AU2002336390B2 - 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents - Google Patents
2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents Download PDFInfo
- Publication number
- AU2002336390B2 AU2002336390B2 AU2002336390A AU2002336390A AU2002336390B2 AU 2002336390 B2 AU2002336390 B2 AU 2002336390B2 AU 2002336390 A AU2002336390 A AU 2002336390A AU 2002336390 A AU2002336390 A AU 2002336390A AU 2002336390 B2 AU2002336390 B2 AU 2002336390B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- methoxy
- quinolin
- optionally substituted
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
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- -1 2,4-disubstituted pyrimidinyl Chemical class 0.000 title claims description 948
- 239000002246 antineoplastic agent Substances 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims description 262
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 221
- 239000000203 mixture Substances 0.000 claims description 202
- 125000001424 substituent group Chemical group 0.000 claims description 146
- 125000000623 heterocyclic group Chemical group 0.000 claims description 124
- 238000000034 method Methods 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 59
- 125000001153 fluoro group Chemical group F* 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 206010028980 Neoplasm Diseases 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 108091000080 Phosphotransferase Proteins 0.000 claims description 34
- 102000020233 phosphotransferase Human genes 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000001246 bromo group Chemical group Br* 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 22
- 241000124008 Mammalia Species 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 14
- 125000005493 quinolyl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- HZQGAYQCXWLOPQ-UHFFFAOYSA-N 4-quinolin-3-yl-1h-pyrimidine-2,4-diamine Chemical compound C1=CNC(N)=NC1(N)C1=CN=C(C=CC=C2)C2=C1 HZQGAYQCXWLOPQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 208000024891 symptom Diseases 0.000 claims description 7
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
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- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
- ITHMKQDIGBAKGT-UHFFFAOYSA-N 4-quinolin-6-yl-1H-pyrimidine-2,4-diamine Chemical compound N1=CC=CC2=CC(=CC=C12)C1(NC(=NC=C1)N)N ITHMKQDIGBAKGT-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
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- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 4
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 4
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- BXWFRIUOWITGEJ-UHFFFAOYSA-N 4-[6-(trifluoromethoxy)quinolin-3-yl]-1H-pyrimidine-2,4-diamine Chemical compound FC(OC=1C=C2C=C(C=NC2=CC=1)C1(NC(=NC=C1)N)N)(F)F BXWFRIUOWITGEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- FHTUWMWXFOIMDW-UHFFFAOYSA-N CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC)N Chemical compound CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC)N FHTUWMWXFOIMDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 14
- 230000000052 comparative effect Effects 0.000 claims 11
- FRDRXZJAYJQJIG-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(C2(N)N=C(N)C=CN2)=C1 FRDRXZJAYJQJIG-UHFFFAOYSA-N 0.000 claims 2
- PJYBZUXUXQRLBZ-UHFFFAOYSA-N 4-(6-methoxyquinolin-3-yl)-1H-pyrimidine-2,4-diamine Chemical compound COC=1C=C2C=C(C=NC2=CC=1)C1(NC(=NC=C1)N)N PJYBZUXUXQRLBZ-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 1
- DTHNDCLPGVAAHV-UHFFFAOYSA-N 2-methoxy-4-[[4-(quinolin-3-ylamino)pyrimidin-2-yl]amino]benzamide Chemical compound C1=C(C(N)=O)C(OC)=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=C1 DTHNDCLPGVAAHV-UHFFFAOYSA-N 0.000 claims 1
