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
Abstract
Spoj formule I: naznačen time što: X je C-R7;X1 je N ili C-R1;R1, R2, R3, R4, R5 i R6 se neovisno bira iz skupine koju čine vodik, izborno supstituirani acil, izborno supstituirani alkil, izborno supstituirani alkoksi, izborno supstituirani acilamino, izborno supstituirani alkoksialkil, (Y1)(Y2)NC(=O)-, (Y1)(Y2)N-, izborno supstituirani alkoksikarbonil, izborno supstituirani aril, izborno supstituirani arilalkil, izborno supstituirani arilalkoksi, izborno supstituirani arilalkiloksialkil, izborno supstituirani ariloksialkil, izborno supstituirani cikloalkenil, izborno supstituirani cikloalkoksialkil, izborno supstituirani cikloalkil, izborno supstituirani cikloalkilalkil, izborno supstituirani cikloalkiloksi, izborno supstituirani heteroarilalkil, izborno supstituirani heteroarilalkoksi, izborno supstituirani heteroarilalkiloksialkil, izborno supstituirani heteroariloksialkil, izborno supstituirani heterocikloalkil, izborno supstituirani heterocikloalkilalkil, izborno supstituirani heterocikloalkiloksi, izborno supstituirani heterocikloalkiloksialkil, halogen, hidroksi, trifluormetil, nitro, izborno supstituirani hidroksialkil, karboksi, te cijano; R7 je vodik, halogen ili izborno supstituirani alkil; iY1 i Y2 su neovisno vodik, izborno supstituirani alkil, izborno supstituirani aril ili izborno supstituirani heteroaril, ili Y1 i Y2, zajedno s dušikom na kojeg su vezani, tvore izborno supstituiranu heteroarilnu skupinu ili izborno supstituiranu heterocikloalkilnu skupinu; heteroaril je aromatski prstenasti sustav s 5 do 14 članova u prstenu, gdje se jedan ili više članova u prstenu bira iz skupine koju čine dušik, kisik i sumpor; heterocikloalkil je nearomatski ili djelomično aromatski prstenasti sustav s 5 do 14 članova u prstenu, gdje se jedan ili više članova u prstenu bira iz skupine koju čine O, S i NY9, gdje Y9 je vodik, izborno supstituirani alkil, izborno supstituirani aril, izborno supstituirani arilalkil, cikloalkilalkil, izborno supstituirani heteroaril ili izborno supstituirani heteroarilalkil; gdje alkilni ostatak i cikloalkenilni ostatak u izborno supstituiranoj skupini može biti supstituiran s jednim ili više supstituenata, koje se bira iz skupine koju čine acil, acilamino, alkoksi, alkoksikarbonil, alkilendioksi, alkilsulfinil, alkilsulfonil, alkiltio, izborno supstituirani aroil, izborno supstituirani aroilamino, izborno supstituirani aril, izborno supstituirani arilalkil, izborno supstituirani arilalkiloksi, izborno supstituirani arilalkiloksikarbonil, izborno supstituirani arilalkiltio, izborno supstituirani ariloksi, izborno supstituirani ariloksikarbonil, izborno supstituirani arilsulfinil, izborno supstituirani arilsulfonil, izborno supstituirani ariltio, karboksi, cijano, cikloalkenil, halogen, izborno supstituirani heteroaroil, izborno supstituirani heteroaril, izborno supstituirani heteroarilalkil, izborno supstituirani heteroarilalkiloksi, izborno supstituirani heteroaroilamino, izborno supstituirani heteroariloksi, izbo
Claims (12)
1. Spoj formule I:
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naznačen time što:
X je C-R7;
X1 je N ili C-R1;
R1, R2, R3, R4, R5 i R6 se neovisno bira iz skupine koju čine vodik, izborno supstituirani acil, izborno supstituirani alkil, izborno supstituirani alkoksi, izborno supstituirani acilamino, izborno supstituirani alkoksialkil, (Y1)(Y2)NC(=O)-, (Y1)(Y2)N-, izborno supstituirani alkoksikarbonil, izborno supstituirani aril, izborno supstituirani arilalkil, izborno supstituirani arilalkoksi, izborno supstituirani arilalkiloksialkil, izborno supstituirani ariloksialkil, izborno supstituirani cikloalkenil, izborno supstituirani cikloalkoksialkil, izborno supstituirani cikloalkil, izborno supstituirani cikloalkilalkil, izborno supstituirani cikloalkiloksi, izborno supstituirani heteroarilalkil, izborno supstituirani heteroarilalkoksi, izborno supstituirani heteroarilalkiloksialkil, izborno supstituirani heteroariloksialkil, izborno supstituirani heterocikloalkil, izborno supstituirani heterocikloalkilalkil, izborno supstituirani heterocikloalkiloksi, izborno supstituirani heterocikloalkiloksialkil, halogen, hidroksi, trifluormetil, nitro, izborno supstituirani hidroksialkil, karboksi, te cijano;
