ZA200201117B - Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. - Google Patents

Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. Download PDF

Info

Publication number: ZA200201117B
Authority: ZA; South Africa
Prior art keywords: thiazol; amino; isopropyl; oxoethyl; acetamide
Prior art date: 1999-08-12

Application number

ZA200201117A

Other languages

English (en)

Inventor

Paolo Pevarello

Raffaella Amici

Manuela Villa

Barbara Salom

Anna Vulpetti

Mario Varasi

Original Assignee

Pharmacia Italia 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.)

1999-08-12

Filing date

2002-02-08

Publication date

2003-04-30

2002-02-08 Application filed by Pharmacia Italia Spa filed Critical Pharmacia Italia Spa

2003-04-30 Publication of ZA200201117B publication Critical patent/ZA200201117B/en

Links

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
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
GXYHQGLODNFTKO-UHFFFAOYSA-N 4-chloro-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)CCCCl)=N1 GXYHQGLODNFTKO-UHFFFAOYSA-N 0.000 claims description 2
LFAYBYGNEDFHQW-UHFFFAOYSA-N 5-methyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]pyrazine-2-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CN=C(C)C=N1 LFAYBYGNEDFHQW-UHFFFAOYSA-N 0.000 claims description 2
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 2
238000009104 chemotherapy regimen Methods 0.000 claims description 2
239000000824 cytostatic agent Substances 0.000 claims description 2
230000001085 cytostatic effect Effects 0.000 claims description 2
239000002254 cytotoxic agent Substances 0.000 claims description 2
231100000599 cytotoxic agent Toxicity 0.000 claims description 2
NWOQJIFMPAVIGL-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-[4-[[2-(5-pyrrolidin-1-yltetrazol-2-yl)acetyl]amino]phenyl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)CN1N=C(N2CCCC2)N=N1 NWOQJIFMPAVIGL-UHFFFAOYSA-N 0.000 claims description 2
TUEBNBSMPGNJLA-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]-2-phenylacetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC=2C=CC=CC=2)=N1 TUEBNBSMPGNJLA-UHFFFAOYSA-N 0.000 claims description 2
BESUAPFNSYBSBZ-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-yl-1,3-thiazole-4-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=2N=C(SC=2)C=2C=NC=CC=2)=N1 BESUAPFNSYBSBZ-UHFFFAOYSA-N 0.000 claims description 2
SHKCCIFLPKKQOC-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]-2-thiophen-3-ylacetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC2=CSC=C2)=N1 SHKCCIFLPKKQOC-UHFFFAOYSA-N 0.000 claims description 2
BYEFXUBTPUCHGJ-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]-1,3-benzodioxole-5-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=C(OCO2)C2=C1 BYEFXUBTPUCHGJ-UHFFFAOYSA-N 0.000 claims description 2
NVQLZWSVSALKDT-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]-4-sulfamoylbenzamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=C(S(N)(=O)=O)C=C1 NVQLZWSVSALKDT-UHFFFAOYSA-N 0.000 claims description 2
SAZHRJACGHUGTH-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]pyridine-3-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 SAZHRJACGHUGTH-UHFFFAOYSA-N 0.000 claims description 2
238000001959 radiotherapy Methods 0.000 claims description 2
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
CLLKUSBHYXKXON-UHFFFAOYSA-N 2-(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=CC=C1N(C)C CLLKUSBHYXKXON-UHFFFAOYSA-N 0.000 claims 2
OTPSCVPEDTYBCE-UHFFFAOYSA-N 2-[2-[[2-(4-methylpiperazin-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(C)CC2)=N1 OTPSCVPEDTYBCE-UHFFFAOYSA-N 0.000 claims 2
WQXGKNUCDHRSAQ-UHFFFAOYSA-N 2-[4-(2,3-dihydroxypropylamino)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)CO)C=C1 WQXGKNUCDHRSAQ-UHFFFAOYSA-N 0.000 claims 2
XBJQOYPQHPMEPL-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-[5-[3-hydroxypropyl(methyl)amino]-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)NC1=NC=C(N(C)CCCO)S1 XBJQOYPQHPMEPL-UHFFFAOYSA-N 0.000 claims 2
DJYPNPCYARISTG-UHFFFAOYSA-N 2-cyano-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)CC#N)C=C1 DJYPNPCYARISTG-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
VDJJBLJFDQPLKF-UHFFFAOYSA-N 3-oxo-3-[[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]amino]propanoic acid Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CC(O)=O)=N1 VDJJBLJFDQPLKF-UHFFFAOYSA-N 0.000 claims 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
150000001412 amines Chemical class 0.000 claims 2
BMJVLRNFMGJTRE-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-[4-[(2-pyridin-3-ylacetyl)amino]phenyl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)CC1=CC=CN=C1 BMJVLRNFMGJTRE-UHFFFAOYSA-N 0.000 claims 2
JBYGGSZCLRLNKB-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]naphthalene-2-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=2C=C3C=CC=CC3=CC=2)=N1 JBYGGSZCLRLNKB-UHFFFAOYSA-N 0.000 claims 2
ZNWCWVAIMNMSSR-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]-2-phenylacetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 ZNWCWVAIMNMSSR-UHFFFAOYSA-N 0.000 claims 2
LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims 1
JUDSXZMOCRCDQM-UHFFFAOYSA-N 1-acetyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]piperidine-4-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C2CCN(CC2)C(C)=O)=N1 JUDSXZMOCRCDQM-UHFFFAOYSA-N 0.000 claims 1
YAQLZSRHHAKUCT-UHFFFAOYSA-N 2-[2-(1-adamantylamino)-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(NC23CC4CC(CC(C4)C2)C3)=N1 YAQLZSRHHAKUCT-UHFFFAOYSA-N 0.000 claims 1
CAYASCWRJUMQAO-UHFFFAOYSA-N 2-[2-[2,3-dihydroxypropyl(methyl)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(N(C)CC(O)CO)=N1 CAYASCWRJUMQAO-UHFFFAOYSA-N 0.000 claims 1
PPDKMURWPGYQSR-UHFFFAOYSA-N 2-[2-[methyl(2-morpholin-4-ylethyl)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(N(C)CCN2CCOCC2)=N1 PPDKMURWPGYQSR-UHFFFAOYSA-N 0.000 claims 1
