HRP20100398T1 - Tienopirazoli - Google Patents
Tienopirazoli Download PDFInfo
- Publication number
- HRP20100398T1 HRP20100398T1 HR20100398T HRP20100398T HRP20100398T1 HR P20100398 T1 HRP20100398 T1 HR P20100398T1 HR 20100398 T HR20100398 T HR 20100398T HR P20100398 T HRP20100398 T HR P20100398T HR P20100398 T1 HRP20100398 T1 HR P20100398T1
- Authority
- HR
- Croatia
- Prior art keywords
- optionally substituted
- thieno
- pyrazol
- indol
- piperidin
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 19
- 239000001257 hydrogen Substances 0.000 claims abstract 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 12
- 125000003118 aryl group Chemical group 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 9
- 125000002252 acyl group Chemical group 0.000 claims abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract 6
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims abstract 6
- 125000003435 aroyl group Chemical group 0.000 claims abstract 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims abstract 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000005239 aroylamino group Chemical group 0.000 claims 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- TTYMOKCRJSJKKL-UHFFFAOYSA-N 1-cyclohexyl-1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]propan-1-ol Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(O)(CC)C1CCCCC1 TTYMOKCRJSJKKL-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- -1 heteroaroyl Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- LRSJJHKUFCCHPI-NRFANRHFSA-N (1S)-1-phenyl-1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]ethanol Chemical compound C1([C@@](O)(C)C=2C=C3C=C(NC3=CC=2)C=2C=3SC=CC=3NN=2)=CC=CC=C1 LRSJJHKUFCCHPI-NRFANRHFSA-N 0.000 claims 1
- DXOQBYZKVAPUSV-QGZVFWFLSA-N (2R)-2-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]butan-2-ol Chemical compound CC[C@@](C)(O)C1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=C1 DXOQBYZKVAPUSV-QGZVFWFLSA-N 0.000 claims 1
- WTJKAISPNGDPIX-UHFFFAOYSA-N (4-pyridin-2-ylpiperazin-1-yl)-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]methanone Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)N(CC1)CCN1C1=CC=CC=N1 WTJKAISPNGDPIX-UHFFFAOYSA-N 0.000 claims 1
- QTSVIJNUFJFMMT-UHFFFAOYSA-N 1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]propan-1-one Chemical compound CCC(=O)C1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=C1 QTSVIJNUFJFMMT-UHFFFAOYSA-N 0.000 claims 1
- YXPQHLHPFKLYMK-UHFFFAOYSA-N 1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]ethanone Chemical compound CC(=O)C1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 YXPQHLHPFKLYMK-UHFFFAOYSA-N 0.000 claims 1
- RQNLAHQTDCNQFN-UHFFFAOYSA-N 1-[2-(pyrrolidin-1-ylmethyl)phenyl]-1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]propan-1-ol Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(O)(CC)C1=CC=CC=C1CN1CCCC1 RQNLAHQTDCNQFN-UHFFFAOYSA-N 0.000 claims 1
- QVGPMYYBAALHGQ-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]oxy]propyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CCCOC1=CC=C(NC(=C2)C=3C=4SC=CC=4NN=3)C2=C1 QVGPMYYBAALHGQ-UHFFFAOYSA-N 0.000 claims 1
- WNGIWKGDQJKXIR-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]oxy]propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCOC1=CC=C(NC(=C2)C=3C=4SC=CC=4NN=3)C2=C1 WNGIWKGDQJKXIR-UHFFFAOYSA-N 0.000 claims 1