R7 je vodik, halogen ili izborno supstituirani alkil; i
Y1 i Y2 su neovisno vodik, izborno supstituirani alkil, izborno supstituirani aril ili izborno supstituirani heteroaril, ili Y1 i Y2, zajedno s dušikom na kojeg su vezani, tvore izborno supstituiranu heteroarilnu skupinu ili izborno supstituiranu heterocikloalkilnu skupinu;
heteroaril je aromatski prstenasti sustav s 5 do 14 članova u prstenu, gdje se jedan ili više članova u prstenu bira iz skupine koju čine dušik, kisik i sumpor;
heterocikloalkil je nearomatski ili djelomično aromatski prstenasti sustav s 5 do 14 članova u prstenu, gdje se jedan ili više članova u prstenu bira iz skupine koju čine O, S i NY9, gdje Y9 je vodik, izborno supstituirani alkil, izborno supstituirani aril, izborno supstituirani arilalkil, cikloalkilalkil, izborno supstituirani heteroaril ili izborno supstituirani heteroarilalkil;
gdje alkilni ostatak i cikloalkenilni ostatak u izborno supstituiranoj skupini može biti supstituiran s jednim ili više supstituenata, koje se bira iz skupine koju čine acil, acilamino, alkoksi, alkoksikarbonil, alkilendioksi, alkilsulfinil, alkilsulfonil, alkiltio, izborno supstituirani aroil, izborno supstituirani aroilamino, izborno supstituirani aril, izborno supstituirani arilalkil, izborno supstituirani arilalkiloksi, izborno supstituirani arilalkiloksikarbonil, izborno supstituirani arilalkiltio, izborno supstituirani ariloksi, izborno supstituirani ariloksikarbonil, izborno supstituirani arilsulfinil, izborno supstituirani arilsulfonil, izborno supstituirani ariltio, karboksi, cijano, cikloalkenil, halogen, izborno supstituirani heteroaroil, izborno supstituirani heteroaril, izborno supstituirani heteroarilalkil, izborno supstituirani heteroarilalkiloksi, izborno supstituirani heteroaroilamino, izborno supstituirani heteroariloksi, izborno supstituirani heterocikloalkil, hidroksi, nitro, okso, trifluormetil, Y7Y8N-, Y7Y8NCO- i Y7Y8NSO2-, gdje Y7 i Y8 su neovisno vodik, alkil, aril, arilalkil, heteroaril ili heteroarilalkil;
cikloalkilni ostatak i heterocikloalkilni ostatak u izborno supstituiranoj skupini može biti supstituiran s jednim ili više supstituenata, koje se bira iz skupine koju čine alkil, acil, acilamino, alkoksi, alkoksikarbonil, alkilendioksi, alkilsulfinil, alkilsulfonil, alkiltio, izborno supstituirani aroil, izborno supstituirani aroilamino, izborno supstituirani aril, izborno supstituirani arilalkil, izborno supstituirani arilalkiloksi, izborno supstituirani arilalkiloksikarbonil, izborno supstituirani arilalkiltio, izborno supstituirani ariloksi, izborno supstituirani ariloksikarbonil, izborno supstituirani arilsulfinil, izborno supstituirani arilsulfonil, izborno supstituirani ariltio, karboksi, cijano, cikloalkenil, halogen, izborno supstituirani heteroaril, izborno supstituirani heteroaril, izborno supstituirani heteroarilalkil, izborno supstituirani heteroarilalkiloksi, izborno supstituirani heteroaroilamino, izborno supstituirani heteroariloksi, izborno supstituirani heterocikloalkil, hidroksi, nitro, okso, trifluormetil, Y7Y8N-, Y7Y8NCO- i Y7Y8NSO2-, gdje Y7 i Y8 su neovisno vodik, alkil, aril, arilalkil, heteroaril ili heteroarilalkil;
arilni ostatak i heteroarilni ostatak u izborno supstituiranoj skupini može biti supstituiran s jednim ili više supstituenata, koje se bira iz skupine koju čine acil, acilamino, alkoksi, alkoksikarbonil, alkil, alkilendioksi, alkilsulfinil, alkilsulfonil, alkiltio, aroil, aroilamino, aril, arilalkil, arilalkiloksi, arilalkiloksikarbonil, arilalkiltio, ariloksi, ariloksikarbonil, arilsulfinil, arilsulfonil, ariltio, karboksi, cijano, halogen, heteroaroil, heteroaril, heteroarilalkil, heteroarilakiloksi, heteroaroilamino, heteroariloksi, heterocikloalkilalkil, hidroksi, nitro, trifluormetil, Y5Y6N-, Y5Y6NCO- i Y5Y6NSO2-, gdje Y5 i Y6 su neovisno vodik, alkil, aril, arilalkil, heteroaril i heteroarilalkil, ili Y5 i Y6, zajedno s atomom dušika na kojeg su vezani, tvore zasićeni aliciklički prsten s dušikom i ima 3 do 7 članova;