OZEYLCOZWGLMSY-UHFFFAOYSA-N 2-[2-[methyl-[2-(4-methylpiperazin-1-yl)ethyl]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(N(C)CCN2CCN(C)CC2)=N1 OZEYLCOZWGLMSY-UHFFFAOYSA-N 0.000 claims 1
XGKFCSOSNIHLTI-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethylamino)phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NCCN1CCOCC1 XGKFCSOSNIHLTI-UHFFFAOYSA-N 0.000 claims 1
FDSHMEHEPHAUDA-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(N2CCN(C)CC2)C=C1 FDSHMEHEPHAUDA-UHFFFAOYSA-N 0.000 claims 1
NLYJIEUTLYYNIT-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-[5-[2-hydroxyethyl(methyl)amino]-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)NC1=NC=C(N(C)CCO)S1 NLYJIEUTLYYNIT-UHFFFAOYSA-N 0.000 claims 1
BEXGHNAZEIPDFE-UHFFFAOYSA-N 2-[4-[(2-amino-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(N)=O)C=C1 BEXGHNAZEIPDFE-UHFFFAOYSA-N 0.000 claims 1
LSFUQQPNYGZMET-UHFFFAOYSA-N 2-[4-[2-(4-methylpiperazin-1-yl)ethylamino]phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NCCN1CCN(C)CC1 LSFUQQPNYGZMET-UHFFFAOYSA-N 0.000 claims 1
BCCWEQFYZCJLCE-UHFFFAOYSA-N 2-[4-[[3-(dimethylamino)-2-hydroxypropyl]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)CN(C)C)C=C1 BCCWEQFYZCJLCE-UHFFFAOYSA-N 0.000 claims 1
XPIHETDVVVKZJO-UHFFFAOYSA-N 2-[4-[methyl(2-morpholin-4-ylethyl)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(N(C)CCN2CCOCC2)C=C1 XPIHETDVVVKZJO-UHFFFAOYSA-N 0.000 claims 1
YSXVDFBVCIQDFG-UHFFFAOYSA-N 2-[4-[methyl-[2-(4-methylpiperazin-1-yl)ethyl]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(N(C)CCN2CCN(C)CC2)C=C1 YSXVDFBVCIQDFG-UHFFFAOYSA-N 0.000 claims 1
NKMGDWUXHNBHHQ-UHFFFAOYSA-N 3,3,3-trifluoro-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)CC(F)(F)F)=N1 NKMGDWUXHNBHHQ-UHFFFAOYSA-N 0.000 claims 1
IRYFRVCELZYNIX-UHFFFAOYSA-N 3,5-dimethyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]-1,2-oxazole-4-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=C(C)ON=C1C IRYFRVCELZYNIX-UHFFFAOYSA-N 0.000 claims 1
YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 claims 1
RXRXQDZXKBXOOY-UHFFFAOYSA-N 3-amino-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)CCN)=N1 RXRXQDZXKBXOOY-UHFFFAOYSA-N 0.000 claims 1
BJSJWNJISVOKHO-UHFFFAOYSA-N 3-cyclopentyl-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)CCC2CCCC2)=N1 BJSJWNJISVOKHO-UHFFFAOYSA-N 0.000 claims 1
206010016629 fibroma Diseases 0.000 claims 1
206010049444 fibromatosis Diseases 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
GELWITVTEPGVTJ-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-(4-pyrrolidin-1-ylphenyl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(N2CCCC2)C=C1 GELWITVTEPGVTJ-UHFFFAOYSA-N 0.000 claims 1
AMLGOMUQBFIHPF-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=2C=CC=CC=2)=N1 AMLGOMUQBFIHPF-UHFFFAOYSA-N 0.000 claims 1
XXCLMDJXKHKFTR-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]prop-2-ynamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C#C)=N1 XXCLMDJXKHKFTR-UHFFFAOYSA-N 0.000 claims 1
229960003966 nicotinamide Drugs 0.000 claims 1
235000005152 nicotinamide Nutrition 0.000 claims 1
239000011570 nicotinamide Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
230000008569 process Effects 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 11
210000004027 cell Anatomy 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
108010033040 Histones Proteins 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000003556 assay Methods 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000000758 substrate Substances 0.000 description 6
210000004881 tumor cell Anatomy 0.000 description 6
239000012267 brine Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
101150073031 cdk2 gene Proteins 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
102000002554 Cyclin A Human genes 0.000 description 4
108010068192 Cyclin A Proteins 0.000 description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000003480 eluent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
238000002821 scintillation proximity assay Methods 0.000 description 4
229960004793 sucrose Drugs 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
108091007914 CDKs Proteins 0.000 description 3
102000003903 Cyclin-dependent kinases Human genes 0.000 description 3
108090000266 Cyclin-dependent kinases Proteins 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
102000006947 Histones Human genes 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000004913 activation Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
239000011324 bead Substances 0.000 description 3
235000013681 dietary sucrose Nutrition 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
JZWQYKGTELBLNN-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound CC(C)C1=CN=C(NC(C)=O)S1 JZWQYKGTELBLNN-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
OYFBZCDKJQUZIV-UHFFFAOYSA-N 2,2,2-trifluoro-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)C(F)(F)F)=N1 OYFBZCDKJQUZIV-UHFFFAOYSA-N 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
OGMDTRHJYJLVSA-UHFFFAOYSA-N 2-(2-acetamido-1,3-thiazol-4-yl)-n-(5-cyclopropyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NC(CC(=O)NC=2SC(=CN=2)C2CC2)=C1 OGMDTRHJYJLVSA-UHFFFAOYSA-N 0.000 description 2
YOKXDVONORYEJY-UHFFFAOYSA-N 2-(2-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(N)=N1 YOKXDVONORYEJY-UHFFFAOYSA-N 0.000 description 2
BYNSJWRUWOHXIW-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(NC(C)=O)C=C1 BYNSJWRUWOHXIW-UHFFFAOYSA-N 0.000 description 2
AADAWDOLHIILDX-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-(5-propan-2-yl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CC=C(N(C)C)C=C1 AADAWDOLHIILDX-UHFFFAOYSA-N 0.000 description 2
YHZPKIWVMUJATI-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-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)CCC=2NC3=CC=CC=C3N=2)=N1 YHZPKIWVMUJATI-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