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims 1
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- 210000002268 wool Anatomy 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
- 229950009233 zinostatin stimalamer Drugs 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin 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(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31433901P | 2001-08-22 | 2001-08-22 | |
| US60/314,339 | 2001-08-22 | ||
| US10/225,783 US6939874B2 (en) | 2001-08-22 | 2002-08-21 | Substituted pyrimidinyl derivatives and methods of use |
| US10/225,783 | 2002-08-21 | ||
| PCT/US2002/026870 WO2003018021A1 (en) | 2001-08-22 | 2002-08-22 | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002336390A1 AU2002336390A1 (en) | 2003-06-05 |
| AU2002336390B2 true AU2002336390B2 (en) | 2005-10-20 |
Family
ID=26919901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002336390A Ceased AU2002336390B2 (en) | 2001-08-22 | 2002-08-22 | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6939874B2 (enExample) |
| EP (1) | EP1427421A1 (enExample) |
| JP (1) | JP2005505535A (enExample) |
| AU (1) | AU2002336390B2 (enExample) |
| CA (1) | CA2457838A1 (enExample) |
| MX (1) | MXPA04001623A (enExample) |
| PL (1) | PL370041A1 (enExample) |
| WO (1) | WO2003018021A1 (enExample) |
Families Citing this family (145)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0402245A3 (en) * | 2001-11-01 | 2010-03-29 | Janssen Pharmaceutica Nv | Pyrimidinyl-aminobenzamide derivatives as glycogen synthase kinase 3betha inhibitors, their use, pharmaceutical compositions containing them and process for producing them |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| IL166241A0 (en) * | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| US7109337B2 (en) | 2002-12-20 | 2006-09-19 | Pfizer Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| ATE458731T1 (de) | 2002-12-20 | 2010-03-15 | Pfizer Prod Inc | Pyrimidin-derivate zur behandlung von anormalem zellwachstum |
| RU2400477C2 (ru) * | 2003-03-14 | 2010-09-27 | Новартис Аг | 2,4-ди(фениламино)пиримидины, применимые при лечении неопластических заболеваний, воспалительных нарушений и нарушений иммунной системы |
| GB0305929D0 (en) * | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| US7201779B2 (en) | 2003-06-16 | 2007-04-10 | L'oreal S.A. | Dye composition comprising at least one direct dye containing mixed chromophores |
| US7172633B2 (en) | 2003-06-16 | 2007-02-06 | L'ORéAL S.A. | Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores |
| US7442698B2 (en) | 2003-07-24 | 2008-10-28 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| RS53109B (sr) * | 2003-07-30 | 2014-06-30 | Rigel Pharmaceuticals Inc. | Jedinjenja 2,4 pirimidindiamina za upotrebu u tretmanu ili prevenciji autoimunih bolesti |
| PL2287156T3 (pl) * | 2003-08-15 | 2013-11-29 | Novartis Ag | 2,4-Di(fenyloamino)-pirymidyny stosowane w leczeniu chorób nowotworowych, chorób zapalnych i zaburzeń układu immunologicznego |
| GB0321710D0 (en) * | 2003-09-16 | 2003-10-15 | Novartis Ag | Organic compounds |
| CA2538413A1 (en) * | 2003-09-18 | 2005-03-24 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| US20050075358A1 (en) * | 2003-10-06 | 2005-04-07 | Carboni Joan M. | Methods for treating IGF1R-inhibitor induced hyperglycemia |
| ATE525377T1 (de) * | 2003-10-15 | 2011-10-15 | Osi Pharm Inc | Imidazoä1,5-aüpyrazine als inhibitoren von tyrosinkinase |
| UA86614C2 (ru) * | 2004-01-23 | 2009-05-12 | Амген Инк | Соединение, которое имеет активность ингибитора киназ, фармацевтическая композиция, которая включает указанное соединение, и их применение для приготовления лекарственного препарата |