- JXPRTVIARIMFQX-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]oxy]propyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CCCOC1=CC=C(NC(=C2)C=3C=4SC=CC=4NN=3)C2=C1 JXPRTVIARIMFQX-UHFFFAOYSA-N 0.000 claims 1
- UDYCXQDEOOWVJJ-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC=CC=4NN=3)C2=C1 UDYCXQDEOOWVJJ-UHFFFAOYSA-N 0.000 claims 1
- GIFLJUPSGFUNAJ-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC=CC=4NN=3)C2=C1 GIFLJUPSGFUNAJ-UHFFFAOYSA-N 0.000 claims 1
- HEETXNSJLNFAMR-UHFFFAOYSA-N 1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC=CC=4NN=3)C2=C1 HEETXNSJLNFAMR-UHFFFAOYSA-N 0.000 claims 1
- REQLZRSNWLKMLZ-UHFFFAOYSA-N 1-[3-[[2-(5-phenyl-1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC(=CC=4NN=3)C=3C=CC=CC=3)C2=C1 REQLZRSNWLKMLZ-UHFFFAOYSA-N 0.000 claims 1
- XDHGRBXHTKTNLW-UHFFFAOYSA-N 1-[3-[[2-[5-(3-methoxyphenyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]oxy]propyl]piperidin-4-ol Chemical compound COC1=CC=CC(C=2SC=3C(C=4NC5=CC(OCCCN6CCC(O)CC6)=CC=C5C=4)=NNC=3C=2)=C1 XDHGRBXHTKTNLW-UHFFFAOYSA-N 0.000 claims 1
- ZSYLOTMNGLLITN-UHFFFAOYSA-N 1-[3-[[2-[5-(phenylmethoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]oxy]propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC(COCC=5C=CC=CC=5)=CC=4NN=3)C2=C1 ZSYLOTMNGLLITN-UHFFFAOYSA-N 0.000 claims 1
- BPQLRKCUGNVVPC-UHFFFAOYSA-N 1-[3-[[2-[5-[2-(dimethylamino)ethyl]-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]oxy]propyl]piperidin-4-ol Chemical compound C1=2SC(CCN(C)C)=CC=2NN=C1C(NC1=C2)=CC1=CC=C2OCCCN1CCC(O)CC1 BPQLRKCUGNVVPC-UHFFFAOYSA-N 0.000 claims 1
- MRYJRWNSFJOEQE-UHFFFAOYSA-N 1-[[3-[6-(3-hydroxypentan-3-yl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]methyl]piperidin-4-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2CN1CCC(O)CC1 MRYJRWNSFJOEQE-UHFFFAOYSA-N 0.000 claims 1
- LOHXKJHTLJSMTD-UHFFFAOYSA-N 1-[[3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(S1)=CC2=C1C(C=1NC3=CC(OCCCN4CCCCC4)=CC=C3C=1)=NN2 LOHXKJHTLJSMTD-UHFFFAOYSA-N 0.000 claims 1
- KNHFJOIKBQUMAA-UHFFFAOYSA-N 1-cyclohexyl-N-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]methyl]methanamine Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1CNCC1CCCCC1 KNHFJOIKBQUMAA-UHFFFAOYSA-N 0.000 claims 1
- LRSJJHKUFCCHPI-UHFFFAOYSA-N 1-phenyl-1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]ethanol Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(O)(C)C1=CC=CC=C1 LRSJJHKUFCCHPI-UHFFFAOYSA-N 0.000 claims 1
- BPOCIGTWUUNXSX-UHFFFAOYSA-N 1-phenyl-N-[[3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]methyl]methanamine Chemical compound C1CCCCN1CCCOC(C=C1N2)=CC=C1C=C2C(C=1S2)=NNC=1C=C2CNCC1=CC=CC=C1 BPOCIGTWUUNXSX-UHFFFAOYSA-N 0.000 claims 1
- WTRFTAAPAMXTCK-UHFFFAOYSA-N 1-pyridin-2-yl-1-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]propan-1-ol Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(O)(CC)C1=CC=CC=N1 WTRFTAAPAMXTCK-UHFFFAOYSA-N 0.000 claims 1
- HEECCHFUOSHPTH-UHFFFAOYSA-N 2-(1H-thieno[3,2-c]pyrazol-3-yl)-N-(2-thiophen-2-ylethyl)-1H-indole-5-carboxamide Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(=O)NCCC1=CC=CS1 HEECCHFUOSHPTH-UHFFFAOYSA-N 0.000 claims 1
- JYWPPSICSZWTJY-UHFFFAOYSA-N 2-(1H-thieno[3,2-c]pyrazol-3-yl)-N-(2-thiophen-2-ylethyl)-1H-indole-6-carboxamide Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)NCCC1=CC=CS1 JYWPPSICSZWTJY-UHFFFAOYSA-N 0.000 claims 1