MENMPXBUKLPJKR-UHFFFAOYSA-N 5-propan-2-yl-1,3-thiazol-2-amine Chemical compound CC(C)C1=CN=C(N)S1 MENMPXBUKLPJKR-UHFFFAOYSA-N 0.000 description 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 2
239000012448 Lithium borohydride Substances 0.000 description 2
206010025323 Lymphomas Diseases 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
208000009905 Neurofibromatoses Diseases 0.000 description 2
102100026379 Neurofibromin Human genes 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
102000001253 Protein Kinase Human genes 0.000 description 2
102100029008 Putative HTLV-1-related endogenous sequence Human genes 0.000 description 2
230000018199 S phase Effects 0.000 description 2
206010039491 Sarcoma Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229940123237 Taxane Drugs 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
229940041181 antineoplastic drug Drugs 0.000 description 2
230000006907 apoptotic process Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000013058 crude material Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229960004679 doxorubicin Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
238000011068 loading method Methods 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
CZHDKSQROZLIFR-UHFFFAOYSA-N n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]prop-2-enamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=C)=N1 CZHDKSQROZLIFR-UHFFFAOYSA-N 0.000 description 2
201000004931 neurofibromatosis Diseases 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
229940080469 phosphocellulose Drugs 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000035755 proliferation Effects 0.000 description 2
108060006633 protein kinase Proteins 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
150000003385 sodium Chemical class 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 2
LIUBVAVJLWQKOY-UHFFFAOYSA-N tert-butyl n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)OC(C)(C)C)=N1 LIUBVAVJLWQKOY-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
KDYOFOADHRBRIZ-UHFFFAOYSA-N 2-(2-acetamido-1,3-thiazol-4-yl)-n-[5-[3-hydroxypropyl(methyl)amino]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(N(CCCO)C)=CN=C1NC(=O)CC1=CSC(NC(C)=O)=N1 KDYOFOADHRBRIZ-UHFFFAOYSA-N 0.000 description 1
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 description 1
ITXDTLFHXZMTLP-UHFFFAOYSA-N 2-[2-[(2-chloroacetyl)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)CCl)=N1 ITXDTLFHXZMTLP-UHFFFAOYSA-N 0.000 description 1
NFPQZYNWZIKULV-UHFFFAOYSA-N 2-[2-[(2-hydroxyacetyl)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)CO)=N1 NFPQZYNWZIKULV-UHFFFAOYSA-N 0.000 description 1
LNUBPLFRRHJPLI-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound CC(C)(C)OC(=O)NC1=NC(CC(O)=O)=CS1 LNUBPLFRRHJPLI-UHFFFAOYSA-N 0.000 description 1
UDNSSCBKEKACHB-UHFFFAOYSA-N 2-[2-[[3-(dimethylamino)-2-hydroxypropyl]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)CN(C)C)=N1 UDNSSCBKEKACHB-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
UYWUGUUZJIONBM-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-(5-nitro-1,3-thiazol-2-yl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)NC1=NC=C([N+]([O-])=O)S1 UYWUGUUZJIONBM-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
RQZWGJCYKAPJGI-UHFFFAOYSA-N 2-isocyanato-1,3-thiazol-4-amine Chemical class NC1=CSC(N=C=O)=N1 RQZWGJCYKAPJGI-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
NHFDRBXTEDBWCZ-ZROIWOOFSA-N 3-[2,4-dimethyl-5-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=CC=C3NC\2=O)=C1C NHFDRBXTEDBWCZ-ZROIWOOFSA-N 0.000 description 1
LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
NTHHUGMFBQYJNU-UHFFFAOYSA-N 3-hydroxy-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)CCO)=N1 NTHHUGMFBQYJNU-UHFFFAOYSA-N 0.000 description 1
ZPUJATOFKHLCJB-UHFFFAOYSA-N 3-methyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]but-2-enamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)C=C(C)C)=N1 ZPUJATOFKHLCJB-UHFFFAOYSA-N 0.000 description 1
AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
BXYAYILDSNLZLU-UHFFFAOYSA-N 5-cyclopropyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1C1CC1 BXYAYILDSNLZLU-UHFFFAOYSA-N 0.000 description 1
SJZVOJXSJJRVFY-UHFFFAOYSA-N 5-methyl-n-[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]phenyl]thiophene-2-carboxamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=C(C)S1 SJZVOJXSJJRVFY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010003571 Astrocytoma Diseases 0.000 description 1
208000003950 B-cell lymphoma Diseases 0.000 description 1
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
206010005003 Bladder cancer Diseases 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
101100439046 Caenorhabditis elegans cdk-2 gene Proteins 0.000 description 1
101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 description 1
101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
101150053721 Cdk5 gene Proteins 0.000 description 1
229940123587 Cell cycle inhibitor Drugs 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
102000002427 Cyclin B Human genes 0.000 description 1
108010068150 Cyclin B Proteins 0.000 description 1
102000003910 Cyclin D Human genes 0.000 description 1
108090000259 Cyclin D Proteins 0.000 description 1
102000003909 Cyclin E Human genes 0.000 description 1
108090000257 Cyclin E Proteins 0.000 description 1
102000000577 Cyclin-Dependent Kinase Inhibitor p27 Human genes 0.000 description 1
108010016777 Cyclin-Dependent Kinase Inhibitor p27 Proteins 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
102000001301 EGF receptor Human genes 0.000 description 1
108060006698 EGF receptor Proteins 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
201000008808 Fibrosarcoma Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
208000032612 Glial tumor Diseases 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
102000009465 Growth Factor Receptors Human genes 0.000 description 1
