DE60316411T2 - Thiazolderivate als npy-rezeptorantagonisten - Google Patents

Info

Publication number

DE60316411T2

DE60316411T2 DE60316411T DE60316411T DE60316411T2 DE 60316411 T2 DE60316411 T2 DE 60316411T2 DE 60316411 T DE60316411 T DE 60316411T DE 60316411 T DE60316411 T DE 60316411T DE 60316411 T2 DE60316411 T2 DE 60316411T2

Authority

DE

Germany

Prior art keywords

thiazol

ylamino

methyl

benzoyl

propyl

Prior art date

2002-02-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 229940044551 receptor antagonist Drugs 0.000 title description 2
• 239000002464 receptor antagonist Substances 0.000 title description 2
• QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical class CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 title 1
• -1 C C 1 -C 8 -alkoxy Chemical group 0.000 claims description 238
• 150000001875 compounds Chemical class 0.000 claims description 208
• 238000006243 chemical reaction Methods 0.000 claims description 155
• 238000000034 method Methods 0.000 claims description 76
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 238000002360 preparation method Methods 0.000 claims description 19
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 17
• 208000008589 Obesity Diseases 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 150000001408 amides Chemical class 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 235000020824 obesity Nutrition 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 15
• 101710151321 Melanostatin Proteins 0.000 claims description 14
• 102100028427 Pro-neuropeptide Y Human genes 0.000 claims description 14
• 229960001243 orlistat Drugs 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
• 238000011321 prophylaxis Methods 0.000 claims description 13
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 10
• 206010003246 arthritis Diseases 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 201000006370 kidney failure Diseases 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 208000030814 Eating disease Diseases 0.000 claims description 8
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 235000014632 disordered eating Nutrition 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• OJBJPKNOXBHZGJ-UHFFFAOYSA-N 2-chloro-n-[3-[[4-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C1=CSC(NCCCNS(=O)(=O)C=2C(=CC=C(C=2)C(F)(F)F)Cl)=N1 OJBJPKNOXBHZGJ-UHFFFAOYSA-N 0.000 claims description 6
• JFZKIMSEVKSNHD-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[3-[[4-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]benzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCNC1=NC(C(=O)C=2C(=CC=CC=2)C)=CS1 JFZKIMSEVKSNHD-UHFFFAOYSA-N 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• VSKXSADWIKAJOW-UHFFFAOYSA-N 2-chloro-n-[3-[[5-(2-chlorobenzoyl)-1,3-thiazol-2-yl]amino]propyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(S(=O)(=O)NCCCNC=2SC(=CN=2)C(=O)C=2C(=CC=CC=2)Cl)=C1 VSKXSADWIKAJOW-UHFFFAOYSA-N 0.000 claims description 5
• WSZRBYPVRMTROP-UHFFFAOYSA-N 2-chloro-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1Cl WSZRBYPVRMTROP-UHFFFAOYSA-N 0.000 claims description 5
• DOAQWUHLLDBVCS-UHFFFAOYSA-N 2-chloro-n-[5-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]pentyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCCCNS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1Cl DOAQWUHLLDBVCS-UHFFFAOYSA-N 0.000 claims description 5
• BFGZPYGHAVNFFS-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]benzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)C)S1 BFGZPYGHAVNFFS-UHFFFAOYSA-N 0.000 claims description 5
• LNHWQOKFWISJLR-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[5-[[4-methyl-5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]pentyl]benzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCCCNC1=NC(C)=C(C(=O)C=2C(=CC=CC=2)C)S1 LNHWQOKFWISJLR-UHFFFAOYSA-N 0.000 claims description 5
