UA72538C2 - Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents - Google Patents

Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents Download PDF

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Publication number: UA72538C2
Authority: UA; Ukraine
Prior art keywords: thiazol; isopropyl; amino; oxoethyl; acetamide
Prior art date: 1999-08-12

Application number

UA2002031948A

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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

2000-11-08

Publication date

2005-03-15

2000-11-08 Application filed filed Critical

2005-03-15 Publication of UA72538C2 publication Critical patent/UA72538C2/uk

Links

230000000259 anti-tumor effect Effects 0.000 title 1
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 27
206010028980 Neoplasm Diseases 0.000 claims abstract description 25
238000011282 treatment Methods 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
201000011510 cancer Diseases 0.000 claims abstract description 11
208000035475 disorder Diseases 0.000 claims abstract description 11
230000002062 proliferating effect Effects 0.000 claims abstract description 11
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 4
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
208000036142 Viral infection Diseases 0.000 claims abstract description 4
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 4
230000009385 viral infection Effects 0.000 claims abstract description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 273
-1 pyrrolidino, morpholino, piperazino Chemical group 0.000 claims description 188
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 120
150000001875 compounds Chemical class 0.000 claims description 119
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
238000000034 method Methods 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 36
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 20
125000004663 dialkyl amino group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 14
102000016736 Cyclin Human genes 0.000 claims description 13
108050006400 Cyclin Proteins 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
230000005764 inhibitory process Effects 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 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
229910052757 nitrogen Inorganic materials 0.000 claims description 11
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 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
108091000080 Phosphotransferase Proteins 0.000 claims description 9
125000001769 aryl amino group Chemical group 0.000 claims description 9
125000005110 aryl thio group Chemical group 0.000 claims description 9
102000020233 phosphotransferase Human genes 0.000 claims description 9
125000003386 piperidinyl group Chemical group 0.000 claims description 9
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 9
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
208000031481 Pathologic Constriction Diseases 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
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 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
208000037804 stenosis Diseases 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 5
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 5
125000005099 aryl alkyl carbonyl group Chemical group 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
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Chemical group 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
230000036262 stenosis Effects 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 4
201000009030 Carcinoma Diseases 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
201000005787 hematologic cancer Diseases 0.000 claims description 4
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229960003966 nicotinamide Drugs 0.000 claims description 4
235000005152 nicotinamide Nutrition 0.000 claims description 4
239000011570 nicotinamide Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
230000002980 postoperative effect Effects 0.000 claims description 4
210000001685 thyroid gland Anatomy 0.000 claims description 4
WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 3
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
201000006107 Familial adenomatous polyposis Diseases 0.000 claims description 3
206010018364 Glomerulonephritis Diseases 0.000 claims description 3
208000007766 Kaposi sarcoma Diseases 0.000 claims description 3
206010027476 Metastases Diseases 0.000 claims description 3
208000009905 Neurofibromatoses Diseases 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
208000004403 Prostatic Hyperplasia Diseases 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
230000002917 arthritic effect Effects 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
208000029664 classic familial adenomatous polyposis Diseases 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
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
201000001441 melanoma Diseases 0.000 claims description 3
230000009401 metastasis Effects 0.000 claims description 3
201000004931 neurofibromatosis Diseases 0.000 claims description 3
210000001428 peripheral nervous system Anatomy 0.000 claims description 3
208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
208000001608 teratocarcinoma Diseases 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
230000004663 cell proliferation Effects 0.000 claims description 2
238000002512 chemotherapy 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
230000014399 negative regulation of angiogenesis Effects 0.000 claims description 2
201000008968 osteosarcoma Diseases 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
206010023347 Keratoacanthoma Diseases 0.000 claims 1
210000002464 muscle smooth vascular Anatomy 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000000049 pigment Substances 0.000 claims 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
230000004770 neurodegeneration Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
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239000000203 mixture Substances 0.000 description 23
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238000002360 preparation method Methods 0.000 description 20
238000005160 1H NMR spectroscopy Methods 0.000 description 18
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239000007787 solid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 10
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239000012266 salt solution Substances 0.000 description 8
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
238000001816 cooling Methods 0.000 description 7
150000002367 halogens Chemical group 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
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108091007914 CDKs Proteins 0.000 description 6
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
238000009835 boiling Methods 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
102000002554 Cyclin A Human genes 0.000 description 5
108010068192 Cyclin A Proteins 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 5
229940090181 propyl acetate Drugs 0.000 description 5
239000000758 substrate Substances 0.000 description 5
210000004881 tumor cell Anatomy 0.000 description 5
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
102000004190 Enzymes Human genes 0.000 description 4
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102000001253 Protein Kinase Human genes 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
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125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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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 3
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230000001988 toxicity Effects 0.000 description 3
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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
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Classifications

