MXPA04011372A - Diaminotiazoles. - Google Patents

Info

Publication number

MXPA04011372A

MXPA04011372A MXPA04011372A MXPA04011372A MXPA04011372A MX PA04011372 A MXPA04011372 A MX PA04011372A MX PA04011372 A MXPA04011372 A MX PA04011372A MX PA04011372 A MXPA04011372 A MX PA04011372A MX PA04011372 A MXPA04011372 A MX PA04011372A

Authority

MX

Mexico

Prior art keywords

amino

phenylamino

thiazol

methanone

phenyl

Prior art date

2002-05-17

Links

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• WKXCZMFWXZRMEZ-UHFFFAOYSA-N 1,3-thiazole-2,4-diamine Chemical class NC1=CSC(N)=N1 WKXCZMFWXZRMEZ-UHFFFAOYSA-N 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 309
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 150000002148 esters Chemical class 0.000 claims abstract description 25
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 239000003814 drug Substances 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 210000001072 colon Anatomy 0.000 claims abstract description 6
• 210000004072 lung Anatomy 0.000 claims abstract description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 246
• -1 2-pyrrolidin-1-yl-ethoxy Chemical group 0.000 claims description 138
• 125000000217 alkyl group Chemical group 0.000 claims description 138
• 238000000034 method Methods 0.000 claims description 136
• 239000011347 resin Substances 0.000 claims description 118
• 229920005989 resin Polymers 0.000 claims description 118
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 125000004429 atom Chemical group 0.000 claims description 25
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 6
• TUQRPBZGEYGHGW-UHFFFAOYSA-N [4-amino-2-[4-(3-aminopropoxy)anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCCN)=CC=2)S1 TUQRPBZGEYGHGW-UHFFFAOYSA-N 0.000 claims description 6
• RNAXYOGSJHEJAT-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN(C)C)=CC=3)S2)N)=C1 RNAXYOGSJHEJAT-UHFFFAOYSA-N 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• PQYFWQYDROQYOA-UHFFFAOYSA-N 3-[4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazole-5-carbonyl]benzonitrile Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C#N)S1 PQYFWQYDROQYOA-UHFFFAOYSA-N 0.000 claims description 5
• SJWTXURWSJGDOI-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCCC3)=CC=2)S1 SJWTXURWSJGDOI-UHFFFAOYSA-N 0.000 claims description 5
• QHFKAWDIEVTHCO-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCC3)=CC=2)S1 QHFKAWDIEVTHCO-UHFFFAOYSA-N 0.000 claims description 5
• MASMEBIOBMMGKM-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound S1C(C(=O)C=2C=C3OCOC3=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 MASMEBIOBMMGKM-UHFFFAOYSA-N 0.000 claims description 5
• RESOAIQZESAJBZ-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 RESOAIQZESAJBZ-UHFFFAOYSA-N 0.000 claims description 5
• OCHCZBZJAGBUPK-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C([C@@H](C)N1CCCC1)OC(C=C1)=CC=C1NC(S1)=NC(N)=C1C(=O)C1=CC=CC(F)=C1 OCHCZBZJAGBUPK-OAHLLOKOSA-N 0.000 claims description 5
• QWOASFZMYYNXRM-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCC(C)(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 QWOASFZMYYNXRM-UHFFFAOYSA-N 0.000 claims description 5
• BUMVLQOZZMNPSW-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C)C=CC=2)S1 BUMVLQOZZMNPSW-UHFFFAOYSA-N 0.000 claims description 5
• QJIDJBIONRJFKP-KRWDZBQOSA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound CN1CCC[C@H]1COC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 QJIDJBIONRJFKP-KRWDZBQOSA-N 0.000 claims description 5
• UUMUREPIJLZIJX-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1N(CC)CCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 UUMUREPIJLZIJX-UHFFFAOYSA-N 0.000 claims description 4
• CVFSHHHSKJDYOE-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound S1C(C(=O)C=2C=C3OCOC3=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 CVFSHHHSKJDYOE-UHFFFAOYSA-N 0.000 claims description 4
• ZUHXRBPQXZBELD-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCOC3=CC=2)S1 ZUHXRBPQXZBELD-UHFFFAOYSA-N 0.000 claims description 4
• PKHGKTDIDRERBR-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 PKHGKTDIDRERBR-UHFFFAOYSA-N 0.000 claims description 4
• FBEOXMSYTZRCPI-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(OC)C=CC=2)S1 FBEOXMSYTZRCPI-UHFFFAOYSA-N 0.000 claims description 4
• KACFBTLJESYLDN-UHFFFAOYSA-N [4-amino-2-[4-[3-(ethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=CC(OCCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(OC)=CC=2)S1 KACFBTLJESYLDN-UHFFFAOYSA-N 0.000 claims description 4
• SSGODMHQNTWPOX-UHFFFAOYSA-N cyanothiourea Chemical compound NC(=S)NC#N SSGODMHQNTWPOX-UHFFFAOYSA-N 0.000 claims description 4