ili njegova farmaceutski prihvatljiva sol ili solvat.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1, R2, R3, R4, R5 i R6 se neovisno bira iz skupine koju čine vodik, izborno supstituirani acil, izborno supstituirani alkoksi, izborno supstituirani alkoksikarbonil, izborno supstituirani alkil, izborno supstituirani aril, karboksi, halogen i (Y1)(Y2)NC(=O)-, gdje Y1 i Y2 su neovisno vodik, izborno supstituirani alkil, izborno supstituirani aril ili izborno supstituirani heteroaril, ili Y1 i Y2, zajedno s dušikom na kojeg su vezani, tvore izborno supstituiranu heteroarilnu skupinu ili izborno supstituiranu heterocikloalkilnu skupinu.
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što X je C-H ili C-halogen, X1 je N, C-H ili C-halogen, jedan od R2 i R3 je vodik, a R6 je vodik.
4. Spoj u skladu s patentnim zahtjevom 2, naznačen time što X1 je C-H; X je C-Br ili C-H.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što jedan od R2 i R3 je vodik, a jedan od R2 i R3 se bira iz skupine koju čine vodik,
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halogen,
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i
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6. Spoj u skladu s patentnim zahtjevom 4, naznačen time što R4 je vodik.
7. Spoj u skladu s patentnim zahtjevom 5, naznačen time što R5 se bira iz skupine koju čine vodik,
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karboksi,
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i
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8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
5-(3-piperidin-1-ilpropoksi)-2-tieno[3,2-c]pirazol-3-il)indol,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-4-ol,
6-(3-piperidin-1-ilpropoksi)-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-3-ol,
(1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-3-il)metanol,
6-[3-(4-etilpiperazin-1-il)propoksi]-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
dimetil{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}amin,
dietil{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}amin,
dialil-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}amin,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}pirolidin-3-ol,
2-(metil{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}amino)etanol,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-iloksi]propil}piperidin-4-ol,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-iloksi]propil}piperidin-3-ol,
(1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-iloksi]propil}piperidin-3-il)metanol,
1-{3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-iloksi]propil}pirolidin-3-ol,
(2-tiofen-2-iletil)amid 2-{1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-karboksilne kiseline,
1-{3-[2-(5-dimetilaminoetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-4-ol,
tert-butilni ester 2-(1-tert-butoksikarbonil-1H-tieno[3,2-c]pirazol-3-il)-5-[tert-butil(dimetil)silaniloksi]indol-1-karboksilne kiseline,
tert-butilni ester 2-(1-tert-butoksikarbonil-1H-tieno[3,2-c]pirazol-3-il)-6-[tert-butil(dimetil)silaniloksi]indol-1-karboksilne kiseline,
tert-butilni ester 2-(1-tert-butoksikarbonil-5-dimetilaminometil-1H-tieno[3,2-c]pirazol-3-il)-6-[tert-butil(dimetil)silaniloksi]indol-1-karboksilne kiseline,
tert-butilni ester 2-(1-tert-butoksikarbonil-5-dimetilaminometil-1H-tieno[3,2-c]pirazol-3-il)-6-hidroksiindol-1-karboksilne kiseline,
[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]metanol,
fenil-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]metanol,
