ZA200104277B - Combination chemotherapy. - Google Patents
Combination chemotherapy. Download PDFInfo
- Publication number
- ZA200104277B ZA200104277B ZA200104277A ZA200104277A ZA200104277B ZA 200104277 B ZA200104277 B ZA 200104277B ZA 200104277 A ZA200104277 A ZA 200104277A ZA 200104277 A ZA200104277 A ZA 200104277A ZA 200104277 B ZA200104277 B ZA 200104277B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenylamino
- methyl
- benzamide
- iodo
- difluoro
- Prior art date
Links
- 238000009096 combination chemotherapy Methods 0.000 title description 2
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 60
- 229940124647 MEK inhibitor Drugs 0.000 claims description 56
- 229940121849 Mitotic inhibitor Drugs 0.000 claims description 51
- -1 phenyl amine compound Chemical class 0.000 claims description 46
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- GFMMXOIFOQCCGU-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 GFMMXOIFOQCCGU-UHFFFAOYSA-N 0.000 claims description 19
- 229930012538 Paclitaxel Natural products 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 229960001592 paclitaxel Drugs 0.000 claims description 19
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 11
- 230000000394 mitotic effect Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 229960003668 docetaxel Drugs 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229960004528 vincristine Drugs 0.000 claims description 9
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 9
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 9
- 102100023266 Dual specificity mitogen-activated protein kinase kinase 2 Human genes 0.000 claims description 8
- 101710146529 Dual specificity mitogen-activated protein kinase kinase 2 Proteins 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 claims description 7
- 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 229960002066 vinorelbine Drugs 0.000 claims description 7
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 229960003048 vinblastine Drugs 0.000 claims description 6
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 6
- VJNZMSLGVUSPCF-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C1CC1CONC(=O)C=1C=C(Br)C(F)=C(F)C=1NC1=CC=C(I)C=C1Cl VJNZMSLGVUSPCF-UHFFFAOYSA-N 0.000 claims description 5
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 claims description 5
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 claims description 5
- UHAXDAKQGVISBZ-UHFFFAOYSA-N N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NOCC1CC1 UHAXDAKQGVISBZ-UHFFFAOYSA-N 0.000 claims description 5
- DVENTWJICBBDAJ-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-4-fluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 DVENTWJICBBDAJ-UHFFFAOYSA-N 0.000 claims description 4
- AANZSIPSXXHMRM-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NOCC1=CC=CC=C1 AANZSIPSXXHMRM-UHFFFAOYSA-N 0.000 claims description 4
- GUAFZVVAOQFCPJ-UHFFFAOYSA-N 5-bromo-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCO GUAFZVVAOQFCPJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 229960000922 vinflunine Drugs 0.000 claims description 4
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 claims description 4
- BZSLAYDTMNXEOY-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4-fluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Cl BZSLAYDTMNXEOY-UHFFFAOYSA-N 0.000 claims description 3
- ROCRLSIAQQGIPN-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclobutylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CCC1 ROCRLSIAQQGIPN-UHFFFAOYSA-N 0.000 claims description 3
- ILYBIGUHBUIMMX-UHFFFAOYSA-N 3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NO ILYBIGUHBUIMMX-UHFFFAOYSA-N 0.000 claims description 3
- DSFQOJWTJQNGSU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 DSFQOJWTJQNGSU-UHFFFAOYSA-N 0.000 claims description 3
- IPJAGDMRFVGHCN-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NO IPJAGDMRFVGHCN-UHFFFAOYSA-N 0.000 claims description 3
- VBFVICYZHVZQIF-UHFFFAOYSA-N 5-bromo-n-cyclopropyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NC1CC1 VBFVICYZHVZQIF-UHFFFAOYSA-N 0.000 claims description 3
- YGRHTDDIYZYUDW-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 YGRHTDDIYZYUDW-UHFFFAOYSA-N 0.000 claims description 3
- PJCPYFYKAWDPLX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 PJCPYFYKAWDPLX-UHFFFAOYSA-N 0.000 claims description 3
- KCOUCDQMKMTOGV-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C KCOUCDQMKMTOGV-UHFFFAOYSA-N 0.000 claims description 3
- CCGNHTHRIVEZPG-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOCC1=CC=CC=C1 CCGNHTHRIVEZPG-UHFFFAOYSA-N 0.000 claims description 3
- JDQKKPHXLMZTFM-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NCCO JDQKKPHXLMZTFM-UHFFFAOYSA-N 0.000 claims description 3
- IDXFBAOJNKCQTB-UHFFFAOYSA-N n-cyclopropyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1CC1 IDXFBAOJNKCQTB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical group COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-UHFFFAOYSA-N 0.000 claims description 2
- UOPHVVWHOCFXFI-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1F UOPHVVWHOCFXFI-UHFFFAOYSA-N 0.000 claims description 2
- MSOPPMSDGHOWLB-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCCCC1 MSOPPMSDGHOWLB-UHFFFAOYSA-N 0.000 claims description 2
- BJULGELJDWFRAX-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NOCC1=CC=CC=C1 BJULGELJDWFRAX-UHFFFAOYSA-N 0.000 claims description 2
- XKRVQEHFHLIYHN-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-n-methyl-5-nitro-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C XKRVQEHFHLIYHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- OSWADHCUFNBMDE-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=NC=C1 OSWADHCUFNBMDE-UHFFFAOYSA-N 0.000 claims description 2
- KEAXMKQPXUVLBO-UHFFFAOYSA-N 3,4-difluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCO KEAXMKQPXUVLBO-UHFFFAOYSA-N 0.000 claims description 2