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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- 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

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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)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Epidemiology (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Dermatology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Communicable Diseases (AREA)
Orthopedic Medicine & Surgery (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Virology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

UA2002031948A 1999-08-12 2000-11-08 Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents UA72538C2 (en)

Applications Claiming Priority (2)

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
PCT/IB2000/001423 WO2001014353A1 (en)	1999-08-12	2000-08-11	Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents

Publications (1)

Publication Number	Publication Date
UA72538C2 true UA72538C2 (en)	2005-03-15

Family

ID=23469806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002031948A UA72538C2 (en)	1999-08-12	2000-11-08	Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents

Country Status (36)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA024672B1 (ru) *	2009-03-20	2016-10-31	Оникс Терапьютикс, Инк.	Кристаллические трипептидные ингибиторы эпоксикетон-протеазы

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
US7125875B2 (en) *	1999-04-15	2006-10-24	Bristol-Myers Squibb Company	Cyclic protein tyrosine kinase inhibitors
TR200102969T2 (tr) *	1999-04-15	2002-08-21	Bristol-Myers Squibb Company	Siklik protein tirozin kinaz önleyicileri.
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
EP1229934B1 (de)	1999-10-01	2014-03-05	Immunogen, Inc.	Zusammensetzungen und verfahren zur behandlung von krebs mittels immunkonjugaten und chemotherapeutischen agenzien
US20040048844A1 (en) *	1999-10-20	2004-03-11	Bristol-Myers Squibb Pharma Company	Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents
US6291504B1 (en)	1999-10-20	2001-09-18	Dupont Pharmaceuticals Company	Acylsemicarbazides and their uses
AU2002215053A1 (en) *	2000-11-27	2002-06-24	Pharmacia Italia S.P.A.	Phenylacetamido- pyrazole derivatives and their use as antitumor agents
WO2002044174A2 (en) *	2000-12-01	2002-06-06	Bristol-Myers Squibb Pharma Company	3-(2,4-dimethylthiazol-5-yl) indeno[1,2-c]pyrazol-4-one derivatives as cdk inhibitors
CA2430376A1 (en)	2000-12-08	2002-06-13	David J. Carini	Semicarbazides and their uses as cyclin dependent kinase inhibitors
EP1347971B1 (de) *	2000-12-21	2006-03-01	Bristol-Myers Squibb Company	Thiazolyl-inhibitoren von tyrosinkinasen der tec-familie
ATE315555T1 (de)	2001-05-11	2006-02-15	Pfizer Prod Inc	Thiazolderivate und ihre verwendung als cdk- inhibitoren
NZ530524A (en) *	2001-07-19	2006-12-22	Pharmacia Italia S	Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents
EP1724270A3 (de)	2001-07-19	2007-01-03	Pfizer Italia S.r.l.	Phenylacetamido-thiazole Verbindungen, Verfahren zu ihren Herstellung und ihre Anwendung als antitumor Mittel
US7087768B2 (en) *	2001-09-27	2006-08-08	Equispharm Co., Ltd.	Fumagillol derivatives and preparing method thereof
BR0215212A (pt) *	2001-12-21	2004-12-07	Novo Nordisk As	Ativador de carboxamida ou sulfonamida de glicoquinase, composto, composição farmacêutica, e, uso de um composto
EP1531815B1 (de) *	2002-06-27	2014-09-24	Novo Nordisk A/S	Glukokinase-aktivatoren
EP1594866A1 (de) *	2003-02-12	2005-11-16	Pfizer Inc.	Antiproliferative 2-(sulfophenyl)aminothiazolderivate
BRPI0407618A (pt) *	2003-02-21	2006-02-21	Pfizer	derivados de tiazole amino substituidos com cicloalquilo contendo n e composições farmacêuticas para inibição da proliferação celular e métodos para a sua utilização
US20060229346A1 (en) *	2003-03-31	2006-10-12	Sucampo Ag	Method for treating vascular hyperpermeable disease
FR2857664B1 (fr) *	2003-07-15	2007-12-14	Oreal	Nouveaux derives thiazoles et utilisation de ces derives pour la teinture des fibres keratiniques