fenil-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]metanon,
1-fenil-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]etanol,
(S)-1-fenil-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]etanol,
1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]propan-1-one,
1-cikloheksil-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]propan-1-ol,
1-cikloheksil-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]propan-1-ol, enantiomer 1,
1-piridin-2-il-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]propan-1-ol,
2-[2-(1H-tieno[3,2-c]pirazaol-3-il)-1H-indol-5-il]butan-2-ol,
(R)-2-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]butan-2-ol,
1-(2-pirolidin-1-ilmetilfenil)-1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]propan-1-ol,
1-tert-butilni ester 5-metilni ester 3-(5-acetil-tert-butoksikarbonil-1H-indol-2-il)-tieno[3,2-c]pirazol-1,5-dikarboksilne kiseline,
metilni ester 3-(5-acetil-1H-indol-2-il)-1H-tieno[3,2-c]pirazol-5-karboksilne kiseline,
3-(5-hidroksimetil-1H-indol-2-il)-1H-tieno[3,2-c]pirazol-5-karboksilna kiselina,
[4-(4-fluorfenil)piperazin-1-il][3-(5-hidroksimetil-1H-indol-2-il)-1H-tieno(3,2-c]pirazol-5-il]metanon,
(3-etoksipropil)amid 3-(5-hidroksimetil-1H-indol-2-il)-1H-tieno[3,2-c]pirazol-5-karboksilne kiseline,
metilni ester 3-(5-hidroksimetil-1H-indol-2-il)-1H-tieno[3,2-c]pirazol-5-karboksilne kiseline,
(piridin-2-ilmetil)amid 3-(5-hidroksimetil-1H-indol-2-il)-1H-tieno[3,2-c]pirazol-5-karboksilne kiseline,
5-bromo-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
metilni ester 2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-karboksilne kiseline,
diciklopropil-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]metanol,
(4-benzo[1,3]dioksol-5-ilmetilpiperazin-1-il)[2-(1H-tieono[3,2-c]pirazol-3-il)-1H-indol-6-il]metanon,
[4-(2-cikloheksiletil)piperazin-1-il][2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]metanon,
(2-hidroksi-2-feniletil)amid 2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-karboksilne kiseline,
(2-cikloheks-1-eniletil)amid 2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-karboksilne kiseline,
(2-tiofen-2-iletil)amid 2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-karboksilne kiseline,
(4-piridin-2-ilpiperazin-il)[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]metanon,
(2-piridin-3-iletil)amid 2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-karboksilne kiseline,
cikloheksilmetil[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-ilmetil]amin,
5-[4-(4-klorbenzil)piperazin-1-ilmetil]-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
[2-(4-fenoksifenil)etil][2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-ilmetil]amin,
1-{3-[2-(5-fenil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-3-ol,
1-{3-[2-(5-fenil-1H-tieno[3,2,c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-4-ol,
2-(5-fenil-1H-tieno[3,2-c]pirazol-3-il)-6-(3-piperidin-1-ilpropoksi)-1H-indol,
1-(3-{2-[5-(3-metoksifenil)-1H-tieno[3,2-c]pirazol-3-il]-1H-indol-6-iloksi}propil)piperidin-4-ol,
5-metoksi-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-pirolo[3,2-b]piridin,
3-amino-6-(3-piperidin-1-ilpropoksi)-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
{3-[6-(3-piperidin-1-ilpropoksi)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-il}metanol,
1-{3-[6-(3-piperidin-1-ilpropoksi)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-ilmetil}piperidine-4-ol,
2-{5-[4-(4-fluorfenil)piperazin-1-ilmetil]-1H-tieno[3,2-c]pirazol-3-il}-6-(3-piperidin-1-ilpropoksi)-1H-indol,
metil{3-[6-(3-pipezadin-1-ilpropoksi)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-ilmetil}piridin-2-ilamin,
benzil{3-[6-(3-piperidin-1-ilpropoksi)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-ilmetil}amin,
6-(3-piperidin-1-ilpropoksi)-2-[5-(4-trifluormetilpiperidin-1-ilmetil)-1H-tieno[3,2-c]pirazol-3-il]-1H-indol,
[2-(5-piperidin-1-ilmetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-5-il]metanol,