- JPFLPYISXHNBBZ-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-phenylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=CC=C1 JPFLPYISXHNBBZ-UHFFFAOYSA-N 0.000 claims description 2
- PFWAYQMMRCDJJX-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-prop-2-enoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC=C PFWAYQMMRCDJJX-UHFFFAOYSA-N 0.000 claims description 2
- IIJDQEBBOFOXKL-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(O)=O IIJDQEBBOFOXKL-UHFFFAOYSA-N 0.000 claims description 2
- GTXGFBQHXPMFRF-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(N)=O GTXGFBQHXPMFRF-UHFFFAOYSA-N 0.000 claims description 2
- IGSVYYMTMKJIDZ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C IGSVYYMTMKJIDZ-UHFFFAOYSA-N 0.000 claims description 2
- DSNSWZOBIUQUBS-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCO DSNSWZOBIUQUBS-UHFFFAOYSA-N 0.000 claims description 2
- JUVFXZWQSKISCB-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 JUVFXZWQSKISCB-UHFFFAOYSA-N 0.000 claims description 2
- RTCMPVBAZMDRHK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(Cl)C=2)NC=2C(=CC(I)=CC=2)C)=C1 RTCMPVBAZMDRHK-UHFFFAOYSA-N 0.000 claims description 2
- ORDKSJQARZCGBK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-methoxybenzamide Chemical compound CONC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C ORDKSJQARZCGBK-UHFFFAOYSA-N 0.000 claims description 2
- NYSBUFZXTTZARS-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 NYSBUFZXTTZARS-UHFFFAOYSA-N 0.000 claims description 2
- BNECLIPSPRXTNW-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(F)C=2)NC=2C(=CC(I)=CC=2)C)=C1 BNECLIPSPRXTNW-UHFFFAOYSA-N 0.000 claims description 2
- NDLMMYHLEMKNIS-UHFFFAOYSA-N 5-fluoro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCO NDLMMYHLEMKNIS-UHFFFAOYSA-N 0.000 claims description 2
- CLOSFYSFDCNULT-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NOCC1=CC=CC=C1 CLOSFYSFDCNULT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- DMGLLVWXKXWTIL-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCCO DMGLLVWXKXWTIL-UHFFFAOYSA-N 0.000 claims description 2
- RJPCFXZBKMJDCK-UHFFFAOYSA-N n-(cyclopropylmethoxy)-2-(4-iodo-2-methylanilino)-4-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(=O)NOCC1CC1 RJPCFXZBKMJDCK-UHFFFAOYSA-N 0.000 claims description 2
- ABMFCKSENBKLRK-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-chloro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCN(CCO)CCO ABMFCKSENBKLRK-UHFFFAOYSA-N 0.000 claims description 2
- XQLIVOYIWQHNST-UHFFFAOYSA-N n-[3-(diethylamino)-2-hydroxypropyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CC(O)CNC(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C XQLIVOYIWQHNST-UHFFFAOYSA-N 0.000 claims description 2
- IKFPRHQBWHOCKH-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C IKFPRHQBWHOCKH-UHFFFAOYSA-N 0.000 claims description 2
- MFTVPZWSFTVKDW-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C MFTVPZWSFTVKDW-UHFFFAOYSA-N 0.000 claims description 2
- ZHKTXUBWPSVDAP-UHFFFAOYSA-N n-cyclohexyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1CCCCC1 ZHKTXUBWPSVDAP-UHFFFAOYSA-N 0.000 claims description 2
- GNBCJLIYQMNLNA-UHFFFAOYSA-N n-cyclopropyl-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NC1CC1 GNBCJLIYQMNLNA-UHFFFAOYSA-N 0.000 claims description 2
- IVKQAKIJQNIBIO-UHFFFAOYSA-N n-hydroxy-2-(4-iodo-2-methylanilino)-4-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(=O)NO IVKQAKIJQNIBIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 23
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 238000011319 anticancer therapy Methods 0.000 claims 5
- 239000012635 anticancer drug combination Substances 0.000 claims 4
- 229940046044 combinations of antineoplastic agent Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- DMXADGCWZHCXBU-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCO DMXADGCWZHCXBU-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- HSDBAZASWXUUHX-UHFFFAOYSA-N 4-fluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NO HSDBAZASWXUUHX-UHFFFAOYSA-N 0.000 claims 2
- YNAWORHNPLOBBU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YNAWORHNPLOBBU-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- HPFQWCKXOZLYJQ-UHFFFAOYSA-N n-but-2-enoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C HPFQWCKXOZLYJQ-UHFFFAOYSA-N 0.000 claims 2
- APDFSUINPPLQLM-UHFFFAOYSA-N n-cyclopropyl-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NC1CC1 APDFSUINPPLQLM-UHFFFAOYSA-N 0.000 claims 2
- IWZZOJQMYWDXJN-UHFFFAOYSA-N 2,3,5-trifluoro-4-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C=C(C(O)=O)C(F)=C1F IWZZOJQMYWDXJN-UHFFFAOYSA-N 0.000 claims 1
- ZHMSIFGQMCBYIY-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-3,4,5-trifluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br ZHMSIFGQMCBYIY-UHFFFAOYSA-N 0.000 claims 1
- XYYUOXLXTADKMW-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-4-fluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Br XYYUOXLXTADKMW-UHFFFAOYSA-N 0.000 claims 1
- NGNWYDBHBYZNEJ-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-chloro-n-(cyclopropylmethoxy)-3,4-difluorobenzamide;2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-4-nitrobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=CC([N+](=O)[O-])=CC=C1C(=O)NOCC1CC1.C=1C=C(I)C=C(Br)C=1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 NGNWYDBHBYZNEJ-UHFFFAOYSA-N 0.000 claims 1
- QMALWSSCPZJMOO-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1Br QMALWSSCPZJMOO-UHFFFAOYSA-N 0.000 claims 1
- RDTSNRQFNRNSCU-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 RDTSNRQFNRNSCU-UHFFFAOYSA-N 0.000 claims 1
- LZRKJVJJXDFWLG-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-4-fluorobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 LZRKJVJJXDFWLG-UHFFFAOYSA-N 0.000 claims 1
- NMGPTKSLPIARAK-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1Br NMGPTKSLPIARAK-UHFFFAOYSA-N 0.000 claims 1
- JHBIWAOIBNORTA-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl JHBIWAOIBNORTA-UHFFFAOYSA-N 0.000 claims 1
- NXUSIIDZHWMSCV-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl NXUSIIDZHWMSCV-UHFFFAOYSA-N 0.000 claims 1
- BOWUZVRUZUWLAM-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-ethoxy-4-nitrobenzamide Chemical compound CCONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1Cl BOWUZVRUZUWLAM-UHFFFAOYSA-N 0.000 claims 1
- BQQMUASDAHOKDU-UHFFFAOYSA-N 2-(2-ethyl-4-iodoanilino)-n-(2-hydroxyethyl)-5-nitrobenzamide Chemical compound CCC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCO BQQMUASDAHOKDU-UHFFFAOYSA-N 0.000 claims 1
- UDMYBSQMRDBEIC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-hydroxyethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCO UDMYBSQMRDBEIC-UHFFFAOYSA-N 0.000 claims 1
- BYNKDEUDKDVPPJ-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-methylprop-2-enoxy)benzamide Chemical compound CC(=C)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C BYNKDEUDKDVPPJ-UHFFFAOYSA-N 0.000 claims 1
- QBTVPUBNRWFMGL-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCOCC1 QBTVPUBNRWFMGL-UHFFFAOYSA-N 0.000 claims 1
- NITWKACUMSHLOB-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 NITWKACUMSHLOB-UHFFFAOYSA-N 0.000 claims 1
- PFLMFENBMHGHFI-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-phenylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=CC=C1 PFLMFENBMHGHFI-UHFFFAOYSA-N 0.000 claims 1
- YGHCZGICKAIMTC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=NC=C1 YGHCZGICKAIMTC-UHFFFAOYSA-N 0.000 claims 1
- MPKKNJJTFVARIP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(3-hydroxypropyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCO MPKKNJJTFVARIP-UHFFFAOYSA-N 0.000 claims 1
- YDOWUWRHGYWZHT-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(furan-3-ylmethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=COC=C1 YDOWUWRHGYWZHT-UHFFFAOYSA-N 0.000 claims 1
- ULZOCHGQJGYENN-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=CC=CS1 ULZOCHGQJGYENN-UHFFFAOYSA-N 0.000 claims 1
- WGIDTTDBLPTUHP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C WGIDTTDBLPTUHP-UHFFFAOYSA-N 0.000 claims 1
- LUDUVSBHPMEVQH-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C LUDUVSBHPMEVQH-UHFFFAOYSA-N 0.000 claims 1
- OKAIUFBLOQNKIS-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluorobenzoic acid Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(O)=O OKAIUFBLOQNKIS-UHFFFAOYSA-N 0.000 claims 1
- RASWBMJSCOCCOP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-[3-(dimethylamino)propyl]-3,4-difluorobenzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C RASWBMJSCOCCOP-UHFFFAOYSA-N 0.000 claims 1
- SLODYXNZAINLFD-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-2-enoxy-3,4-difluorobenzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C SLODYXNZAINLFD-UHFFFAOYSA-N 0.000 claims 1
- LWZBCTIJTITZBA-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-3-ynoxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCC#C LWZBCTIJTITZBA-UHFFFAOYSA-N 0.000 claims 1
- OPSQYIMKGZTWMH-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=CC=C(I)C=C1C OPSQYIMKGZTWMH-UHFFFAOYSA-N 0.000 claims 1
- WRIPZDWCGAIYEF-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 WRIPZDWCGAIYEF-UHFFFAOYSA-N 0.000 claims 1
- LFKXETJHTXTXSA-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitrobenzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(O)=O LFKXETJHTXTXSA-UHFFFAOYSA-N 0.000 claims 1
- XLTVXGORWXCJNJ-UHFFFAOYSA-N 2-(4-iodoanilino)-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC=C(I)C=C1 XLTVXGORWXCJNJ-UHFFFAOYSA-N 0.000 claims 1
- BTHLVVULQLRTBK-UHFFFAOYSA-N 2-propan-2-yloxybenzamide Chemical compound CC(C)OC1=CC=CC=C1C(N)=O BTHLVVULQLRTBK-UHFFFAOYSA-N 0.000 claims 1
- IKYHHUKKYADHCL-UHFFFAOYSA-N 3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(O)=O IKYHHUKKYADHCL-UHFFFAOYSA-N 0.000 claims 1
- HDLXUSUTCIBXQZ-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-methylprop-2-enoxy)benzamide Chemical compound CC(=C)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C HDLXUSUTCIBXQZ-UHFFFAOYSA-N 0.000 claims 1
- HYIXUGDJHLKVGF-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 HYIXUGDJHLKVGF-UHFFFAOYSA-N 0.000 claims 1
- RLUBNNSZZPDBIV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-phenylprop-2-ynoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC=C1 RLUBNNSZZPDBIV-UHFFFAOYSA-N 0.000 claims 1
- JWVMVMKROCWQQV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCN1CCCCC1 JWVMVMKROCWQQV-UHFFFAOYSA-N 0.000 claims 1
- UYUHIMXYEAWUTA-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCC1=CC=NC=C1 UYUHIMXYEAWUTA-UHFFFAOYSA-N 0.000 claims 1
- HAONTWSXIVMMHV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=CC=CS1 HAONTWSXIVMMHV-UHFFFAOYSA-N 0.000 claims 1
- ZWXXSMYLKXWUIM-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#C ZWXXSMYLKXWUIM-UHFFFAOYSA-N 0.000 claims 1
- XRNCNLRJMNWXRG-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(O)=O XRNCNLRJMNWXRG-UHFFFAOYSA-N 0.000 claims 1
- XKKPRURDQYWGIU-UHFFFAOYSA-N 3,4-difluoro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCO XKKPRURDQYWGIU-UHFFFAOYSA-N 0.000 claims 1
- YPKLFSUXFMFTNP-UHFFFAOYSA-N 3,4-difluoro-n-(furan-3-ylmethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=COC=C1 YPKLFSUXFMFTNP-UHFFFAOYSA-N 0.000 claims 1
- LEYZOHZNXYPUBL-UHFFFAOYSA-N 4-chloro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC(Cl)=CC=C1C(O)=O LEYZOHZNXYPUBL-UHFFFAOYSA-N 0.000 claims 1
- HUNHDWQNBANZPB-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCN1CCOCC1 HUNHDWQNBANZPB-UHFFFAOYSA-N 0.000 claims 1
- XYPDOWBXGOOEOA-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 XYPDOWBXGOOEOA-UHFFFAOYSA-N 0.000 claims 1
- TXVFFQLHNCTHDG-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=NC=C1 TXVFFQLHNCTHDG-UHFFFAOYSA-N 0.000 claims 1
- ALEXORMOTRNKGS-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCN1CCCC1 ALEXORMOTRNKGS-UHFFFAOYSA-N 0.000 claims 1
- FXKGVPODJZKPSN-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-thiophen-2-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=CS1 FXKGVPODJZKPSN-UHFFFAOYSA-N 0.000 claims 1
- KYPCIWQNEIGNMW-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2h-tetrazol-5-yl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NC1=NN=NN1 KYPCIWQNEIGNMW-UHFFFAOYSA-N 0.000 claims 1
- IURDPGNSPNCXAT-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCCN1CCCCC1 IURDPGNSPNCXAT-UHFFFAOYSA-N 0.000 claims 1
- PBAMOEUDSFIDGM-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1=CC=CS1 PBAMOEUDSFIDGM-UHFFFAOYSA-N 0.000 claims 1
- PEZQORQECWUYJA-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C PEZQORQECWUYJA-UHFFFAOYSA-N 0.000 claims 1
- HHSBHFSKYJRNAR-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C HHSBHFSKYJRNAR-UHFFFAOYSA-N 0.000 claims 1
- IVJXLCPTSRJPLQ-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1=CC=CC=C1 IVJXLCPTSRJPLQ-UHFFFAOYSA-N 0.000 claims 1
- VFLRZRPXLGMONP-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC#C VFLRZRPXLGMONP-UHFFFAOYSA-N 0.000 claims 1
- WOHHWWLIRJXRJT-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C WOHHWWLIRJXRJT-UHFFFAOYSA-N 0.000 claims 1
- COEXMYRMIABFRK-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(N)=O COEXMYRMIABFRK-UHFFFAOYSA-N 0.000 claims 1
- DWXSHLDPWGVUAY-UHFFFAOYSA-N 4-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCO DWXSHLDPWGVUAY-UHFFFAOYSA-N 0.000 claims 1
- PJMHNOKJJUERIL-UHFFFAOYSA-N 4-fluoro-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCCN1CCN(CCO)CC1 PJMHNOKJJUERIL-UHFFFAOYSA-N 0.000 claims 1
- BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 claims 1
- RPWNJSYAWBWAFW-UHFFFAOYSA-N 5-bromo-2-(2-bromo-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br RPWNJSYAWBWAFW-UHFFFAOYSA-N 0.000 claims 1
- ZMFXUELOZZCDTA-UHFFFAOYSA-N 5-bromo-2-(2-bromo-4-iodoanilino)-n-ethoxy-3,4-difluorobenzamide Chemical compound CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br ZMFXUELOZZCDTA-UHFFFAOYSA-N 0.000 claims 1
- SRMDAFUJVQJZFI-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl SRMDAFUJVQJZFI-UHFFFAOYSA-N 0.000 claims 1
- YGSACSKOTDWEIY-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YGSACSKOTDWEIY-UHFFFAOYSA-N 0.000 claims 1
- KACROHVGLWUBCA-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCOCC1 KACROHVGLWUBCA-UHFFFAOYSA-N 0.000 claims 1
- IAVNIGIRNWGCLU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCCCC1 IAVNIGIRNWGCLU-UHFFFAOYSA-N 0.000 claims 1
- MXCDWFRGCXEWHI-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(Br)C=2)NC=2C(=CC(I)=CC=2)C)=C1 MXCDWFRGCXEWHI-UHFFFAOYSA-N 0.000 claims 1
- JSROFQXNBQJWGD-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCOCC1 JSROFQXNBQJWGD-UHFFFAOYSA-N 0.000 claims 1
- QTDDKGUPEPKNIP-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCCCC1 QTDDKGUPEPKNIP-UHFFFAOYSA-N 0.000 claims 1
- LOWHNAGNDJCFSR-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCC1=CC=NC=C1 LOWHNAGNDJCFSR-UHFFFAOYSA-N 0.000 claims 1
- RDSDFNHYHOTLTQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCCC1 RDSDFNHYHOTLTQ-UHFFFAOYSA-N 0.000 claims 1
- NKRZYDJKGYMRDY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-methylbut-2-enoxy)benzamide Chemical compound CC(C)=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C NKRZYDJKGYMRDY-UHFFFAOYSA-N 0.000 claims 1
- HCJZFECDFDVVFQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-methylpent-2-en-4-ynoxy)benzamide Chemical compound C#CC(C)=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C HCJZFECDFDVVFQ-UHFFFAOYSA-N 0.000 claims 1
- CYHKFEHMDJDUCY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-3-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=CC=CN=C1 CYHKFEHMDJDUCY-UHFFFAOYSA-N 0.000 claims 1
- SQGHOLDHMVSJEQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCC1=CC=NC=C1 SQGHOLDHMVSJEQ-UHFFFAOYSA-N 0.000 claims 1
- JDYMILCDQZFLCK-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC#C JDYMILCDQZFLCK-UHFFFAOYSA-N 0.000 claims 1
- IHCADDZQYYEXFH-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(O)=O IHCADDZQYYEXFH-UHFFFAOYSA-N 0.000 claims 1
- CWFCDWVXNAFAHX-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-[(4-iodo-2-methylphenyl)methyl]-n-[5-(3-methoxyphenyl)-3-methylpent-2-en-4-ynoxy]benzamide Chemical compound COC1=CC=CC(C#CC(C)=CCONC(=O)C=2C(=C(F)C(F)=C(Br)C=2)CC=2C(=CC(I)=CC=2)C)=C1 CWFCDWVXNAFAHX-UHFFFAOYSA-N 0.000 claims 1
- OKRDHHWCFHEDRY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-(furan-3-ylmethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=COC=C1 OKRDHHWCFHEDRY-UHFFFAOYSA-N 0.000 claims 1
- PADIEEAWBNJBQS-UHFFFAOYSA-N 5-bromo-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCO PADIEEAWBNJBQS-UHFFFAOYSA-N 0.000 claims 1
- WBQVEORRHAMIPY-UHFFFAOYSA-N 5-bromo-n-(cyclobutylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CCC1 WBQVEORRHAMIPY-UHFFFAOYSA-N 0.000 claims 1
- PHJXBTSQFDDWJS-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound FC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 PHJXBTSQFDDWJS-UHFFFAOYSA-N 0.000 claims 1
- YUKGGEUVPFOCFI-UHFFFAOYSA-N 5-bromo-n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YUKGGEUVPFOCFI-UHFFFAOYSA-N 0.000 claims 1
- JETNCDYHKNDALF-UHFFFAOYSA-N 5-bromo-n-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C JETNCDYHKNDALF-UHFFFAOYSA-N 0.000 claims 1
- GNQPYQRZLIRIAD-UHFFFAOYSA-N 5-bromo-n-cyclohexyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NC1CCCCC1 GNQPYQRZLIRIAD-UHFFFAOYSA-N 0.000 claims 1
- HXACAYXLBFGWMG-UHFFFAOYSA-N 5-bromo-n-ethoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C HXACAYXLBFGWMG-UHFFFAOYSA-N 0.000 claims 1
- MKRVIYRPNNYISB-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl MKRVIYRPNNYISB-UHFFFAOYSA-N 0.000 claims 1
- LVSSVNULIKSVNX-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C LVSSVNULIKSVNX-UHFFFAOYSA-N 0.000 claims 1
- AMBAWPSSVDPNGB-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCN1CCOCC1 AMBAWPSSVDPNGB-UHFFFAOYSA-N 0.000 claims 1
- HFKKIAJNJRTIFR-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(oxan-2-yloxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NOC1OCCCC1 HFKKIAJNJRTIFR-UHFFFAOYSA-N 0.000 claims 1
- MBXXUKAZBOOXOL-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(O)=O MBXXUKAZBOOXOL-UHFFFAOYSA-N 0.000 claims 1
- RCKXWJPGNUQSAX-UHFFFAOYSA-N 5-chloro-3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NO RCKXWJPGNUQSAX-UHFFFAOYSA-N 0.000 claims 1
- FZJKEESBPVPDBV-UHFFFAOYSA-N 5-chloro-n,n-diethyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C FZJKEESBPVPDBV-UHFFFAOYSA-N 0.000 claims 1
- IHNKPBIVPDAOMS-UHFFFAOYSA-N 5-chloro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCCO IHNKPBIVPDAOMS-UHFFFAOYSA-N 0.000 claims 1
- WPTQCTMJDFCZSI-UHFFFAOYSA-N 5-chloro-n-[2-(diethylamino)ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C WPTQCTMJDFCZSI-UHFFFAOYSA-N 0.000 claims 1
- TUWOHSIPLLUTFB-UHFFFAOYSA-N 5-chloro-n-[2-[di(propan-2-yl)amino]ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C TUWOHSIPLLUTFB-UHFFFAOYSA-N 0.000 claims 1
- XNAJEOYTSSBCFU-UHFFFAOYSA-N 5-chloro-n-[3-(diethylamino)-2-hydroxypropyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CC(O)CNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C XNAJEOYTSSBCFU-UHFFFAOYSA-N 0.000 claims 1
- OQWXTWHGTZIWBE-UHFFFAOYSA-N 5-chloro-n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C OQWXTWHGTZIWBE-UHFFFAOYSA-N 0.000 claims 1
- YPPGTJWMYLGECO-UHFFFAOYSA-N 5-chloro-n-cyclohexyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NC1CCCCC1 YPPGTJWMYLGECO-UHFFFAOYSA-N 0.000 claims 1
- NRQYGGWYEHEXEJ-UHFFFAOYSA-N 5-chloro-n-cyclopropyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NC1CC1 NRQYGGWYEHEXEJ-UHFFFAOYSA-N 0.000 claims 1
- HHLZFIBFGYVDRZ-UHFFFAOYSA-N 5-chloro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NO HHLZFIBFGYVDRZ-UHFFFAOYSA-N 0.000 claims 1
- TYGDKZJTFRTMAO-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN1CCCCC1 TYGDKZJTFRTMAO-UHFFFAOYSA-N 0.000 claims 1
- SFKIHCBPGXCYLE-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN1CCCC1 SFKIHCBPGXCYLE-UHFFFAOYSA-N 0.000 claims 1
- XTIXMUNFVWCJGM-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCN1CCCCC1 XTIXMUNFVWCJGM-UHFFFAOYSA-N 0.000 claims 1
- LTGBDYINTUIVIR-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(oxan-2-yloxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOC1OCCCC1 LTGBDYINTUIVIR-UHFFFAOYSA-N 0.000 claims 1
- PPBHPHGQDGGSHX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(O)=O PPBHPHGQDGGSHX-UHFFFAOYSA-N 0.000 claims 1
- YSXVOTVVUSIKNI-UHFFFAOYSA-N 5-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCO YSXVOTVVUSIKNI-UHFFFAOYSA-N 0.000 claims 1
- FUJLYVVUOAQPRQ-UHFFFAOYSA-N 5-fluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NO FUJLYVVUOAQPRQ-UHFFFAOYSA-N 0.000 claims 1
- LOUSDJOLFFYIHT-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 LOUSDJOLFFYIHT-UHFFFAOYSA-N 0.000 claims 1
- ISSKCCWEUYSNQW-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(I)=CC=C1NC1=CC=C(I)C=C1C ISSKCCWEUYSNQW-UHFFFAOYSA-N 0.000 claims 1
- KOXXMRABYKWLII-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(O)=O KOXXMRABYKWLII-UHFFFAOYSA-N 0.000 claims 1
- BHHBGJUZEPKYTF-UHFFFAOYSA-N CCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C.CC=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C Chemical compound CCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C.CC=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C BHHBGJUZEPKYTF-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- PNWJMZMIJSAVRR-UHFFFAOYSA-N [2-(4-iodo-2-methylanilino)-5-nitrophenyl]methanol Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1CO PNWJMZMIJSAVRR-UHFFFAOYSA-N 0.000 claims 1
- QAFJIVFPYARMAT-UHFFFAOYSA-N [5-bromo-2-(4-iodo-2-methylanilino)phenyl]methanol Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1CO QAFJIVFPYARMAT-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- SKMCJUSFAIWLJG-UHFFFAOYSA-N n,n-diethyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CCN(CC)C(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C SKMCJUSFAIWLJG-UHFFFAOYSA-N 0.000 claims 1
- PINUTQQQUYREAM-UHFFFAOYSA-N n,n-diethyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)C(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C PINUTQQQUYREAM-UHFFFAOYSA-N 0.000 claims 1
- HVMSAZSBXQHNDL-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCC(O)CO HVMSAZSBXQHNDL-UHFFFAOYSA-N 0.000 claims 1
- RYOCQJVSICWPKA-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCO RYOCQJVSICWPKA-UHFFFAOYSA-N 0.000 claims 1
- TYHIZTJRCMNBDH-UHFFFAOYSA-N n-(cyclopropylmethoxy)-2-(2-fluoro-4-iodoanilino)-4-nitrobenzamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=CC([N+](=O)[O-])=CC=C1C(=O)NOCC1CC1 TYHIZTJRCMNBDH-UHFFFAOYSA-N 0.000 claims 1
- DQHARHQBVRLSQS-UHFFFAOYSA-N n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 DQHARHQBVRLSQS-UHFFFAOYSA-N 0.000 claims 1
- HGXUEXUZCRYPLV-UHFFFAOYSA-N n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 HGXUEXUZCRYPLV-UHFFFAOYSA-N 0.000 claims 1
- ZQRHTXJWJRVYGA-UHFFFAOYSA-N n-(cyclopropylmethoxy)-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 ZQRHTXJWJRVYGA-UHFFFAOYSA-N 0.000 claims 1
- HDYUNAODPNRHCT-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C HDYUNAODPNRHCT-UHFFFAOYSA-N 0.000 claims 1
- QFICQLHYTPHHHZ-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-bromo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN(CCO)CCO QFICQLHYTPHHHZ-UHFFFAOYSA-N 0.000 claims 1
- RESDNAOQJMJZLG-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN(CCO)CCO RESDNAOQJMJZLG-UHFFFAOYSA-N 0.000 claims 1
- RYONWGDKFMCGQK-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C RYONWGDKFMCGQK-UHFFFAOYSA-N 0.000 claims 1
- PMRYRJFGVUNXAW-UHFFFAOYSA-N n-benzyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCC1=CC=CC=C1 PMRYRJFGVUNXAW-UHFFFAOYSA-N 0.000 claims 1
- VWFSFOHXGXBXFO-UHFFFAOYSA-N n-but-3-yn-2-yloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound C#CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C VWFSFOHXGXBXFO-UHFFFAOYSA-N 0.000 claims 1
- QVEIDMMXXOMGHZ-UHFFFAOYSA-N n-butyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCCCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C QVEIDMMXXOMGHZ-UHFFFAOYSA-N 0.000 claims 1
- OMWXQRPRACBVAD-UHFFFAOYSA-N n-cyclobutyloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCC1 OMWXQRPRACBVAD-UHFFFAOYSA-N 0.000 claims 1
- ZTMPSQKWWVAXQV-UHFFFAOYSA-N n-cyclohexyl-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NC1CCCCC1 ZTMPSQKWWVAXQV-UHFFFAOYSA-N 0.000 claims 1
- NVABLGSLZIYASV-UHFFFAOYSA-N n-cyclopentyloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCCC1 NVABLGSLZIYASV-UHFFFAOYSA-N 0.000 claims 1
- MBSHGFWRDZJDMZ-UHFFFAOYSA-N n-ethoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C MBSHGFWRDZJDMZ-UHFFFAOYSA-N 0.000 claims 1
- CDOZIVZPNPKUPY-UHFFFAOYSA-N n-ethyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C CDOZIVZPNPKUPY-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 102000029749 Microtubule Human genes 0.000 description 7
- 108091022875 Microtubule Proteins 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 210000004688 microtubule Anatomy 0.000 description 7
- 102000004243 Tubulin Human genes 0.000 description 3
- 108090000704 Tubulin Proteins 0.000 description 3
- 230000000547 effect on apoptosis Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 108060006698 EGF receptor Proteins 0.000 description 2
- 102000001301 EGF receptor Human genes 0.000 description 2
- 102000019149 MAP kinase activity proteins Human genes 0.000 description 2
- 108040008097 MAP kinase activity proteins Proteins 0.000 description 2
- 102000043136 MAP kinase family Human genes 0.000 description 2
- 108091054455 MAP kinase family Proteins 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003226 mitogen Substances 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VGCAUBADGNQYOE-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-nitrobenzoic acid 2-(4-bromo-2-methylanilino)-3,4-difluorobenzoic acid 2-(4-bromo-2-methylanilino)-4-fluorobenzoic acid Chemical compound BrC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)C.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].BrC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1)F)C VGCAUBADGNQYOE-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- HNXJNPOQVWVOGW-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C HNXJNPOQVWVOGW-UHFFFAOYSA-N 0.000 description 1
- LUVODTHAYCCRJL-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-cyclobutyloxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCC1 LUVODTHAYCCRJL-UHFFFAOYSA-N 0.000 description 1
- FUDMVYZZNQDLOV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C FUDMVYZZNQDLOV-UHFFFAOYSA-N 0.000 description 1
- OEYRWOJRMOBKSM-UHFFFAOYSA-N 3,4-difluoro-n-[3-(2-fluorophenyl)prop-2-ynoxy]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC=C1F OEYRWOJRMOBKSM-UHFFFAOYSA-N 0.000 description 1
- HPPOAFGKJXHOLJ-UHFFFAOYSA-N 3-bromo-n-(cyclobutylmethoxy)-4,5-difluorobenzamide Chemical compound BrC1=C(F)C(F)=CC(C(=O)NOCC2CCC2)=C1 HPPOAFGKJXHOLJ-UHFFFAOYSA-N 0.000 description 1
- HOCFDFIQDORVTE-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide;4-fluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCN1CCOCC1.CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCCN1CCCCC1 HOCFDFIQDORVTE-UHFFFAOYSA-N 0.000 description 1
- HIDZKFBLBMEGIG-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCN1CCCCC1 HIDZKFBLBMEGIG-UHFFFAOYSA-N 0.000 description 1
- DNTAOAAQWZAAQE-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide;5-bromo-n-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C.CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCOCC1 DNTAOAAQWZAAQE-UHFFFAOYSA-N 0.000 description 1
- ANJGKWAYKBLXEK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCCN1CCCCC1 ANJGKWAYKBLXEK-UHFFFAOYSA-N 0.000 description 1
- MYXJMTKOGODVJC-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide;5-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCO.CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCO MYXJMTKOGODVJC-UHFFFAOYSA-N 0.000 description 1
- WLRFUQMWNIHSLX-UHFFFAOYSA-N 5-fluoro-N-hydroxy-2-(4-iodo-2-methylanilino)benzamide 4-fluoro-2-(4-iodo-2-methylanilino)-N-phenylmethoxybenzamide Chemical compound FC=1C=CC(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NOCC2=CC=CC=C2)C=C1)NC1=C(C=C(C=C1)I)C WLRFUQMWNIHSLX-UHFFFAOYSA-N 0.000 description 1
- USDURDZZSHBDOA-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(I)C=2)NC=2C(=CC(I)=CC=2)C)=C1 USDURDZZSHBDOA-UHFFFAOYSA-N 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- SKMQXQZKZOAOJP-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1F)F SKMQXQZKZOAOJP-UHFFFAOYSA-N 0.000 description 1
- FATOFNYONVLPRK-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F FATOFNYONVLPRK-UHFFFAOYSA-N 0.000 description 1
- FTSVGYFONYQFDU-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F FTSVGYFONYQFDU-UHFFFAOYSA-N 0.000 description 1
- DOUCLRHHTDCTFK-UHFFFAOYSA-N BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCC2=CC=NC=C2)C=CC(=C1F)F)C.FC1=CC(=C(C(=O)NCCC2=CC=NC=C2)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCC2=CC=NC=C2)C=CC(=C1F)F)C.FC1=CC(=C(C(=O)NCCC2=CC=NC=C2)C=C1)NC1=C(C=C(C=C1)I)C DOUCLRHHTDCTFK-UHFFFAOYSA-N 0.000 description 1
- HSSQHMBHNBTMAG-UHFFFAOYSA-N BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCN2CCCC2)C=CC(=C1F)F)C.BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCCO)C=CC(=C1F)F)C Chemical compound BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCN2CCCC2)C=CC(=C1F)F)C.BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCCO)C=CC(=C1F)F)C HSSQHMBHNBTMAG-UHFFFAOYSA-N 0.000 description 1
- WUIHAZBDMOYABC-UHFFFAOYSA-N BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCO)C=CC(=C1F)F)C.C(C1=CC=CC=C1)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O Chemical compound BrC1=CC(=C(C=C1)NC1=C(C(=O)NCCO)C=CC(=C1F)F)C.C(C1=CC=CC=C1)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O WUIHAZBDMOYABC-UHFFFAOYSA-N 0.000 description 1
- NXRBKJMWVPKIAV-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)N(C)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)N(CC)CC)C1)NC1=C(C=C(C=C1)I)C.C(CCC)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O Chemical compound BrC=1C=CC(=C(C(=O)N(C)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)N(CC)CC)C1)NC1=C(C=C(C=C1)I)C.C(CCC)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O NXRBKJMWVPKIAV-UHFFFAOYSA-N 0.000 description 1
- YHTKHDNULVFDMG-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)NCC2=CC(=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CCCCC2)C1)NC1=C(C=C(C=C1)I)C.C1(CCCCC1)NC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O Chemical compound BrC=1C=CC(=C(C(=O)NCC2=CC(=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CCCCC2)C1)NC1=C(C=C(C=C1)I)C.C1(CCCCC1)NC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O YHTKHDNULVFDMG-UHFFFAOYSA-N 0.000 description 1
- LXGZYCXMQVRVDR-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NCCC)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NCC(=O)O)C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NCCC)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NCC(=O)O)C1)NC1=C(C=C(C=C1)I)C LXGZYCXMQVRVDR-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- DNLREKHLBCOMIH-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)C.BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Br)F)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)C.BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Br)F)F DNLREKHLBCOMIH-UHFFFAOYSA-N 0.000 description 1
- SAHKSTUKOOYEPV-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.FC=1C(=C(C(=O)NO)C=CC1F)NC1=C(C=C(C=C1)I)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.FC=1C(=C(C(=O)NO)C=CC1F)NC1=C(C=C(C=C1)I)F SAHKSTUKOOYEPV-UHFFFAOYSA-N 0.000 description 1
- QPHAYFMRZOZDNO-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC)C=CC(=C1)[N+](=O)[O-].BrC=1C(=C(C(=C(C(=O)NOCC)C1)NC1=C(C=C(C=C1)I)Br)F)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC)C=CC(=C1)[N+](=O)[O-].BrC=1C(=C(C(=C(C(=O)NOCC)C1)NC1=C(C=C(C=C1)I)Br)F)F QPHAYFMRZOZDNO-UHFFFAOYSA-N 0.000 description 1
- NSJYYUSKALBFIU-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F NSJYYUSKALBFIU-UHFFFAOYSA-N 0.000 description 1
- HTRFPXSKIBKVJQ-UHFFFAOYSA-N ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)F)F)F.C1(CC1)CONC(C1=C(C(=C(C(=C1)F)F)F)NC1=C(C=C(C=C1)I)F)=O Chemical compound ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)F)F)F.C1(CC1)CONC(C1=C(C(=C(C(=C1)F)F)F)NC1=C(C=C(C=C1)I)F)=O HTRFPXSKIBKVJQ-UHFFFAOYSA-N 0.000 description 1
- SXSKGCLAGXUWAS-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C Chemical compound ClC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C SXSKGCLAGXUWAS-UHFFFAOYSA-N 0.000 description 1
- OKTRPHWEGHANPE-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C.OCCNC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O Chemical compound ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C.OCCNC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O OKTRPHWEGHANPE-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000010831 Cytoskeletal Proteins Human genes 0.000 description 1
- 108010037414 Cytoskeletal Proteins Proteins 0.000 description 1
- 102100023275 Dual specificity mitogen-activated protein kinase kinase 3 Human genes 0.000 description 1
- 108030004793 Dual-specificity kinases Proteins 0.000 description 1
- IJPWOLXIVFMSIK-UHFFFAOYSA-N FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)[N+](=O)[O-] Chemical compound FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)[N+](=O)[O-] IJPWOLXIVFMSIK-UHFFFAOYSA-N 0.000 description 1
- LOLUAXMEWHZFKV-UHFFFAOYSA-N FC1=CC(=C(C(=O)NOC)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound FC1=CC(=C(C(=O)NOC)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)C LOLUAXMEWHZFKV-UHFFFAOYSA-N 0.000 description 1
- RRMCYONWALUEOB-UHFFFAOYSA-N FC=1C(=C(C(=O)NOCC)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOC)C=CC1F)NC1=C(C=C(C=C1)Br)C Chemical compound FC=1C(=C(C(=O)NOCC)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOC)C=CC1F)NC1=C(C=C(C=C1)Br)C RRMCYONWALUEOB-UHFFFAOYSA-N 0.000 description 1
- FKFRYJQJVPEAAM-UHFFFAOYSA-N FC=1C(=C(C(=O)NOCC=CC)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC(=C)C)C=CC1F)NC1=C(C=C(C=C1)Br)C Chemical compound FC=1C(=C(C(=O)NOCC=CC)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC(=C)C)C=CC1F)NC1=C(C=C(C=C1)Br)C FKFRYJQJVPEAAM-UHFFFAOYSA-N 0.000 description 1
- CIGLTSMILQDCMO-UHFFFAOYSA-N FC=1C(=C(C(=O)NOCC=CC)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)NOCC)C=CC1F)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C(=C(C(=O)NOCC=CC)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)NOCC)C=CC1F)NC1=C(C=C(C=C1)I)C CIGLTSMILQDCMO-UHFFFAOYSA-N 0.000 description 1
- VLPCNUHAEWDBKJ-UHFFFAOYSA-N FC=1C(=C(C(=O)NOCCC#C)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC=2SC=CC2)C=CC1F)NC1=C(C=C(C=C1)Br)C Chemical compound FC=1C(=C(C(=O)NOCCC#C)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC=2SC=CC2)C=CC1F)NC1=C(C=C(C=C1)Br)C VLPCNUHAEWDBKJ-UHFFFAOYSA-N 0.000 description 1
- CHXHPIRRYRGXBG-UHFFFAOYSA-N FC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C CHXHPIRRYRGXBG-UHFFFAOYSA-N 0.000 description 1
- IYNYOWHOUWWBSK-UHFFFAOYSA-N FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.C(C1=CC=CC=C1)ONC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O Chemical compound FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.C(C1=CC=CC=C1)ONC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O IYNYOWHOUWWBSK-UHFFFAOYSA-N 0.000 description 1
- 101001115394 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 3 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- IFURCWJGLVRZIA-UHFFFAOYSA-N IC1=CC(=C(C=C1)NC1=C(C(=O)N(C2=CC=CC=C2)C)C=C(C=C1)[N+](=O)[O-])C.OCCNC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)CC)=O Chemical compound IC1=CC(=C(C=C1)NC1=C(C(=O)N(C2=CC=CC=C2)C)C=C(C=C1)[N+](=O)[O-])C.OCCNC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)CC)=O IFURCWJGLVRZIA-UHFFFAOYSA-N 0.000 description 1
- BOVFVEGNAAVDHQ-UHFFFAOYSA-M IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-])C.BrC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)[O-])C1)NC1=C(C=C(C=C1)I)C.[Na+] Chemical compound IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-])C.BrC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)[O-])C1)NC1=C(C=C(C=C1)I)C.[Na+] BOVFVEGNAAVDHQ-UHFFFAOYSA-M 0.000 description 1
- ZAEMJXGAUGRRQO-UHFFFAOYSA-N IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=C1)C.ClC1=CC(=C(C(=O)O)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=C1)C.ClC1=CC(=C(C(=O)O)C=C1)NC1=C(C=C(C=C1)I)C ZAEMJXGAUGRRQO-UHFFFAOYSA-N 0.000 description 1
- 206010022095 Injection Site reaction Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 102100037611 Lysophospholipase Human genes 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 108091008606 PDGF receptors Proteins 0.000 description 1
- 108010058864 Phospholipases A2 Proteins 0.000 description 1
- 102000014750 Phosphorylase Kinase Human genes 0.000 description 1
- 108010064071 Phosphorylase Kinase Proteins 0.000 description 1
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 1
- 229940078123 Ras inhibitor Drugs 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 1
- 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940044684 anti-microtubule agent Drugs 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- FKURQLBTBBUUAQ-UHFFFAOYSA-N n-cyclohexyl-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NC1CCCCC1 FKURQLBTBBUUAQ-UHFFFAOYSA-N 0.000 description 1
- ISERPJZNOJTETH-UHFFFAOYSA-N n-cyclopentyloxy-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOC1CCCC1 ISERPJZNOJTETH-UHFFFAOYSA-N 0.000 description 1
- NSECATTVHWALCK-UHFFFAOYSA-N n-ethyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide;4-fluoro-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C.CN(C)C(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C NSECATTVHWALCK-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 229940108949 paclitaxel injection Drugs 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009703 regulation of cell differentiation Effects 0.000 description 1
- 230000025053 regulation of cell proliferation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-XAZOAEDWSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11329198P | 1998-12-22 | 1998-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104277B true ZA200104277B (en) | 2002-08-26 |
Family
ID=27733552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104277A ZA200104277B (en) | 1998-12-22 | 2001-05-24 | Combination chemotherapy. |
Country Status (2)
| Country | Link |
|---|---|
| CR (1) | CR6395A (es) |
| ZA (1) | ZA200104277B (es) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
-
2001
- 2001-05-24 ZA ZA200104277A patent/ZA200104277B/en unknown
- 2001-06-19 CR CR6395A patent/CR6395A/es not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| EP3028699A1 (en) | 2010-02-25 | 2016-06-08 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| CR6395A (es) | 2004-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6972298B2 (en) | Method of treating or inhibiting neutrophil chemotaxis by administering a MEK inhibitor | |
| CA2346448A1 (en) | Treatment of arthritis with mek inhibitors | |
| JP6532878B2 (ja) | 組合せ医薬 | |
| US6251943B1 (en) | Method of treating or preventing septic shock by administering a MEK inhibitor | |
| RU2202344C2 (ru) | Антагонисты ноцицептина, производные амида, аналгетик, способ инициирования антагонистического действия к ноцицептину, способ лечения боли, фармацевтические композиции | |
| CA2352326A1 (en) | Combination chemotherapy | |
| ZA200104000B (en) | Antiviral method using MEK inhibitors. | |
| DK1912640T3 (en) | USE OF THE HDAC INHIBITOR PANOBINOSTAT FOR THE TREATMENT OF MYELOMA | |
| US20090247582A1 (en) | Methods of treating atherosclerosis | |
| HRP20050115A2 (en) | Combinations of drugs for the treatment of neoplasms | |
| CA2362381A1 (en) | Amide compounds and medicinal use thereof | |
| EP1202726A2 (en) | Method for treating chronic pain using mek inhibitors | |
| CA2346684A1 (en) | Use of a mek inhibitor for preventing transplant rejection | |
| CA2498210C (en) | Combination of a) n-{5-[4-(4-methyl-piperazino-methyl)-benzoylamido]-2-methylphenyl}-4-(3-pyridyl)-2-pyrimidine-amine and b) a histone deacetylase inhibitor for the treatment of leukemia | |
| JP2001516718A5 (es) | ||
| ZA200104277B (en) | Combination chemotherapy. | |
| US20040171632A1 (en) | Combination chemotherapy | |
| ES2365387T3 (es) | Composiciones analgésicas y antiflamatorias que contienen celecoxib e ibuprofeno. | |
| JP2006508118A5 (es) | ||
| WO2006083214A1 (en) | Pharmaceutical composition comprising a p2x7 receptor antagonist and a hmg-coa reductase inhibitor | |
| JP2013538810A (ja) | Ｈｄａｃ阻害剤と血小板減少症薬との組合せ | |
| CA3150893A1 (en) | Combination therapies comprising panobinostat for the treatment of cholangiocarcinoma |