108010009202 Growth Factor Receptors Proteins 0.000 description 1
208000002250 Hematologic Neoplasms Diseases 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000021519 Hodgkin lymphoma Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102100037852 Insulin-like growth factor I Human genes 0.000 description 1
101150076933 KIP gene Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
108091054455 MAP kinase family Proteins 0.000 description 1
102000043136 MAP kinase family Human genes 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
101001055320 Myxine glutinosa Insulin-like growth factor Proteins 0.000 description 1
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
108091008606 PDGF receptors Proteins 0.000 description 1
108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
102000003923 Protein Kinase C Human genes 0.000 description 1
108090000315 Protein Kinase C Proteins 0.000 description 1
229940123924 Protein kinase C inhibitor Drugs 0.000 description 1
206010041067 Small cell lung cancer Diseases 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
108010090804 Streptavidin Proteins 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
206010042971 T-cell lymphoma Diseases 0.000 description 1
208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
102000004243 Tubulin Human genes 0.000 description 1
108090000704 Tubulin Proteins 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000033 alkoxyamino group Chemical group 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000004037 angiogenesis inhibitor Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940045799 anthracyclines and related substance Drugs 0.000 description 1
230000002942 anti-growth Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
238000011394 anticancer treatment Methods 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-O azanium;hydron;hydroxide Chemical compound [NH4+].O VHUUQVKOLVNVRT-UHFFFAOYSA-O 0.000 description 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
201000001531 bladder carcinoma Diseases 0.000 description 1
206010006007 bone sarcoma Diseases 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
229960000590 celecoxib Drugs 0.000 description 1
230000006369 cell cycle progression Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
238000004590 computer program Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
229940111134 coxibs Drugs 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
208000023965 endometrium neoplasm Diseases 0.000 description 1
229960001904 epirubicin Drugs 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
229960001842 estramustine Drugs 0.000 description 1
OILYEROQTRYBTF-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]amino]acetate Chemical compound S1C(NC(=O)C(=O)OCC)=NC(CC(=O)NC=2SC(=CN=2)C(C)C)=C1 OILYEROQTRYBTF-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
210000000232 gallbladder Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
230000003394 haemopoietic effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229940022353 herceptin Drugs 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229940125697 hormonal agent Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
239000000677 immunologic agent Substances 0.000 description 1
229940124541 immunological agent Drugs 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
201000005296 lung carcinoma Diseases 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
235000012254 magnesium hydroxide Nutrition 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000037353 metabolic pathway Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
230000031864 metaphase Effects 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
SCQBDADQAVXTMZ-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC1=NC=CS1 SCQBDADQAVXTMZ-UHFFFAOYSA-N 0.000 description 1
FGMNBHJNHMFEEO-UHFFFAOYSA-N n-(5-propan-2-yl-1,3-thiazol-2-yl)-2-[2-[(2-pyridin-4-ylsulfanylacetyl)amino]-1,3-thiazol-4-yl]acetamide Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CSC=2C=CN=CC=2)=N1 FGMNBHJNHMFEEO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
229940086322 navelbine Drugs 0.000 description 1
208000007538 neurilemmoma Diseases 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000001814 pectin Substances 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical compound NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000003881 protein kinase C inhibitor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
201000009410 rhabdomyosarcoma Diseases 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
208000000587 small cell lung carcinoma Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
102000009076 src-Family Kinases Human genes 0.000 description 1
108010087686 src-Family Kinases Proteins 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
102000013498 tau Proteins Human genes 0.000 description 1
108010026424 tau Proteins Proteins 0.000 description 1
239000003277 telomerase inhibitor Substances 0.000 description 1
SEAMSPZUVYLAGF-UHFFFAOYSA-N tert-butyl 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]ethyl]carbamate Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CNC(=O)OC(C)(C)C)=N1 SEAMSPZUVYLAGF-UHFFFAOYSA-N 0.000 description 1
DRWKBQLNDVZUHF-UHFFFAOYSA-N tert-butyl n-[3-oxo-3-[[4-[2-oxo-2-[(5-propan-2-yl-1,3-thiazol-2-yl)amino]ethyl]-1,3-thiazol-2-yl]amino]propyl]carbamate Chemical compound S1C(C(C)C)=CN=C1NC(=O)CC1=CSC(NC(=O)CCNC(=O)OC(C)(C)C)=N1 DRWKBQLNDVZUHF-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000003558 transferase inhibitor Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Immunology (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Communicable Diseases (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Pulmonology (AREA)
Psychiatry (AREA)
Virology (AREA)
Rheumatology (AREA)
Oncology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

