UA61047C2 - 6-aryl pyrido[2,3-d]pyrimidines and naphthyridines derivatives, a pharmaceutical composition having inhibitory action of cellular proliferation caused by protein tyrosinc kinase, and a method for inhibition of cellular proliferation - Google Patents
6-aryl pyrido[2,3-d]pyrimidines and naphthyridines derivatives, a pharmaceutical composition having inhibitory action of cellular proliferation caused by protein tyrosinc kinase, and a method for inhibition of cellular proliferation Download PDFInfo
- Publication number
- UA61047C2 UA61047C2 UA97062801A UA97062801A UA61047C2 UA 61047 C2 UA61047 C2 UA 61047C2 UA 97062801 A UA97062801 A UA 97062801A UA 97062801 A UA97062801 A UA 97062801A UA 61047 C2 UA61047 C2 UA 61047C2
- Authority
- UA
- Ukraine
- Prior art keywords
- dichlorophenyl
- pyrido
- group
- tert
- pyrimidin
- Prior art date
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- 230000004663 cell proliferation Effects 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 84
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 230000002401 inhibitory effect Effects 0.000 title claims description 10
- 150000005054 naphthyridines Chemical class 0.000 title abstract description 5
- 102000004169 proteins and genes Human genes 0.000 title description 8
- 108090000623 proteins and genes Proteins 0.000 title description 8
- 230000005764 inhibitory process Effects 0.000 title description 6
- 102000001253 Protein Kinase Human genes 0.000 title description 2
- 108060006633 protein kinase Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 20
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- -1 2,6-dichlorophenyl Chemical group 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000006308 propyl amino group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052709 silver Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 11
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 11
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
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- 125000001424 substituent group Chemical group 0.000 claims description 7
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- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
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- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- CMMSUVYMWKBPQK-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine-2,4-diamine Chemical compound N1=CC=CC2=NC(N)=NC(N)=C21 CMMSUVYMWKBPQK-UHFFFAOYSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 229940052907 telazol Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 108091005990 tyrosine-phosphorylated proteins Proteins 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
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- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33905194A | 1994-11-14 | 1994-11-14 | |
PCT/US1995/014700 WO1996015128A2 (en) | 1994-11-14 | 1995-11-13 | 6-ARYL PYRIDO[2,3-d]PYRIMIDINES AND NAPHTHYRIDINES FOR INHIBITING PROTEIN TYROSINE KINASE MEDIATED CELLULAR PROLIFERATION |
Publications (1)
Publication Number | Publication Date |
---|---|
UA61047C2 true UA61047C2 (en) | 2003-11-17 |
Family
ID=23327276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA97062801A UA61047C2 (en) | 1994-11-14 | 1995-11-13 | 6-aryl pyrido[2,3-d]pyrimidines and naphthyridines derivatives, a pharmaceutical composition having inhibitory action of cellular proliferation caused by protein tyrosinc kinase, and a method for inhibition of cellular proliferation |
Country Status (7)
Country | Link |
---|---|
US (1) | US5733913A (ko) |
JP (1) | JP4221530B2 (ko) |
KR (1) | KR100385520B1 (ko) |
IL (1) | IL115256A0 (ko) |
SI (1) | SI0790997T1 (ko) |
UA (1) | UA61047C2 (ko) |
ZA (1) | ZA959675B (ko) |
Families Citing this family (76)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5945422A (en) * | 1997-02-05 | 1999-08-31 | Warner-Lambert Company | N-oxides of amino containing pyrido 2,3-D! pyrimidines |
EA200200643A1 (ru) * | 2000-01-25 | 2002-12-26 | Уорнер-Ламберт Компани | ПИРИДО[2,3-d]ПИРИМИДИН-2,7-ДИАМИНОВЫЕ ИНГИБИТОРЫ КИНАЗ |
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-
1995
- 1995-09-12 IL IL11525695A patent/IL115256A0/xx unknown
- 1995-11-06 US US08/539,410 patent/US5733913A/en not_active Expired - Lifetime
- 1995-11-13 SI SI9530385T patent/SI0790997T1/xx unknown
- 1995-11-13 KR KR1019970703225A patent/KR100385520B1/ko not_active IP Right Cessation
- 1995-11-13 JP JP51624096A patent/JP4221530B2/ja not_active Expired - Fee Related
- 1995-11-13 UA UA97062801A patent/UA61047C2/uk unknown
- 1995-11-14 ZA ZA959675A patent/ZA959675B/xx unknown
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SI0790997T1 (en) | 2000-06-30 |
JPH10509452A (ja) | 1998-09-14 |
JP4221530B2 (ja) | 2009-02-12 |
US5733913A (en) | 1998-03-31 |
ZA959675B (en) | 1996-05-29 |
KR100385520B1 (ko) | 2003-10-10 |
IL115256A0 (en) | 1995-12-31 |
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