ZA200102869B - 2-ureido-thiazole derivatives, process for their preparation, and their use as antitumor agents. - Google Patents

Info

Publication number

ZA200102869B

ZA200102869B ZA200102869A ZA200102869A ZA200102869B ZA 200102869 B ZA200102869 B ZA 200102869B ZA 200102869 A ZA200102869 A ZA 200102869A ZA 200102869 A ZA200102869 A ZA 200102869A ZA 200102869 B ZA200102869 B ZA 200102869B

Authority

ZA

South Africa

Prior art keywords

thiazol

urea

isopropyl

phenyl

amino

Prior art date

1998-10-30

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 46
• YTQDJZOARIHJGS-UHFFFAOYSA-N 1,3-thiazol-2-ylurea Chemical class NC(=O)NC1=NC=CS1 YTQDJZOARIHJGS-UHFFFAOYSA-N 0.000 title claims description 17
• 238000002360 preparation method Methods 0.000 title description 16
• 239000002246 antineoplastic agent Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 134
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 126
• 239000004202 carbamide Substances 0.000 claims description 95
• -1 trifluoromethylphenyl Chemical group 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 229910052799 carbon Inorganic materials 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 206010028980 Neoplasm Diseases 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Chemical group 0.000 claims description 11
• 208000035475 disorder Diseases 0.000 claims description 11
• 230000000694 effects Effects 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 230000005764 inhibitory process Effects 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 230000002062 proliferating effect Effects 0.000 claims description 11
• 108091000080 Phosphotransferase Proteins 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 102000020233 phosphotransferase Human genes 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 229920000642 polymer Polymers 0.000 claims description 9
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000001769 aryl amino group Chemical group 0.000 claims description 7
• 235000010233 benzoic acid Nutrition 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000005110 aryl thio group Chemical group 0.000 claims description 6
• 230000004663 cell proliferation Effects 0.000 claims description 6
• NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 201000009030 Carcinoma Diseases 0.000 claims description 5
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 230000036262 stenosis Effects 0.000 claims description 5
• 208000037804 stenosis Diseases 0.000 claims description 5
• 230000002792 vascular Effects 0.000 claims description 5
• CUDYXZOOORMACN-UHFFFAOYSA-N 1-phenyl-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC=CC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 CUDYXZOOORMACN-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 201000005787 hematologic cancer Diseases 0.000 claims description 4
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 210000001685 thyroid gland Anatomy 0.000 claims description 4
• WEYDYKHFODVPIK-UHFFFAOYSA-N (4-methoxyphenyl)methylurea Chemical compound COC1=CC=C(CNC(N)=O)C=C1 WEYDYKHFODVPIK-UHFFFAOYSA-N 0.000 claims description 3
• IXRIXDYRKUXVCS-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC2=CC=CC=C2S1 IXRIXDYRKUXVCS-UHFFFAOYSA-N 0.000 claims description 3
• ODTPBEJMYMHQBH-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CC=C1O ODTPBEJMYMHQBH-UHFFFAOYSA-N 0.000 claims description 3
• PQHTXYBCYAQVEF-UHFFFAOYSA-N 1-(3-aminophenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CC(N)=C1 PQHTXYBCYAQVEF-UHFFFAOYSA-N 0.000 claims description 3
• MGEPHWQYBZGHHX-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-(5-cyclopropyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC(Cl)=CC=1N(C(=O)N)C(S1)=NC=C1C1CC1 MGEPHWQYBZGHHX-UHFFFAOYSA-N 0.000 claims description 3