• SEZOMSCCWVONAJ-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[5-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]pentyl]benzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)C)S1 SEZOMSCCWVONAJ-UHFFFAOYSA-N 0.000 claims description 5
• AKHLFPVCUFCQSQ-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[5-[[5-(pyridine-2-carbonyl)-1,3-thiazol-2-yl]amino]pentyl]benzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2N=CC=CC=2)S1 AKHLFPVCUFCQSQ-UHFFFAOYSA-N 0.000 claims description 5
• YSYAZDMYCKSANN-UHFFFAOYSA-N 4-methoxy-n-[5-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]pentyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)C)S1 YSYAZDMYCKSANN-UHFFFAOYSA-N 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
• YFZMRHFEVGODEE-UHFFFAOYSA-N n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]thiophene-2-sulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC=CS1 YFZMRHFEVGODEE-UHFFFAOYSA-N 0.000 claims description 5
• KYZCONUNJLEHBB-UHFFFAOYSA-N n-[5-[[5-(2-chlorobenzoyl)-1,3-thiazol-2-yl]amino]pentyl]-2-fluorobenzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)Cl)S1 KYZCONUNJLEHBB-UHFFFAOYSA-N 0.000 claims description 5
• KITOQPGNBHIXGH-UHFFFAOYSA-N n-[5-[[5-(2-chlorobenzoyl)-1,3-thiazol-2-yl]amino]pentyl]-2-methoxy-5-methylbenzenesulfonamide Chemical compound COC1=CC=C(C)C=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)Cl)S1 KITOQPGNBHIXGH-UHFFFAOYSA-N 0.000 claims description 5
• XJTXAAPTCQPFDF-UHFFFAOYSA-N n-[5-[[5-(2-chlorobenzoyl)-1,3-thiazol-2-yl]amino]pentyl]-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NCCCCCNC1=NC=C(C(=O)C=2C(=CC=CC=2)Cl)S1 XJTXAAPTCQPFDF-UHFFFAOYSA-N 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• WUMYVSGSTKZLKN-UHFFFAOYSA-N 2,5-dimethoxy-n-[4-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]butyl]benzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NCCCCNC=2SC(=CN=2)C(=O)C=2C(=CC=CC=2)C)=C1 WUMYVSGSTKZLKN-UHFFFAOYSA-N 0.000 claims description 4
• MOAWCMYHSCPOHS-UHFFFAOYSA-N 2-chloro-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl MOAWCMYHSCPOHS-UHFFFAOYSA-N 0.000 claims description 4
• HHBPUXHVLPSPRC-UHFFFAOYSA-N 4-chloro-n-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(C)CCCNC(S1)=NC=C1C(=O)C1=CC=CC=C1C HHBPUXHVLPSPRC-UHFFFAOYSA-N 0.000 claims description 4
• MWJPZYAHWVJURU-UHFFFAOYSA-N 5-fluoro-2-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC(F)=CC=C1C MWJPZYAHWVJURU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• AOMFSYVEJWWWOZ-UHFFFAOYSA-N n,2-dimethyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]benzenesulfonamide Chemical compound C=1C=CC=C(C)C=1S(=O)(=O)N(C)CCCNC(S1)=NC=C1C(=O)C1=CC=CC=C1C AOMFSYVEJWWWOZ-UHFFFAOYSA-N 0.000 claims description 4
• ZJACVTXUARJMKK-UHFFFAOYSA-N n-[3-[[5-(2-chlorobenzoyl)-1,3-thiazol-2-yl]amino]propyl]thiophene-2-sulfonamide Chemical compound ClC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC=CS1 ZJACVTXUARJMKK-UHFFFAOYSA-N 0.000 claims description 4
• WTDLBONHJHWXJS-UHFFFAOYSA-N n-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]-4-nitrobenzenesulfonamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1S(=O)(=O)N(C)CCCNC(S1)=NC=C1C(=O)C1=CC=CC=C1C WTDLBONHJHWXJS-UHFFFAOYSA-N 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 3
• KINDPLVJEGXZBU-UHFFFAOYSA-N 5-chloro-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]thiophene-2-sulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCNS(=O)(=O)C1=CC=C(Cl)S1 KINDPLVJEGXZBU-UHFFFAOYSA-N 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• CSNICAGFSAQDIK-UHFFFAOYSA-N n-[4-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]butyl]thiophene-2-sulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(S1)=CN=C1NCCCCNS(=O)(=O)C1=CC=CS1 CSNICAGFSAQDIK-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• QPKQMQKFALBADC-UHFFFAOYSA-N 5-chloro-n-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]thiophene-2-sulfonamide Chemical compound C=1C=C(Cl)SC=1S(=O)(=O)N(C)CCCNC(S1)=NC=C1C(=O)C1=CC=CC=C1C QPKQMQKFALBADC-UHFFFAOYSA-N 0.000 claims 1