ZA200201117A 1999-08-12 2002-02-08 Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents. ZA200201117B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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

Publications (1)

Publication Number	Publication Date
ZA200201117B true ZA200201117B (en)	2003-04-30

Family

ID=23469806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200201117A ZA200201117B (en)	1999-08-12	2002-02-08	Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents.

Country Status (36)

Country	Link
US (3)	US6114365A (no)
EP (1)	EP1204649B1 (no)
JP (1)	JP4864260B2 (no)
KR (2)	KR100773709B1 (no)
CN (1)	CN100410245C (no)
AP (1)	AP1853A (no)
AT (1)	ATE375987T1 (no)
AU (1)	AU782882B2 (no)
BG (1)	BG65484B1 (no)
BR (1)	BR0013281A (no)
CA (1)	CA2381097C (no)
CY (1)	CY1107108T1 (no)
CZ (1)	CZ303138B6 (no)
DE (1)	DE60036803T2 (no)
DK (1)	DK1204649T3 (no)
EA (1)	EA005375B1 (no)
EE (1)	EE04939B1 (no)
ES (1)	ES2295056T3 (no)
GE (1)	GEP20053475B (no)
HK (1)	HK1054233B (no)
HR (1)	HRP20020127B1 (no)
HU (1)	HUP0202492A3 (no)
IL (2)	IL147924A0 (no)
IS (1)	IS2594B (no)
MA (1)	MA25433A1 (no)
MX (1)	MXPA02001508A (no)
NO (1)	NO323576B1 (no)
NZ (1)	NZ517236A (no)
OA (1)	OA12047A (no)
PT (1)	PT1204649E (no)
RS (1)	RS50300B (no)
SI (1)	SI1204649T1 (no)
SK (1)	SK287373B6 (no)
UA (1)	UA72538C2 (no)
WO (1)	WO2001014353A1 (no)
ZA (1)	ZA200201117B (no)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US6610846B1 (en) *	1999-03-29	2003-08-26	Hoffman-La Roche Inc.	Heteroaromatic glucokinase activators
US6320050B1 (en) *	1999-03-29	2001-11-20	Hoffmann-La Roche Inc.	Heteroaromatic glucokinase activators
IL144910A0 (en)	1999-04-15	2002-06-30	Bristol Myers Squibb Co	Cyclic compounds and pharmaceutical compositions containing the same
US7125875B2 (en) *	1999-04-15	2006-10-24	Bristol-Myers Squibb Company	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
EP2266607A3 (en)	1999-10-01	2011-04-20	Immunogen, Inc.	Immunoconjugates for treating cancer
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
AU2002228692A1 (en) *	2000-12-01	2002-06-11	Bristol-Myers Squibb Pharma Company	3-(2,4-dimethylthiazol-5-yl) indeno(1,2-c)pyrazol-4-one derivatives as cdk inhibitors
CA2430376A1 (en)	2000-12-08	2002-06-13	David J. Carini	Semicarbazides and their uses as cyclin dependent kinase inhibitors
ATE318812T1 (de) *	2000-12-21	2006-03-15	Bristol Myers Squibb Co	Thiazolyl-inhibitoren von tyrosinkinasen der tec- familie
ES2254611T3 (es) *	2001-05-11	2006-06-16	Pfizer Products Inc.	Derivados de tiazol.
IL159570A0 (en) *	2001-07-19	2004-06-01	Pharmacia Italia Spa	Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents
EP1724270A3 (en)	2001-07-19	2007-01-03	Pfizer Italia S.r.l.	Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents
US7087768B2 (en) *	2001-09-27	2006-08-08	Equispharm Co., Ltd.	Fumagillol derivatives and preparing method thereof
WO2003055482A1 (en) *	2001-12-21	2003-07-10	Novo Nordisk A/S	Amide derivatives as gk activators
EP1531815B1 (en) *	2002-06-27	2014-09-24	Novo Nordisk A/S	Glucokinase activators
WO2004072070A1 (en) *	2003-02-12	2004-08-26	Pfizer Inc.	Antiproliferative 2-(sulfo-phenyl)-aminothiazole derivatives
EP1597256A1 (en) *	2003-02-21	2005-11-23	Pfizer Inc.	N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors
US20060229346A1 (en) *	2003-03-31	2006-10-12	Sucampo Ag	Method for treating vascular hyperpermeable disease
WO2005014591A1 (en) *	2003-07-15	2005-02-17	L'oreal	2-acylamino or 2-sulfonylamino-1, 3-thiazoles as couplers for the oxidation dyeing of keratin fibres
FR2857664B1 (fr) *	2003-07-15	2007-12-14	Oreal	Nouveaux derives thiazoles et utilisation de ces derives pour la teinture des fibres keratiniques
US7351727B2 (en) *	2003-09-02	2008-04-01	Bristol-Myers Squibb Company	Inhibitors of 15-lipoxygenase
US20050074424A1 (en) *	2003-10-03	2005-04-07	Lev Salnikov	Using polyion polymers with glucose infusion for a cancer selective chemotherapy compound and method
WO2005060956A1 (en) *	2003-12-12	2005-07-07	University Of Maryland, Baltimore	IMMUNOMODULATORY COMPOUNDS THAT TARGET AND INHIBIT THE pY+3 BINDING SITE OF TYROSENE KINASE p56 LCK SH2 DOMAIN
