HRP20020451A2 - 1-tia-3-aza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediates for preparation thereof - Google Patents

Info

Publication number

HRP20020451A2

HRP20020451A2 HR20020451A HRP20020451A HRP20020451A2 HR P20020451 A2 HRP20020451 A2 HR P20020451A2 HR 20020451 A HR20020451 A HR 20020451A HR P20020451 A HRP20020451 A HR P20020451A HR P20020451 A2 HRP20020451 A2 HR P20020451A2

Authority

HR

Croatia

Prior art keywords

dibenzo

aza

dithia

azulene

trifluoromethyl

Prior art date

2002-05-23

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• 238000002360 preparation method Methods 0.000 title claims description 21
• 238000004519 manufacturing process Methods 0.000 title claims description 12
• 239000000543 intermediate Substances 0.000 title claims description 6
• 108060008682 Tumor Necrosis Factor Proteins 0.000 title description 38
• 239000003112 inhibitor Substances 0.000 title description 7
• 102000003390 tumor necrosis factor Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 103
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
• 238000006243 chemical reaction Methods 0.000 claims description 37
• -1 C1-C4-alkoxycarbonyl Chemical group 0.000 claims description 36
• 229910052717 sulfur Inorganic materials 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000003435 aroyl group Chemical group 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
• 102000004127 Cytokines Human genes 0.000 claims description 5
• 108090000695 Cytokines Proteins 0.000 claims description 5
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 230000001575 pathological effect Effects 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• PTVFNZZZZATPQA-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(CO)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(CO)=N2 PTVFNZZZZATPQA-UHFFFAOYSA-N 0.000 claims description 3
• WFILCHQWYZCTFT-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(CO)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(CO)=N2 WFILCHQWYZCTFT-UHFFFAOYSA-N 0.000 claims description 3
• GQMHIIXRIBMULE-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(C=C)=N2 Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(C=C)=N2 GQMHIIXRIBMULE-UHFFFAOYSA-N 0.000 claims description 3
• YSWWQBXFHGXJMY-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CCOCCCN(C)C)=N2 Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CCOCCCN(C)C)=N2 YSWWQBXFHGXJMY-UHFFFAOYSA-N 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• MTCBIAFZEQYHCD-UHFFFAOYSA-N (5-fluoro-1,8-dithia-3-aza-dibenzo[e,h]azulene-2-yl)-methanol Chemical compound C12=CC=CC=C2SC2=CC=C(F)C=C2C2=C1SC(CO)=N2 MTCBIAFZEQYHCD-UHFFFAOYSA-N 0.000 claims description 2
• JUZFUOIIPXZSEP-UHFFFAOYSA-N (6-chloro-1,8-dithia-3-aza-dibenzo[e,h]azulene-2-yl)-acetonitrile Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CC#N)=N2 JUZFUOIIPXZSEP-UHFFFAOYSA-N 0.000 claims description 2
• AOWMZDRASCRFAM-UHFFFAOYSA-N 13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethanol Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(CO)=N2 AOWMZDRASCRFAM-UHFFFAOYSA-N 0.000 claims description 2
• PEXIGZVSSOKOKY-UHFFFAOYSA-N 13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaene-4-carbaldehyde Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(C=O)=N2 PEXIGZVSSOKOKY-UHFFFAOYSA-N 0.000 claims description 2
• QXVIZBQTDRQEST-UHFFFAOYSA-N 2-(10-chloro-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)ethanol Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CCO)=N2 QXVIZBQTDRQEST-UHFFFAOYSA-N 0.000 claims description 2
• CNZVOASUSIRXRP-UHFFFAOYSA-N 2-(3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethoxy)-N,N-dimethylethanamine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(COCCN(C)C)=N2 CNZVOASUSIRXRP-UHFFFAOYSA-N 0.000 claims description 2
• OAHMBFKSFPVRDM-UHFFFAOYSA-N 2-[(9-chloro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylethanamine Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(COCCN(C)C)=N2 OAHMBFKSFPVRDM-UHFFFAOYSA-N 0.000 claims description 2
• CSDNVMZGFFVXEF-UHFFFAOYSA-N 2-[(9-fluoro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylethanamine Chemical compound C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(COCCN(C)C)=N2 CSDNVMZGFFVXEF-UHFFFAOYSA-N 0.000 claims description 2
• VVIWCPJFLVYJHE-UHFFFAOYSA-N 3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaene-4-carbaldehyde Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(C=O)=N2 VVIWCPJFLVYJHE-UHFFFAOYSA-N 0.000 claims description 2
• ZMKDSCQDEWVIBS-UHFFFAOYSA-N 3-[(9-chloro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(COCCCN(C)C)=N2 ZMKDSCQDEWVIBS-UHFFFAOYSA-N 0.000 claims description 2
• DIGZMTZERQUQEZ-UHFFFAOYSA-N 3-[(9-fluoro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(COCCCN(C)C)=N2 DIGZMTZERQUQEZ-UHFFFAOYSA-N 0.000 claims description 2
• MVPXMPNBDVTAOR-UHFFFAOYSA-N 4-methyl-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaene Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(C)=N2 MVPXMPNBDVTAOR-UHFFFAOYSA-N 0.000 claims description 2
• DKYJVDQOJFXBLK-UHFFFAOYSA-N 4-phenyl-10-(trifluoromethyl)-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3SC3=CC(C(F)(F)F)=CC=C3C=2N=C1C1=CC=CC=C1 DKYJVDQOJFXBLK-UHFFFAOYSA-N 0.000 claims description 2
• PRFOWOWBVPKKOR-UHFFFAOYSA-N 4-pyridin-4-yl-10-(trifluoromethyl)-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3OC3=CC(C(F)(F)F)=CC=C3C=2N=C1C1=CC=NC=C1 PRFOWOWBVPKKOR-UHFFFAOYSA-N 0.000 claims description 2
• WQTCKGFCFBQLEL-UHFFFAOYSA-N 5-fluoro-2-methyl-8-oxa-1-thia-3-aza-dibenzo[e,h]azulene Chemical compound C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(C)=N2 WQTCKGFCFBQLEL-UHFFFAOYSA-N 0.000 claims description 2
• GSDSWPKSDAVWOY-UHFFFAOYSA-N 8-oxa-1-thia-3-aza-dibenzo[e,h]azulene Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC=N2 GSDSWPKSDAVWOY-UHFFFAOYSA-N 0.000 claims description 2
• AOBRMDCJPLVRLM-UHFFFAOYSA-N 9-chloro-4-methyl-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound C12=CC=CC=C2SC2=CC=C(Cl)C=C2C2=C1SC(C)=N2 AOBRMDCJPLVRLM-UHFFFAOYSA-N 0.000 claims description 2
• MBNZQQXTJWCFKY-UHFFFAOYSA-N 9-fluoro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound C12=CC(F)=CC=C2OC2=CC=CC=C2C2=C1N=CS2 MBNZQQXTJWCFKY-UHFFFAOYSA-N 0.000 claims description 2
• QJNKULLSGCYTJL-UHFFFAOYSA-N 9-fluoro-13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene-4-carbaldehyde Chemical compound C12=CC(F)=CC=C2OC2=CC=CC=C2C2=C1N=C(C=O)S2 QJNKULLSGCYTJL-UHFFFAOYSA-N 0.000 claims description 2
• UQXKDMBOYBZGIN-UHFFFAOYSA-N C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1N=C(C=O)S2 Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1N=C(C=O)S2 UQXKDMBOYBZGIN-UHFFFAOYSA-N 0.000 claims description 2
• KSTGEIMMMMARBK-UHFFFAOYSA-N C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1N=CS2 Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1N=CS2 KSTGEIMMMMARBK-UHFFFAOYSA-N 0.000 claims description 2
• YOIZOQXXVDNKFG-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(C)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(C)=N2 YOIZOQXXVDNKFG-UHFFFAOYSA-N 0.000 claims description 2
• KYXBLOQUMUCDQC-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(CC(=O)OC)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(Cl)C=C2C2=C1SC(CC(=O)OC)=N2 KYXBLOQUMUCDQC-UHFFFAOYSA-N 0.000 claims description 2
• MXAFZQDNNYLDIP-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(CC(=O)OC)=N2 Chemical compound C12=CC=CC=C2OC2=CC=C(F)C=C2C2=C1SC(CC(=O)OC)=N2 MXAFZQDNNYLDIP-UHFFFAOYSA-N 0.000 claims description 2
• CZBPKQWNAFJZLQ-UHFFFAOYSA-N C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(COCCCN(C)C)=N2 Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(COCCCN(C)C)=N2 CZBPKQWNAFJZLQ-UHFFFAOYSA-N 0.000 claims description 2
• HHQUNALPRILPRY-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(Br)=CC=C2C2=C1SC(C)=N2 Chemical compound C12=CC=CC=C2SC2=CC(Br)=CC=C2C2=C1SC(C)=N2 HHQUNALPRILPRY-UHFFFAOYSA-N 0.000 claims description 2
• KUKPVBMCEVICHP-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(C(=O)OCC)=N2 Chemical compound C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(C(=O)OCC)=N2 KUKPVBMCEVICHP-UHFFFAOYSA-N 0.000 claims description 2
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• CVSRFBLIIQQYNC-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(CO)=N2 Chemical compound C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(CO)=N2 CVSRFBLIIQQYNC-UHFFFAOYSA-N 0.000 claims description 2
• SVXNNSHPJURTOR-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(COCCN(C)C)=N2 Chemical compound C12=CC=CC=C2SC2=CC(C(F)(F)F)=CC=C2C2=C1SC(COCCN(C)C)=N2 SVXNNSHPJURTOR-UHFFFAOYSA-N 0.000 claims description 2
• ADGPUESFYPJUBC-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(C)=N2 Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(C)=N2 ADGPUESFYPJUBC-UHFFFAOYSA-N 0.000 claims description 2
• JSMSTFXDNBSBEE-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CC(=O)OCC)=N2 Chemical compound C12=CC=CC=C2SC2=CC(Cl)=CC=C2C2=C1SC(CC(=O)OCC)=N2 JSMSTFXDNBSBEE-UHFFFAOYSA-N 0.000 claims description 2
• MRFCKYOLXVBYAY-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=C(Br)C=C2C2=C1SC(C)=N2 Chemical compound C12=CC=CC=C2SC2=CC=C(Br)C=C2C2=C1SC(C)=N2 MRFCKYOLXVBYAY-UHFFFAOYSA-N 0.000 claims description 2
• ZCYRHWMGMZHLGA-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=C(F)C=C2C2=C1SC(C(=O)OCC)=N2 Chemical compound C12=CC=CC=C2SC2=CC=C(F)C=C2C2=C1SC(C(=O)OCC)=N2 ZCYRHWMGMZHLGA-UHFFFAOYSA-N 0.000 claims description 2
• KJGCUADBMGUVBQ-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(CO)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(CO)=N2 KJGCUADBMGUVBQ-UHFFFAOYSA-N 0.000 claims description 2
• ZXXNXABMRBCTHB-UHFFFAOYSA-N C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(COCCCN(C)C)=N2 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC(COCCCN(C)C)=N2 ZXXNXABMRBCTHB-UHFFFAOYSA-N 0.000 claims description 2
• XOKLDXCTYVNPES-UHFFFAOYSA-N N,N-dimethyl-2-(13-oxa-3-thia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaen-4-ylmethoxy)ethanamine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1SC(COCCN(C)C)=N2 XOKLDXCTYVNPES-UHFFFAOYSA-N 0.000 claims description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• IKGOXVIGOYMVPQ-UHFFFAOYSA-N [3-(5-fluoro-1,8-dithia-3-aza-dibenzo[e,h]azulene-2-ylmethoxy)-propyl]-dimethylamine Chemical compound C12=CC=CC=C2SC2=CC=C(F)C=C2C2=C1SC(COCCCN(C)C)=N2 IKGOXVIGOYMVPQ-UHFFFAOYSA-N 0.000 claims description 2
• FJPDXFMXDIINIM-UHFFFAOYSA-N ctk3b6033 Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1SC=N2 FJPDXFMXDIINIM-UHFFFAOYSA-N 0.000 claims description 2
• 231100000252 nontoxic Toxicity 0.000 claims description 2
• 230000003000 nontoxic effect Effects 0.000 claims description 2
• 229910052698 phosphorus Inorganic materials 0.000 claims description 2
• 239000011574 phosphorus Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 6
• CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims 2
• GREMVYZPMVTGTO-UHFFFAOYSA-N 10-(trifluoromethyl)-4-[3-(trifluoromethyl)phenyl]-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound FC(F)(F)C1=CC=CC(C=2SC3=C(C4=CC=C(C=C4SC4=CC=CC=C43)C(F)(F)F)N=2)=C1 GREMVYZPMVTGTO-UHFFFAOYSA-N 0.000 claims 1
• HZMKCIKUGRDZGA-UHFFFAOYSA-N 10-(trifluoromethyl)-4-[4-(trifluoromethyl)pyridin-3-yl]-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3SC3=CC(C(F)(F)F)=CC=C3C=2N=C1C1=CN=CC=C1C(F)(F)F HZMKCIKUGRDZGA-UHFFFAOYSA-N 0.000 claims 1
• DHGUYWBWZHODRI-UHFFFAOYSA-N 10-(trifluoromethyl)-4-[6-(trifluoromethyl)pyridin-2-yl]-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3SC3=CC(C(F)(F)F)=CC=C3C=2N=C1C1=CC=CC(C(F)(F)F)=N1 DHGUYWBWZHODRI-UHFFFAOYSA-N 0.000 claims 1
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• RBFQPQDCLJVUBH-UHFFFAOYSA-N 10-chloro-9-fluoro-4-pyridin-4-yl-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7,9,11,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3SC=3C=C(Cl)C(F)=CC=3C=2N=C1C1=CC=NC=C1 RBFQPQDCLJVUBH-UHFFFAOYSA-N 0.000 claims 1
• ZPLRCBZZVGCQDW-UHFFFAOYSA-N 10-methyl-4-pyridin-4-yl-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound S1C=2C3=CC=CC=C3SC3=CC(C)=CC=C3C=2N=C1C1=CC=NC=C1 ZPLRCBZZVGCQDW-UHFFFAOYSA-N 0.000 claims 1
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• IQMQGNVTKXUTBH-UHFFFAOYSA-N 11-chloro-9-fluoro-4-pyridin-4-yl-3,13-dithia-5-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2(6),4,7(12),8,10,14,16-octaene Chemical compound N=1C=2C3=CC(F)=CC(Cl)=C3SC3=CC=CC=C3C=2SC=1C1=CC=NC=C1 IQMQGNVTKXUTBH-UHFFFAOYSA-N 0.000 claims 1
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