1-{3-[2-(5-benziloksimetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-iloksi]propil}piperidin-4-ol,
3-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-[2-(5-benziloksimetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol i
[2-(5-benziloksimetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]dipiridin-2-ilmetanol;
ili njihove farmaceutski prihvatljive soli ili solvati.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
1-{3-[6-(1-etil-1-hidroksipropil)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-ilmetil}piperidin-4-ol,
3-[2-(5-dimetilaminometil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-(2-{5-[4-(piridin-4-iloksi)piperidin-1-ilmetil]-1H-tieno[3,2-c]pirazol-3-il}-1H-indol-6-il)pentan-3-ol,
3-[2-(5-piperazin-1-ilmetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-[2-(5-piperazin-1-il-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-{2-[5-(3-ciklopropil-1,2,4-oksadiazol-5-il)-1H-tieno[3,2-c]pirazol-3-il]-1H-indol-6-il}pentan-3-ol,
3-[2-(5-piridin-4-il-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
bis(1-metilpiperidin-4-il)[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]metanol,
3-[2-(5-difluommetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
4-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]piperidin-4-ol,
6-(4-fluorpiperidin-4-il)-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol,
2-[2-(1H-tieno[3,2-c]piraksol-3-il)-1H-indol-6-il]butan-2-ol,
1-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]etanon,
3-[3-piperidin-4-il-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-[3-piridin-4-il-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-[3-(4-metilpiperazin-1-il)-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
3-[3-morfolin-4-ilmetil-2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]pentan-3-ol,
4-[2-(1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]tetrahidropiran-4-ol,
3-{2-[5-(1-hidroksi-1-metiletil)-1H-tieno[3,2-c]pirazol-3-il]-1H-indol-6-il}pentan-3-ol,
3-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-3-piridin-4-il-1H-indol-6-il]pentan-3-ol,
4-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-1H-indol-6-il]tetrahidropiran-4-ol,
3-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-3-piperazin-1-il-1H-indol-6-il]pentan-3-ol,
3-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-3-morfolin-4-ilmetil-1H-indol-6-il]pentan-3-ol,
2-{3-[6-(1-etil-1-hidroksipropil)-1H-indol-2-il]-1H-tieno[3,2-c]pirazol-5-il}tetrahidrofuran-3-karbonitril,
3-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-3-metil-1H-indol-6-il]pentan-3-ol i
3-[2-(5-metoksimetil-1H-tieno[3,2-c]pirazol-3-il)-3-piperidin-4-il-1H-indol-6-il]pentan-3-ol;
ili njihove farmaceutski prihvatljive soli ili solvati.
10. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje patološkog stanja povezanog s hiperprodukcijom citokina Th2.
11. Upotreba u skladu s patentnim zahtjevom 10, naznačena time što patološko stanje je astma.
12. Farmaceutski proizvod, naznačen time što sadrži aktivni sastojak i farmaceutski prihvatljivu pomoćnu tvar, gdje je navedeni aktivni sastojak spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9.
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 (hr) |
| JP (1) | JP4879739B2 (hr) |
| KR (1) | KR20060069490A (hr) |
| CN (1) | CN100398545C (hr) |
| AT (1) | ATE468341T1 (hr) |
| AU (1) | AU2004272507B2 (hr) |
| BR (1) | BRPI0414215A (hr) |
| CA (1) | CA2538032C (hr) |
| CR (1) | CR8255A (hr) |
| DE (1) | DE602004027288D1 (hr) |
| DK (1) | DK1682553T3 (hr) |
| EC (1) | ECSP066411A (hr) |
| ES (1) | ES2345257T3 (hr) |
| HK (1) | HK1095587A1 (hr) |
| HR (1) | HRP20100398T1 (hr) |
| IL (1) | IL173916A (hr) |
| MA (1) | MA28038A1 (hr) |
| ME (1) | MEP20908A (hr) |
| MX (1) | MXPA06001827A (hr) |
| MY (1) | MY144339A (hr) |
| NO (1) | NO20061626L (hr) |
| NZ (1) | NZ545421A (hr) |
| OA (1) | OA13252A (hr) |
| PT (1) | PT1682553E (hr) |
| RS (2) | RS51846B (hr) |
| RU (1) | RU2358978C2 (hr) |
| TN (1) | TNSN06058A1 (hr) |
