ZA200209360B - Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. - Google Patents

Info

Publication number

ZA200209360B

ZA200209360B ZA200209360A ZA200209360A ZA200209360B ZA 200209360 B ZA200209360 B ZA 200209360B ZA 200209360 A ZA200209360 A ZA 200209360A ZA 200209360 A ZA200209360 A ZA 200209360A ZA 200209360 B ZA200209360 B ZA 200209360B

Authority

ZA

South Africa

Prior art keywords

thiazol

ethyl

amino

chloro

sulfonyl

Prior art date

2000-05-22

Links

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• 239000003112 inhibitor Substances 0.000 title description 8
• 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title description 2
• 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title description 2
• -1 di-substituted, amide Chemical class 0.000 claims description 729
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 421
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 187
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 164
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 91
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• 239000001257 hydrogen Substances 0.000 claims description 72
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 150000002431 hydrogen Chemical group 0.000 claims description 48
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 43
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 150000001875 compounds Chemical class 0.000 claims description 35
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229940124530 sulfonamide Drugs 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• 239000004305 biphenyl Substances 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 23
• 235000010290 biphenyl Nutrition 0.000 claims description 21
• 150000001412 amines Chemical class 0.000 claims description 19
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 18
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 230000008878 coupling Effects 0.000 claims description 18
• 238000010168 coupling process Methods 0.000 claims description 18
• 238000005859 coupling reaction Methods 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 17
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 125000002757 morpholinyl group Chemical group 0.000 claims description 16
• 150000001408 amides Chemical class 0.000 claims description 15
• 206010012601 diabetes mellitus Diseases 0.000 claims description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 14
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
• 239000000203 mixture Substances 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• 208000010412 Glaucoma Diseases 0.000 claims description 9
• 208000001132 Osteoporosis Diseases 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 150000003456 sulfonamides Chemical class 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
• 230000002519 immonomodulatory effect Effects 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 239000012453 solvate Substances 0.000 claims description 7
• 208000011580 syndromic disease Diseases 0.000 claims description 7
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
• UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
• 125000001769 aryl amino group Chemical group 0.000 claims description 6
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
• 125000005110 aryl thio group Chemical group 0.000 claims description 6
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 150000001733 carboxylic acid esters Chemical class 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 6
• SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 6
• 229910052763 palladium Inorganic materials 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
• 201000008827 tuberculosis Diseases 0.000 claims description 6
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 5
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
• MWZDUDLJCVHQQA-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-[methyl(methylsulfonyl)amino]ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CS(=O)(=O)N(C)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MWZDUDLJCVHQQA-UHFFFAOYSA-N 0.000 claims description 5
• IKWXQEULPZNLEH-UHFFFAOYSA-N 3-chloro-n-[4-[2-(methanesulfonamido)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(C)(=O)=O)=CS1 IKWXQEULPZNLEH-UHFFFAOYSA-N 0.000 claims description 5
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 5
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
• OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 241000700605 Viruses Species 0.000 claims description 5
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 5
• OBFRWCVXUAAEQG-UHFFFAOYSA-N ethyl 2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=N1 OBFRWCVXUAAEQG-UHFFFAOYSA-N 0.000 claims description 5