| US7303591B2 (en) | 2004-02-27 | 2007-12-04 | L'oreal S.A. | Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes |
| US7300471B2 (en) | 2004-02-27 | 2007-11-27 | L'oreal S.A. | Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes. |
| US7288121B2 (en) | 2004-02-27 | 2007-10-30 | L'oreal S.A. | Composition comprising at least one mixed dye comprising at least one chromophore chosen from compounds of the methine family and/or the carbonyl family, dyeing process and kit, and mixed dyes |
| EP2168968B1 (en) | 2004-04-02 | 2017-08-23 | OSI Pharmaceuticals, LLC | 6,6-bicyclic ring substituted heterobicyclic protein kinase inhibitors |
| EP1758887A1 (en) | 2004-05-14 | 2007-03-07 | Pfizer Products Incorporated | Pyrimidine derivatives for the treatment of abnormal cell growth |
| CA2566332A1 (en) | 2004-05-14 | 2005-11-24 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
| JP2007537235A (ja) | 2004-05-14 | 2007-12-20 | ファイザー・プロダクツ・インク | 異常細胞増殖の治療用ピリミジン誘導体 |
| AR053090A1 (es) | 2004-07-20 | 2007-04-25 | Osi Pharm Inc | Imidazotriazinas como inhibidores de proteina quinasas y su uso para la preparacion de medicamentos |
| MX2007001399A (es) | 2004-08-02 | 2007-04-18 | Osi Pharm Inc | Compuestos que inhiben pirrolopirimidina multi-cinasa aril-amino sustituidas. |
| GB0419160D0 (en) | 2004-08-27 | 2004-09-29 | Novartis Ag | Organic compounds |
| CN101039919A (zh) * | 2004-10-13 | 2007-09-19 | 惠氏公司 | 经n－苯磺酰基取代的苯胺基嘧啶类似物 |
| ES2380550T3 (es) * | 2004-11-24 | 2012-05-16 | Rigel Pharmaceuticals, Inc. | Compuestos de espiro-2,4-pirimidindiamina y sus usos |
| JP5208516B2 (ja) * | 2004-12-30 | 2013-06-12 | エグゼリクシス， インコーポレイテッド | キナーゼモジュレーターとしてのピリミジン誘導体および使用方法 |
| NZ555947A (en) * | 2005-01-19 | 2010-11-26 | Rigel Pharmaceuticals Inc | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US20080161278A1 (en) * | 2005-03-23 | 2008-07-03 | Astrazeneca Ab | 2-Azetidinyl-4-(1H-Pyrazol-3-Ylamino) Pyrimidines as Inhibitors of Insulin-Like Growth Factor-1 Receptor Activity |
| ATE404554T1 (de) * | 2005-04-05 | 2008-08-15 | Astrazeneca Ab | Pyrimidinderivate zur verwendung als antikrebsmittel |
| GB0506886D0 (en) * | 2005-04-05 | 2005-05-11 | Astrazeneca Ab | Chemical compounds |
| GB0507347D0 (en) * | 2005-04-12 | 2005-05-18 | Astrazeneca Ab | Chemical compounds |
| DE102005016634A1 (de) * | 2005-04-12 | 2006-10-19 | Merck Patent Gmbh | Neuartige Aza-Hetercyclen als Kinase-Inhibitoren |
| CA2604551A1 (en) * | 2005-05-03 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Jak kinase inhibitors and their uses |
| MX286273B (es) * | 2005-06-08 | 2011-05-04 | Rigel Pharmaceuticals Inc | Composiciones y metodos para inhibicion de la via jak. |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| BRPI0613452A2 (pt) * | 2005-07-11 | 2011-01-11 | Sanofi Aventis | derivados de 2,4-dianilino pirimidinas, o respectivo preparo, a tìtulo de medicamentos, composições farmacêuticas e notadamente como inibidores de ikk |
| FR2888239B1 (fr) * | 2005-07-11 | 2008-05-09 | Sanofi Aventis Sa | Nouveaux derives de 2,4-dianilinopyrimidines, leur preparation, a titre de medicaments, compositions pharmaceutiques et notamment comme inhibiteurs de ikk |
| US7566721B2 (en) * | 2005-08-08 | 2009-07-28 | Osi Pharmaceuticals, Inc. | Substituted thienol[2,3-d]pyrimidines as kinase inhibitors |
| FR2889954B1 (fr) | 2005-08-26 | 2007-10-19 | Oreal | Colorants mixtes cationiques comprenant un chromophore anthraquinone et leur utilisation en colorant capillaire |
| JP2009508833A (ja) * | 2005-09-16 | 2009-03-05 | アストラゼネカ アクチボラグ | Ｉｇｆ−１ｒチロシンキナーゼ活性の阻害のためのピリミジン誘導体類 |