PT1723128E (pt) *	2004-01-06	2013-02-27	Novo Nordisk As	Heteroaril-ureias e o seu uso como activadores da glicoquinase
US20080146555A1 (en)	2004-06-18	2008-06-19	Gpc Biotech, Inc	Uses of Kinase Inhibitors and Compositions Thereof
EP1621539A1 (en) *	2004-07-27	2006-02-01	Aventis Pharma S.A.	Heterocycle -substituted cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors
EP1621536A1 (en) *	2004-07-27	2006-02-01	Aventis Pharma S.A.	Amino cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors
ES2401138T3 (es) *	2004-08-13	2013-04-17	Genentech, Inc.	Inhibidores basados en tiazol de enzimas que usan ATP
DE602004021404D1 (de)	2004-12-23	2009-07-16	Gpc Biotech Ag	Quadratsäurederivate mit antiproliferativer Wirkung
CN101208089A (zh) *	2005-06-03	2008-06-25	泽农医药公司	氨基噻唑衍生物作为人硬酯酰-CoA去饱和酶抑制剂
US7999114B2 (en) *	2005-07-08	2011-08-16	Novo Nordisk A/S	Dicycloalkylcarbamoyl ureas as glucokinase activators
US7884210B2 (en)	2005-07-14	2011-02-08	Novo Nordisk A/S	Ureido-thiazole glucokinase activators
EP1914234A1 (en) *	2006-10-16	2008-04-23	GPC Biotech Inc.	Pyrido[2,3-d]pyrimidines and their use as kinase inhibitors
WO2008084043A1 (en) *	2007-01-09	2008-07-17	Novo Nordisk A/S	Urea glucokinase activators
AU2008204530B2 (en)	2007-01-11	2013-08-01	Vtv Therapeutics Llc	Urea glucokinase activators
US8153792B2 (en) *	2007-02-13	2012-04-10	Ab Science	Process for the synthesis of 2-aminothiazole compounds as kinase inhibitors
US8450348B2 (en) *	2007-02-21	2013-05-28	Forma Tm, Llc	Derivatives of squaric acid with anti-proliferative activity
TWI437986B (zh) *	2008-01-31	2014-05-21	R Tech Ueno Ltd	噻唑衍生物及使用該衍生物作為ｖａｐ－１抑制劑之用途
US8232402B2 (en)	2008-03-12	2012-07-31	Link Medicine Corporation	Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications
EP2112150B1 (en)	2008-04-22	2013-10-16	Forma Therapeutics, Inc.	Improved raf inhibitors
EP2112152A1 (en)	2008-04-22	2009-10-28	GPC Biotech AG	Dihydropteridinones as Plk Inhibitors
WO2010057006A1 (en)	2008-11-13	2010-05-20	Link Medicine Corporation	Azaquinolinone derivatives and uses thereof
UA103918C2 (en) *	2009-03-02	2013-12-10	Айерем Элелси	N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators
AR075899A1 (es) *	2009-03-20	2011-05-04	Onyx Therapeutics Inc	Tripeptidos epoxicetonas cristalinos inhibidores de proteasa
EP2440556A1 (en) *	2009-06-10	2012-04-18	Vertex Pharmaceuticals Incorporated	Inhibitors of phosphatidylinositol 3-kinase
DE102009043260A1 (de) *	2009-09-28	2011-04-28	Merck Patent Gmbh	Pyridinyl-imidazolonderivate
EP2325185A1 (en)	2009-10-28	2011-05-25	GPC Biotech AG	Plk inhibitor
HU0900798D0 (en)	2009-12-21	2010-03-01	Vichem Chemie Kutato Kft	4-phenylamino-pyrimidine derivatives having protein kinase inhibitor activity
US8883793B2 (en)	2010-12-29	2014-11-11	Development Center For Biotechnology	Tubulin inhibitors and methods of using the same
RU2011122942A (ru)	2011-06-08	2012-12-20	Общество С Ограниченной Ответственностью "Асинэкс Медхим"	Новые ингибиторы киназ
CN103387551B (zh) *	2012-05-11	2015-05-20	中国人民解放军军事医学科学院毒物药物研究所	噻唑类化合物及其用途
PL2887943T3 (pl)	2012-08-23	2018-05-30	Virostatics Srl	Nowe 4,6-dipodstawione pochodne aminopirymidyny
KR102431257B1 (ko)	2016-04-11	2022-08-10	장피트	담즙정체성 및 섬유증 질환의 치료 방법
AU2018380132B2 (en)	2017-12-06	2023-11-09	Lin Bioscience, Inc.	Tubulin inhibitors
JP7184383B2 (ja) *	2018-02-01	2022-12-06	ザ・ユニバーシティ・オブ・シドニー	抗癌性化合物
CA3093025A1 (en)	2018-06-12	2019-12-19	Vtv Therapeutics Llc	Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs
EP3712127A1 (en)	2019-03-22	2020-09-23	Deutsches Krebsforschungszentrum	Novel inhibitors of histone deacetylase 10
WO2020193431A1 (en)	2019-03-22	2020-10-01	Deutsches Krebsforschungszentrum	Novel inhibitors of histone deacetylase 10
EP4104835A4 (en) *	2020-02-10	2024-05-01	Juntendo Educational Found	TYPE-2 RYANODINE RECEPTOR ACTIVITY INHIBITOR
CN115322208B (zh) *	2021-05-10	2023-04-11	中国药科大学	2-氨基噻唑类衍生物及其制备方法和医药用途
WO2023182780A1 (ko) *	2022-03-22	2023-09-28	오토텔릭바이오 주식회사	티아졸 유도체 화합물 및 이의 용도