• 210000002307 prostate Anatomy 0.000 claims description 4
• IBIXIAHOAPMZTJ-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCCC4)=CC=3)S2)N)=C1 IBIXIAHOAPMZTJ-UHFFFAOYSA-N 0.000 claims description 3
• FVTSKHLUDRUVSK-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OC1CCCNC1 FVTSKHLUDRUVSK-UHFFFAOYSA-N 0.000 claims description 3
• IFXOVSQDVVTNDS-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCCC4)=CC=3)S2)N)=C1 IFXOVSQDVVTNDS-UHFFFAOYSA-N 0.000 claims description 3
• DIYHPWPVOVXELI-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 DIYHPWPVOVXELI-UHFFFAOYSA-N 0.000 claims description 3
• GHEKTLVREQLKIT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 GHEKTLVREQLKIT-UHFFFAOYSA-N 0.000 claims description 3
• NMTDYVUTYCNVNT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CN(CC)CC4)=CC=3)S2)N)=C1 NMTDYVUTYCNVNT-UHFFFAOYSA-N 0.000 claims description 3
• JBEWFBPHPDHEKY-UHFFFAOYSA-N [4-amino-2-[4-(2-imidazol-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4C=NC=C4)=CC=3)S2)N)=C1 JBEWFBPHPDHEKY-UHFFFAOYSA-N 0.000 claims description 3
• JQYOOPVLXZGSKP-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 JQYOOPVLXZGSKP-UHFFFAOYSA-N 0.000 claims description 3
• KJTQECUCLSKETJ-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 KJTQECUCLSKETJ-UHFFFAOYSA-N 0.000 claims description 3
• CZJMEJVHIWOBOC-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methyl-2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound C1=C2C(C)COC2=CC=C1C(=O)C(=C(N=1)N)SC=1NC(C=C1)=CC=C1OCCN1CCCC1 CZJMEJVHIWOBOC-UHFFFAOYSA-N 0.000 claims description 3
• MPJMUPXNCBXSED-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(4-ethyl-3-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCN3CCCC3)=CC=2)S1 MPJMUPXNCBXSED-UHFFFAOYSA-N 0.000 claims description 3
• UUQWCSLNCKAQHP-CQSZACIVSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N(C)C)=CC=3)S2)N)=C1 UUQWCSLNCKAQHP-CQSZACIVSA-N 0.000 claims description 3
• PKHGKTDIDRERBR-CYBMUJFWSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OC[C@@H](C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 PKHGKTDIDRERBR-CYBMUJFWSA-N 0.000 claims description 3
• CQLWHHFYBLHEIJ-QGZVFWFLSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C([C@@H](C)N1CCCC1)OC(C=C1)=CC=C1NC(S1)=NC(N)=C1C(=O)C(C=1)=CC=CC=1C1CC1 CQLWHHFYBLHEIJ-QGZVFWFLSA-N 0.000 claims description 3
• NUIRIOMUOLZYKJ-QGZVFWFLSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N4CCCC4)=CC=3)S2)N)=C1 NUIRIOMUOLZYKJ-QGZVFWFLSA-N 0.000 claims description 3
• WWBQVIMIWSCQEZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(OC)=CC=2)S1 WWBQVIMIWSCQEZ-UHFFFAOYSA-N 0.000 claims description 3
• XWEJXUMHVXPUSS-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCCOC3=CC=2)S1 XWEJXUMHVXPUSS-UHFFFAOYSA-N 0.000 claims description 3
• KCLVVBCHPZJWBZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 KCLVVBCHPZJWBZ-UHFFFAOYSA-N 0.000 claims description 3
• GVCMCRIPYSUCJX-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-nitrophenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)S1 GVCMCRIPYSUCJX-UHFFFAOYSA-N 0.000 claims description 3
• IWGPPWKRMBZHSQ-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCOC3=CC=2)S1 IWGPPWKRMBZHSQ-UHFFFAOYSA-N 0.000 claims description 3
• GLJAZVDIWLYFBM-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3CCOC3=CC=2)S1 GLJAZVDIWLYFBM-UHFFFAOYSA-N 0.000 claims description 3
• FIWHTKIXUIAOTG-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 FIWHTKIXUIAOTG-UHFFFAOYSA-N 0.000 claims description 3
• 238000007911 parenteral administration Methods 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 claims description 2
• BWQIMYBVXAAHBJ-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(C=CC=2)C2CC2)=C(N)N=C1NC(C=C1)=CC=C1OC1CCNC1 BWQIMYBVXAAHBJ-UHFFFAOYSA-N 0.000 claims description 2
• ZDUFKQZIJRVRSN-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 ZDUFKQZIJRVRSN-UHFFFAOYSA-N 0.000 claims description 2
• KXUOSZRFGUIVQI-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=C(F)C(C)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCC3)=CC=2)S1 KXUOSZRFGUIVQI-UHFFFAOYSA-N 0.000 claims description 2
• ASBJJBCTLYXARJ-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 ASBJJBCTLYXARJ-UHFFFAOYSA-N 0.000 claims description 2
• LDWASAYFOGXWAO-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(4-methoxy-3-nitrophenyl)methanone Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCN3CCCC3)=CC=2)S1 LDWASAYFOGXWAO-UHFFFAOYSA-N 0.000 claims description 2
• JNJCWPVQZGQMFX-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N(C)C)=CC=3)S2)N)=C1 JNJCWPVQZGQMFX-OAHLLOKOSA-N 0.000 claims description 2
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