| JP5055284B2 (ja) | 2005-09-20 | 2012-10-24 | オーエスアイ・フアーマシユーテイカルズ・エル・エル・シー | インシュリン様成長因子−１受容体キナーゼ阻害剤に対する抗癌応答を予測する生物学的マーカー |
| AR057960A1 (es) | 2005-12-02 | 2007-12-26 | Osi Pharm Inc | Inhibidores de proteina quinasa biciclicos |
| US8575164B2 (en) * | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
| GB0526246D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| TW200736232A (en) * | 2006-01-26 | 2007-10-01 | Astrazeneca Ab | Pyrimidine derivatives |
| CA2642229C (en) | 2006-02-24 | 2015-05-12 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| RU2008152195A (ru) * | 2006-06-15 | 2010-07-20 | БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) | 2-анилино-4-(гетероциклил)аминопиримидины, как ингибиторы протеинкиназы с-альфа |
| CN101506176A (zh) | 2006-06-15 | 2009-08-12 | 贝林格尔.英格海姆国际有限公司 | 2-苯胺基-4-氨基亚烷基氨基嘧啶 |
| US8222256B2 (en) | 2006-07-05 | 2012-07-17 | Exelixis, Inc. | Methods of using IGFIR and ABL kinase modulators |
| JP5161233B2 (ja) | 2006-10-19 | 2013-03-13 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 自己免疫疾患の処置のためのｊａｋキナーゼの阻害剤としての２，４−ピリミジンアミン誘導体 |
| NZ576425A (en) | 2006-10-23 | 2012-04-27 | Cephalon Inc | Fused bicyclic derivatives of 2,4-diaminopyrimidine as alk and c-met inhibitors |
| CN101616895A (zh) | 2006-12-08 | 2009-12-30 | Irm责任有限公司 | 作为蛋白激酶抑制剂的化合物和组合物 |
| EP2120964A2 (en) | 2006-12-15 | 2009-11-25 | Abraxis BioScience, Inc. | Triazine derivatives and their therapeutical applications |
| US20080269266A1 (en) * | 2007-03-27 | 2008-10-30 | Astrazeneca Ab | Novel compounds 747 |
| WO2009010794A1 (en) * | 2007-07-19 | 2009-01-22 | Astrazeneca Ab | 2,4-diamino-pyrimidine derivatives |
| US8431608B2 (en) | 2007-08-17 | 2013-04-30 | Icagen Inc. | Heterocycles as potassium channel modulators |
| ES2400604T3 (es) * | 2007-08-17 | 2013-04-11 | Icagen, Inc. | Heterociclos como moduladores del canal de potasio |
| MX2010002336A (es) * | 2007-08-28 | 2010-03-25 | Irm Llc | Derivados de 2-bifenil-amino-4-amino-pirimidina como inhibidores de cinasa. |
| AP2010005347A0 (en) | 2008-01-11 | 2010-08-31 | Natco Pharma Ltd | Novel pyrazolo [3,4-D] pyrimidine derivatives as anti-cancer agents |
| EP2250173A1 (en) * | 2008-01-18 | 2010-11-17 | OSI Pharmaceuticals, Inc. | Imidazopyrazinol derivatives for the treatment of cancers |
| ES2396613T3 (es) * | 2008-05-19 | 2013-02-22 | OSI Pharmaceuticals, LLC | Imidazopirazinas e imidazotriazinas sustituidas |
| PE20100087A1 (es) | 2008-06-25 | 2010-02-08 | Irm Llc | Compuestos y composiciones como inhibidores de cinasa |
| US8445505B2 (en) | 2008-06-25 | 2013-05-21 | Irm Llc | Pyrimidine derivatives as kinase inhibitors |
| NZ589843A (en) | 2008-06-27 | 2012-12-21 | Avila Therapeutics Inc | Pyrimidine heteroaryl compounds and uses thereof as protein kinase inhibitors |
| US11351168B1 (en) | 2008-06-27 | 2022-06-07 | Celgene Car Llc | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| US8338439B2 (en) * | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| MX2011004824A (es) | 2008-11-07 | 2012-01-12 | Triact Therapeutics Inc | Uso de derivados de butano catecólico en terapia contra el cáncer. |
| WO2010072155A1 (zh) * | 2008-12-26 | 2010-07-01 | 复旦大学 | 一种嘧啶类衍生物及其制备方法和用途 |
| EP2400985A2 (en) | 2009-02-25 | 2012-01-04 | OSI Pharmaceuticals, LLC | Combination of an either an anti-igf-1r antibody or an igf binding protein and a small molecule igf-1r kinase inhibitor |
| JP2012519170A (ja) | 2009-02-26 | 2012-08-23 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 生体内の腫瘍細胞のｅｍｔステータスをモニターするためのｉｎｓｉｔｕ法 |