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL125062C (no) *	1960-04-20
JPH1095777A (ja) *	1996-07-31	1998-04-14	Otsuka Pharmaceut Co Ltd	チアゾール誘導体
TW513418B (en) *	1996-07-31	2002-12-11	Otsuka Pharma Co Ltd	Thiazole derivatives, their production and use
US6794392B1 (en) *	1996-09-30	2004-09-21	Schering Aktiengesellschaft	Cell differentiation inducer
IL135574A0 (en) *	1997-10-27	2001-05-20	Agouron Pharma	Substituted 4-amino-thiazol-2-yl compounds as cdk inhibitors
US6040321A (en) *	1997-11-12	2000-03-21	Bristol-Myers Squibb Company	Aminothiazole inhibitors of cyclin dependent kinases
JP2002518380A (ja) *	1998-06-18	2002-06-25	ブリストル−マイヤーズスクイブカンパニー	サイクリン依存キナーゼの炭素置換アミノチアゾール抑制剤
GB9823871D0 (en) *	1998-10-30	1998-12-23	Pharmacia & Upjohn Spa	2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents
IL144910A0 (en) *	1999-04-15	2002-06-30	Bristol Myers Squibb Co	Cyclic compounds and pharmaceutical compositions containing the same
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
US6992081B2 (en) *	2000-03-23	2006-01-31	Elan Pharmaceuticals, Inc.	Compounds to treat Alzheimer's disease
SE0102440D0 (sv) *	2001-07-05	2001-07-05	Astrazeneca Ab	New compound
US6936629B2 (en) *	2001-12-21	2005-08-30	Virochem Pharma Inc.	Compounds and methods for the treatment or prevention of flavivirus infections
CA2514573A1 (en) *	2003-01-27	2004-08-12	Astellas Pharma Inc.	Thiazole derivatives and their use as vap-1 inhibitors