• LMUWHAMXLLIQOX-UHFFFAOYSA-N n-methyl-n-[3-[[5-(2-methylbenzoyl)-1,3-thiazol-2-yl]amino]propyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C)CCCNC(S1)=NC=C1C(=O)C1=CC=CC=C1C LMUWHAMXLLIQOX-UHFFFAOYSA-N 0.000 claims 1
• 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 290
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
• 239000003153 chemical reaction reagent Substances 0.000 description 100
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• 239000002585 base Substances 0.000 description 59
• 239000000203 mixture Substances 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 53
• 239000002904 solvent Substances 0.000 description 53
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 43
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
• HLABGJLUTKJSBA-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CN=C(NCCCN)S1 HLABGJLUTKJSBA-UHFFFAOYSA-N 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
• 238000004458 analytical method Methods 0.000 description 29
• 239000000376 reactant Substances 0.000 description 28
• 239000000243 solution Substances 0.000 description 27
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• IRVLCEMGFDBWAF-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-(2-chlorophenyl)methanone Chemical compound S1C(NCCCN)=NC=C1C(=O)C1=CC=CC=C1Cl IRVLCEMGFDBWAF-UHFFFAOYSA-N 0.000 description 22
• 239000002253 acid Substances 0.000 description 22
• MWXYNRSDYAGUBL-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-(2-ethylphenyl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C1=CN=C(NCCCN)S1 MWXYNRSDYAGUBL-UHFFFAOYSA-N 0.000 description 21
• 125000000753 cycloalkyl group Chemical group 0.000 description 21
• ZMZRUMCPNAJPPN-UHFFFAOYSA-N tert-butyl n-[3-(dimethylaminomethylidenecarbamothioylamino)propyl]carbamate Chemical compound CN(C)C=NC(=S)NCCCNC(=O)OC(C)(C)C ZMZRUMCPNAJPPN-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 150000007979 thiazole derivatives Chemical class 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• NTMQRZKPLYIFMC-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-4-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CSC(NCCCN)=N1 NTMQRZKPLYIFMC-UHFFFAOYSA-N 0.000 description 18
• WUPWWMXYQFNPOB-UHFFFAOYSA-N [2-[3-(methylamino)propylamino]-1,3-thiazol-5-yl]-(2-methylphenyl)methanone Chemical compound S1C(NCCCNC)=NC=C1C(=O)C1=CC=CC=C1C WUPWWMXYQFNPOB-UHFFFAOYSA-N 0.000 description 18
• QXLPEATYACFYRX-UHFFFAOYSA-N [2-(2-aminobutylamino)-1,3-thiazol-5-yl]-(2-methylphenyl)methanone Chemical compound S1C(NCC(N)CC)=NC=C1C(=O)C1=CC=CC=C1C QXLPEATYACFYRX-UHFFFAOYSA-N 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000010438 heat treatment Methods 0.000 description 15
• 229940124530 sulfonamide Drugs 0.000 description 15
• 150000003456 sulfonamides Chemical class 0.000 description 15
• KDRUKMQPSTVING-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-(4-methylpyridin-3-yl)methanone Chemical compound CC1=CC=NC=C1C(=O)C1=CN=C(NCCCN)S1 KDRUKMQPSTVING-UHFFFAOYSA-N 0.000 description 14
• 230000002411 adverse Effects 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• NIOKEQAGNVAFRY-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound S1C(NCCCN)=NC=C1C(=O)C1=CC=CC=C1C(F)(F)F NIOKEQAGNVAFRY-UHFFFAOYSA-N 0.000 description 13
• 230000002829 reductive effect Effects 0.000 description 13
• 150000003672 ureas Chemical class 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• UULOZENNGZPQKV-UHFFFAOYSA-N [2-(5-aminopentylamino)-1,3-thiazol-5-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CN=C(NCCCCCN)S1 UULOZENNGZPQKV-UHFFFAOYSA-N 0.000 description 12
• LJERBHQAGPSVCE-UHFFFAOYSA-N [2-(5-aminopentylamino)-1,3-thiazol-5-yl]-pyridin-2-ylmethanone Chemical compound S1C(NCCCCCN)=NC=C1C(=O)C1=CC=CC=N1 LJERBHQAGPSVCE-UHFFFAOYSA-N 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
• 125000006239 protecting group Chemical group 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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