SK4732001A3 - 2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents - Google Patents

2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents Download PDF

Info

Publication number: SK4732001A3
Authority: SK; Slovakia
Prior art keywords: thiazol; urea; isopropyl; phenyl; amino
Prior art date: 1998-10-30

Application number

SK473-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Paolo Pevarello

Raffaella Amici

Gabriella Traquandi

Manuela Villa

Anna Vulpetti

Antonella Isacchi

Original Assignee

Pharmacia & Upjohn Spa

Priority date (The priority date 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 date listed.)

1998-10-30

Filing date

1999-10-27

Publication date

2001-12-03

1999-10-27 Application filed by Pharmacia & Upjohn Spa filed Critical Pharmacia & Upjohn Spa

2001-12-03 Publication of SK4732001A3 publication Critical patent/SK4732001A3/sk

Links

238000002360 preparation method Methods 0.000 title claims description 28
238000000034 method Methods 0.000 title claims description 25
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title abstract 2
239000002246 antineoplastic agent Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 135
125000000217 alkyl group Chemical group 0.000 claims abstract description 59
125000003118 aryl group Chemical group 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 26
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 21
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
230000000694 effects Effects 0.000 claims abstract description 14
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 13
125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
108091000080 Phosphotransferase Proteins 0.000 claims abstract description 10
102000020233 phosphotransferase Human genes 0.000 claims abstract description 10
230000002062 proliferating effect Effects 0.000 claims abstract description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
-1 nitro, amino, substituted amino Chemical group 0.000 claims description 131
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 61
239000004202 carbamide Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 26
206010028980 Neoplasm Diseases 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 19
YTQDJZOARIHJGS-UHFFFAOYSA-N 1,3-thiazol-2-ylurea Chemical class NC(=O)NC1=NC=CS1 YTQDJZOARIHJGS-UHFFFAOYSA-N 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical group 0.000 claims description 15
210000004027 cell Anatomy 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 12
230000005764 inhibitory process Effects 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
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 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
229910052794 bromium Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000001769 aryl amino group Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000005110 aryl thio group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
210000000329 smooth muscle myocyte Anatomy 0.000 claims description 6
CNRKRRIACAOSRB-UHFFFAOYSA-N 3-[(5-propan-2-yl-1,3-thiazol-2-yl)carbamoylamino]benzoic acid Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=CC(C(O)=O)=C1 CNRKRRIACAOSRB-UHFFFAOYSA-N 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 5
208000031481 Pathologic Constriction Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
125000004104 aryloxy group Chemical group 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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
230000004663 cell proliferation Effects 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
230000002980 postoperative effect Effects 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
MIIUOQTXCFSCTJ-UHFFFAOYSA-N 1-(2-methoxyphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC=C1N(C(N)=O)C1=NC=C(C(C)C)S1 MIIUOQTXCFSCTJ-UHFFFAOYSA-N 0.000 claims description 4
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 4
YOUJCIXYCSRUGY-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(5-methyl-1,3-thiazol-2-yl)urea Chemical compound S1C(C)=CN=C1NC(=O)NC1=CC=C(F)C=C1 YOUJCIXYCSRUGY-UHFFFAOYSA-N 0.000 claims description 4
JJDOYZXRKIFULW-UHFFFAOYSA-N 1-(5-bromo-1,3-thiazol-2-yl)-3-phenylurea Chemical compound S1C(Br)=CN=C1NC(=O)NC1=CC=CC=C1 JJDOYZXRKIFULW-UHFFFAOYSA-N 0.000 claims description 4
ZLYRZKMHCYAWNC-UHFFFAOYSA-N 1-(5-methyl-1,3-thiazol-2-yl)-3-phenylurea Chemical compound S1C(C)=CN=C1NC(=O)NC1=CC=CC=C1 ZLYRZKMHCYAWNC-UHFFFAOYSA-N 0.000 claims description 4
PKOGEJUUQGCYAK-UHFFFAOYSA-N 1-phenyl-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=CC=C1 PKOGEJUUQGCYAK-UHFFFAOYSA-N 0.000 claims description 4
201000009030 Carcinoma Diseases 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000006501 nitrophenyl group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
XXBQLHATYQHJQC-UHFFFAOYSA-N 1,2-dihydroquinoxaline Chemical compound C1=CC=C2N=CCNC2=C1 XXBQLHATYQHJQC-UHFFFAOYSA-N 0.000 claims description 3
BZOJQPULWSWMQO-UHFFFAOYSA-N 1-(1-oxo-2,3-dihydroinden-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)CC2)C2=C1 BZOJQPULWSWMQO-UHFFFAOYSA-N 0.000 claims description 3
SJGMIHUMEXKSOV-UHFFFAOYSA-N 1-(1h-indazol-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=NN2)C2=C1 SJGMIHUMEXKSOV-UHFFFAOYSA-N 0.000 claims description 3
BOZUJVGGARBPSX-UHFFFAOYSA-N 1-(1h-indol-6-yl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=C(C=CN2)C2=C1 BOZUJVGGARBPSX-UHFFFAOYSA-N 0.000 claims description 3
PPZZUNWQMFHEJL-UHFFFAOYSA-N 1-(2-methoxy-4-phenylphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC(C=2C=CC=CC=2)=CC=C1N(C(N)=O)C1=NC=C(C(C)C)S1 PPZZUNWQMFHEJL-UHFFFAOYSA-N 0.000 claims description 3
RMLQEVRTONQCAG-UHFFFAOYSA-N 1-(2-methoxyphenyl)-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC=C1N(C(N)=O)C1=NC=C(C=2C=CC=CC=2)S1 RMLQEVRTONQCAG-UHFFFAOYSA-N 0.000 claims description 3
AAYFECGTTOZUJL-UHFFFAOYSA-N 1-(2-methyl-5-phenylpyrazol-3-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=2C=CC=CC=2)=NN1C AAYFECGTTOZUJL-UHFFFAOYSA-N 0.000 claims description 3
CJGOXPFEJROODW-UHFFFAOYSA-N 1-(2-methylquinolin-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(N=C(C)C=C2)C2=C1 CJGOXPFEJROODW-UHFFFAOYSA-N 0.000 claims description 3
HWCODOIWKMUZQZ-UHFFFAOYSA-N 1-(2-morpholin-4-ylphenyl)-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=C1N1CCOCC1 HWCODOIWKMUZQZ-UHFFFAOYSA-N 0.000 claims description 3
NVAHSTHGJIALQU-UHFFFAOYSA-N 1-(2-phenylphenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 NVAHSTHGJIALQU-UHFFFAOYSA-N 0.000 claims description 3
GPBWFWGZOFREGO-UHFFFAOYSA-N 1-(3-ethynylphenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=CC(C#C)=C1 GPBWFWGZOFREGO-UHFFFAOYSA-N 0.000 claims description 3
KXTHRUUXCZBWOO-UHFFFAOYSA-N 1-(3-methoxyphenyl)-1-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC(N(C(N)=O)C=2SC(=CN=2)C=2C=CC=CC=2)=C1 KXTHRUUXCZBWOO-UHFFFAOYSA-N 0.000 claims description 3
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 3
IRSIMXOWOOOURS-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=CC=C(F)C=C1 IRSIMXOWOOOURS-UHFFFAOYSA-N 0.000 claims description 3
QSMATKRKEUTYIE-UHFFFAOYSA-N 1-(4-imidazo[1,2-a]pyridin-2-ylphenyl)-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=2N=C3C=CC=CN3C=2)C=C1 QSMATKRKEUTYIE-UHFFFAOYSA-N 0.000 claims description 3
ARPKRUGLZXKWIS-UHFFFAOYSA-N 1-(4-phenoxyphenyl)-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)C(C=C1)=CC=C1OC1=CC=CC=C1 ARPKRUGLZXKWIS-UHFFFAOYSA-N 0.000 claims description 3
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 3
WJTJFTYBSXSATJ-UHFFFAOYSA-N 1-(5-methyl-1,3-thiazol-2-yl)-1-(5-oxo-1,2-dihydropyrazol-3-yl)urea Chemical compound Cc1cnc(s1)N(C(N)=O)c1cc(O)[nH]n1 WJTJFTYBSXSATJ-UHFFFAOYSA-N 0.000 claims description 3