| WO2010099364A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| WO2010099138A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| EP2401614A1 (en) | 2009-02-27 | 2012-01-04 | OSI Pharmaceuticals, LLC | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| US8513415B2 (en) | 2009-04-20 | 2013-08-20 | OSI Pharmaceuticals, LLC | Preparation of C-pyrazine-methylamines |
| JP5918693B2 (ja) | 2009-05-05 | 2016-05-18 | ダナ ファーバー キャンサー インスティテュート インコーポレイテッド | Ｅｇｆｒ阻害剤及び疾患の治療方法 |
| WO2010129740A1 (en) * | 2009-05-07 | 2010-11-11 | Osi Pharmaceuticals, Inc. | Use of osi-906 for treating adrenocortical carcinoma |
| CN102459236B (zh) * | 2009-05-27 | 2014-10-29 | Abbvie公司 | 激酶活性的嘧啶抑制剂 |
| JP2012529517A (ja) | 2009-06-09 | 2012-11-22 | アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー | ベンジル置換トリアジン誘導体類及びそれらの治療応用 |
| KR101457027B1 (ko) | 2009-06-09 | 2014-10-31 | 캘리포니아 캐피탈 에쿼티, 엘엘씨 | 트리아진 유도체와 이들의 치료적 용도 |
| JP6073677B2 (ja) | 2009-06-12 | 2017-02-01 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | 縮合複素環式化合物およびそれらの使用 |
| WO2011017178A1 (en) * | 2009-07-28 | 2011-02-10 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| EP2519517B1 (en) | 2009-12-29 | 2015-03-25 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| US20110217309A1 (en) | 2010-03-03 | 2011-09-08 | Buck Elizabeth A | Biological markers predictive of anti-cancer response to insulin-like growth factor-1 receptor kinase inhibitors |
| WO2011109572A2 (en) | 2010-03-03 | 2011-09-09 | OSI Pharmaceuticals, LLC | Biological markers predictive of anti-cancer response to insulin-like growth factor-1 receptor kinase inhibitors |
| WO2011112666A1 (en) | 2010-03-09 | 2011-09-15 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| WO2011140338A1 (en) * | 2010-05-05 | 2011-11-10 | Gatekeeper Pharmaceuticals, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
| CN103003264B (zh) | 2010-05-21 | 2014-08-06 | 切米利亚股份公司 | 嘧啶衍生物 |
| ES2617763T3 (es) | 2010-08-10 | 2017-06-19 | Celgene Avilomics Research, Inc. | Sal de besilato de un inhibidor de BTK |
| WO2012061299A1 (en) | 2010-11-01 | 2012-05-10 | Avila Therapeutics, Inc. | Heterocyclic compounds and uses thereof |
| US9238629B2 (en) | 2010-11-01 | 2016-01-19 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| EP2637502B1 (en) | 2010-11-10 | 2018-01-10 | Celgene CAR LLC | Mutant-selective egfr inhibitors and uses thereof |
| WO2012116040A1 (en) | 2011-02-22 | 2012-08-30 | OSI Pharmaceuticals, LLC | Biological markers predictive of anti-cancer response to insulin-like growth factor-1 receptor kinase inhibitors in hepatocellular carcinoma |
| AU2012230229A1 (en) | 2011-03-24 | 2013-10-10 | Noviga Research Ab | Novel pyrimidine derivatives |
| JP2014519813A (ja) | 2011-04-25 | 2014-08-21 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 癌薬剤発見、診断、および治療におけるｅｍｔ遺伝子シグネチャーの使用 |
| JP2014532658A (ja) | 2011-10-28 | 2014-12-08 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | ブルトン型チロシンキナーゼ疾患または障害を治療する方法 |
| JP6106685B2 (ja) * | 2011-11-17 | 2017-04-05 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | Ｃ−ｊｕｎ−ｎ−末端キナーゼ（ｊｎｋ）の阻害剤 |
| US8993614B2 (en) * | 2012-03-15 | 2015-03-31 | F. Hoffmann-La Roche Ag | Substituted pyrrolidine-2-carboxamides |
| WO2013138495A1 (en) | 2012-03-15 | 2013-09-19 | Celgene Avilomics Research, Inc. | Solid forms of an epidermal growth factor receptor kinase inhibitor |
| JP6317320B2 (ja) | 2012-03-15 | 2018-04-25 | セルジーン シーエーアール エルエルシー | 上皮成長因子受容体キナーゼ阻害剤の塩 |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| US10112927B2 (en) | 2012-10-18 | 2018-10-30 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
| US10000483B2 (en) | 2012-10-19 | 2018-06-19 | Dana-Farber Cancer Institute, Inc. | Bone marrow on X chromosome kinase (BMX) inhibitors and uses thereof |
| US9758522B2 (en) | 2012-10-19 | 2017-09-12 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged small molecules as inducers of protein degradation |