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
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
US20070196395A1 (en) *	2003-12-12	2007-08-23	Mackerell Alexander	Immunomodulatory compounds that target and inhibit the py'binding site of tyrosene kinase p56 lck sh2 domain
BRPI0506662B8 (pt) *	2004-01-06	2021-05-25	Novo Nordisk As	compostos ativadores de glucoquinase
CA2584493A1 (en)	2004-06-18	2006-01-05	Gpc Biotech, Inc.	Kinase inhibitors for treating cancers
EP1621539A1 (de) *	2004-07-27	2006-02-01	Aventis Pharma S.A.	Heterocyclische-substituirte cyclische Harnstoffderivate, Verfaren zu ihrer Herstellung, und ihre pharmaceutische Verwendung als Kinase Inhibitoren
EP1621536A1 (de) *	2004-07-27	2006-02-01	Aventis Pharma S.A.	Amino zyklische Urea-Derivaten, ihre Herstellung und deren pharmazeutische Verwendungen als Kinase Inhibitoren
MX2007001727A (es) *	2004-08-13	2007-04-20	Genentech Inc	Compuestos a base de 2-amido-tiazol que exhiben actividad inhibidora de enzima que utiliza atp y composiciones y usos de los mismos.
DE602004021404D1 (de)	2004-12-23	2009-07-16	Gpc Biotech Ag	Quadratsäurederivate mit antiproliferativer Wirkung
EP2029138A1 (de) *	2005-06-03	2009-03-04	Xenon Pharmaceuticals Inc.	Aminothiazolderivate als humane stearoyl-coa desaturasehemmer
US7999114B2 (en) *	2005-07-08	2011-08-16	Novo Nordisk A/S	Dicycloalkylcarbamoyl ureas as glucokinase activators
CN101263131B (zh) *	2005-07-14	2013-04-24	特兰斯特克药品公司	脲葡糖激酶活化剂
EP1914234A1 (de) *	2006-10-16	2008-04-23	GPC Biotech Inc.	Pyrido[2,3-d]pyrimidinen und ihre Verwendung als kinase Inhibitoren
JP2010515701A (ja) *	2007-01-09	2010-05-13	ノボ・ノルデイスク・エー／エス	ウレアグルコキナーゼアクチベーター
AU2008204530B2 (en) *	2007-01-11	2013-08-01	Vtv Therapeutics Llc	Urea glucokinase activators
ES2369617T3 (es) *	2007-02-13	2011-12-02	Ab Science	Procedimiento para la síntesis de compuestos de 2-aminotiazol como inhibidores de la quinasa.
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
WO2009151683A2 (en)	2008-03-12	2009-12-17	Link Medicine Corporation	Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications
EP2112152A1 (de)	2008-04-22	2009-10-28	GPC Biotech AG	Dihydropteridinones als Plk-Inhibitoren
EP2112150B1 (de)	2008-04-22	2013-10-16	Forma Therapeutics, Inc.	Verbesserte Raf-Inhibitoren
EP2370436A1 (de)	2008-11-13	2011-10-05	Link Medicine Corporation	Azachinolinonderivate und deren verwendungen
UA103918C2 (en) *	2009-03-02	2013-12-10	Айерем Элелси	N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators
EP2440556A1 (de) *	2009-06-10	2012-04-18	Vertex Pharmaceuticals Incorporated	Phosphatidylinositol 3-kinasehemmer
DE102009043260A1 (de) *	2009-09-28	2011-04-28	Merck Patent Gmbh	Pyridinyl-imidazolonderivate
EP2325185A1 (de)	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
EP2887943B1 (de)	2012-08-23	2017-12-06	Virostatics Srl	Neuartige 4,6-disubstituierte aminopyrimidinderivate
PT3777855T (pt)	2016-04-11	2023-01-10	Genfit	Métodos de tratamento para doenças fibróticas
US11040945B2 (en)	2017-12-06	2021-06-22	Lin Bioscience Pty Ltd.	Tubulin inhibitors
EP3746422A4 (de) *	2018-02-01	2021-06-09	The University Of Sydney	Antikrebsverbindungen
MX2020008905A (es)	2018-06-12	2020-12-03	Vtv Therapeutics Llc	Usos terapeuticos de activadores de glucoquinasa en combinacion con insulina o analogos de insulinas.
WO2020193431A1 (en)	2019-03-22	2020-10-01	Deutsches Krebsforschungszentrum	Novel inhibitors of histone deacetylase 10
EP3712127A1 (de)	2019-03-22	2020-09-23	Deutsches Krebsforschungszentrum	Neuartige inhibitoren der histon-deacetylase 10
WO2021060888A2 (ko) *	2019-09-25	2021-04-01	한국원자력의학원	신규 트리플루오로메틸페닐피라졸 유도체를 유효성분으로 함유하는 암 예방 또는 치료용 조성물
EP4104835A4 (de) *	2020-02-10	2024-05-01	Juntendo Educational Foundation	Typ-2-ryanodinrezeptoraktivitätsinhibitor
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
AU2023239988A1 (en) *	2022-03-22	2024-10-10	Autotelic Bio Inc.	Thiazole derivative compound and uses thereof