JDEUGJVXDYIFJI-UHFFFAOYSA-N 1-(5-methyl-1,3-thiazol-2-yl)-1-pyridin-3-ylurea Chemical compound S1C(C)=CN=C1N(C(N)=O)C1=CC=CN=C1 JDEUGJVXDYIFJI-UHFFFAOYSA-N 0.000 claims description 3
PNOSONOEWDJCGG-UHFFFAOYSA-N 1-(5-oxo-7,8-dihydro-6H-naphthalen-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=CC=C(C(=O)CCC2)C2=C1 PNOSONOEWDJCGG-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
NGFVWMBYVGHEDU-UHFFFAOYSA-N 1-(5-phenyl-1h-pyrazol-3-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=2C=CC=CC=2)=NN1 NGFVWMBYVGHEDU-UHFFFAOYSA-N 0.000 claims description 3
LYYFJNMGCAEMAV-UHFFFAOYSA-N 1-(5-propan-2-yl-1,3-thiazol-2-yl)-1-(pyridin-3-ylmethyl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)CC1=CC=CN=C1 LYYFJNMGCAEMAV-UHFFFAOYSA-N 0.000 claims description 3
CHWQPKNZZDQGEG-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NCC1=CC=CO1 CHWQPKNZZDQGEG-UHFFFAOYSA-N 0.000 claims description 3
DXMLMYOLEZJTPJ-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-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=C1Cl DXMLMYOLEZJTPJ-UHFFFAOYSA-N 0.000 claims description 3
AZQNQVVNBIRPIA-UHFFFAOYSA-N 1-[(2-methoxyphenyl)methyl]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC=CC=C1CNC(=O)NC1=NC=C(C(C)C)S1 AZQNQVVNBIRPIA-UHFFFAOYSA-N 0.000 claims description 3
BCCFVEQHDFIOMO-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1N(C(N)=O)CC1=CC=C(Cl)C(Cl)=C1 BCCFVEQHDFIOMO-UHFFFAOYSA-N 0.000 claims description 3
WMYPLTFSIWKREX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=O)NC1=NC=C(C(C)C)S1 WMYPLTFSIWKREX-UHFFFAOYSA-N 0.000 claims description 3
DXHYYHPHWPHDOI-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-1-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound COC1=CC(OC)=CC(CN(C(N)=O)C=2SC(=CN=2)C(C)C)=C1 DXHYYHPHWPHDOI-UHFFFAOYSA-N 0.000 claims description 3
ZGTPUYIFHNMRFP-UHFFFAOYSA-N 1-[3-(3-hydroxybut-1-ynyl)phenyl]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound CC(O)C#CC1=CC=CC(NC(=O)NC=2SC(=CN=2)C(C)C)=C1 ZGTPUYIFHNMRFP-UHFFFAOYSA-N 0.000 claims description 3
ANYRBLCKQZNCAH-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3-ethyl-1,2-oxazol-5-yl]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(Cl)C=CC=1C=1C(CC)=NOC=1NC(=O)NC1=NC=C(C(C)C)S1 ANYRBLCKQZNCAH-UHFFFAOYSA-N 0.000 claims description 3
SODPJCVXXRAYPK-UHFFFAOYSA-N 1-[4-[ethyl(propan-2-yl)amino]phenyl]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(N(C(C)C)CC)=CC=C1NC(=O)NC1=NC=C(C(C)C)S1 SODPJCVXXRAYPK-UHFFFAOYSA-N 0.000 claims description 3
PNUGLMFUYSBJSN-GFCCVEGCSA-N 1-[[(2R)-2-amino-2-phenylacetyl]amino]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C(C)(C)C1=CN=C(S1)NC(=O)NNC([C@H](N)C1=CC=CC=C1)=O PNUGLMFUYSBJSN-GFCCVEGCSA-N 0.000 claims description 3
PNUGLMFUYSBJSN-LBPRGKRZSA-N 1-[[(2S)-2-amino-2-phenylacetyl]amino]-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C(C)(C)C1=CN=C(S1)NC(=O)NNC([C@@H](N)C1=CC=CC=C1)=O PNUGLMFUYSBJSN-LBPRGKRZSA-N 0.000 claims description 3
JAAWNUHSLSEMIK-UHFFFAOYSA-N 1-benzyl-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound S1C(C(C)C)=CN=C1NC(=O)NCC1=CC=CC=C1 JAAWNUHSLSEMIK-UHFFFAOYSA-N 0.000 claims description 3
JIPLNIKAMDJGJC-UHFFFAOYSA-N 1-ethyl-1-phenyl-3-(5-propan-2-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC=CC=1N(CC)C(=O)NC1=NC=C(C(C)C)S1 JIPLNIKAMDJGJC-UHFFFAOYSA-N 0.000 claims description 3
JYPRMOWNNXGDET-UHFFFAOYSA-N 1-phenyl-3-(5-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC=CC=1NC(=O)NC(S1)=NC=C1C1=CC=CC=C1 JYPRMOWNNXGDET-UHFFFAOYSA-N 0.000 claims description 3
FWMGUFKJLIUQRO-UHFFFAOYSA-N 1-phenyl-5-[(5-propan-2-yl-1,3-thiazol-2-yl)carbamoylamino]pyrazole-4-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)NC1=C(C(N)=O)C=NN1C1=CC=CC=C1 FWMGUFKJLIUQRO-UHFFFAOYSA-N 0.000 claims description 3
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HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/426—1,3-Thiazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof

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SK473-2001A 1998-10-30 1999-10-27 2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents SK4732001A3 (en)

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Application Number	Priority Date	Filing Date	Title
GBGB9823871.0A GB9823871D0 (en)	1998-10-30	1998-10-30	2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents
PCT/EP1999/008306 WO2000026202A1 (en)	1998-10-30	1999-10-27	2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents

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SK4732001A3 true SK4732001A3 (en)	2001-12-03

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KR (1)	KR20010085977A (de)
CN (1)	CN1325389A (de)
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AT (1)	ATE294785T1 (de)
AU (2)	AU766193B2 (de)
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1998
- 1998-10-30 GB GBGB9823871.0A patent/GB9823871D0/en not_active Ceased
1999
- 1999-10-27 CA CA002347188A patent/CA2347188A1/en not_active Abandoned
- 1999-10-27 TW TW088118558A patent/TWI222447B/zh active
- 1999-10-27 CZ CZ20011414A patent/CZ20011414A3/cs unknown
- 1999-10-27 SK SK473-2001A patent/SK4732001A3/sk unknown
- 1999-10-27 US US09/807,962 patent/US7037929B1/en not_active Expired - Fee Related
- 1999-10-27 HU HU0104200A patent/HUP0104200A3/hu unknown
- 1999-10-27 NZ NZ510965A patent/NZ510965A/en unknown
- 1999-10-27 EP EP99955931A patent/EP1124810B9/de not_active Expired - Lifetime
- 1999-10-27 JP JP2000579591A patent/JP2002528537A/ja active Pending
- 1999-10-27 WO PCT/EP1999/008306 patent/WO2000026202A1/en not_active Ceased
- 1999-10-27 AT AT99955931T patent/ATE294785T1/de not_active IP Right Cessation
- 1999-10-27 DE DE69925145T patent/DE69925145T2/de not_active Expired - Fee Related
- 1999-10-27 HK HK02102811.1A patent/HK1041261A1/zh unknown
- 1999-10-27 CN CN99812926A patent/CN1325389A/zh active Pending
- 1999-10-27 AU AU12679/00A patent/AU766193B2/en not_active Ceased
- 1999-10-27 ID IDW00200101146A patent/ID28623A/id unknown
- 1999-10-27 MX MXPA01004278A patent/MXPA01004278A/es unknown
- 1999-10-27 EA EA200100487A patent/EA005575B1/ru not_active IP Right Cessation
- 1999-10-27 IL IL14237199A patent/IL142371A0/xx unknown
- 1999-10-27 PL PL99347505A patent/PL347505A1/xx not_active Application Discontinuation
- 1999-10-27 KR KR1020017005374A patent/KR20010085977A/ko not_active Ceased
- 1999-10-27 ES ES99955931T patent/ES2241338T3/es not_active Expired - Lifetime
- 1999-10-27 PT PT99955931T patent/PT1124810E/pt unknown
- 1999-10-29 AR ARP990105474A patent/AR025276A1/es unknown
2001
- 2001-04-06 ZA ZA200102870A patent/ZA200102870B/en unknown
- 2001-04-26 NO NO20012057A patent/NO20012057L/no not_active Application Discontinuation
2004
- 2004-01-09 AU AU2004200096A patent/AU2004200096A1/en not_active Abandoned

Also Published As

Publication number	Publication date
ATE294785T1 (de)	2005-05-15
EA005575B1 (ru)	2005-04-28
HK1041261A1 (zh)	2002-07-05
HUP0104200A3 (en)	2003-12-29
NZ510965A (en)	2003-10-31
CZ20011414A3 (cs)	2001-09-12
NO20012057L (no)	2001-06-28
AU766193B2 (en)	2003-10-09
EA200100487A1 (ru)	2001-10-22
AR025276A1 (es)	2002-11-20
CA2347188A1 (en)	2000-05-11
NO20012057D0 (no)	2001-04-26
PT1124810E (pt)	2005-09-30
DE69925145D1 (de)	2005-06-09
AU1267900A (en)	2000-05-22
EP1124810B1 (de)	2005-05-04
HUP0104200A2 (hu)	2002-03-28
IL142371A0 (en)	2002-03-10
MXPA01004278A (es)	2002-06-21
DE69925145T2 (de)	2006-02-16
AU2004200096A1 (en)	2004-02-05
GB9823871D0 (en)	1998-12-23
TWI222447B (en)	2004-10-21
ES2241338T3 (es)	2005-10-16
PL347505A1 (en)	2002-04-08
CN1325389A (zh)	2001-12-05
ZA200102870B (en)	2001-10-10
ID28623A (id)	2001-06-21
EP1124810A1 (de)	2001-08-22
EP1124810B9 (de)	2005-12-28
KR20010085977A (ko)	2001-09-07
US7037929B1 (en)	2006-05-02
JP2002528537A (ja)	2002-09-03
WO2000026202A1 (en)	2000-05-11

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