino, hydroxy Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005418 aryl aryl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 125000004434 sulfur atoms Chemical group 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000005842 heteroatoms Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 102100015379 CTSS Human genes 0.000 claims description 2
- 108090000613 Cathepsin S Proteins 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 241001024304 Mino Species 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- HRXPLNARFGLXAV-UHFFFAOYSA-N 1-(4-cyano-6-morpholin-4-yl-1,3,5-triazin-2-yl)-N,N-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C1=NC(C#N)=NC(N2CCOCC2)=N1 HRXPLNARFGLXAV-UHFFFAOYSA-N 0.000 claims 1
- CMRHBNMOCLQRSF-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-6-ylamino)-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(C#N)=NC(NC=2C=C3OCCOC3=CC=2)=NC=1N1CCOCC1 CMRHBNMOCLQRSF-UHFFFAOYSA-N 0.000 claims 1
- XWCQLQFUUUVLRU-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-6-(4-chloroanilino)-5-methoxypyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CCC(N)CC2)C(OC)=C1NC1=CC=C(Cl)C=C1 XWCQLQFUUUVLRU-UHFFFAOYSA-N 0.000 claims 1
- YPDSLCXUIXJXNJ-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-6-(4-chloroanilino)pyrimidine-2-carbonitrile Chemical compound C1CC(N)CCN1C1=CC(NC=2C=CC(Cl)=CC=2)=NC(C#N)=N1 YPDSLCXUIXJXNJ-UHFFFAOYSA-N 0.000 claims 1
- NMABGHZGYRXDKI-UHFFFAOYSA-N 4-(4-chloroanilino)-5-methoxy-6-(3-oxopiperazin-1-yl)pyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CC(=O)NCC2)C(OC)=C1NC1=CC=C(Cl)C=C1 NMABGHZGYRXDKI-UHFFFAOYSA-N 0.000 claims 1
- BTZKIHBFNQJXTB-UHFFFAOYSA-N 4-(4-chloroanilino)-5-methoxy-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CCOCC2)C(OC)=C1NC1=CC=C(Cl)C=C1 BTZKIHBFNQJXTB-UHFFFAOYSA-N 0.000 claims 1
- WUUXAWFBPPBXII-UHFFFAOYSA-N 4-(4-chloroanilino)-5-methoxy-6-piperazin-1-ylpyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CCNCC2)C(OC)=C1NC1=CC=C(Cl)C=C1 WUUXAWFBPPBXII-UHFFFAOYSA-N 0.000 claims 1
- PQVMVGGJDJIQEL-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(2-piperidin-1-ylethylamino)-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(NCCN2CCCCC2)=NC(C#N)=N1 PQVMVGGJDJIQEL-UHFFFAOYSA-N 0.000 claims 1
- ZPTOAFOTEBXFRX-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(3-hydroxypyrrolidin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound C1C(O)CCN1C1=NC(NC=2C=CC(Cl)=CC=2)=NC(C#N)=N1 ZPTOAFOTEBXFRX-UHFFFAOYSA-N 0.000 claims 1
- LNLMQGVSOHPCFR-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(3-pyrrolidin-1-ylpropylamino)pyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(NCCCN2CCCC2)=NC(C#N)=N1 LNLMQGVSOHPCFR-UHFFFAOYSA-N 0.000 claims 1
- XFOOFOWYROOZEA-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(4-methylpiperazin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound C1CN(C)CCN1C1=NC(NC=2C=CC(Cl)=CC=2)=NC(C#N)=N1 XFOOFOWYROOZEA-UHFFFAOYSA-N 0.000 claims 1
- XJKDWNYTZZEYQD-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(4-phenylpiperidin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCC(CC2)C=2C=CC=CC=2)=N1 XJKDWNYTZZEYQD-UHFFFAOYSA-N 0.000 claims 1
- BBAKVKGWOAPQKH-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(N2CCC(CC2)N2CCCC2)=NC(C#N)=N1 BBAKVKGWOAPQKH-UHFFFAOYSA-N 0.000 claims 1
- JEGOOIZAHWJJSB-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(cyclopropylamino)pyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(NC2CC2)=NC(C#N)=N1 JEGOOIZAHWJJSB-UHFFFAOYSA-N 0.000 claims 1
- NMWMRLWGNJUBRC-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(dimethylamino)-1,3,5-triazine-2-carbonitrile Chemical compound N#CC1=NC(N(C)C)=NC(NC=2C=CC(Cl)=CC=2)=N1 NMWMRLWGNJUBRC-UHFFFAOYSA-N 0.000 claims 1
- FKNPVHLJQRYZPP-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(dimethylamino)-5-methoxypyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N(C)C)C(OC)=C1NC1=CC=C(Cl)C=C1 FKNPVHLJQRYZPP-UHFFFAOYSA-N 0.000 claims 1
- VCUKMSHUJDBTKR-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(dimethylamino)pyrimidine-2-carbonitrile Chemical compound N#CC1=NC(N(C)C)=CC(NC=2C=CC(Cl)=CC=2)=N1 VCUKMSHUJDBTKR-UHFFFAOYSA-N 0.000 claims 1
- CFTYWZFVQURLDD-UHFFFAOYSA-N 4-(4-chloroanilino)-6-(ethylamino)-1,3,5-triazine-2-carbonitrile Chemical compound N#CC1=NC(NCC)=NC(NC=2C=CC(Cl)=CC=2)=N1 CFTYWZFVQURLDD-UHFFFAOYSA-N 0.000 claims 1
- VSBXRTMJVIITDW-UHFFFAOYSA-N 4-(4-chloroanilino)-6-[4-[3-(dimethylamino)propyl]piperazin-1-yl]-5-methoxypyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CCN(CCCN(C)C)CC2)C(OC)=C1NC1=CC=C(Cl)C=C1 VSBXRTMJVIITDW-UHFFFAOYSA-N 0.000 claims 1
- GKWVLGLOAVNKNN-UHFFFAOYSA-N 4-(4-chloroanilino)-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCOCC2)=N1 GKWVLGLOAVNKNN-UHFFFAOYSA-N 0.000 claims 1
- ARIOMJSONVMVHM-UHFFFAOYSA-N 4-(4-chloroanilino)-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(N2CCOCC2)=NC(C#N)=N1 ARIOMJSONVMVHM-UHFFFAOYSA-N 0.000 claims 1
- PHRFVDJKWANIIJ-UHFFFAOYSA-N 4-(4-chloroanilino)-6-piperazin-1-ylpyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(N2CCNCC2)=NC(C#N)=N1 PHRFVDJKWANIIJ-UHFFFAOYSA-N 0.000 claims 1
- XUABEUVVOXVCEQ-UHFFFAOYSA-N 4-(4-chloroanilino)-6-piperidin-1-yl-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCCCC2)=N1 XUABEUVVOXVCEQ-UHFFFAOYSA-N 0.000 claims 1
- FNIDFZPHGCXTQD-UHFFFAOYSA-N 4-(4-chloroanilino)-6-pyrrolidin-1-yl-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCCC2)=N1 FNIDFZPHGCXTQD-UHFFFAOYSA-N 0.000 claims 1
- JBJHOQKLHPKKNE-UHFFFAOYSA-N 4-(4-chloroanilino)-6-pyrrolidin-1-ylpyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=CC(N2CCCC2)=NC(C#N)=N1 JBJHOQKLHPKKNE-UHFFFAOYSA-N 0.000 claims 1
- RCCAPSQQOVDJIJ-UHFFFAOYSA-N 4-(4-chlorophenoxy)-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1OC1=CC(N2CCOCC2)=NC(C#N)=N1 RCCAPSQQOVDJIJ-UHFFFAOYSA-N 0.000 claims 1
- ICWNIFGBCIVBTL-UHFFFAOYSA-N 4-(4-imidazol-1-ylpiperidin-1-yl)-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(C#N)=NC(N2CCOCC2)=NC=1N(CC1)CCC1N1C=CN=C1 ICWNIFGBCIVBTL-UHFFFAOYSA-N 0.000 claims 1
- NLPJWWPRAXCQIW-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]heptan-7-yl)-6-(4-chloroanilino)-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2C3CCC2CC3)=N1 NLPJWWPRAXCQIW-UHFFFAOYSA-N 0.000 claims 1
- ZOZJTLLDGHUBPY-UHFFFAOYSA-N 4-(azetidin-1-yl)-6-(4-chloroanilino)-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCC2)=N1 ZOZJTLLDGHUBPY-UHFFFAOYSA-N 0.000 claims 1
- JACOZRXEUWTVOP-UHFFFAOYSA-N 4-(cyclohexylamino)-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C=1C(N2CCOCC2)=NC(C#N)=NC=1NC1CCCCC1 JACOZRXEUWTVOP-UHFFFAOYSA-N 0.000 claims 1
- SWHVKIKRWPLXPK-UHFFFAOYSA-N 4-[(1-methylpiperidin-4-yl)amino]-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1CN(C)CCC1NC1=CC(N2CCOCC2)=NC(C#N)=N1 SWHVKIKRWPLXPK-UHFFFAOYSA-N 0.000 claims 1
- WOXKHFVEAVYTRX-UHFFFAOYSA-N 4-[(3-chlorophenyl)methylamino]-6-(dimethylamino)-1,3,5-triazine-2-carbonitrile Chemical compound N#CC1=NC(N(C)C)=NC(NCC=2C=C(Cl)C=CC=2)=N1 WOXKHFVEAVYTRX-UHFFFAOYSA-N 0.000 claims 1
- KJLDVJFLNOBWQC-NSHDSACASA-N 4-[(3S)-3-aminopyrrolidin-1-yl]-6-(4-chloroanilino)-5-methoxypyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2C[C@@H](N)CC2)C(OC)=C1NC1=CC=C(Cl)C=C1 KJLDVJFLNOBWQC-NSHDSACASA-N 0.000 claims 1
- QTUPPQQZNILLGV-UHFFFAOYSA-N 4-[(4-methylcyclohexyl)amino]-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1CC(C)CCC1NC1=CC(N2CCOCC2)=NC(C#N)=N1 QTUPPQQZNILLGV-UHFFFAOYSA-N 0.000 claims 1
- FBBDIKHSVMXWNJ-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)amino]-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1=NC(Cl)=CC=C1NC1=CC(N2CCOCC2)=NC(C#N)=N1 FBBDIKHSVMXWNJ-UHFFFAOYSA-N 0.000 claims 1
- HKYNATOIQKWVMA-UHFFFAOYSA-N 4-[2-(furan-2-yl)ethylamino]-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(N2CCOCC2)=NC(C#N)=NC=1NCCC1=CC=CO1 HKYNATOIQKWVMA-UHFFFAOYSA-N 0.000 claims 1
- AGZVGTBMPVFJME-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound COC1=CC=CC=C1N1CCN(C=2N=C(N=C(N=2)C#N)N2CCOCC2)CC1 AGZVGTBMPVFJME-UHFFFAOYSA-N 0.000 claims 1
- QBVCDJOMJPOECH-UHFFFAOYSA-N 4-[4-(4-chlorobenzoyl)piperidin-1-yl]-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(C=2N=C(N=C(N=2)C#N)N2CCOCC2)CC1 QBVCDJOMJPOECH-UHFFFAOYSA-N 0.000 claims 1
- NSXYUBSJTLTVOX-UHFFFAOYSA-N 4-[4-(5-chloropyridin-2-yl)piperazin-1-yl]-6-morpholin-4-yl-1,3,5-triazine-2-carbonitrile Chemical compound N1=CC(Cl)=CC=C1N1CCN(C=2N=C(N=C(N=2)C#N)N2CCOCC2)CC1 NSXYUBSJTLTVOX-UHFFFAOYSA-N 0.000 claims 1
- VVFZSWNCOHTYQS-UHFFFAOYSA-N 4-morpholin-4-yl-6-(2-pyridin-3-ylethylamino)-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(N2CCOCC2)=NC(C#N)=NC=1NCCC1=CC=CN=C1 VVFZSWNCOHTYQS-UHFFFAOYSA-N 0.000 claims 1
- ACPGGAROWYBYCA-UHFFFAOYSA-N 4-morpholin-4-yl-6-(3-phenylpiperidin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(C#N)=NC(N2CCOCC2)=NC=1N(C1)CCCC1C1=CC=CC=C1 ACPGGAROWYBYCA-UHFFFAOYSA-N 0.000 claims 1
- RSBVTQNOBXLYGL-UHFFFAOYSA-N 4-morpholin-4-yl-6-(4-morpholin-4-ylanilino)-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(N2CCOCC2)=NC(C#N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 RSBVTQNOBXLYGL-UHFFFAOYSA-N 0.000 claims 1
- KHPHMGJSXDODOC-UHFFFAOYSA-N 4-morpholin-4-yl-6-(4-phenoxypiperidin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(C#N)=NC(N2CCOCC2)=NC=1N(CC1)CCC1OC1=CC=CC=C1 KHPHMGJSXDODOC-UHFFFAOYSA-N 0.000 claims 1
- URMHHFDWPPZHIV-UHFFFAOYSA-N 4-morpholin-4-yl-6-(4-piperidin-1-ylpiperidin-1-yl)-1,3,5-triazine-2-carbonitrile Chemical compound N=1C(C#N)=NC(N2CCOCC2)=NC=1N(CC1)CCC1N1CCCCC1 URMHHFDWPPZHIV-UHFFFAOYSA-N 0.000 claims 1
- JORNRTNWRASXHW-UHFFFAOYSA-N 4-morpholin-4-yl-6-[3-(2-oxopyrrolidin-1-yl)propylamino]-1,3,5-triazine-2-carbonitrile Chemical compound O=C1CCCN1CCCNC1=NC(C#N)=NC(N2CCOCC2)=N1 JORNRTNWRASXHW-UHFFFAOYSA-N 0.000 claims 1
- HLVUUIRENGTYML-UHFFFAOYSA-N 5-amino-4-(4-chloroanilino)-6-(ethylamino)pyrimidine-2-carbonitrile Chemical compound CCNC1=NC(C#N)=NC(NC=2C=CC(Cl)=CC=2)=C1N HLVUUIRENGTYML-UHFFFAOYSA-N 0.000 claims 1
- GJHNZJNXSKYROP-UHFFFAOYSA-N 5-amino-4-(4-chloroanilino)-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C(N2CCOCC2)C(N)=C1NC1=CC=C(Cl)C=C1 GJHNZJNXSKYROP-UHFFFAOYSA-N 0.000 claims 1
- JLEVFFZEGQVAOR-UHFFFAOYSA-N 5-chloro-4-(4-chloroanilino)-6-morpholin-4-ylpyrimidine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1NC1=NC(C#N)=NC(N2CCOCC2)=C1Cl JLEVFFZEGQVAOR-UHFFFAOYSA-N 0.000 claims 1
- 108010005843 Cysteine Proteases Proteins 0.000 claims 1
- 102000005927 Cysteine Proteases Human genes 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims 1
- 229940113083 morpholine Drugs 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- 125000004193 piperazinyl group Chemical class 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005466 alkylenyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 125000003375 sulfoxide group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N Benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 230000001548 androgenic Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
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SE0201976A SE0201976D0 (sv) | 2002-06-24 | 2002-06-24 | Novel compounds |
PCT/SE2003/001078 WO2004000819A1 (en) | 2002-06-24 | 2003-06-23 | New use of pyrimidine - or triazine- 2-carbonitiles for treating diseases associated with cysteine protease activity and novel pyrimidine-2-carbonitile derivatives |
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JP2005533803A JP2005533803A (ja) | 2005-11-10 |
JP2005533803A5 true JP2005533803A5 (US20050059668A1-20050317-C00061.png) | 2006-08-17 |
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JP2004515328A Pending JP2005533803A (ja) | 2002-06-24 | 2003-06-23 | システインプロテアーゼ活性と関連する疾患の処置のためのピリミジン−またはトリアジン−2−カルボニトリルの新規使用および新規ピリミジン−2−カルボニトリル誘導体 |
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-
2002
- 2002-06-24 SE SE0201976A patent/SE0201976D0/xx unknown
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2003
- 2003-06-23 WO PCT/SE2003/001078 patent/WO2004000819A1/en active IP Right Grant
- 2003-06-23 DE DE60311820T patent/DE60311820T2/de not_active Expired - Fee Related
- 2003-06-23 ES ES03761001T patent/ES2280794T3/es not_active Expired - Lifetime
- 2003-06-23 JP JP2004515328A patent/JP2005533803A/ja active Pending
- 2003-06-23 AU AU2003243095A patent/AU2003243095A1/en not_active Abandoned
- 2003-06-23 US US10/518,817 patent/US7125881B2/en not_active Expired - Fee Related
- 2003-06-23 EP EP03761001A patent/EP1532121B1/en not_active Expired - Lifetime
- 2003-06-23 AT AT03761001T patent/ATE353880T1/de not_active IP Right Cessation
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