• PWVFWMRVAJPZQZ-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 PWVFWMRVAJPZQZ-UHFFFAOYSA-N 0.000 claims description 5
• HMGOOODTJVJVDK-CMDGGOBGSA-N ethyl 2-[2-[[(e)-2-phenylethenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)\C=C\C=2C=CC=CC=2)=N1 HMGOOODTJVJVDK-CMDGGOBGSA-N 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 201000001421 hyperglycemia Diseases 0.000 claims description 5
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 5
• 201000008980 hyperinsulinism Diseases 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 5
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 4
• DGWGQUBCSAZGGX-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-cyclohexyl-n-methylacetamide Chemical compound C=1SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=NC=1CC(=O)N(C)C1CCCCC1 DGWGQUBCSAZGGX-UHFFFAOYSA-N 0.000 claims description 4
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• SKFUKFDKZSDFRR-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound O1C(C)=NN=C1CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 SKFUKFDKZSDFRR-UHFFFAOYSA-N 0.000 claims description 4
• PMDHDRBKLSNVTO-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethoxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCOCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 PMDHDRBKLSNVTO-UHFFFAOYSA-N 0.000 claims description 4
• NOLMXNHBTMCQLS-UHFFFAOYSA-N 4-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound OCCC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 NOLMXNHBTMCQLS-UHFFFAOYSA-N 0.000 claims description 4
• 208000028698 Cognitive impairment Diseases 0.000 claims description 4
• 208000013016 Hypoglycemia Diseases 0.000 claims description 4
• 241000236488 Lepra Species 0.000 claims description 4
• 206010024229 Leprosy Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• JVAFXOOYGZUHAM-UHFFFAOYSA-N ethyl 2-[2-(quinolin-8-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)=N1 JVAFXOOYGZUHAM-UHFFFAOYSA-N 0.000 claims description 4
• JDBWRECUZVWGNO-UHFFFAOYSA-N ethyl 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 JDBWRECUZVWGNO-UHFFFAOYSA-N 0.000 claims description 4
• LNAGTOPKTFQIIS-UHFFFAOYSA-N ethyl 2-[2-[(2-methylsulfonylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)S(C)(=O)=O)=N1 LNAGTOPKTFQIIS-UHFFFAOYSA-N 0.000 claims description 4
• ZCNWUMGMIAXUQD-UHFFFAOYSA-N ethyl 2-[2-[(2-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZCNWUMGMIAXUQD-UHFFFAOYSA-N 0.000 claims description 4
• XQETZYRGNIDJBQ-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)F)=N1 XQETZYRGNIDJBQ-UHFFFAOYSA-N 0.000 claims description 4
• MSBRGTIONVCFPM-UHFFFAOYSA-N ethyl 2-[2-[(4-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=N1 MSBRGTIONVCFPM-UHFFFAOYSA-N 0.000 claims description 4
• AXHPKOPJFWOGEG-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)=N1 AXHPKOPJFWOGEG-UHFFFAOYSA-N 0.000 claims description 4
• 230000002218 hypoglycaemic effect Effects 0.000 claims description 4
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
• WVSCPCGKOUHZLV-UHFFFAOYSA-N 2,4-dichloro-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 WVSCPCGKOUHZLV-UHFFFAOYSA-N 0.000 claims description 3
• HBSWMTRBCJGKNK-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl benzoate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC(=O)C=2C=CC=CC=2)=CS1 HBSWMTRBCJGKNK-UHFFFAOYSA-N 0.000 claims description 3
• MNYDWIWWEGDUMZ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MNYDWIWWEGDUMZ-UHFFFAOYSA-N 0.000 claims description 3
• VISGQGQJQWSXHJ-UHFFFAOYSA-N 2-[2-[(4-acetamidophenyl)sulfonylamino]-4-thiazolyl]acetic acid ethyl ester Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=N1 VISGQGQJQWSXHJ-UHFFFAOYSA-N 0.000 claims description 3
• LPCMLZYSJNPYRP-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 LPCMLZYSJNPYRP-UHFFFAOYSA-N 0.000 claims description 3
• YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims description 3
• LRSHRBXCWRJSCQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxopentyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCCC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 LRSHRBXCWRJSCQ-UHFFFAOYSA-N 0.000 claims description 3
• GQMBSMSODYSGSD-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(morpholin-4-ylmethyl)-1,3-thiazol-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CN2CCOCC2)=CS1 GQMBSMSODYSGSD-UHFFFAOYSA-N 0.000 claims description 3
• NZQVGMPKUSPJFJ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(methylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CNCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NZQVGMPKUSPJFJ-UHFFFAOYSA-N 0.000 claims description 3
• UZWQRKFUNIGEEO-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(trifluoromethylsulfonylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(=O)(=O)C(F)(F)F)=CS1 UZWQRKFUNIGEEO-UHFFFAOYSA-N 0.000 claims description 3
• XNIJTLZWWZHATQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-chloroethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCl)=CS1 XNIJTLZWWZHATQ-UHFFFAOYSA-N 0.000 claims description 3
• JOVCZOADHRKCLI-UHFFFAOYSA-N 3-chloro-n-[4-(2-methoxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound COCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 JOVCZOADHRKCLI-UHFFFAOYSA-N 0.000 claims description 3
• UOTYWFJEHQSZLC-UHFFFAOYSA-N 3-chloro-n-[4-(3-hydroxypropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCO)=CS1 UOTYWFJEHQSZLC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims description 3
• JJWLUBGKRMKXNK-UHFFFAOYSA-N ethyl 2-[2-(naphthalen-2-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 JJWLUBGKRMKXNK-UHFFFAOYSA-N 0.000 claims description 3
• CAAGINURIJZJFA-UHFFFAOYSA-N ethyl 2-[2-[(1-methylimidazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2N=CN(C)C=2)=N1 CAAGINURIJZJFA-UHFFFAOYSA-N 0.000 claims description 3
• FUOFZFZFISSASM-UHFFFAOYSA-N ethyl 2-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 FUOFZFZFISSASM-UHFFFAOYSA-N 0.000 claims description 3
• BOFWWAXNVWTGKH-UHFFFAOYSA-N ethyl 2-[2-[(3-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(F)C=CC=2)=N1 BOFWWAXNVWTGKH-UHFFFAOYSA-N 0.000 claims description 3
• MHIBAPFQSMMVMN-UHFFFAOYSA-N ethyl 2-[2-[(4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(F)=CC=2)=N1 MHIBAPFQSMMVMN-UHFFFAOYSA-N 0.000 claims description 3
• IGKYRCNENBYGMB-UHFFFAOYSA-N ethyl 2-[2-[[5-(2-methylsulfanylpyrimidin-4-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C=2N=C(SC)N=CC=2)=N1 IGKYRCNENBYGMB-UHFFFAOYSA-N 0.000 claims description 3
• BNACUUGAPKFPRZ-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 BNACUUGAPKFPRZ-UHFFFAOYSA-N 0.000 claims description 3
• ZTUGURUGCPZKNN-UHFFFAOYSA-N methyl 2-[2-[(4-chlorophenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 ZTUGURUGCPZKNN-UHFFFAOYSA-N 0.000 claims description 3
• QAJVSRSYPVAURA-UHFFFAOYSA-N methyl 2-[2-[[4-(3-chloro-2-cyanophenoxy)phenyl]sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1C#N QAJVSRSYPVAURA-UHFFFAOYSA-N 0.000 claims description 3
• AWAACVVVLZSRMV-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetamide Chemical compound C1=C2OCOC2=CC(CNC(CC=2N=C(NS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)SC=2)=O)=C1 AWAACVVVLZSRMV-UHFFFAOYSA-N 0.000 claims description 3
• UFEUINZZSPOMIB-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]-n-(2-hydroxyethyl)furan-2-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN(CCO)C(=O)C=2OC=CC=2)=CS1 UFEUINZZSPOMIB-UHFFFAOYSA-N 0.000 claims description 3
• ITSYGEVZNPQFOG-UHFFFAOYSA-N n-ethyl-n-methyl-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 ITSYGEVZNPQFOG-UHFFFAOYSA-N 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
• KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
• JBKXGULGNQEDPS-UHFFFAOYSA-N 2-[2-[(2,4-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 JBKXGULGNQEDPS-UHFFFAOYSA-N 0.000 claims description 2
• OQUSPHXWLUOJKV-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 OQUSPHXWLUOJKV-UHFFFAOYSA-N 0.000 claims description 2
• NSIMZMOFHFLYCX-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methyl-n-propan-2-ylacetamide Chemical compound CC(C)N(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NSIMZMOFHFLYCX-UHFFFAOYSA-N 0.000 claims description 2
• HCVDPOLLLJHUPC-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 HCVDPOLLLJHUPC-UHFFFAOYSA-N 0.000 claims description 2
• NUSJTMYRJVRWGH-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NUSJTMYRJVRWGH-UHFFFAOYSA-N 0.000 claims description 2
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 2
• YWCBGZLJKFQWCX-UHFFFAOYSA-N 2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(OC(F)(F)F)=CC=2)C)=N1 YWCBGZLJKFQWCX-UHFFFAOYSA-N 0.000 claims description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
• BZJKTWZDZSLMID-UHFFFAOYSA-N 3-chloro-n-[4-[3-(2-hydroxyethylamino)propyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrate;hydrochloride Chemical compound O.Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCNCCO)=CS1 BZJKTWZDZSLMID-UHFFFAOYSA-N 0.000 claims description 2
• ZHLZAFKVZBBSST-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2OC3=CC=CC=C3C=2)=NC=1CC(=O)N1CCOCC1 ZHLZAFKVZBBSST-UHFFFAOYSA-N 0.000 claims description 2
• TZNDCHUGTISBJP-UHFFFAOYSA-N 4-(5-chlorothiophen-2-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(Cl)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 TZNDCHUGTISBJP-UHFFFAOYSA-N 0.000 claims description 2
• QFDBISKHFLCXAV-UHFFFAOYSA-N 4-morpholin-4-yl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1N1CCOCC1 QFDBISKHFLCXAV-UHFFFAOYSA-N 0.000 claims description 2
• NHXSTXWKZVAVOQ-UHFFFAOYSA-N Ethyl furoate Chemical compound CCOC(=O)C1=CC=CO1 NHXSTXWKZVAVOQ-UHFFFAOYSA-N 0.000 claims description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