| TW (1) | TWI352705B (hr) |
| WO (1) | WO2005026175A1 (hr) |
| ZA (1) | ZA200601947B (hr) |
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 |
| JP2009520831A (ja) * | 2005-12-20 | 2009-05-28 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｔｅｃキナーゼインヒビター |
| EP2151433A1 (en) | 2008-08-05 | 2010-02-10 | Institut Pasteur | Alkoxypyrazoles and the process for their preparation |
| EP2151434A1 (en) | 2008-08-05 | 2010-02-10 | Institut Pasteur | Alkoxypyrazoles and the process for their preparation |
| 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 |
| JP2016538270A (ja) | 2013-10-25 | 2016-12-08 | ファーマサイクリックス エルエルシー | 移植片対宿主病を処置し予防する方法 |
| AR099052A1 (es) | 2014-01-09 | 2016-06-29 | Takeda Pharmaceuticals Co | Derivados de azaindol |
| 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 |
| MA45973A (fr) | 2015-08-31 | 2019-06-26 | Pharmacyclics Llc | Combinaisons d'inhibiteurs de btk pour le traitement du myélome multiple |
| MX2019005029A (es) | 2016-11-03 | 2019-10-24 | Juno Therapeutics Inc | Terapia de combinación de una terapia de células t y un inhibidor de tirosina cinasa de bruton (btk). |
| EP3787751A1 (en) | 2018-05-03 | 2021-03-10 | 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 |
| ATE301651T1 (de) * | 1999-06-23 | 2005-08-15 | Aventis Pharma 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 |
| US7101884B2 (en) * | 2001-09-14 | 2006-09-05 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| JP5039268B2 (ja) * | 2001-10-26 | 2012-10-03 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用 |
| 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 |
-
2004
- 2004-07-23 RS RS20060162A patent/RS51846B/en unknown
- 2004-07-23 MY MYPI20042959A patent/MY144339A/en unknown
- 2004-07-23 OA OA1200600080A patent/OA13252A/en unknown
- 2004-07-23 WO PCT/US2004/023814 patent/WO2005026175A1/en active Application Filing
- 2004-07-23 TW TW093122172A patent/TWI352705B/zh active
- 2004-07-23 CA CA2538032A patent/CA2538032C/en not_active Expired - Fee Related
- 2004-07-23 JP JP2006525328A patent/JP4879739B2/ja not_active Expired - Fee Related
- 2004-07-23 CN CNB2004800257424A patent/CN100398545C/zh not_active Expired - Fee Related
- 2004-07-23 ES ES04779049T patent/ES2345257T3/es active Active
- 2004-07-23 MX MXPA06001827A patent/MXPA06001827A/es active IP Right Grant
- 2004-07-23 BR BRPI0414215-2A patent/BRPI0414215A/pt not_active IP Right Cessation
- 2004-07-23 AU AU2004272507A patent/AU2004272507B2/en not_active Ceased
- 2004-07-23 AT AT04779049T patent/ATE468341T1/de active
- 2004-07-23 RS YUP-2006/0162A patent/RS20060162A/sr unknown
- 2004-07-23 DE DE602004027288T patent/DE602004027288D1/de active Active
- 2004-07-23 NZ NZ545421A patent/NZ545421A/en not_active IP Right Cessation
- 2004-07-23 KR KR1020067004795A patent/KR20060069490A/ko active IP Right Grant
- 2004-07-23 ME MEP-209/08A patent/MEP20908A/xx unknown
- 2004-07-23 RU RU2006111470/04A patent/RU2358978C2/ru not_active IP Right Cessation
- 2004-07-23 DK DK04779049.8T patent/DK1682553T3/da active
- 2004-07-23 PT PT04779049T patent/PT1682553E/pt unknown
-
2006
- 2006-02-15 TN TNP2006000058A patent/TNSN06058A1/en unknown
- 2006-02-23 CR CR8255A patent/CR8255A/es not_active Application Discontinuation
- 2006-02-23 IL IL173916A patent/IL173916A/en not_active IP Right Cessation
- 2006-03-06 US US11/368,566 patent/US7518000B2/en not_active Expired - Fee Related
- 2006-03-06 EC EC2006006411A patent/ECSP066411A/es unknown
- 2006-03-07 ZA ZA200601947A patent/ZA200601947B/en unknown
- 2006-03-13 MA MA28871A patent/MA28038A1/fr unknown
- 2006-04-10 NO NO20061626A patent/NO20061626L/no not_active Application Discontinuation
-
2007
- 2007-01-17 HK HK07100592A patent/HK1095587A1/xx not_active IP Right Cessation
-
2009
- 2009-03-26 US US12/411,818 patent/US7928231B2/en not_active Expired - Fee Related
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2010
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