| US9126950B2 (en) | 2012-12-21 | 2015-09-08 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| AU2014214846A1 (en) | 2013-02-08 | 2015-07-23 | Celgene Avilomics Research, Inc. | ERK inhibitors and uses thereof |
| US9834575B2 (en) | 2013-02-26 | 2017-12-05 | Triact Therapeutics, Inc. | Cancer therapy |
| US10202356B2 (en) * | 2013-03-14 | 2019-02-12 | Tolero Pharmaceuticals, Inc. | JAK2 and ALK2 inhibitors and methods for their use |
| US10150742B2 (en) | 2013-03-15 | 2018-12-11 | President And Fellows Of Harvard College | Substituted heterocyclic compounds for treating or preventing viral infections |
| US9492471B2 (en) | 2013-08-27 | 2016-11-15 | Celgene Avilomics Research, Inc. | Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase |
| EP3044593A4 (en) | 2013-09-09 | 2017-05-17 | Triact Therapeutics, Inc. | Cancer therapy |
| AU2014337122B2 (en) | 2013-10-18 | 2019-01-03 | Dana-Farber Cancer Institute, Inc. | Heteroaromatic compounds useful for the treatment of proliferative diseases |
| AU2014337044A1 (en) | 2013-10-18 | 2016-05-05 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7) |
| US9415049B2 (en) | 2013-12-20 | 2016-08-16 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| WO2015154038A1 (en) | 2014-04-04 | 2015-10-08 | Syros Pharmaceuticals, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| WO2015164614A1 (en) | 2014-04-23 | 2015-10-29 | Dana-Farber Cancer Institute, Inc. | Janus kinase inhibitors and uses thereof |
| WO2015164604A1 (en) | 2014-04-23 | 2015-10-29 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged janus kinase inhibitors and uses thereof |
| WO2016008048A1 (en) | 2014-07-15 | 2016-01-21 | Ontario Institute For Cancer Research | Methods and devices for predicting anthracycline treatment efficacy |
| WO2016025561A1 (en) | 2014-08-13 | 2016-02-18 | Celgene Avilomics Research, Inc. | Forms and compositions of an erk inhibitor |
| CN105601573B (zh) * | 2014-11-24 | 2021-07-02 | 中国科学院上海药物研究所 | 2-氨基嘧啶类化合物及其药物组合物和应用 |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 |
| AU2016243529B2 (en) | 2015-03-27 | 2021-03-25 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| AU2016276963C1 (en) | 2015-06-12 | 2021-08-05 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| JP7028766B2 (ja) | 2015-09-09 | 2022-03-02 | ダナ－ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼの阻害剤 |
| US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
| US11034690B2 (en) | 2016-11-11 | 2021-06-15 | Saginiet Biosciences Inc. | Heterocyclic modulators of lipid synthesis |
| US11440904B2 (en) * | 2017-08-28 | 2022-09-13 | Zhihong Chen | Substituted pyrimidines, pharmaceutical compositions and therapeutic methods thereof |
| BR112020020246A8 (pt) | 2018-04-05 | 2022-10-18 | Sumitomo Dainippon Pharma Oncology Inc | Inibidores de cinase axl e uso dos mesmos |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| EP3826684A4 (en) | 2018-07-26 | 2022-04-06 | Sumitomo Dainippon Pharma Oncology, Inc. | METHODS OF TREATMENT OF DISEASES ASSOCIATED WITH ABNORMAL ACVR1 EXPRESSION AND ACVR1 INHIBITORS FOR USE IN THE SAME |
| CN111362928A (zh) * | 2018-12-26 | 2020-07-03 | 上海喆邺生物科技有限公司 | 2,4-二氨基嘧啶衍生物 |
| AU2019413694B2 (en) | 2018-12-28 | 2025-03-20 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 and uses thereof |
| TW202115042A (zh) * | 2019-06-21 | 2021-04-16 | 大陸商江蘇豪森藥業集團有限公司 | 芳基磷氧化物類衍生物抑制劑、其製備方法和應用 |
| WO2021163629A1 (en) * | 2020-02-14 | 2021-08-19 | Salk Institute For Biological Studies | Inhibitors of ulk1/2 and methods of using same |
| CN113549018B (zh) * | 2020-04-24 | 2024-02-27 | 中国药科大学 | 蛋白激酶抑制剂及其衍生物，制备方法、药物组合物和应用 |
| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Ａｌｋ﹘５抑制劑和彼之用途 |
| KR102560221B1 (ko) * | 2021-02-24 | 2023-07-27 | 서울대학교산학협력단 | 멀티키나제 억제제 및 이를 포함하는 암 예방 또는 치료용 조성물 |
| KR20230155351A (ko) * | 2022-05-03 | 2023-11-10 | 한국화학연구원 | 5-클로로-2,4-다이아미노피리미딘을 포함하는 키나아제 억제 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 |
| CN115141150B (zh) * | 2022-07-25 | 2024-04-26 | 南通大学 | 2,4,5-三取代嘧啶羟胺酰衍生物及其制备方法与应用 |
| US20250171431A1 (en) * | 2023-08-02 | 2025-05-29 | Horizon Therapeutics Ireland Dac | Heterocyclic inhibitors of igf-1r for treatment of disease |
| KR20250041906A (ko) * | 2023-09-19 | 2025-03-26 | (주)엠디바이오팜 | Hpk1 및 mlk3 저해 활성을 갖는 신규한 화합물 및 이를 함유하는 항암용 조성물 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2585972A (en) * | 1948-11-05 | 1952-02-19 | Muriel Ruth Curd | Process for the manufacture of diquaternary salts of pyrimidylaminoquinolines |
| US2585979A (en) * | 1948-11-05 | 1952-02-19 | Ici Ltd | Process for the manufacture of quaternary salts of pyrimidylamino quinolines |
| US2585910A (en) * | 1948-11-05 | 1952-02-19 | Muriel Ruth Curd | Process for preparing diquaternary salts of pyrimidylamino quinolines |
| US2643253A (en) * | 1950-12-06 | 1953-06-23 | Muriel Ruth Curd | Di-quaternary salts of 4-amino-6-(2'-amino pyrimidyl-4'-amino) quinazoline and process of preparing same |
| GB794043A (en) * | 1955-06-03 | 1958-04-30 | Ici Ltd | New quinoline derivatives |
| WO1998041512A1 (en) * | 1997-03-14 | 1998-09-24 | Celltech Therapeutics Limited | Substituted 2-anilinopyrimidines useful as protein kinase inhibitors |
| US5958935A (en) * | 1995-11-20 | 1999-09-28 | Celltech Therapeutics Limited | Substituted 2-anilinopyrimidines useful as protein kinase inhibitors |
| WO2001040218A1 (fr) * | 1999-11-29 | 2001-06-07 | Aventis Pharma S.A. | Derives arylamines et leur application comme agent antitelomerase |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU206337B (en) | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| US4983608A (en) | 1989-09-05 | 1991-01-08 | Hoechst-Roussell Pharmaceuticals, Inc. | N-substituted-4-pyrimidinamines and pyrimidinediamines |
| US5043317A (en) | 1990-12-14 | 1991-08-27 | Eastman Kodak Company | Yellow dye mixture for thermal color proofing |
| GB9309573D0 (en) | 1993-05-10 | 1993-06-23 | Merck Sharp & Dohme | Therapeutic agents |
| TW574214B (en) | 1994-06-08 | 2004-02-01 | Pfizer | Corticotropin releasing factor antagonists |
| US5935966A (en) | 1995-09-01 | 1999-08-10 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
| DE19750701A1 (de) | 1997-11-15 | 1999-05-20 | Dystar Textilfarben Gmbh & Co | Verfahren zur Umsetzung von fluorsubstituierten Heterocyclen mit Aminen in Gegenwart von Phasentransfer-Katalysatoren |
| ATE401312T1 (de) | 1997-12-15 | 2008-08-15 | Astellas Pharma Inc | Pyrimidin-5-carboxamid-derivate |
| ATE245641T1 (de) | 1998-02-17 | 2003-08-15 | Tularik Inc | Antivirale pyrimidinderivate |
| EP1245567B1 (en) | 1998-03-27 | 2011-03-02 | Janssen Pharmaceutica NV | HIV inhibiting pyrimidine derivatives |
| CA2350801C (en) | 1998-11-10 | 2008-05-20 | Janssen Pharmaceutica N.V. | Hiv replication inhibiting pyrimidines |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| EP1040831A3 (en) | 1999-04-02 | 2003-05-02 | Pfizer Products Inc. | Use of corticotropin releasing factor (CRF) antagonists to prevent sudden death |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| ATE253915T1 (de) | 1999-06-30 | 2003-11-15 | Merck & Co Inc | Src-kinase hemmende verbindungen |
| CA2393896A1 (en) | 1999-09-15 | 2001-03-22 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| KR100820605B1 (ko) | 1999-09-24 | 2008-04-08 | 얀센 파마슈티카 엔.브이. | 항바이러스 조성물 |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| JP2003519143A (ja) | 1999-12-28 | 2003-06-17 | ファーマコピーア，インコーポレーティッド | ピリミジン及びトリアジン系キナーゼ阻害剤 |
| AU2001228638A1 (en) * | 2000-01-28 | 2001-08-07 | Astrazeneca Ab | Chemical compounds |
| CA2400447C (en) | 2000-02-17 | 2008-04-22 | Amgen Inc. | Kinase inhibitors |
| GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| AU4262901A (en) | 2000-03-29 | 2001-10-08 | Cyclacel Ltd | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatmetn of proliferative disorders |
| US7276510B2 (en) | 2000-05-08 | 2007-10-02 | Janssen Pharmaceutica, Inc. | HIV replication inhibitors |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA03005001A (es) | 2000-12-05 | 2003-09-05 | Vertex Pharma | Inhibidores de n- terminal c-jun cinasas (jnk) y otras proteinas cinasas. |
| US7129242B2 (en) | 2000-12-06 | 2006-10-31 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as JNK pathway inhibitors and compositions and methods related thereto |
| US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
| AU2002228922A1 (en) | 2000-12-12 | 2002-06-24 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| EP1377573B1 (en) | 2000-12-15 | 2005-07-27 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| EP1341788B1 (en) | 2000-12-15 | 2005-08-10 | Glaxo Group Limited | Pyrazolopyridines |
| AP2003002825A0 (en) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| DK1343782T3 (da) | 2000-12-21 | 2009-08-24 | Smithkline Beecham Corp | Pyrimidinaminer som angiogenesemodulatorer |
-
2002
- 2002-08-21 US US10/225,783 patent/US6939874B2/en not_active Expired - Fee Related
- 2002-08-22 WO PCT/US2002/026870 patent/WO2003018021A1/en not_active Ceased
- 2002-08-22 MX MXPA04001623A patent/MXPA04001623A/es active IP Right Grant
- 2002-08-22 AU AU2002336390A patent/AU2002336390B2/en not_active Ceased
- 2002-08-22 EP EP02773237A patent/EP1427421A1/en not_active Withdrawn
- 2002-08-22 PL PL02370041A patent/PL370041A1/xx not_active Application Discontinuation
- 2002-08-22 JP JP2003522539A patent/JP2005505535A/ja active Pending
- 2002-08-22 CA CA002457838A patent/CA2457838A1/en not_active Abandoned
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2585972A (en) * | 1948-11-05 | 1952-02-19 | Muriel Ruth Curd | Process for the manufacture of diquaternary salts of pyrimidylaminoquinolines |
| US2585979A (en) * | 1948-11-05 | 1952-02-19 | Ici Ltd | Process for the manufacture of quaternary salts of pyrimidylamino quinolines |
| US2585910A (en) * | 1948-11-05 | 1952-02-19 | Muriel Ruth Curd | Process for preparing diquaternary salts of pyrimidylamino quinolines |
| US2643253A (en) * | 1950-12-06 | 1953-06-23 | Muriel Ruth Curd | Di-quaternary salts of 4-amino-6-(2'-amino pyrimidyl-4'-amino) quinazoline and process of preparing same |
| GB794043A (en) * | 1955-06-03 | 1958-04-30 | Ici Ltd | New quinoline derivatives |
| US5958935A (en) * | 1995-11-20 | 1999-09-28 | Celltech Therapeutics Limited | Substituted 2-anilinopyrimidines useful as protein kinase inhibitors |
| WO1998041512A1 (en) * | 1997-03-14 | 1998-09-24 | Celltech Therapeutics Limited | Substituted 2-anilinopyrimidines useful as protein kinase inhibitors |
| WO2001040218A1 (fr) * | 1999-11-29 | 2001-06-07 | Aventis Pharma S.A. | Derives arylamines et leur application comme agent antitelomerase |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040063705A1 (en) | 2004-04-01 |
| US6939874B2 (en) | 2005-09-06 |
| WO2003018021A1 (en) | 2003-03-06 |
| PL370041A1 (en) | 2005-05-16 |
| JP2005505535A (ja) | 2005-02-24 |
| EP1427421A1 (en) | 2004-06-16 |
| MXPA04001623A (es) | 2004-07-08 |
| CA2457838A1 (en) | 2003-03-06 |
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