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL263812A (de) *	1960-04-20
TW513418B (en) *	1996-07-31	2002-12-11	Otsuka Pharma Co Ltd	Thiazole derivatives, their production and use
JPH1095777A (ja) *	1996-07-31	1998-04-14	Otsuka Pharmaceut Co Ltd	チアゾール誘導体
US6794392B1 (en) *	1996-09-30	2004-09-21	Schering Aktiengesellschaft	Cell differentiation inducer
PL342447A1 (en)	1997-10-27	2001-06-04	Agouron Pharma	Substituted 4-amino thiazol-2-yl compounds as inhibitors of cyclin-dependent kinases
US6040321A (en) *	1997-11-12	2000-03-21	Bristol-Myers Squibb Company	Aminothiazole inhibitors of cyclin dependent kinases
WO1999065884A1 (en) *	1998-06-18	1999-12-23	Bristol-Myers Squibb Company	Carbon substituted aminothiazole inhibitors of cyclin dependent kinases
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
TR200102969T2 (tr) *	1999-04-15	2002-08-21	Bristol-Myers Squibb Company	Siklik protein tirozin kinaz önleyicileri.
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
DE60221627D1 (de) *	2001-12-21	2007-09-20	Virochem Pharma Inc	Thiazolderivate und ihre Verwendung zur Behandlung oder Vorbeugung von Infektionen durch Flaviviren
TWI336696B (en) *	2003-01-27	2011-02-01	Astellas Pharma Inc	Thiazole derivatives

1999
- 1999-08-12 US US09/372,832 patent/US6114365A/en not_active Expired - Lifetime
2000
- 2000-08-11 CA CA002381097A patent/CA2381097C/en not_active Expired - Fee Related
- 2000-08-11 EE EEP200200064A patent/EE04939B1/xx not_active IP Right Cessation
- 2000-08-11 SI SI200030974T patent/SI1204649T1/sl unknown
- 2000-08-11 WO PCT/IB2000/001423 patent/WO2001014353A1/en active IP Right Grant
- 2000-08-11 IL IL14792400A patent/IL147924A0/xx active IP Right Grant
- 2000-08-11 US US10/048,474 patent/US6784198B1/en not_active Expired - Fee Related
- 2000-08-11 PT PT00962760T patent/PT1204649E/pt unknown
- 2000-08-11 JP JP2001518441A patent/JP4864260B2/ja not_active Expired - Fee Related
- 2000-08-11 BR BR0013281-0A patent/BR0013281A/pt not_active IP Right Cessation
- 2000-08-11 AT AT00962760T patent/ATE375987T1/de active
- 2000-08-11 MX MXPA02001508A patent/MXPA02001508A/es active IP Right Grant
- 2000-08-11 KR KR1020027001844A patent/KR100773709B1/ko not_active IP Right Cessation
- 2000-08-11 EA EA200200247A patent/EA005375B1/ru not_active IP Right Cessation
- 2000-08-11 OA OA1200200052A patent/OA12047A/en unknown
- 2000-08-11 DK DK00962760T patent/DK1204649T3/da active
- 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 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 ES ES00962760T patent/ES2295056T3/es not_active Expired - Lifetime
- 2000-08-11 CZ CZ20020486A patent/CZ303138B6/cs not_active IP Right Cessation
- 2000-08-11 EP EP00962760A patent/EP1204649B1/de not_active Expired - Lifetime
- 2000-08-11 RS YUP-97/02A patent/RS50300B/sr unknown
- 2000-08-11 NZ NZ517236A patent/NZ517236A/en not_active IP Right Cessation
- 2000-08-11 SK SK180-2002A patent/SK287373B6/sk not_active IP Right Cessation
- 2000-08-11 DE DE60036803T patent/DE60036803T2/de not_active Expired - Lifetime
- 2000-08-11 HU HU0202492A patent/HUP0202492A3/hu unknown
- 2000-08-11 GE GE4757A patent/GEP20053475B/en unknown
- 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 IS IS6264A patent/IS2594B/is unknown
- 2002-02-11 NO NO20020683A patent/NO323576B1/no not_active IP Right Cessation
- 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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA024672B1 (ru) *	2009-03-20	2016-10-31	Оникс Терапьютикс, Инк.	Кристаллические трипептидные ингибиторы эпоксикетон-протеазы