• DXRZITAMHWFERV-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=CC(O)=C1 DXRZITAMHWFERV-UHFFFAOYSA-N 0.000 claims description 3
• FFNFJMSVUQKCNO-UHFFFAOYSA-N 1-(3-nitrophenyl)-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC([N+]([O-])=O)=CC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 FFNFJMSVUQKCNO-UHFFFAOYSA-N 0.000 claims description 3
• RQTVRHSXYTZRLJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(5-cyclopropyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(Cl)C=CC=1N(C(=O)N)C(S1)=NC=C1C1CC1 RQTVRHSXYTZRLJ-UHFFFAOYSA-N 0.000 claims description 3
• IPBFBHGCUHKYSR-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OC)=CC=C1N(C(N)=O)C1=NC=C(C(C)C)S1 IPBFBHGCUHKYSR-UHFFFAOYSA-N 0.000 claims description 3
• KLPXFFUFLVYRSA-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-1-(4-sulfamoylphenyl)urea Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1N(C(=O)N)C1=NC=C(Br)S1 KLPXFFUFLVYRSA-UHFFFAOYSA-N 0.000 claims description 3
• KHLVFPANSYGLID-UHFFFAOYSA-N 1-(5-cyclopropyl-1,3-thiazol-2-yl)-1-phenylurea Chemical compound C=1C=CC=CC=1N(C(=O)N)C(S1)=NC=C1C1CC1 KHLVFPANSYGLID-UHFFFAOYSA-N 0.000 claims description 3
• AFXKKLAODPOSPX-UHFFFAOYSA-N 1-(5-phenyl-1,3-thiazol-2-yl)-1-pyridin-2-ylurea Chemical compound C=1C=CC=NC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 AFXKKLAODPOSPX-UHFFFAOYSA-N 0.000 claims description 3
• QOORKGHMGUEMNU-UHFFFAOYSA-N 1-(5-phenyl-1,3-thiazol-2-yl)-1-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 QOORKGHMGUEMNU-UHFFFAOYSA-N 0.000 claims description 3
• FXAYTGUHKGABFB-UHFFFAOYSA-N 1-(5-propan-2-yl-1,3-thiazol-2-yl)-1-pyridin-3-ylurea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CN=C1 FXAYTGUHKGABFB-UHFFFAOYSA-N 0.000 claims description 3
• OXPCYIHYVYCGEJ-UHFFFAOYSA-N 1-benzyl-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)CC1=CC=CC=C1 OXPCYIHYVYCGEJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 3
• 206010027476 Metastases Diseases 0.000 claims description 3
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 3
• 102100026379 Neurofibromin Human genes 0.000 claims description 3
• 201000010208 Seminoma Diseases 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000003325 follicular Effects 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
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• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
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• 201000008968 osteosarcoma Diseases 0.000 claims description 3
• 210000001428 peripheral nervous system Anatomy 0.000 claims description 3
• 208000015768 polyposis Diseases 0.000 claims description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
• 208000001608 teratocarcinoma Diseases 0.000 claims description 3
• 230000005747 tumor angiogenesis Effects 0.000 claims description 3
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
• HAQVOMUKHGSSMH-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-1-(5-cyclopropyl-1,3-thiazol-2-yl)urea Chemical compound C=1C2=CC=CC=C2SC=1N(C(=O)N)C(S1)=NC=C1C1CC1 HAQVOMUKHGSSMH-UHFFFAOYSA-N 0.000 claims description 2
• RNRQMZXYNUZUJX-UHFFFAOYSA-N 1-(1h-indol-6-yl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=C(C=CN2)C2=C1 RNRQMZXYNUZUJX-UHFFFAOYSA-N 0.000 claims description 2
• IIZYGNSELZATBT-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=C(C)C=C1C IIZYGNSELZATBT-UHFFFAOYSA-N 0.000 claims description 2
• XZSADQUEMHCPTJ-UHFFFAOYSA-N 1-(2-chlorophenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CC=C1Cl XZSADQUEMHCPTJ-UHFFFAOYSA-N 0.000 claims description 2
• JOAAOGSMFIFPOW-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=NC=C(C=2C=CC=CC=2)S1 JOAAOGSMFIFPOW-UHFFFAOYSA-N 0.000 claims description 2
• IJHLLNHALNCUKT-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound OC1=CC=CC=C1NC(=O)NC1=NC=C(C=2C=CC=CC=2)S1 IJHLLNHALNCUKT-UHFFFAOYSA-N 0.000 claims description 2
• WXJFELWNTUDKQQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=NC=C(C=2C=CC=CC=2)S1 WXJFELWNTUDKQQ-UHFFFAOYSA-N 0.000 claims description 2
• PRFSINOAXIWHMA-UHFFFAOYSA-N 1-(2-methyl-1,3-dioxoisoindol-5-yl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=C(C(=O)N(C)C2=O)C2=C1 PRFSINOAXIWHMA-UHFFFAOYSA-N 0.000 claims description 2
• GFLXMXAQYQLRRY-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=C(OC)C=C(C=C1)N(C(N)=O)C1=NC=C(S1)C(C)C GFLXMXAQYQLRRY-UHFFFAOYSA-N 0.000 claims description 2
• HKBOINYJYFEMIU-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC(C)=CC(C)=C1 HKBOINYJYFEMIU-UHFFFAOYSA-N 0.000 claims description 2
• GOLKGFGWNQQGRP-UHFFFAOYSA-N 1-(3-aminophenyl)-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC(N)=CC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 GOLKGFGWNQQGRP-UHFFFAOYSA-N 0.000 claims description 2
• RIMCHQXDRYKOHO-UHFFFAOYSA-N 1-(3-fluorophenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CC(F)=C1 RIMCHQXDRYKOHO-UHFFFAOYSA-N 0.000 claims description 2
• AJAGKYGHATZUFX-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound OC1=CC=CC(NC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)=C1 AJAGKYGHATZUFX-UHFFFAOYSA-N 0.000 claims description 2
• PTECRYPEILTWRD-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)=C1 PTECRYPEILTWRD-UHFFFAOYSA-N 0.000 claims description 2
• RFCSBRAZZVIUAY-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2SC(=CN=2)C(C)C)=C1 RFCSBRAZZVIUAY-UHFFFAOYSA-N 0.000 claims description 2
• AMLBLIVGHLZAGB-UHFFFAOYSA-N 1-(3-nitrophenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=CC([N+]([O-])=O)=C1 AMLBLIVGHLZAGB-UHFFFAOYSA-N 0.000 claims description 2
• JZPQKNPUZAZXOF-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=C(NC=N2)C2=C1 JZPQKNPUZAZXOF-UHFFFAOYSA-N 0.000 claims description 2
• QCTULOZMDIFQOP-UHFFFAOYSA-N 1-(4-aminophenyl)-1-(5-cyclopropyl-1,3-thiazol-2-yl)urea Chemical compound NC(=O)N(C1=NC=C(S1)C1CC1)C1=CC=C(N)C=C1 QCTULOZMDIFQOP-UHFFFAOYSA-N 0.000 claims description 2
• FSQYZONMAFCZTR-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(Cl)C=CC=1N(C(=O)N)C(S1)=NC=C1C1=CC=CC=C1 FSQYZONMAFCZTR-UHFFFAOYSA-N 0.000 claims description 2
• JKVMQUUKYDWYQS-UHFFFAOYSA-N 1-(4-cyanophenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C1=CC=C(C#N)C=C1 JKVMQUUKYDWYQS-UHFFFAOYSA-N 0.000 claims description 2
• QPPDWRQBVWCCPE-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=NC=C(C=2C=CC=CC=2)S1 QPPDWRQBVWCCPE-UHFFFAOYSA-N 0.000 claims description 2
• KGRRAAAPLYYVLK-UHFFFAOYSA-N 1-(4-methylphenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=C(C)C=C1 KGRRAAAPLYYVLK-UHFFFAOYSA-N 0.000 claims description 2
• WXFNESHRRUNQNR-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-1-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(N(C(N)=O)C=2SC(Br)=CN=2)=C1 WXFNESHRRUNQNR-UHFFFAOYSA-N 0.000 claims description 2
• LSPHGORSSNAJRZ-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-1-pyridin-4-ylurea Chemical compound C=1C=NC=CC=1N(C(=O)N)C1=NC=C(Br)S1 LSPHGORSSNAJRZ-UHFFFAOYSA-N 0.000 claims description 2
• VFIXMTNPMMXRKC-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-3-(2-chlorophenyl)urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=NC=C(Br)S1 VFIXMTNPMMXRKC-UHFFFAOYSA-N 0.000 claims description 2
• SLVZJUAXVBGIJU-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=NC=C(Br)S1 SLVZJUAXVBGIJU-UHFFFAOYSA-N 0.000 claims description 2
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• VOCGTUUQPVZBDY-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-3-pyridin-3-ylurea Chemical compound S1C(Br)=CN=C1NC(=O)NC1=CC=CN=C1 VOCGTUUQPVZBDY-UHFFFAOYSA-N 0.000 claims description 2
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