MX2009000220A - Compuestos de pirimido fusionados. - Google Patents
Compuestos de pirimido fusionados.Info
- Publication number
- MX2009000220A MX2009000220A MX2009000220A MX2009000220A MX2009000220A MX 2009000220 A MX2009000220 A MX 2009000220A MX 2009000220 A MX2009000220 A MX 2009000220A MX 2009000220 A MX2009000220 A MX 2009000220A MX 2009000220 A MX2009000220 A MX 2009000220A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- carbon atoms
- group
- alkyl
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 272
- 238000000034 method Methods 0.000 claims abstract description 52
- 230000008569 process Effects 0.000 claims abstract description 42
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 947
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 298
- 229910052739 hydrogen Inorganic materials 0.000 claims description 189
- 229910052799 carbon Inorganic materials 0.000 claims description 186
- -1 piperazinylcarbonyl Chemical group 0.000 claims description 183
- 239000001257 hydrogen Substances 0.000 claims description 182
- 125000000217 alkyl group Chemical group 0.000 claims description 173
- 125000005842 heteroatom Chemical group 0.000 claims description 146
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 126
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 122
- 150000002431 hydrogen Chemical group 0.000 claims description 96
- 229920006395 saturated elastomer Polymers 0.000 claims description 86
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 75
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 229910052757 nitrogen Inorganic materials 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 150000001721 carbon Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000004414 alkyl thio group Chemical group 0.000 claims description 54
- 125000003282 alkyl amino group Chemical group 0.000 claims description 53
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 43
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 206010028980 Neoplasm Diseases 0.000 claims description 23
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- 125000003386 piperidinyl group Chemical group 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000002757 morpholinyl group Chemical group 0.000 claims description 20
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000005977 Ethylene Substances 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 16
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 16
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 229910003827 NRaRb Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- ODWVFJUVKLPMDM-UHFFFAOYSA-N 9-methyl-9-azabicyclo[3.3.1]nonane Chemical class C1CCC2CCCC1N2C ODWVFJUVKLPMDM-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 claims 2
- IUBVHENRQMZUQG-UHFFFAOYSA-N 1,2-bis(1,3-benzodioxol-5-yl)ethane-1,2-dione Chemical compound C1=C2OCOC2=CC(C(C(=O)C=2C=C3OCOC3=CC=2)=O)=C1 IUBVHENRQMZUQG-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- PIYDNEWDZZFKKO-ILVMPNSOSA-N n-[(1s)-3-[7-(2-methylbenzimidazol-1-yl)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl]-1-phenylpropyl]cyclobutanecarboxamide Chemical class N([C@@H](CCN1C2COCC1CC(C2)N1C2=CC=CC=C2N=C1C)C=1C=CC=CC=1)C(=O)C1CCC1 PIYDNEWDZZFKKO-ILVMPNSOSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 620
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 150
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 140
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 129
- 238000005481 NMR spectroscopy Methods 0.000 description 113
- 239000000543 intermediate Substances 0.000 description 102
- 239000007787 solid Substances 0.000 description 85
- 239000000047 product Substances 0.000 description 79
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 59
- 229910021529 ammonia Inorganic materials 0.000 description 55
- 239000000203 mixture Substances 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 49
- 238000004007 reversed phase HPLC Methods 0.000 description 48
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 37
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 36
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- 229960005419 nitrogen Drugs 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 21
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 20
- 239000007821 HATU Substances 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 16
- 229960001124 trientine Drugs 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 230000014759 maintenance of location Effects 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 15
- 229940039407 aniline Drugs 0.000 description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 11
- XBYFLVPPIOYEJF-UHFFFAOYSA-N 4-amino-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NC2CCN(C)CC2)=C1 XBYFLVPPIOYEJF-UHFFFAOYSA-N 0.000 description 10
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US81887806P | 2006-07-06 | 2006-07-06 | |
| PCT/GB2007/002490 WO2008003958A2 (en) | 2006-07-06 | 2007-07-05 | Fused pyrimido compounds |
Publications (1)
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|---|---|
| MX2009000220A true MX2009000220A (es) | 2009-01-22 |
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| MX2009000220A MX2009000220A (es) | 2006-07-06 | 2007-07-05 | Compuestos de pirimido fusionados. |
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| EP (1) | EP2046793A2 (https=) |
| JP (1) | JP2009542613A (https=) |
| KR (1) | KR20090038895A (https=) |
| CN (1) | CN101511836A (https=) |
| AR (1) | AR061850A1 (https=) |
| AU (1) | AU2007270931A1 (https=) |
| BR (1) | BRPI0714045A2 (https=) |
| CA (1) | CA2656936A1 (https=) |
| CL (1) | CL2007001973A1 (https=) |
| EC (1) | ECSP099044A (https=) |
| IL (1) | IL196207A0 (https=) |
| MX (1) | MX2009000220A (https=) |
| NO (1) | NO20090052L (https=) |
| RU (1) | RU2009103810A (https=) |
| TW (1) | TW200808325A (https=) |
| UY (1) | UY30472A1 (https=) |
| WO (1) | WO2008003958A2 (https=) |
| ZA (1) | ZA200900073B (https=) |
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| US8063050B2 (en) * | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| EP2049500B1 (en) | 2006-07-06 | 2011-09-07 | Array Biopharma, Inc. | Cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| WO2008113711A1 (en) | 2007-03-22 | 2008-09-25 | F. Hoffmann-La Roche Ag | Substituted pyrimidodiazepines useful as plk1 inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| CN101918373B (zh) | 2007-07-05 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| CA2695753A1 (en) * | 2007-08-15 | 2009-02-19 | Vertex Pharmaceuticals Incorporated | Compounds useful as protein kinases inhibitors |
| WO2009042711A1 (en) * | 2007-09-25 | 2009-04-02 | Takeda Pharmaceutical Company Limited | Polo-like kinase inhibitors |
| EP2205603B1 (en) | 2007-09-28 | 2014-01-15 | Cyclacel Limited | Pyrimidine derivatives as protein kinase inhibitors |
| WO2009067547A1 (en) * | 2007-11-19 | 2009-05-28 | Takeda Pharmaceutical Company Limited | Polo-like kinase inhibitors |
| NZ586346A (en) | 2008-01-09 | 2012-02-24 | Array Biopharma Inc | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US8853216B2 (en) | 2008-01-09 | 2014-10-07 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor |
| JP2011527667A (ja) | 2008-06-18 | 2011-11-04 | 武田薬品工業株式会社 | ハロ置換ピリミドジアゼピン |
| EP4585589A3 (en) * | 2008-12-03 | 2025-11-19 | The Scripps Research Institute | Stem cell cultures |
| EP2379559B1 (en) | 2009-01-06 | 2017-10-25 | Dana-Farber Cancer Institute, Inc. | Pyrimido-diazepinone kinase scaffold compounds and methods of treating disorders |
| RS57869B1 (sr) | 2009-06-17 | 2018-12-31 | Vertex Pharma | Inhibitori replikacije virusa gripa |
| TWI399551B (zh) * | 2009-06-26 | 2013-06-21 | Senao Networks Inc | Burner device and burner method |
| SG179206A1 (en) | 2009-09-25 | 2012-04-27 | Vertex Pharma | Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors |
| CA2773827A1 (en) * | 2009-09-25 | 2011-03-31 | Vertex Pharmaceuticals Incorporated | Methods for preparing pyrimidine derivatives useful as protein kinase inhibitors |
| US8466155B2 (en) * | 2009-10-02 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Pyrimidines |
| US20110218295A1 (en) * | 2010-03-02 | 2011-09-08 | Basf Se | Anionic associative rheology modifiers |
| US8673275B2 (en) | 2010-03-02 | 2014-03-18 | Basf Se | Block copolymers and their use |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| TR201815685T4 (tr) | 2011-04-01 | 2018-11-21 | Genentech Inc | Kanser tedavisi için akt ve mek inhibe edici bileşiklerin kombinasyonları. |
| KR102021157B1 (ko) | 2011-04-01 | 2019-09-11 | 제넨테크, 인크. | Ａｋｔ 억제제 화합물 및 아비라테론의 조합물, 및 사용 방법 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| GB201205752D0 (en) * | 2012-03-30 | 2012-05-16 | Cyclacel Ltd | Treatment |
| HRP20181272T1 (hr) | 2013-11-13 | 2018-10-05 | Vertex Pharmaceuticals Incorporated | Postupci priprave inhibitora replikacije virusa influence |
| RS59144B1 (sr) | 2013-11-13 | 2019-09-30 | Vertex Pharma | Inhibitori replikacije virusa influence |
| GB201403536D0 (en) | 2014-02-28 | 2014-04-16 | Cancer Rec Tech Ltd | Inhibitor compounds |
| JP6857617B2 (ja) | 2015-05-13 | 2021-04-14 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤 |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| CN107949279A (zh) * | 2015-07-06 | 2018-04-20 | 得克萨斯系统大学评议会 | 可用作用于治疗人类癌症的抗癌剂的苯甲酰胺或苯扎明化合物 |
| US11155556B2 (en) * | 2016-04-07 | 2021-10-26 | Dana-Farber Cancer Institute, Inc. | Pyrimido-diazepinone kinase scaffold compounds and methods for treating PI3K-mediated disorders |
| CN115485025A (zh) * | 2020-02-28 | 2022-12-16 | 雷密克斯医疗公司 | 用于调节剪接的化合物和方法 |
| WO2022145989A1 (ko) * | 2020-12-31 | 2022-07-07 | (주) 업테라 | 선택적 plk1 억제제로서의 피리미도디아제핀 유도체 |
| EP4157849A4 (en) * | 2021-08-10 | 2024-12-11 | Uppthera, Inc. | NOVEL PLK1 DEGRADATION-INDUCING COMPOUND |
| WO2023034812A1 (en) * | 2021-08-30 | 2023-03-09 | Remix Therapeutics Inc. | Compounds and methods for modulating splicing |
| CN114392258B (zh) * | 2021-12-30 | 2024-04-16 | 北京朗瑞邦科技有限公司 | 一种4H-吡喃并[2,3-c]吡啶-4-酮类化合物药物制剂及其制备方法 |
| CN113999244B (zh) * | 2021-12-30 | 2022-05-20 | 北京鑫开元医药科技有限公司 | 一种4H-吡喃并[2,3-c]吡啶-4-酮类化合物及其制备方法 |
| TW202345806A (zh) | 2022-03-31 | 2023-12-01 | 美商艾伯維有限公司 | 噻唑并〔５，４－ｂ〕吡啶ｍａｌｔ－１抑制劑 |
Family Cites Families (17)
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| PT1427730E (pt) | 2001-09-04 | 2006-11-30 | Boehringer Ingelheim Pharma | Novas di-hidropteridinonas, processo para sua preparação e sua utilização como medicamento |
| US6806272B2 (en) | 2001-09-04 | 2004-10-19 | Boehringer Ingelheim Pharma Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| BR0318145A (pt) | 2003-02-26 | 2006-02-21 | Boehringer Ingelheim Pharma | dihidropteridinonas, processos para a sua preparação e sua aplicação como medicamento |
| US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| DE102004029784A1 (de) | 2004-06-21 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004034623A1 (de) | 2004-07-16 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 6-Formyl-tetrahydropteridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US20060074088A1 (en) | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
| US7759485B2 (en) | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
| US7728134B2 (en) * | 2004-08-14 | 2010-06-01 | Boehringer Ingelheim International Gmbh | Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| US20060035903A1 (en) | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
| EP1632493A1 (de) | 2004-08-25 | 2006-03-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1630163A1 (de) | 2004-08-25 | 2006-03-01 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| CA2575804A1 (en) | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim International Gmbh | Pteridinones used as plk (polo like kinase) inhibitors |
| JP2008510771A (ja) | 2004-08-27 | 2008-04-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ジヒドロプテリジノン、その製造方法および医薬薬剤としてのその使用 |
| US7439358B2 (en) | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
| TW200804389A (en) | 2006-02-14 | 2008-01-16 | Vertex Pharma | Dihydrodiazepines useful as inhibitors of protein kinases |
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2007
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- 2007-07-05 MX MX2009000220A patent/MX2009000220A/es not_active Application Discontinuation
- 2007-07-05 CA CA002656936A patent/CA2656936A1/en not_active Abandoned
- 2007-07-05 US US11/773,674 patent/US7709471B2/en not_active Expired - Fee Related
- 2007-07-05 KR KR1020097002535A patent/KR20090038895A/ko not_active Withdrawn
- 2007-07-05 RU RU2009103810/04A patent/RU2009103810A/ru not_active Application Discontinuation
- 2007-07-05 EP EP07733455A patent/EP2046793A2/en not_active Withdrawn
- 2007-07-05 WO PCT/GB2007/002490 patent/WO2008003958A2/en not_active Ceased
- 2007-07-05 CN CNA2007800331017A patent/CN101511836A/zh active Pending
- 2007-07-05 BR BRPI0714045-2A patent/BRPI0714045A2/pt not_active IP Right Cessation
- 2007-07-05 CL CL200701973A patent/CL2007001973A1/es unknown
- 2007-07-05 AU AU2007270931A patent/AU2007270931A1/en not_active Abandoned
- 2007-07-05 JP JP2009517423A patent/JP2009542613A/ja active Pending
- 2007-07-06 UY UY30472A patent/UY30472A1/es unknown
- 2007-07-06 AR ARP070103042A patent/AR061850A1/es not_active Application Discontinuation
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2008
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- 2009-01-06 NO NO20090052A patent/NO20090052L/no not_active Application Discontinuation
- 2009-01-09 EC EC2009009044A patent/ECSP099044A/es unknown
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| WO2008003958A3 (en) | 2008-03-06 |
| ZA200900073B (en) | 2010-06-30 |
| US7709471B2 (en) | 2010-05-04 |
| US20080009482A1 (en) | 2008-01-10 |
| EP2046793A2 (en) | 2009-04-15 |
| KR20090038895A (ko) | 2009-04-21 |
| CN101511836A (zh) | 2009-08-19 |
| UY30472A1 (es) | 2008-02-29 |
| JP2009542613A (ja) | 2009-12-03 |
| TW200808325A (en) | 2008-02-16 |
| AR061850A1 (es) | 2008-09-24 |
| IL196207A0 (en) | 2009-09-22 |
| AU2007270931A1 (en) | 2008-01-10 |
| CL2007001973A1 (es) | 2008-04-04 |
| CA2656936A1 (en) | 2008-01-10 |
| BRPI0714045A2 (pt) | 2012-12-11 |
| RU2009103810A (ru) | 2010-08-20 |
| WO2008003958A2 (en) | 2008-01-10 |
| NO20090052L (no) | 2009-01-28 |
| ECSP099044A (es) | 2009-02-27 |
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