- HBQMRTZDVYCFFQ-UHFFFAOYSA-N 2-(4-phenoxyphenyl)-N-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]methyl]ethanamine Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1CNCCC(C=C1)=CC=C1OC1=CC=CC=C1 HBQMRTZDVYCFFQ-UHFFFAOYSA-N 0.000 claims 1
- DXOQBYZKVAPUSV-UHFFFAOYSA-N 2-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]butan-2-ol Chemical compound CCC(C)(O)C1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=C1 DXOQBYZKVAPUSV-UHFFFAOYSA-N 0.000 claims 1
- QZRREJIJXYPVOF-UHFFFAOYSA-N 2-[3-[6-(3-hydroxypentan-3-yl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]oxolane-3-carbonitrile Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2C1OCCC1C#N QZRREJIJXYPVOF-UHFFFAOYSA-N 0.000 claims 1
- OONCLYMIXNGRIH-UHFFFAOYSA-N 2-[methyl-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]amino]ethanol Chemical compound OCCN(C)CCCOC1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 OONCLYMIXNGRIH-UHFFFAOYSA-N 0.000 claims 1
- MZXZWJOZGIUDSA-UHFFFAOYSA-N 3-(5-bromo-1H-indol-2-yl)-1H-thieno[3,2-c]pyrazole Chemical compound BrC1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=C1 MZXZWJOZGIUDSA-UHFFFAOYSA-N 0.000 claims 1
- HYDFIGJRGGSFOQ-UHFFFAOYSA-N 3-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)-1H-thieno[3,2-c]pyrazole Chemical compound COC1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=N1 HYDFIGJRGGSFOQ-UHFFFAOYSA-N 0.000 claims 1
- NSECBOSACCVWHK-UHFFFAOYSA-N 3-[2-(5-piperazin-1-yl-1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2N1CCNCC1 NSECBOSACCVWHK-UHFFFAOYSA-N 0.000 claims 1
- SIDOUDTVEGQWQR-UHFFFAOYSA-N 3-[2-(5-pyridin-4-yl-1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2C1=CC=NC=C1 SIDOUDTVEGQWQR-UHFFFAOYSA-N 0.000 claims 1
- MSELBTXMNDQOMK-UHFFFAOYSA-N 3-[2-[5-(2-hydroxypropan-2-yl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound CCC(O)(CC)C1=CC=C2C=C(C=3C=4SC(=CC=4NN=3)C(C)(C)O)NC2=C1 MSELBTXMNDQOMK-UHFFFAOYSA-N 0.000 claims 1
- QNWZOWWSIMLUNU-UHFFFAOYSA-N 3-[2-[5-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2C(ON=1)=NC=1C1CC1 QNWZOWWSIMLUNU-UHFFFAOYSA-N 0.000 claims 1
- JESNQRJNHAPTCT-UHFFFAOYSA-N 3-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-3-(morpholin-4-ylmethyl)-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=C(COC)SC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1CN1CCOCC1 JESNQRJNHAPTCT-UHFFFAOYSA-N 0.000 claims 1
- FESNCMIENNSFPO-UHFFFAOYSA-N 3-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-3-methyl-1H-indol-6-yl]pentan-3-ol Chemical compound CCC(O)(CC)C1=CC=C2C(C)=C(C=3C=4SC(COC)=CC=4NN=3)NC2=C1 FESNCMIENNSFPO-UHFFFAOYSA-N 0.000 claims 1
- BVXTXGMOTISRBR-UHFFFAOYSA-N 3-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-3-piperazin-1-yl-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=C(COC)SC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1N1CCNCC1 BVXTXGMOTISRBR-UHFFFAOYSA-N 0.000 claims 1
- MJDGBNSJAGKWAZ-UHFFFAOYSA-N 3-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-3-piperidin-4-yl-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=C(COC)SC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1C1CCNCC1 MJDGBNSJAGKWAZ-UHFFFAOYSA-N 0.000 claims 1
- RRVVIQFHOKJSDT-UHFFFAOYSA-N 3-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-3-pyridin-4-yl-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=C(COC)SC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1C1=CC=NC=C1 RRVVIQFHOKJSDT-UHFFFAOYSA-N 0.000 claims 1