• 230000010933 acylation Effects 0.000 claims description 2
• 238000005917 acylation reaction Methods 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
• 230000021235 carbamoylation Effects 0.000 claims description 2
• AYEZJMCEEUOZBO-UHFFFAOYSA-N ethyl 2-[2-[(2,3,4-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 AYEZJMCEEUOZBO-UHFFFAOYSA-N 0.000 claims description 2
• CBVGFYLRKFMWIY-UHFFFAOYSA-N ethyl 2-[2-[(2,3-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=N1 CBVGFYLRKFMWIY-UHFFFAOYSA-N 0.000 claims description 2
• DFVBAXVWJFEVIE-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonyl-methylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(N(C)S(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 DFVBAXVWJFEVIE-UHFFFAOYSA-N 0.000 claims description 2
• PZARFSJHMREGLA-UHFFFAOYSA-N ethyl 2-[2-[(3-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(OC)C=CC=2)=N1 PZARFSJHMREGLA-UHFFFAOYSA-N 0.000 claims description 2
• UHAQMGZZUVKJHH-UHFFFAOYSA-N ethyl 2-[2-[(4-acetamido-3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(NC(C)=O)=CC=2)=N1 UHAQMGZZUVKJHH-UHFFFAOYSA-N 0.000 claims description 2
• UWYFMDJTWUHYCH-UHFFFAOYSA-N ethyl 2-[2-[(4-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=N1 UWYFMDJTWUHYCH-UHFFFAOYSA-N 0.000 claims description 2
• LSUOHCBWXCYLMG-UHFFFAOYSA-N ethyl 2-[2-[[4-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC=C(C=2)S(=O)(=O)C=2C=CC=CC=2)=N1 LSUOHCBWXCYLMG-UHFFFAOYSA-N 0.000 claims description 2
• REWJMTLJYJXMPA-UHFFFAOYSA-N ethyl 2-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)=N1 REWJMTLJYJXMPA-UHFFFAOYSA-N 0.000 claims description 2
• JPINMSJPGIZMAC-UHFFFAOYSA-N ethyl 2-[2-[[5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C2=NN(C)C(=C2)C(F)(F)F)=N1 JPINMSJPGIZMAC-UHFFFAOYSA-N 0.000 claims description 2
• PVWVVNUNHXAKGT-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 PVWVVNUNHXAKGT-UHFFFAOYSA-N 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• ZYBLYLRTWNHTON-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl ZYBLYLRTWNHTON-UHFFFAOYSA-N 0.000 claims description 2
• POQSMNSPMDVTHU-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OC)=C(C)S1 POQSMNSPMDVTHU-UHFFFAOYSA-N 0.000 claims description 2
• IERVETIQARVCNC-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 IERVETIQARVCNC-UHFFFAOYSA-N 0.000 claims description 2
• FGEITWLWOHALNM-UHFFFAOYSA-N propan-2-yl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CC(C)OC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 FGEITWLWOHALNM-UHFFFAOYSA-N 0.000 claims description 2
• 238000007127 saponification reaction Methods 0.000 claims description 2
• 150000003585 thioureas Chemical class 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 4
• XTSPBSIOOVDLFL-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2F)F)=N1 XTSPBSIOOVDLFL-UHFFFAOYSA-N 0.000 claims 4
• PMRYJIFBBGSVKP-UHFFFAOYSA-N ethyl 2-[2-[(2-methoxy-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2)OC)=N1 PMRYJIFBBGSVKP-UHFFFAOYSA-N 0.000 claims 4
• ZTCSTONMUHDFKJ-UHFFFAOYSA-N ethyl 2-[2-[(3-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Br)C=CC=2)=N1 ZTCSTONMUHDFKJ-UHFFFAOYSA-N 0.000 claims 4
• WZQBUAOAZRGEBW-UHFFFAOYSA-N ethyl 2-[2-[(3-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C)C=CC=2)=N1 WZQBUAOAZRGEBW-UHFFFAOYSA-N 0.000 claims 4
• PGUXTMPTPRTMHK-UHFFFAOYSA-N ethyl 2-[2-[(4-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=N1 PGUXTMPTPRTMHK-UHFFFAOYSA-N 0.000 claims 4
• GGFUIBCPKURKMT-UHFFFAOYSA-N ethyl 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 GGFUIBCPKURKMT-UHFFFAOYSA-N 0.000 claims 4
• JIHXZUUTKHVLNU-UHFFFAOYSA-N ethyl 2-[2-[(4-phenoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 JIHXZUUTKHVLNU-UHFFFAOYSA-N 0.000 claims 4
• HTGLZCFZWSAEEN-UHFFFAOYSA-N ethyl 2-[2-[(4-propan-2-ylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(C)C)=N1 HTGLZCFZWSAEEN-UHFFFAOYSA-N 0.000 claims 4
• VJZNBJUIDMRTPW-UHFFFAOYSA-N ethyl 2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 VJZNBJUIDMRTPW-UHFFFAOYSA-N 0.000 claims 4
• GJLFAKWHOGZISU-UHFFFAOYSA-N ethyl 2-[2-[[2-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 GJLFAKWHOGZISU-UHFFFAOYSA-N 0.000 claims 4
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 4
• ULPWFZWHDRXKJM-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 ULPWFZWHDRXKJM-UHFFFAOYSA-N 0.000 claims 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
• PCURMNYHJKIXIK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-phenylmethoxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCC=2C=CC=CC=2)=CS1 PCURMNYHJKIXIK-UHFFFAOYSA-N 0.000 claims 3
• UZLWJPBUKCZYIM-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(2,2,2-trifluoroethoxy)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCC(F)(F)F)=CS1 UZLWJPBUKCZYIM-UHFFFAOYSA-N 0.000 claims 3