1999
- 1999-08-12 US US09/372,832 patent/US6114365A/en not_active Expired - Lifetime
2000
- 2000-08-11 KR KR1020027001844A patent/KR100773709B1/ko not_active IP Right Cessation
- 2000-08-11 EP EP00962760A patent/EP1204649B1/en not_active Expired - Lifetime
- 2000-08-11 DE DE60036803T patent/DE60036803T2/de not_active Expired - Lifetime
- 2000-08-11 US US10/048,474 patent/US6784198B1/en not_active Expired - Fee Related
- 2000-08-11 KR KR1020077014635A patent/KR100827563B1/ko not_active IP Right Cessation
- 2000-08-11 AU AU74400/00A patent/AU782882B2/en not_active Ceased
- 2000-08-11 IL IL14792400A patent/IL147924A0/xx active IP Right Grant
- 2000-08-11 ES ES00962760T patent/ES2295056T3/es not_active Expired - Lifetime
- 2000-08-11 CA CA002381097A patent/CA2381097C/en not_active Expired - Fee Related
- 2000-08-11 EA EA200200247A patent/EA005375B1/ru not_active IP Right Cessation
- 2000-08-11 CN CNB008127336A patent/CN100410245C/zh not_active Expired - Fee Related
- 2000-08-11 AP APAP/P/2002/002441A patent/AP1853A/en active
- 2000-08-11 WO PCT/IB2000/001423 patent/WO2001014353A1/en active IP Right Grant
- 2000-08-11 HU HU0202492A patent/HUP0202492A3/hu unknown
- 2000-08-11 PT PT00962760T patent/PT1204649E/pt unknown
- 2000-08-11 NZ NZ517236A patent/NZ517236A/en not_active IP Right Cessation
- 2000-08-11 RS YUP-97/02A patent/RS50300B/sr unknown
- 2000-08-11 MX MXPA02001508A patent/MXPA02001508A/es active IP Right Grant
- 2000-08-11 DK DK00962760T patent/DK1204649T3/da active
- 2000-08-11 OA OA1200200052A patent/OA12047A/en unknown
- 2000-08-11 EE EEP200200064A patent/EE04939B1/xx not_active IP Right Cessation
- 2000-08-11 BR BR0013281-0A patent/BR0013281A/pt not_active IP Right Cessation
- 2000-08-11 SI SI200030974T patent/SI1204649T1/sl unknown
- 2000-08-11 CZ CZ20020486A patent/CZ303138B6/cs not_active IP Right Cessation
- 2000-08-11 JP JP2001518441A patent/JP4864260B2/ja not_active Expired - Fee Related
- 2000-08-11 SK SK180-2002A patent/SK287373B6/sk not_active IP Right Cessation
- 2000-08-11 GE GE4757A patent/GEP20053475B/en unknown
- 2000-08-11 AT AT00962760T patent/ATE375987T1/de active
- 2000-11-08 UA UA2002031948A patent/UA72538C2/uk unknown
2002
- 2002-01-31 IL IL147924A patent/IL147924A/en not_active IP Right Cessation
- 2002-02-08 ZA ZA200201117A patent/ZA200201117B/en unknown
- 2002-02-11 NO NO20020683A patent/NO323576B1/no not_active IP Right Cessation
- 2002-02-11 IS IS6264A patent/IS2594B/is unknown
- 2002-02-12 HR HR20020127A patent/HRP20020127B1/xx not_active IP Right Cessation
- 2002-03-05 BG BG106481A patent/BG65484B1/bg unknown
- 2002-03-11 MA MA26547A patent/MA25433A1/fr unknown
2003
- 2003-09-11 HK HK03106484.7A patent/HK1054233B/zh not_active IP Right Cessation
2004
- 2004-07-29 US US10/902,326 patent/US20050004120A1/en not_active Abandoned
2007
- 2007-12-20 CY CY20071101629T patent/CY1107108T1/el unknown

Also Published As

Publication number	Publication date
HK1054233A1 (en)	2003-11-21
EA200200247A1 (ru)	2002-08-29
NO20020683D0 (no)	2002-02-11
DE60036803T2 (de)	2008-07-24
US6114365A (en)	2000-09-05
IL147924A (en)	2008-03-20
CY1107108T1 (el)	2012-10-24
ES2295056T3 (es)	2008-04-16
US20050004120A1 (en)	2005-01-06
YU9702A (sh)	2004-11-25
EE200200064A (et)	2003-04-15
AU7440000A (en)	2001-03-19
NZ517236A (en)	2004-11-26
JP2003507461A (ja)	2003-02-25
AP2002002441A0 (en)	2002-03-31
JP4864260B2 (ja)	2012-02-01
NO20020683L (no)	2002-04-10
IL147924A0 (en)	2002-08-14
MA25433A1 (fr)	2002-04-01
KR100773709B1 (ko)	2007-11-09
CN1425009A (zh)	2003-06-18
OA12047A (en)	2006-05-02
CA2381097A1 (en)	2001-03-01
IS6264A (is)	2002-02-11
DK1204649T3 (da)	2007-12-03
PT1204649E (pt)	2008-01-10
UA72538C2 (en)	2005-03-15
US6784198B1 (en)	2004-08-31
KR20020060159A (ko)	2002-07-16
GEP20053475B (en)	2005-03-25
CZ303138B6 (cs)	2012-04-25
KR100827563B1 (ko)	2008-05-07
HRP20020127B1 (en)	2010-08-31
BR0013281A (pt)	2002-06-18
EP1204649A1 (en)	2002-05-15
ATE375987T1 (de)	2007-11-15
BG106481A (en)	2002-09-30
HUP0202492A2 (hu)	2002-11-28
CA2381097C (en)	2009-06-16
HRP20020127A2 (en)	2003-04-30
EP1204649B1 (en)	2007-10-17
NO323576B1 (no)	2007-06-11
CN100410245C (zh)	2008-08-13
RS50300B (sr)	2009-09-08
MXPA02001508A (es)	2003-07-21
CZ2002486A3 (cs)	2002-11-13
DE60036803D1 (de)	2007-11-29
WO2001014353A1 (en)	2001-03-01
KR20070074003A (ko)	2007-07-10
HK1054233B (zh)	2009-05-29
AP1853A (en)	2008-05-29
HUP0202492A3 (en)	2004-12-28
EE04939B1 (et)	2007-12-17
IS2594B (is)	2010-03-15
SK287373B6 (sk)	2010-08-09
BG65484B1 (bg)	2008-09-30
SK1802002A3 (en)	2003-05-02
AU782882B2 (en)	2005-09-08
EA005375B1 (ru)	2005-02-24
SI1204649T1 (sl)	2008-02-29
PL353588A1 (en)	2003-12-01

Publication	Publication Date	Title
US6784198B1 (en)	2004-08-31	Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents
AU766193B2 (en)	2003-10-09	2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents
US6218418B1 (en)	2001-04-17	3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents
EP1202734B1 (en)	2007-05-02	3(5)-ureido-pyrazole derivatives, process for their preparation and their use as antitumor agents
US6455559B1 (en)	2002-09-24	Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents
AU2002325860B2 (en)	2008-03-13	Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents