ZA200201117B - Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. - Google Patents
Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. Download PDFInfo
- Publication number
- ZA200201117B ZA200201117B ZA200201117A ZA200201117A ZA200201117B ZA 200201117 B ZA200201117 B ZA 200201117B ZA 200201117 A ZA200201117 A ZA 200201117A ZA 200201117 A ZA200201117 A ZA 200201117A ZA 200201117 B ZA200201117 B ZA 200201117B
- Authority
- ZA
- South Africa
- Prior art keywords
- thiazol
- amino
- isopropyl
- oxoethyl
- acetamide
- Prior art date
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- 239000002246 antineoplastic agent Substances 0.000 title description 11
- -1 pyrrolidino, morpholino, piperazino Chemical group 0.000 claims description 142
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 138
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 102
- 229910052799 carbon Inorganic materials 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 16
- 102000016736 Cyclin Human genes 0.000 claims description 14
- 108050006400 Cyclin Proteins 0.000 claims description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 108091000080 Phosphotransferase Proteins 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 102000020233 phosphotransferase Human genes 0.000 claims description 10
- 230000002062 proliferating effect Effects 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 8
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 7
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 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 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000022131 cell cycle Effects 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- FSTRSZJZPLCPAX-UHFFFAOYSA-N 2-cyclopropyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC2CC2)=N1 FSTRSZJZPLCPAX-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- PPPBHWXGZXJZLF-UHFFFAOYSA-N n-(5-cyclopropyl-1,3-thiazol-2-yl)-2-[4-(dimethylamino)phenyl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)NC1=NC=C(C2CC2)S1 PPPBHWXGZXJZLF-UHFFFAOYSA-N 0.000 claims description 4
- SLEGSQHSICIILJ-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]-2-pyridin-3-ylacetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC=2C=NC=CC=2)=N1 SLEGSQHSICIILJ-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 230000036262 stenosis Effects 0.000 claims description 4
- 208000037804 stenosis Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 210000001685 thyroid gland Anatomy 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- FWDNBSRTVKBKBT-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]propanamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C(F)(F)C(F)(F)F)=N1 FWDNBSRTVKBKBT-UHFFFAOYSA-N 0.000 claims description 3
- MBYNYEYAXWXQQV-UHFFFAOYSA-N 2-[2-[(2-aminoacetyl)amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CN)=N1 MBYNYEYAXWXQQV-UHFFFAOYSA-N 0.000 claims description 3
- XEFKMYIIGXFLDW-UHFFFAOYSA-N 2-[2-[[2-(4-benzylpiperazin-1-yl)acetyl]amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CN2CCN(CC=3C=CC=CC=3)CC2)=N1 XEFKMYIIGXFLDW-UHFFFAOYSA-N 0.000 claims description 3
- JUYXRYAKOREOPH-UHFFFAOYSA-N 2-[2-[[2-(dimethylamino)acetyl]amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CN(C)C)=N1 JUYXRYAKOREOPH-UHFFFAOYSA-N 0.000 claims description 3
- ZEYSLZVCVAIGKV-UHFFFAOYSA-N 2-[4-[(2-methoxyacetyl)amino]phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound C1=CC(NC(=O)COC)=CC=C1CC(=O)NC1=NC=C(C(C)C)S1 ZEYSLZVCVAIGKV-UHFFFAOYSA-N 0.000 claims description 3
- PICNHPJFNQSDDN-UHFFFAOYSA-N 2-[4-[[2-(dimethylamino)-2-oxoethyl]amino]phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(NCC(=O)N(C)C)C=C1 PICNHPJFNQSDDN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 3
- DPVFQMSMVQLHFL-UHFFFAOYSA-N 2-chloro-2,2-difluoro-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(NC(=O)C(F)(F)Cl)C=C1 DPVFQMSMVQLHFL-UHFFFAOYSA-N 0.000 claims description 3
- UGMDPLFPVDXIKU-UHFFFAOYSA-N 2-cyano-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC#N)=N1 UGMDPLFPVDXIKU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- JJBBAUPEODHZSQ-UHFFFAOYSA-N 4-(dimethylamino)-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]benzamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=C(N(C)C)C=C1 JJBBAUPEODHZSQ-UHFFFAOYSA-N 0.000 claims description 3
- NUZDYTKXGWBRIE-UHFFFAOYSA-N 4-acetamido-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]benzamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=C(NC(C)=O)C=C1 NUZDYTKXGWBRIE-UHFFFAOYSA-N 0.000 claims description 3
- RMDJWTUKVUYSTH-UHFFFAOYSA-N 4-amino-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]butanamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CCCN)=N1 RMDJWTUKVUYSTH-UHFFFAOYSA-N 0.000 claims description 3
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 3
- LGEPXMXHJWNJLH-UHFFFAOYSA-N 4-hydroxy-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]butanamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CCCO)=N1 LGEPXMXHJWNJLH-UHFFFAOYSA-N 0.000 claims description 3
- OKBUQUMSRZIFKC-UHFFFAOYSA-N 5-methyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]pyrazine-2-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=2N=CC(C)=NC=2)=N1 OKBUQUMSRZIFKC-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 201000010208 Seminoma Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 229940127089 cytotoxic agent Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000003325 follicular Effects 0.000 claims description 3
- 201000005787 hematologic cancer Diseases 0.000 claims description 3
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- NODPGLXZZWPCLB-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-[2-[[2-(tetrazol-1-yl)acetyl]amino]-1,3-thiazol-4-yl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CN2N=NN=C2)=N1 NODPGLXZZWPCLB-UHFFFAOYSA-N 0.000 claims description 3
- LDLZLAXIZMHZPA-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-[4-[(2-thiophen-3-ylacetyl)amino]phenyl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)CC1=CSC=C1 LDLZLAXIZMHZPA-UHFFFAOYSA-N 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 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
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 208000001608 teratocarcinoma Diseases 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 230000005747 tumor angiogenesis Effects 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- RIKYCZGUVPYLAO-UHFFFAOYSA-N 1-acetyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]piperidine-4-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1CCN(C(C)=O)CC1 RIKYCZGUVPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- XIOYUHHRRBDMCO-UHFFFAOYSA-N 2-(2-acetamido-1,3-thiazol-4-yl)-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(C)=O)=N1 XIOYUHHRRBDMCO-UHFFFAOYSA-N 0.000 claims description 2
- TWBBOTXKVOUKMX-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(N2CCOCC2)C=C1 TWBBOTXKVOUKMX-UHFFFAOYSA-N 0.000 claims description 2
- IOHLVTZUFQWZJS-UHFFFAOYSA-N 2-[2-[(2-amino-2-oxoethyl)amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NCC(N)=O)=N1 IOHLVTZUFQWZJS-UHFFFAOYSA-N 0.000 claims description 2
- QCQWRTATHSYOGH-UHFFFAOYSA-N 2-[2-[(2-fluoroacetyl)amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CF)=N1 QCQWRTATHSYOGH-UHFFFAOYSA-N 0.000 claims description 2
- BOSRJMNRRJKWKC-UHFFFAOYSA-N 2-[2-[(2-methoxyacetyl)amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)COC)=NC(CC(=O)NC=2SC(=CN=2)C(C)C)=C1 BOSRJMNRRJKWKC-UHFFFAOYSA-N 0.000 claims description 2
- JQNYZDGLVPUFGS-UHFFFAOYSA-N 2-[2-[[2-(dimethylamino)-2-oxoethyl]amino]-1,3-thiazol-4-yl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NCC(=O)N(C)C)=N1 JQNYZDGLVPUFGS-UHFFFAOYSA-N 0.000 claims description 2