Also Published As

Publication number	Publication date
DE60036803T2 (de)	2008-07-24
RS50300B (sr)	2009-09-08
EE200200064A (et)	2003-04-15
IL147924A (en)	2008-03-20
KR100827563B1 (ko)	2008-05-07
HK1054233A1 (en)	2003-11-21
BG65484B1 (bg)	2008-09-30
HK1054233B (zh)	2009-05-29
CZ303138B6 (cs)	2012-04-25
CY1107108T1 (el)	2012-10-24
EA200200247A1 (ru)	2002-08-29
NZ517236A (en)	2004-11-26
ATE375987T1 (de)	2007-11-15
MXPA02001508A (es)	2003-07-21
IL147924A0 (en)	2002-08-14
NO20020683D0 (no)	2002-02-11
AU7440000A (en)	2001-03-19
CN1425009A (zh)	2003-06-18
YU9702A (sh)	2004-11-25
CA2381097C (en)	2009-06-16
DE60036803D1 (de)	2007-11-29
AP1853A (en)	2008-05-29
BG106481A (en)	2002-09-30
PL353588A1 (en)	2003-12-01
AP2002002441A0 (en)	2002-03-31
EA005375B1 (ru)	2005-02-24
IS2594B (is)	2010-03-15
ES2295056T3 (es)	2008-04-16
HUP0202492A3 (en)	2004-12-28
AU782882B2 (en)	2005-09-08
GEP20053475B (en)	2005-03-25
OA12047A (en)	2006-05-02
CZ2002486A3 (cs)	2002-11-13
EP1204649A1 (de)	2002-05-15
JP2003507461A (ja)	2003-02-25
US20050004120A1 (en)	2005-01-06
KR100773709B1 (ko)	2007-11-09
EE04939B1 (et)	2007-12-17
CN100410245C (zh)	2008-08-13
KR20070074003A (ko)	2007-07-10
KR20020060159A (ko)	2002-07-16
NO323576B1 (no)	2007-06-11
SK287373B6 (sk)	2010-08-09
PT1204649E (pt)	2008-01-10
US6784198B1 (en)	2004-08-31
NO20020683L (no)	2002-04-10
WO2001014353A1 (en)	2001-03-01
HRP20020127B1 (en)	2010-08-31
HRP20020127A2 (en)	2003-04-30
IS6264A (is)	2002-02-11
EP1204649B1 (de)	2007-10-17
JP4864260B2 (ja)	2012-02-01
SI1204649T1 (sl)	2008-02-29
HUP0202492A2 (hu)	2002-11-28
ZA200201117B (en)	2003-04-30
US6114365A (en)	2000-09-05
BR0013281A (pt)	2002-06-18
MA25433A1 (fr)	2002-04-01
DK1204649T3 (da)	2007-12-03
SK1802002A3 (en)	2003-05-02
CA2381097A1 (en)	2001-03-01

Publication	Publication Date	Title
UA72538C2 (en)	2005-03-15	Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents
EP1124810B1 (de)	2005-05-04	2-aminothiazolederivate, verfahren zu ihrer herstellung und ihre verwendung als antitumormittel
US6218418B1 (en)	2001-04-17	3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents
CN104507923B (zh)	2018-02-09	作为激酶抑制剂的取代的吡咯类活性剂
SK4752001A3 (en)	2002-02-05	2-aminothiazole derivatives, process for their preparation, and their use as antitumor agents
KR20030010739A (ko)	2003-02-05	아자인돌 유도체, 이의 제조방법 및 항종양제로서의 이의용도
EA007392B1 (ru)	2006-10-27	Фенилацетамидотиазольные производные, способ их получения и их использования в качестве противоопухолевых средств
US20040116497A1 (en)	2004-06-17	Chromane derivatives, process for their preparation and their use as antitumor agents
PL203424B1 (pl)	2009-10-30	Pochodne 2-amino-1,3-tiazolu, sposoby ich wytwarzania, ich zastosowanie oraz ich kompozycje farmaceutyczne

UA72538C2 - Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents - Google Patents

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