• MIBSEMNJJNDMIY-UHFFFAOYSA-N 3-chloro-n-[4-(2-imidazol-1-ylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;dihydrate Chemical compound O.O.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C=NC=C2)=CS1 MIBSEMNJJNDMIY-UHFFFAOYSA-N 0.000 claims 3
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 3
• FFIWDZOIZSYFCK-UHFFFAOYSA-N ethyl 2-[2-[(2,3,4-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(F)C(F)=CC=2)F)=N1 FFIWDZOIZSYFCK-UHFFFAOYSA-N 0.000 claims 3
• AZFIPTGNCDPGCH-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 AZFIPTGNCDPGCH-UHFFFAOYSA-N 0.000 claims 3
• IQHJPEZHJFMMKA-UHFFFAOYSA-N ethyl 2-[2-[(2-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=N1 IQHJPEZHJFMMKA-UHFFFAOYSA-N 0.000 claims 3
• FIUOJUMQXLUVOT-UHFFFAOYSA-N ethyl 2-[2-[(2-chloro-4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)Cl)=N1 FIUOJUMQXLUVOT-UHFFFAOYSA-N 0.000 claims 3
• IWJABBCLSCEYRG-UHFFFAOYSA-N ethyl 2-[2-[(2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C)=N1 IWJABBCLSCEYRG-UHFFFAOYSA-N 0.000 claims 3
• XJVXNSMNVRSDPC-UHFFFAOYSA-N ethyl 2-[2-[(3,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=N1 XJVXNSMNVRSDPC-UHFFFAOYSA-N 0.000 claims 3
• CWRLDLCBUSKDDE-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=N1 CWRLDLCBUSKDDE-UHFFFAOYSA-N 0.000 claims 3
• GJLYEXVGTDRIDB-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 GJLYEXVGTDRIDB-UHFFFAOYSA-N 0.000 claims 3
• SKMXVSXCYNCVLY-UHFFFAOYSA-N ethyl 2-[2-[[2,4-bis(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)C(F)(F)F)=N1 SKMXVSXCYNCVLY-UHFFFAOYSA-N 0.000 claims 3
• FLDPZLUGDUXEOR-UHFFFAOYSA-N ethyl 2-[2-[[3-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=N1 FLDPZLUGDUXEOR-UHFFFAOYSA-N 0.000 claims 3
• MZTOQUINLWUTBG-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzamidomethyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(CNC(=O)C=3C=CC=CC=3)=CC=2)=N1 MZTOQUINLWUTBG-UHFFFAOYSA-N 0.000 claims 3
• IEGXMLXVLNHQQR-UHFFFAOYSA-N ethyl 3-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]propanoate Chemical compound CCOC(=O)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 IEGXMLXVLNHQQR-UHFFFAOYSA-N 0.000 claims 3
• RTBBWCJKGBZVGL-UHFFFAOYSA-N ethyl morpholine-4-carboxylate Chemical compound CCOC(=O)N1CCOCC1 RTBBWCJKGBZVGL-UHFFFAOYSA-N 0.000 claims 3
• VYJPKJQHXPFNGR-UHFFFAOYSA-N n,n-diethyl-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N(CC)CC)=CS1 VYJPKJQHXPFNGR-UHFFFAOYSA-N 0.000 claims 3
• DIVHULOBFPKRPY-UHFFFAOYSA-N n-[4-(2-bromoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCBr)=CS1 DIVHULOBFPKRPY-UHFFFAOYSA-N 0.000 claims 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
• 238000002560 therapeutic procedure Methods 0.000 claims 3
• RPZCXMXPXXVKKM-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C RPZCXMXPXXVKKM-UHFFFAOYSA-N 0.000 claims 2
• DHILZBKTQNBASR-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl furan-2-carboxylate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC(=O)C=2OC=CC=2)=CS1 DHILZBKTQNBASR-UHFFFAOYSA-N 0.000 claims 2
• AYKJIFPXBJZYOI-UHFFFAOYSA-N 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 AYKJIFPXBJZYOI-UHFFFAOYSA-N 0.000 claims 2
• OEUIPTZTKZPHFU-UHFFFAOYSA-N 2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 OEUIPTZTKZPHFU-UHFFFAOYSA-N 0.000 claims 2
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
• RQENMSXJKNRXFR-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-morpholin-4-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2CCOCC2)=CS1 RQENMSXJKNRXFR-UHFFFAOYSA-N 0.000 claims 2
• AKQKZSLUWUYCND-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-[methyl(trifluoromethylsulfonyl)amino]ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(C)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 AKQKZSLUWUYCND-UHFFFAOYSA-N 0.000 claims 2
• PSIMSLBVQXNOEQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCO)=CS1 PSIMSLBVQXNOEQ-UHFFFAOYSA-N 0.000 claims 2
• IBCZFVVJSBMGBI-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-hydroxyethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNCCO)=CS1 IBCZFVVJSBMGBI-UHFFFAOYSA-N 0.000 claims 2
• XXJRBYRRYDXBAK-UHFFFAOYSA-N 3-chloro-n-[4-[2-(3,4-dihydro-1h-isoquinolin-2-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CC3=CC=CC=C3CC2)=CS1 XXJRBYRRYDXBAK-UHFFFAOYSA-N 0.000 claims 2
• GVEMPLKGNIFWOE-UHFFFAOYSA-N 3-chloro-n-[4-[2-(ethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCNCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GVEMPLKGNIFWOE-UHFFFAOYSA-N 0.000 claims 2
• KQXSRJQWBZKFPM-UHFFFAOYSA-N 3-chloro-n-[4-[2-[(3-chloro-2-methylphenyl)sulfonyl-methylamino]ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C=1C=CC(Cl)=C(C)C=1S(=O)(=O)N(C)CCC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C KQXSRJQWBZKFPM-UHFFFAOYSA-N 0.000 claims 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
• ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims 2
• 101100095563 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SEO1 gene Proteins 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• IJNMHHJKXLKFJT-UHFFFAOYSA-N ethyl 2-[2-(benzenesulfonamido)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC=CC=2)=N1 IJNMHHJKXLKFJT-UHFFFAOYSA-N 0.000 claims 2
• LFHRKMQLRBNRKC-UHFFFAOYSA-N ethyl 2-[2-[(2,4-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 LFHRKMQLRBNRKC-UHFFFAOYSA-N 0.000 claims 2
• KACQGQGBDKICBL-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=N1 KACQGQGBDKICBL-UHFFFAOYSA-N 0.000 claims 2
• FCKASCFOIWCCQJ-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(OC)C=2)OC)=N1 FCKASCFOIWCCQJ-UHFFFAOYSA-N 0.000 claims 2
• HAGXVJTVTTUNAP-UHFFFAOYSA-N ethyl 2-[2-[(2-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C#N)=N1 HAGXVJTVTTUNAP-UHFFFAOYSA-N 0.000 claims 2
• PFPFBIQZBIPXNF-UHFFFAOYSA-N ethyl 2-[2-[(3,4-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(OC)C(OC)=CC=2)=N1 PFPFBIQZBIPXNF-UHFFFAOYSA-N 0.000 claims 2
• GZLJHVLKSZQICO-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GZLJHVLKSZQICO-UHFFFAOYSA-N 0.000 claims 2
• YTRIEVDHWCSHLN-UHFFFAOYSA-N ethyl 2-[2-[(3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=N1 YTRIEVDHWCSHLN-UHFFFAOYSA-N 0.000 claims 2
• WDZSIANQAZTVEH-UHFFFAOYSA-N ethyl 2-[2-[(3-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C#N)=N1 WDZSIANQAZTVEH-UHFFFAOYSA-N 0.000 claims 2
• JWPFFPNIEBVQBS-UHFFFAOYSA-N ethyl 2-[2-[(4,5-dichlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 JWPFFPNIEBVQBS-UHFFFAOYSA-N 0.000 claims 2
• GTGYIXMGPVAEAW-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2,5-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=C(F)C=2)F)=N1 GTGYIXMGPVAEAW-UHFFFAOYSA-N 0.000 claims 2
• CDXAXVDUNJWIEK-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,1,3-benzoxadiazol-7-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NON=C3C(Cl)=CC=2)=N1 CDXAXVDUNJWIEK-UHFFFAOYSA-N 0.000 claims 2
• OAGJLQCJTUZHMJ-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,6-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)C)=N1 OAGJLQCJTUZHMJ-UHFFFAOYSA-N 0.000 claims 2
• AAWVIKWDCOANTH-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)C)=N1 AAWVIKWDCOANTH-UHFFFAOYSA-N 0.000 claims 2
• DGMIUIWULBYPQP-UHFFFAOYSA-N ethyl 2-[2-[(5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=CC=2)=N1 DGMIUIWULBYPQP-UHFFFAOYSA-N 0.000 claims 2
• HKEFYAKHKFYMMG-UHFFFAOYSA-N ethyl 2-[2-[(5-fluoro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(F)C=2)C)=N1 HKEFYAKHKFYMMG-UHFFFAOYSA-N 0.000 claims 2
• FAJOFAUMOBXWQR-UHFFFAOYSA-N ethyl 2-[2-[[2-methyl-4-(trifluoromethoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(OC(F)(F)F)=CC=2)C)=N1 FAJOFAUMOBXWQR-UHFFFAOYSA-N 0.000 claims 2
• DAFDNRSHQQFNSQ-UHFFFAOYSA-N ethyl 2-[2-[[4-(3-chloro-2-cyanophenoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=N1 DAFDNRSHQQFNSQ-UHFFFAOYSA-N 0.000 claims 2
• SEMYPGMDNTYNAW-UHFFFAOYSA-N ethyl 2-[2-[[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C2=NOC=C2)=N1 SEMYPGMDNTYNAW-UHFFFAOYSA-N 0.000 claims 2
• SSTFTUKNWXIXKH-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 SSTFTUKNWXIXKH-UHFFFAOYSA-N 0.000 claims 2
• SRRCAMPLVRPDHC-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C(=O)C(=O)OCC)=CS1 SRRCAMPLVRPDHC-UHFFFAOYSA-N 0.000 claims 2
• VAJCYQHLYBTSHG-UHFFFAOYSA-N ethyl n,n-diethylcarbamate Chemical compound CCOC(=O)N(CC)CC VAJCYQHLYBTSHG-UHFFFAOYSA-N 0.000 claims 2
• GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 claims 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
• XGRFANQSTSFERT-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 XGRFANQSTSFERT-UHFFFAOYSA-N 0.000 claims 2
• KASYRVNOWHARGW-UHFFFAOYSA-N n,n-di(propan-2-yl)-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N(C(C)C)C(C)C)=CS1 KASYRVNOWHARGW-UHFFFAOYSA-N 0.000 claims 2
• FDKSCNNPNTWASM-UHFFFAOYSA-N n,n-diethyl-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 FDKSCNNPNTWASM-UHFFFAOYSA-N 0.000 claims 2
• IABWJYRLNHRIAD-UHFFFAOYSA-N n-[3-[4-[[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]sulfamoyl]phenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)=C1 IABWJYRLNHRIAD-UHFFFAOYSA-N 0.000 claims 2
• RGRYQXXKBMGOMW-UHFFFAOYSA-N n-[4-(2-aminoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN)=CS1 RGRYQXXKBMGOMW-UHFFFAOYSA-N 0.000 claims 2
• NSBJXAREJWGDLL-UHFFFAOYSA-N n-ethyl-n-methyl-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 NSBJXAREJWGDLL-UHFFFAOYSA-N 0.000 claims 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
• CSUYPAKJHXXDPC-UHFFFAOYSA-N phenyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)OC=2C=CC=CC=2)=CS1 CSUYPAKJHXXDPC-UHFFFAOYSA-N 0.000 claims 2
• DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 claims 2