- WVHNYEQAOBRRDE-UHFFFAOYSA-N 3-[2-[5-(phenylmethoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2COCC1=CC=CC=C1 WVHNYEQAOBRRDE-UHFFFAOYSA-N 0.000 claims 1
- UFPCLAQHZTUQPJ-UHFFFAOYSA-N 3-[2-[5-(piperazin-1-ylmethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2CN1CCNCC1 UFPCLAQHZTUQPJ-UHFFFAOYSA-N 0.000 claims 1
- GVWVHQDDTRAANN-UHFFFAOYSA-N 3-[2-[5-[(4-pyridin-4-yloxypiperidin-1-yl)methyl]-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound N1C2=CC(C(O)(CC)CC)=CC=C2C=C1C(C=1S2)=NNC=1C=C2CN(CC1)CCC1OC1=CC=NC=C1 GVWVHQDDTRAANN-UHFFFAOYSA-N 0.000 claims 1
- OZCPQNNZBUEZLS-UHFFFAOYSA-N 3-[2-[5-[(dimethylamino)methyl]-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]pentan-3-ol Chemical compound CCC(O)(CC)C1=CC=C2C=C(C=3C=4SC(CN(C)C)=CC=4NN=3)NC2=C1 OZCPQNNZBUEZLS-UHFFFAOYSA-N 0.000 claims 1
- FXLMSEFHRAWPEW-UHFFFAOYSA-N 3-[3-(4-methylpiperazin-1-yl)-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=CSC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1N1CCN(C)CC1 FXLMSEFHRAWPEW-UHFFFAOYSA-N 0.000 claims 1
- XIFIPZSAQHEEDA-UHFFFAOYSA-N 3-[3-(morpholin-4-ylmethyl)-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=CSC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1CN1CCOCC1 XIFIPZSAQHEEDA-UHFFFAOYSA-N 0.000 claims 1
- DPNKJZFYLHXYTJ-UHFFFAOYSA-N 3-[3-piperidin-4-yl-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=CSC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1C1CCNCC1 DPNKJZFYLHXYTJ-UHFFFAOYSA-N 0.000 claims 1
- KSJIOHVWHCGZNM-UHFFFAOYSA-N 3-[3-pyridin-4-yl-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]pentan-3-ol Chemical compound N=1NC=2C=CSC=2C=1C=1NC2=CC(C(O)(CC)CC)=CC=C2C=1C1=CC=NC=C1 KSJIOHVWHCGZNM-UHFFFAOYSA-N 0.000 claims 1
- IWJSNRHTGNSMAH-UHFFFAOYSA-N 3-[5-(hydroxymethyl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole-5-carboxylic acid Chemical compound OCC1=CC=C2NC(C=3C=4SC(=CC=4NN=3)C(O)=O)=CC2=C1 IWJSNRHTGNSMAH-UHFFFAOYSA-N 0.000 claims 1
- JRIYVUJOCVFXTD-UHFFFAOYSA-N 3-[5-(hydroxymethyl)-1H-indol-2-yl]-N-(pyridin-2-ylmethyl)-1H-thieno[3,2-c]pyrazole-5-carboxamide Chemical compound C=1C2=CC(CO)=CC=C2NC=1C(C=1S2)=NNC=1C=C2C(=O)NCC1=CC=CC=N1 JRIYVUJOCVFXTD-UHFFFAOYSA-N 0.000 claims 1
- BSCGZUXAMOELEG-UHFFFAOYSA-N 3-[5-[[4-[(4-chlorophenyl)methyl]piperazin-1-yl]methyl]-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C1=CC(Cl)=CC=C1CN1CCN(CC=2C=C3C=C(NC3=CC=2)C=2C=3SC=CC=3NN=2)CC1 BSCGZUXAMOELEG-UHFFFAOYSA-N 0.000 claims 1
- MGXZCFYKPJKJIV-UHFFFAOYSA-N 3-[5-acetyl-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]thieno[3,2-c]pyrazole-1,5-dicarboxylic acid Chemical compound CC(=O)C1=CC=C2N(C(=O)OC(C)(C)C)C(C=3C=4SC(=CC=4N(C(O)=O)N=3)C(O)=O)=CC2=C1 MGXZCFYKPJKJIV-UHFFFAOYSA-N 0.000 claims 1
- YZRIJWMDPGIYDN-UHFFFAOYSA-N 3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1OCCCN1CCCCC1 YZRIJWMDPGIYDN-UHFFFAOYSA-N 0.000 claims 1
- PJFINGMXSIIAQN-UHFFFAOYSA-N 3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-5-[[4-(trifluoromethyl)piperidin-1-yl]methyl]-1H-thieno[3,2-c]pyrazole Chemical compound C1CC(C(F)(F)F)CCN1CC(S1)=CC2=C1C(C=1NC3=CC(OCCCN4CCCCC4)=CC=C3C=1)=NN2 PJFINGMXSIIAQN-UHFFFAOYSA-N 0.000 claims 1
- XQRGMPBDXZACPU-UHFFFAOYSA-N 3-[6-(4-fluoropiperidin-4-yl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C1(F)CCNCC1 XQRGMPBDXZACPU-UHFFFAOYSA-N 0.000 claims 1
- VNXFCEKVBNODTE-UHFFFAOYSA-N 3-[6-[3-(4-ethylpiperazin-1-yl)propoxy]-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C1CN(CC)CCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC=CC=4NN=3)C2=C1 VNXFCEKVBNODTE-UHFFFAOYSA-N 0.000 claims 1
- JMCXWCFGDHFCDP-UHFFFAOYSA-N 4-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxan-4-ol Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C1(O)CCOCC1 JMCXWCFGDHFCDP-UHFFFAOYSA-N 0.000 claims 1
- SNQXUBZJXJOAFY-UHFFFAOYSA-N 4-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]piperidin-4-ol Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C1(O)CCNCC1 SNQXUBZJXJOAFY-UHFFFAOYSA-N 0.000 claims 1
- GUISTLUPWUOULL-UHFFFAOYSA-N 4-[2-[5-(methoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]oxan-4-ol Chemical compound C1=2SC(COC)=CC=2NN=C1C(NC1=C2)=CC1=CC=C2C1(O)CCOCC1 GUISTLUPWUOULL-UHFFFAOYSA-N 0.000 claims 1
- YFPAFQFOHZODPG-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C1=CC(F)=CC=C1N1CCN(CC=2SC=3C(C=4NC5=CC(OCCCN6CCCCC6)=CC=C5C=4)=NNC=3C=2)CC1 YFPAFQFOHZODPG-UHFFFAOYSA-N 0.000 claims 1
- DQLPPAZQHDULGL-UHFFFAOYSA-N 5-phenyl-3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole Chemical compound C1CCCCN1CCCOC(C=C1N2)=CC=C1C=C2C(C=1S2)=NNC=1C=C2C1=CC=CC=C1 DQLPPAZQHDULGL-UHFFFAOYSA-N 0.000 claims 1
- IXPUSVSGGMKMJU-UHFFFAOYSA-N 6-(3-piperidin-1-ylpropoxy)-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-3-amine Chemical compound Nc1c([nH]c2cc(OCCCN3CCCCC3)ccc12)-c1n[nH]c2ccsc12 IXPUSVSGGMKMJU-UHFFFAOYSA-N 0.000 claims 1
- 125000006416 CBr Chemical group BrC* 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- SNXVTEMZFIXKMJ-UHFFFAOYSA-N N,N-diethyl-3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propan-1-amine Chemical compound CCN(CC)CCCOC1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 SNXVTEMZFIXKMJ-UHFFFAOYSA-N 0.000 claims 1
- WVVFXYZPQMLMDS-UHFFFAOYSA-N N,N-dimethyl-3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propan-1-amine Chemical compound CN(C)CCCOC1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 WVVFXYZPQMLMDS-UHFFFAOYSA-N 0.000 claims 1
- ALTCXRFWHKVYDD-UHFFFAOYSA-N N-(2-hydroxy-2-phenylethyl)-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indole-6-carboxamide Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)NCC(O)C1=CC=CC=C1 ALTCXRFWHKVYDD-UHFFFAOYSA-N 0.000 claims 1
- OBUIXEWSVZYYPU-UHFFFAOYSA-N N-(2-pyridin-3-ylethyl)-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indole-6-carboxamide Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)NCCC1=CC=CN=C1 OBUIXEWSVZYYPU-UHFFFAOYSA-N 0.000 claims 1
- DDUVWIRGEDFLOX-UHFFFAOYSA-N N-(3-ethoxypropyl)-3-[5-(hydroxymethyl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole-5-carboxamide Chemical compound OCC1=CC=C2NC(C3=NNC=4C=C(SC=43)C(=O)NCCCOCC)=CC2=C1 DDUVWIRGEDFLOX-UHFFFAOYSA-N 0.000 claims 1
- ITMNGPLKCPTRKL-UHFFFAOYSA-N N-[2-(cyclohexen-1-yl)ethyl]-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indole-6-carboxamide Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)NCCC1=CCCCC1 ITMNGPLKCPTRKL-UHFFFAOYSA-N 0.000 claims 1
- MRLBGQJMWFGSJU-UHFFFAOYSA-N [1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]oxy]propyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1CCCOC1=CC=C(NC(=C2)C=3C=4SC=CC=4NN=3)C2=C1 MRLBGQJMWFGSJU-UHFFFAOYSA-N 0.000 claims 1
- WJYVOODKWFUAGF-UHFFFAOYSA-N [1-[3-[[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]oxy]propyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1CCCOC1=CC=C(C=C(N2)C=3C=4SC=CC=4NN=3)C2=C1 WJYVOODKWFUAGF-UHFFFAOYSA-N 0.000 claims 1
- MPZMCNZFQJBEGD-UHFFFAOYSA-N [2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]methanol Chemical compound OCC1=CC=C2NC(C=3C=4SC=CC=4NN=3)=CC2=C1 MPZMCNZFQJBEGD-UHFFFAOYSA-N 0.000 claims 1
- CYNPTXVWWJJDST-UHFFFAOYSA-N [2-[5-(phenylmethoxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-6-yl]-dipyridin-2-ylmethanol Chemical compound C=1C=CC=NC=1C(C=1N=CC=CC=1)(O)C(C=C1N2)=CC=C1C=C2C(C=1S2)=NNC=1C=C2COCC1=CC=CC=C1 CYNPTXVWWJJDST-UHFFFAOYSA-N 0.000 claims 1
- LCMBLVQUOMCZES-UHFFFAOYSA-N [2-[5-(piperidin-1-ylmethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-1H-indol-5-yl]methanol Chemical compound C=1C2=CC(CO)=CC=C2NC=1C(C=1S2)=NNC=1C=C2CN1CCCCC1 LCMBLVQUOMCZES-UHFFFAOYSA-N 0.000 claims 1
- UGBASCAWZGZRCF-UHFFFAOYSA-N [3-[6-(3-piperidin-1-ylpropoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]methanol Chemical compound C1=2SC(CO)=CC=2NN=C1C(NC1=C2)=CC1=CC=C2OCCCN1CCCCC1 UGBASCAWZGZRCF-UHFFFAOYSA-N 0.000 claims 1
- HEQXXMNXXNRRCC-UHFFFAOYSA-N [4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]methanone Chemical compound C1=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC(C(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=O)=C1 HEQXXMNXXNRRCC-UHFFFAOYSA-N 0.000 claims 1
- QKNXULHDBHOODD-UHFFFAOYSA-N [4-(2-cyclohexylethyl)piperazin-1-yl]-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]methanone Chemical compound C=1C=C2C=C(C=3C=4SC=CC=4NN=3)NC2=CC=1C(=O)N(CC1)CCN1CCC1CCCCC1 QKNXULHDBHOODD-UHFFFAOYSA-N 0.000 claims 1
- XCTQVDKXQIBMSU-UHFFFAOYSA-N [4-(4-fluorophenyl)piperazin-1-yl]-[3-[5-(hydroxymethyl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-yl]methanone Chemical compound C=1C2=CC(CO)=CC=C2NC=1C(C=1S2)=NNC=1C=C2C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 XCTQVDKXQIBMSU-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- DIXGMUOGPVYGGQ-UHFFFAOYSA-N bis(1-methylpiperidin-4-yl)-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]methanol Chemical compound C1CN(C)CCC1C(O)(C=1C=C2NC(=CC2=CC=1)C=1C=2SC=CC=2NN=1)C1CCN(C)CC1 DIXGMUOGPVYGGQ-UHFFFAOYSA-N 0.000 claims 1
- OHAIFZDRLDEOAC-UHFFFAOYSA-N chembl2017553 Chemical compound CCC(O)(CC)C1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 OHAIFZDRLDEOAC-UHFFFAOYSA-N 0.000 claims 1
- CQZZZUNOWZUNNG-UHFFFAOYSA-N chembl2017556 Chemical compound CCC(O)(CC)C1=CC=C2C=C(C=3C=4SC(=CC=4NN=3)C(F)F)NC2=C1 CQZZZUNOWZUNNG-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- WWTJBFXCGGJTMI-UHFFFAOYSA-N dicyclopropyl-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-6-yl]methanol Chemical compound C1CC1C(C=1C=C2NC(=CC2=CC=1)C=1C=2SC=CC=2NN=1)(O)C1CC1 WWTJBFXCGGJTMI-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- SMMBOXPLNPXHLZ-UHFFFAOYSA-N methyl 2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=C(C=3C=4SC=CC=4NN=3)NC2=C1 SMMBOXPLNPXHLZ-UHFFFAOYSA-N 0.000 claims 1
- VCNIHYAPZMKVQI-UHFFFAOYSA-N methyl 3-(5-acetyl-1H-indol-2-yl)-1H-thieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)C1=CC=C2NC(C3=NNC=4C=C(SC=43)C(=O)OC)=CC2=C1 VCNIHYAPZMKVQI-UHFFFAOYSA-N 0.000 claims 1
- SATYSRLXHMALNE-UHFFFAOYSA-N methyl 3-[5-(hydroxymethyl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole-5-carboxylate Chemical compound OCC1=CC=C2NC(C3=NNC=4C=C(SC=43)C(=O)OC)=CC2=C1 SATYSRLXHMALNE-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- NZLLSNRJBHQTRA-UHFFFAOYSA-N phenyl-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]methanol Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(O)C1=CC=CC=C1 NZLLSNRJBHQTRA-UHFFFAOYSA-N 0.000 claims 1
- BCNWQQAZEXXASV-UHFFFAOYSA-N phenyl-[2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]methanone Chemical compound C=1C=C2NC(C=3C=4SC=CC=4NN=3)=CC2=CC=1C(=O)C1=CC=CC=C1 BCNWQQAZEXXASV-UHFFFAOYSA-N 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- DFFQMBBFMDZDKQ-UHFFFAOYSA-N tert-butyl 3-[5-[tert-butyl(dimethyl)silyl]oxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]thieno[3,2-c]pyrazole-1-carboxylate Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=C2N(C(=O)OC(C)(C)C)C(C3=NN(C=4C=CSC=43)C(=O)OC(C)(C)C)=CC2=C1 DFFQMBBFMDZDKQ-UHFFFAOYSA-N 0.000 claims 1
- DGBWMYPWIKJLLZ-UHFFFAOYSA-N tert-butyl 3-[6-[tert-butyl(dimethyl)silyl]oxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]-5-[(dimethylamino)methyl]thieno[3,2-c]pyrazole-1-carboxylate Chemical compound C1=C(O[Si](C)(C)C(C)(C)C)C=C2N(C(=O)OC(C)(C)C)C(C3=NN(C=4C=C(SC=43)CN(C)C)C(=O)OC(C)(C)C)=CC2=C1 DGBWMYPWIKJLLZ-UHFFFAOYSA-N 0.000 claims 1
- AQQXRQMLCOXKES-UHFFFAOYSA-N tert-butyl 3-[6-[tert-butyl(dimethyl)silyl]oxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]thieno[3,2-c]pyrazole-1-carboxylate Chemical compound C1=C(O[Si](C)(C)C(C)(C)C)C=C2N(C(=O)OC(C)(C)C)C(C3=NN(C=4C=CSC=43)C(=O)OC(C)(C)C)=CC2=C1 AQQXRQMLCOXKES-UHFFFAOYSA-N 0.000 claims 1
- GLCQPLHAOSQKLG-UHFFFAOYSA-N tert-butyl 5-[(dimethylamino)methyl]-3-[6-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]thieno[3,2-c]pyrazole-1-carboxylate Chemical compound C1=C(O)C=C2N(C(=O)OC(C)(C)C)C(C3=NN(C=4C=C(SC=43)CN(C)C)C(=O)OC(C)(C)C)=CC2=C1 GLCQPLHAOSQKLG-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
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 abstract 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50115903P | 2003-09-08 | 2003-09-08 | |
| PCT/US2004/023814 WO2005026175A1 (en) | 2003-09-08 | 2004-07-23 | Thienopyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100398T1 true HRP20100398T1 (hr) | 2010-09-30 |
Family
ID=34312256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100398T HRP20100398T1 (hr) | 2003-09-08 | 2010-07-20 | Tienopirazoli |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US7518000B2 (de) |
| JP (1) | JP4879739B2 (de) |
| KR (1) | KR20060069490A (de) |
| CN (1) | CN100398545C (de) |
| AT (1) | ATE468341T1 (de) |
| AU (1) | AU2004272507B2 (de) |
| BR (1) | BRPI0414215A (de) |
| CA (1) | CA2538032C (de) |
| CR (1) | CR8255A (de) |
| DE (1) | DE602004027288D1 (de) |
| DK (1) | DK1682553T3 (de) |
| EC (1) | ECSP066411A (de) |
| ES (1) | ES2345257T3 (de) |
| HK (1) | HK1095587A1 (de) |
| HR (1) | HRP20100398T1 (de) |
| IL (1) | IL173916A (de) |
| MA (1) | MA28038A1 (de) |
| ME (1) | MEP20908A (de) |
| MX (1) | MXPA06001827A (de) |
| MY (1) | MY144339A (de) |
| NO (1) | NO20061626L (de) |
| NZ (1) | NZ545421A (de) |
| OA (1) | OA13252A (de) |
| PT (1) | PT1682553E (de) |
| RS (2) | RS20060162A (de) |
| RU (1) | RU2358978C2 (de) |
| TN (1) | TNSN06058A1 (de) |
| TW (1) | TWI352705B (de) |
| WO (1) | WO2005026175A1 (de) |
| ZA (1) | ZA200601947B (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006101454A1 (en) * | 2005-03-21 | 2006-09-28 | S*Bio Pte Ltd | Benzothiophene derivatives: preparation and pharmaceutical applications |
| EP1968580A2 (de) * | 2005-12-20 | 2008-09-17 | Boehringer Ingelheim International Gmbh | 2-(ih-thieno [3,2-c] pyrazol-3yl)-ih-indol-derivate und damit zusammenhängende verbindungen als tec-kinase-hemmer zur behandlung von entzündungen und immunologischen erkrankungen |
| EP2151434A1 (de) | 2008-08-05 | 2010-02-10 | Institut Pasteur | Allkoxypyrazole und Verfahren zu ihrer Herstellung |
| EP2151433A1 (de) | 2008-08-05 | 2010-02-10 | Institut Pasteur | Alkoxypyrazole und Verfahren zu ihrer Herstellung |
| US8299070B2 (en) * | 2009-11-25 | 2012-10-30 | Japan Tobacco Inc. | Indole compounds and pharmaceutical use thereof |
| US20130158066A1 (en) * | 2011-12-20 | 2013-06-20 | Hoffmann-La Roche Inc. | 4-azaindole inhibitors of crac |
| WO2013153539A1 (en) | 2012-04-13 | 2013-10-17 | Glenmark Pharmaceuticals S.A. | Tricyclic compounds as tec kinase inhibitors |
| CN103467481B (zh) * | 2012-06-07 | 2016-08-31 | 上海汇伦生命科技有限公司 | 二氢吡啶类化合物、其组合物、制备方法和用途 |
| TW201414734A (zh) | 2012-07-10 | 2014-04-16 | Takeda Pharmaceutical | 氮雜吲哚衍生物 |
| WO2014041518A1 (en) * | 2012-09-14 | 2014-03-20 | Glenmark Pharmaceuticals S.A. | Thienopyrrole derivatives as itk inhibitors |
| CN103720694A (zh) * | 2012-10-11 | 2014-04-16 | 韩冰 | 一类治疗脑性瘫痪的化合物及其用途 |
| CN103772391A (zh) * | 2012-10-23 | 2014-05-07 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
| KR101571590B1 (ko) * | 2012-11-21 | 2015-11-25 | 주식회사 두산 | 유기 화합물 및 이를 이용하는 유기 전계 발광 소자 |
| CA3103411A1 (en) | 2013-10-25 | 2015-04-30 | Pharmacyclics Llc | Use of ibrutinib for treating and preventing chronic graft versus host disease |
| TW201620904A (zh) | 2014-01-09 | 2016-06-16 | 武田藥品工業有限公司 | 氮雜吲哚衍生物 |
| WO2016010108A1 (ja) * | 2014-07-18 | 2016-01-21 | 塩野義製薬株式会社 | 含窒素複素環誘導体およびそれらを含有する医薬組成物 |
| CN108135904A (zh) | 2015-08-31 | 2018-06-08 | 药品循环有限责任公司 | 用于治疗多发性骨髓瘤的btk抑制剂组合 |
| JP2019532997A (ja) | 2016-11-03 | 2019-11-14 | ジュノー セラピューティクス インコーポレイテッド | Ｔ細胞療法とｂｔｋ阻害剤との併用療法 |
| US20210121466A1 (en) | 2018-05-03 | 2021-04-29 | Juno Therapeutics, Inc. | Combination therapy of a chimeric antigen receptor (car) t cell therapy and a kinase inhibitor |
| WO2023139248A1 (en) * | 2022-01-21 | 2023-07-27 | Ecole Polytechnique Federale De Lausanne (Epfl) | Inhibitors of acyl protein thioesterases against microbial infections |
| WO2023220655A1 (en) | 2022-05-11 | 2023-11-16 | Celgene Corporation | Methods to overcome drug resistance by re-sensitizing cancer cells to treatment with a prior therapy via treatment with a t cell therapy |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6462036B1 (en) * | 1998-11-06 | 2002-10-08 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
| US6297238B1 (en) * | 1999-04-06 | 2001-10-02 | Basf Aktiengesellschaft | Therapeutic agents |
| WO2001000610A1 (de) * | 1999-06-23 | 2001-01-04 | Aventis Pharma Deutschland Gmbh | Substituierte benzimidazole |
| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| WO2003024969A1 (en) * | 2001-09-14 | 2003-03-27 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| IL161576A0 (en) * | 2001-10-26 | 2004-09-27 | Aventis Pharma Inc | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| FR2831536A1 (fr) * | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
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- 2004-07-23 ES ES04779049T patent/ES2345257T3/es active Active
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