ZA200601947B - Thienopyrazoles - Google Patents

Info

Publication number

ZA200601947B

ZA200601947B ZA200601947A ZA200601947A ZA200601947B ZA 200601947 B ZA200601947 B ZA 200601947B ZA 200601947 A ZA200601947 A ZA 200601947A ZA 200601947 A ZA200601947 A ZA 200601947A ZA 200601947 B ZA200601947 B ZA 200601947B

Authority

ZA

South Africa

Prior art keywords

thieno

pyrazol

indol

optionally substituted

piperidin

Prior art date

2003-09-08

Links

• Espacenet
• Global Dossier
• Discuss

• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 207
• 239000000203 mixture Substances 0.000 claims description 169
• 150000001875 compounds Chemical class 0.000 claims description 141
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 74
• -1 2-thiophen-2-yl-ethyl Chemical group 0.000 claims description 69
• 238000000034 method Methods 0.000 claims description 64
• 150000003839 salts Chemical class 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 41
• 239000002253 acid Substances 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 19
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 239000000126 substance Substances 0.000 claims description 15
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
• 229940002612 prodrug Drugs 0.000 claims description 14
• 239000000651 prodrug Substances 0.000 claims description 14
• 125000003107 substituted aryl group Chemical group 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003435 aroyl group Chemical group 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 8
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 8
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 8
• 125000005110 aryl thio group Chemical group 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000005239 aroylamino group Chemical group 0.000 claims description 7
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 7
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 6
• 125000001475 halogen functional group Chemical group 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• AQIXEPGDORPWBJ-UHFFFAOYSA-N diethyl carbinol Natural products CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• UMHLJYMJTZWSTJ-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-1H-thieno[3,2-c]pyrazole Chemical compound C1=CC=C2NC(C3=NNC=4C=CSC=43)=NC2=C1 UMHLJYMJTZWSTJ-UHFFFAOYSA-N 0.000 claims description 4
• 108090000695 Cytokines Proteins 0.000 claims description 4
• 102000004127 Cytokines Human genes 0.000 claims description 4
• 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 description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 150000001555 benzenes Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 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 description 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
• 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• PGZUCEHHEMJFTH-UHFFFAOYSA-N 1-o-tert-butyl 5-o-methyl 3-[5-acetyl-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]thieno[3,2-c]pyrazole-1,5-dicarboxylate Chemical compound CC(=O)C1=CC=C2N(C(=O)OC(C)(C)C)C(C3=NN(C=4C=C(SC=43)C(=O)OC)C(=O)OC(C)(C)C)=CC2=C1 PGZUCEHHEMJFTH-UHFFFAOYSA-N 0.000 claims description 2
• BEIGNMUXNMORNR-UHFFFAOYSA-N 3-(6-methoxy-1H-benzimidazol-2-yl)-2H-[1]benzothiolo[3,2-c]pyrazole Chemical compound C12=CC=CC=C2SC2=C1NN=C2C1=NC2=CC=C(OC)C=C2N1 BEIGNMUXNMORNR-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 230000001575 pathological effect Effects 0.000 claims 6
• 238000012261 overproduction Methods 0.000 claims 4
• 238000004519 manufacturing process Methods 0.000 claims 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims 2
• 229940127557 pharmaceutical product Drugs 0.000 claims 2
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 125000006416 CBr Chemical group BrC* 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
• 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
• 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
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 1
• LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 claims 1
• 229940023942 remeron Drugs 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
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 669
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 360
• 239000000543 intermediate Substances 0.000 description 221
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 210
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 191
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 184
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 161
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