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
• CGPRKKGTHPOISW-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 CGPRKKGTHPOISW-UHFFFAOYSA-N 0.000 claims 1
• UDSFXWYSYFILMF-UHFFFAOYSA-N 2,4,6-trichloro-n-[5-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound N=1C(CC(=O)N2CCOCC2)=C(C)SC=1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl UDSFXWYSYFILMF-UHFFFAOYSA-N 0.000 claims 1
• IBGZNXCMLFPZRU-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 IBGZNXCMLFPZRU-UHFFFAOYSA-N 0.000 claims 1
• DOTRAHDBXAHCSW-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-morpholin-4-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CCN2CCOCC2)=CS1 DOTRAHDBXAHCSW-UHFFFAOYSA-N 0.000 claims 1
• HIFGQHGWMTZMOH-UHFFFAOYSA-N 2-(trifluoromethoxy)benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F HIFGQHGWMTZMOH-UHFFFAOYSA-N 0.000 claims 1
• WSKHSWHWEKUKCK-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WSKHSWHWEKUKCK-UHFFFAOYSA-N 0.000 claims 1
• RBJALPGWPKFZJQ-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethyl-n-methylacetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 RBJALPGWPKFZJQ-UHFFFAOYSA-N 0.000 claims 1
• HEMVPFSRVDOYIS-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 HEMVPFSRVDOYIS-UHFFFAOYSA-N 0.000 claims 1
• QOLLTXJGTDTYQY-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-dipropylacetamide Chemical compound CCCN(CCC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 QOLLTXJGTDTYQY-UHFFFAOYSA-N 0.000 claims 1
• NSBLVGFETONCLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethyl-n-methylacetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NSBLVGFETONCLJ-UHFFFAOYSA-N 0.000 claims 1
• MWLVRQCUVOUIBF-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MWLVRQCUVOUIBF-UHFFFAOYSA-N 0.000 claims 1
• ZFZSPBPBECULLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 ZFZSPBPBECULLJ-UHFFFAOYSA-N 0.000 claims 1
• PBNMKZXABHYGGL-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(N)=O)=CS1 PBNMKZXABHYGGL-UHFFFAOYSA-N 0.000 claims 1
• WBXQHDLZILRZTA-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WBXQHDLZILRZTA-UHFFFAOYSA-N 0.000 claims 1
• VYZWVMVWGHXNGP-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOS(C)(=O)=O)=CS1 VYZWVMVWGHXNGP-UHFFFAOYSA-N 0.000 claims 1
• VKMTYZOUAYGZLK-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl propanoate Chemical compound CCC(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 VKMTYZOUAYGZLK-UHFFFAOYSA-N 0.000 claims 1
• KIYPUUWMSLECQJ-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-(furan-2-ylmethyl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NCC=2OC=CC=2)=CS1 KIYPUUWMSLECQJ-UHFFFAOYSA-N 0.000 claims 1
• SFYSOCDXRYVHSP-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-(oxolan-2-ylmethyl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NCC2OCCC2)=CS1 SFYSOCDXRYVHSP-UHFFFAOYSA-N 0.000 claims 1
• SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims 1
• ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 claims 1
• VNCUBHRMXCJHJU-UHFFFAOYSA-N 2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CC1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 VNCUBHRMXCJHJU-UHFFFAOYSA-N 0.000 claims 1
• RHMRHGLMZBCOKT-UHFFFAOYSA-N 2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1S(N)(=O)=O RHMRHGLMZBCOKT-UHFFFAOYSA-N 0.000 claims 1
• QZZZWEIWYVXIHQ-UHFFFAOYSA-N 2-propylbenzenesulfonamide Chemical compound CCCC1=CC=CC=C1S(N)(=O)=O QZZZWEIWYVXIHQ-UHFFFAOYSA-N 0.000 claims 1
• HBNANTYKOKNNMC-UHFFFAOYSA-N 3-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]propyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCOS(C)(=O)=O)=CS1 HBNANTYKOKNNMC-UHFFFAOYSA-N 0.000 claims 1
• JQAGIZSPAQASSK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 JQAGIZSPAQASSK-UHFFFAOYSA-N 0.000 claims 1
• RJBYZNYPFAZOTP-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-propan-2-yloxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC(C)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RJBYZNYPFAZOTP-UHFFFAOYSA-N 0.000 claims 1
• FEBDOOGGNQMLEA-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-pyridin-2-ylsulfanylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCSC=2N=CC=CC=2)=CS1 FEBDOOGGNQMLEA-UHFFFAOYSA-N 0.000 claims 1
• YDPRNGAPPNPYQQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YDPRNGAPPNPYQQ-UHFFFAOYSA-N 0.000 claims 1
• MQNNPMUEUFLKRU-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-fluoroethoxy)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCCF)=CS1 MQNNPMUEUFLKRU-UHFFFAOYSA-N 0.000 claims 1
• GDULMDVSHSQBBG-UHFFFAOYSA-N 3-chloro-n-[4-[2-(diethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CCN(CC)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GDULMDVSHSQBBG-UHFFFAOYSA-N 0.000 claims 1
• CUVAORAJJTXNTP-GFCCVEGCSA-N 3-chloro-n-[4-[2-[(2r)-2,4-dimethylpiperazin-1-yl]-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C[C@@H]1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 CUVAORAJJTXNTP-GFCCVEGCSA-N 0.000 claims 1
• KUXWEFJHUYNBNN-TXEJJXNPSA-N 3-chloro-n-[4-[2-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 KUXWEFJHUYNBNN-TXEJJXNPSA-N 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• UMJPVWFIBILILQ-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanamide Chemical compound CC(C)C(C(C)C)C(N)=O UMJPVWFIBILILQ-UHFFFAOYSA-N 0.000 claims 1
• QKLDLIUPDVKUJI-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=C3OCOC3=CC=2)=NC=1CC(=O)N1CCOCC1 QKLDLIUPDVKUJI-UHFFFAOYSA-N 0.000 claims 1
• RUTGRVOKCXTIRW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 RUTGRVOKCXTIRW-UHFFFAOYSA-N 0.000 claims 1
• NHKHEYOGWVQQDI-UHFFFAOYSA-N 4-bromo-2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Br)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 NHKHEYOGWVQQDI-UHFFFAOYSA-N 0.000 claims 1
• MUUXKDKJIARHTQ-UHFFFAOYSA-N 4-chloro-2,6-dimethyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(C)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 MUUXKDKJIARHTQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
• HEFXLFQNUYNJHA-UHFFFAOYSA-N 4-phenyl-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 HEFXLFQNUYNJHA-UHFFFAOYSA-N 0.000 claims 1
• NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
• BRAIZMGEVOORLF-UHFFFAOYSA-N C1CSCC(N1O)O Chemical compound C1CSCC(N1O)O BRAIZMGEVOORLF-UHFFFAOYSA-N 0.000 claims 1
• SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 1
• PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 claims 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
• 241001024304 Mino Species 0.000 claims 1
• BBRFCFZVRCJPHU-UHFFFAOYSA-N N-[4-[[2-amino-4-(chloromethyl)-1,3-thiazol-5-yl]sulfonyl]phenyl]acetamide Chemical compound N(C(=O)C)C1=CC=C(C=C1)S(=O)(=O)C1=C(N=C(S1)N)CCl BBRFCFZVRCJPHU-UHFFFAOYSA-N 0.000 claims 1
• PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims 1
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 claims 1
• 125000000068 chlorophenyl group Chemical group 0.000 claims 1
• 229940016681 dipropylacetamide Drugs 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• DFPIHKZQUYAUSJ-UHFFFAOYSA-N ethyl 2-[2-[(2,4,5-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 DFPIHKZQUYAUSJ-UHFFFAOYSA-N 0.000 claims 1
• CQCXDXXEKHBZCA-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 CQCXDXXEKHBZCA-UHFFFAOYSA-N 0.000 claims 1
• RXLDVKZBTUCMEB-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 RXLDVKZBTUCMEB-UHFFFAOYSA-N 0.000 claims 1
• WYLIDXHKCNSRSG-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WYLIDXHKCNSRSG-UHFFFAOYSA-N 0.000 claims 1
• GIDZENNFVLMYKK-UHFFFAOYSA-N ethyl 2-[2-[(3-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=N1 GIDZENNFVLMYKK-UHFFFAOYSA-N 0.000 claims 1
• KKXBMETYIBLJLL-UHFFFAOYSA-N ethyl 2-[2-[(4-butoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 KKXBMETYIBLJLL-UHFFFAOYSA-N 0.000 claims 1
• DVAQZPOPYAJLPP-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=N1 DVAQZPOPYAJLPP-UHFFFAOYSA-N 0.000 claims 1
• IITATKCUYSUFMF-UHFFFAOYSA-N ethyl 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 IITATKCUYSUFMF-UHFFFAOYSA-N 0.000 claims 1
• UZBKVHNVGKVIBK-UHFFFAOYSA-N ethyl 2-[2-[(4-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC)=CC=2)=N1 UZBKVHNVGKVIBK-UHFFFAOYSA-N 0.000 claims 1
• OGXYMEROVHKCKW-UHFFFAOYSA-N ethyl 2-[2-[(4-methylsulfonylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 OGXYMEROVHKCKW-UHFFFAOYSA-N 0.000 claims 1
• ZODUISOKTTXHTP-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 ZODUISOKTTXHTP-UHFFFAOYSA-N 0.000 claims 1
• RWZWQUOQHYQFEY-UHFFFAOYSA-N ethyl 4-[[2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 RWZWQUOQHYQFEY-UHFFFAOYSA-N 0.000 claims 1
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims 1
• PDEPXTWYXQSUAK-UHFFFAOYSA-N methyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl PDEPXTWYXQSUAK-UHFFFAOYSA-N 0.000 claims 1
• KCIZIKWZFCENMB-UHFFFAOYSA-N n,n-di(propan-2-yl)-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 KCIZIKWZFCENMB-UHFFFAOYSA-N 0.000 claims 1
• ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 claims 1
• HEOXDBQVGHVNLH-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]-2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC=C2C(CCNC(CC=3N=C(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)SC=3)=O)=CNC2=C1 HEOXDBQVGHVNLH-UHFFFAOYSA-N 0.000 claims 1
• HDGAICTWOOQDHI-UHFFFAOYSA-N n-[4-(2-azidoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN=[N+]=[N-])=CS1 HDGAICTWOOQDHI-UHFFFAOYSA-N 0.000 claims 1
• KDWZXHHMVXZGSZ-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-2,4-bis(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 KDWZXHHMVXZGSZ-UHFFFAOYSA-N 0.000 claims 1
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