- VQMVANCXTQOOCP-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)CC1=CC=C(N(C)C)C=C1 VQMVANCXTQOOCP-UHFFFAOYSA-N 0.000 claims description 2
- OHEUFVNRSDNVBQ-UHFFFAOYSA-N 2-methoxy-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(OC)C(=O)NC(C=C1)=CC=C1CC(=O)NC1=NC=C(C(C)C)S1 OHEUFVNRSDNVBQ-UHFFFAOYSA-N 0.000 claims description 2
- OTDNZOGQKZNOHQ-UHFFFAOYSA-N 2-methyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]propanamide Chemical compound S1C(NC(=O)C(C)C)=NC(CC(=O)NC=2SC(=CN=2)C(C)C)=C1 OTDNZOGQKZNOHQ-UHFFFAOYSA-N 0.000 claims description 2
- UGDYPAHFZAZUBO-UHFFFAOYSA-N 2-oxo-2-[[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]amino]acetic acid Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C(O)=O)=N1 UGDYPAHFZAZUBO-UHFFFAOYSA-N 0.000 claims description 2
- DLMWGTVXJQJYBH-UHFFFAOYSA-N 3,3,3-trifluoro-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]propanamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(NC(=O)CC(F)(F)F)C=C1 DLMWGTVXJQJYBH-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- 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
- A61K31/426—1,3-Thiazoles
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Epidemiology (AREA)
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- Biomedical Technology (AREA)
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- Urology & Nephrology (AREA)
- Dermatology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Oncology (AREA)
- Cardiology (AREA)
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- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| US09/372,832 US6114365A (en) | 1999-08-12 | 1999-08-12 | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
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| ZA200201117B true ZA200201117B (en) | 2003-04-30 |
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| ZA200201117A ZA200201117B (en) | 1999-08-12 | 2002-02-08 | Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. |
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| BR (1) | BR0013281A (ru) |
| CA (1) | CA2381097C (ru) |
| CY (1) | CY1107108T1 (ru) |
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| ES (1) | ES2295056T3 (ru) |
| GE (1) | GEP20053475B (ru) |
| HK (1) | HK1054233B (ru) |
| HR (1) | HRP20020127B1 (ru) |
| HU (1) | HUP0202492A3 (ru) |
| IL (2) | IL147924A0 (ru) |
| IS (1) | IS2594B (ru) |
| MA (1) | MA25433A1 (ru) |
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| US20020150921A1 (en) * | 1996-02-09 | 2002-10-17 | Francis Barany | Detection of nucleic acid sequence differences using the ligase detection reaction with addressable arrays |
| US6407103B2 (en) | 1998-04-21 | 2002-06-18 | Bristol-Myers Squibb Pharma Company | Indeno [1,2-c] pyrazol-4-ones and their uses |
| US6320050B1 (en) * | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
| US6610846B1 (en) * | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| US7125875B2 (en) * | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| WO2000062778A1 (en) * | 1999-04-15 | 2000-10-26 | Bristol-Myers Squibb Co. | Cyclic protein tyrosine kinase inhibitors |
| US6114365A (en) | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| US20040048844A1 (en) * | 1999-10-20 | 2004-03-11 | Bristol-Myers Squibb Pharma Company | Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents |
| US6291504B1 (en) | 1999-10-20 | 2001-09-18 | Dupont Pharmaceuticals Company | Acylsemicarbazides and their uses |
| AU2002215053A1 (en) * | 2000-11-27 | 2002-06-24 | Pharmacia Italia S.P.A. | Phenylacetamido- pyrazole derivatives and their use as antitumor agents |
| WO2002044174A2 (en) * | 2000-12-01 | 2002-06-06 | Bristol-Myers Squibb Pharma Company | 3-(2,4-dimethylthiazol-5-yl) indeno[1,2-c]pyrazol-4-one derivatives as cdk inhibitors |
| US6849631B2 (en) | 2000-12-08 | 2005-02-01 | Bristol Myers Squibb Pharma Company | Semicarbazides and their uses |
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