ES2366489T3 - Compuesto de pirido (2,3-d) piridinona y sus uso como inhibidores de pi3. - Google Patents
Compuesto de pirido (2,3-d) piridinona y sus uso como inhibidores de pi3. Download PDFInfo
- Publication number
- ES2366489T3 ES2366489T3 ES07804890T ES07804890T ES2366489T3 ES 2366489 T3 ES2366489 T3 ES 2366489T3 ES 07804890 T ES07804890 T ES 07804890T ES 07804890 T ES07804890 T ES 07804890T ES 2366489 T3 ES2366489 T3 ES 2366489T3
- Authority
- ES
- Spain
- Prior art keywords
- amino
- methyl
- pyrimidin
- alkyl
- group
- 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.)
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- -1 PIRID COMPOUND Chemical class 0.000 title claims abstract description 255
- 239000003112 inhibitor Substances 0.000 title description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 367
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 80
- 125000003118 aryl group Chemical group 0.000 claims abstract description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 61
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 38
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000005631 S-sulfonamido group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 73
- 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 46
- 238000011282 treatment Methods 0.000 claims description 29
- 230000010261 cell growth Effects 0.000 claims description 25
- 230000002159 abnormal effect Effects 0.000 claims description 24
- WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 7
- LPJUKWATMDFWDN-UHFFFAOYSA-N 2-amino-6-bromo-8-[4-(2-hydroxyethoxy)cyclohexyl]-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(Br)=CC=2C(C)=NC(N)=NC=2N1C1CCC(OCCO)CC1 LPJUKWATMDFWDN-UHFFFAOYSA-N 0.000 claims description 6
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
- FWILAFBSYLISCN-UHFFFAOYSA-N 2-amino-4-methyl-7-oxo-8-propan-2-yl-n-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C(=O)NC1=CC=NN1 FWILAFBSYLISCN-UHFFFAOYSA-N 0.000 claims description 3
- PDCGXSKEKLYDRP-GASCZTMLSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@H]1CC[C@@H](OCCO)CC1 PDCGXSKEKLYDRP-GASCZTMLSA-N 0.000 claims description 3
- OGLHIMZEXBTIEM-UHFFFAOYSA-N N-(1H-pyrazol-5-yl)pyrimidine-4-carboxamide Chemical compound N1=CN=C(C=C1)C(=O)NC1=CC=NN1 OGLHIMZEXBTIEM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- SPZLNUYSXWJTDI-UHFFFAOYSA-N 8-cyclopentyl-4-methyl-2-(methylamino)-7-oxo-n-pyridin-2-ylpyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC(C)=C2C=C1C(=O)NC1=CC=CC=N1 SPZLNUYSXWJTDI-UHFFFAOYSA-N 0.000 claims description 2
- WOMVHFKOGGCXMG-SHTZXODSSA-N C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=C(F)C(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 WOMVHFKOGGCXMG-SHTZXODSSA-N 0.000 claims description 2
- PCOJUVWPYNNKBZ-ULQDDVLXSA-N C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OC[C@@H](O)CO)CC1 PCOJUVWPYNNKBZ-ULQDDVLXSA-N 0.000 claims description 2
- UAADDCZXGPRVQO-HDJSIYSDSA-N O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CNN=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 UAADDCZXGPRVQO-HDJSIYSDSA-N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- KMYHNHSRXMFXAJ-QAQDUYKDSA-N C1=NC(N(C)C)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 Chemical compound C1=NC(N(C)C)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1CC[C@@H](OCCO)CC1 KMYHNHSRXMFXAJ-QAQDUYKDSA-N 0.000 claims 1
- ISROHHNFTMLKES-JOCQHMNTSA-N C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 Chemical compound C1=NC(OC)=NC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1[C@@H]1C[C@@H](OCCO)C1 ISROHHNFTMLKES-JOCQHMNTSA-N 0.000 claims 1
- BPRLASJBTWVPSB-SHTZXODSSA-N O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=CN(C)N=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 BPRLASJBTWVPSB-SHTZXODSSA-N 0.000 claims 1
- GPUZESZBHMOJPX-JOCQHMNTSA-N O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1[C@H]1CC[C@H](OCCO)CC1 GPUZESZBHMOJPX-JOCQHMNTSA-N 0.000 claims 1
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 416
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 347
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
- 238000005481 NMR spectroscopy Methods 0.000 description 139
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
- 239000000243 solution Substances 0.000 description 117
- 239000000203 mixture Substances 0.000 description 109
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 97
- 238000000034 method Methods 0.000 description 90
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
- 238000005160 1H NMR spectroscopy Methods 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 59
- 239000002904 solvent Substances 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000007787 solid Substances 0.000 description 57
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 47
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
- 239000012267 brine Substances 0.000 description 38
- 239000003795 chemical substances by application Substances 0.000 description 38
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 36
- 206010028980 Neoplasm Diseases 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 230000002829 reductive effect Effects 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- 238000003818 flash chromatography Methods 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 23
- 239000002246 antineoplastic agent Substances 0.000 description 22
- 239000012043 crude product Substances 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- 201000011510 cancer Diseases 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 18
- 201000010099 disease Diseases 0.000 description 18
- 229940086542 triethylamine Drugs 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 238000009472 formulation Methods 0.000 description 17
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 17
- 235000011181 potassium carbonates Nutrition 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 239000012453 solvate Substances 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
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- 229910052794 bromium Inorganic materials 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 11
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 11
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- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
- PZNBITSSQHGPKM-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-4-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC)=NC(C)=C2C=C(Br)C(=O)N1C1CCCC1 PZNBITSSQHGPKM-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- 108091007960 PI3Ks Proteins 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 8
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Classifications
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- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
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| US947852P | 2007-07-03 | ||
| US95262807P | 2007-07-30 | 2007-07-30 | |
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| PCT/IB2007/002578 WO2008032162A1 (en) | 2006-09-15 | 2007-09-03 | Pyrido (2, 3-d) pyrimidin0ne compounds and their use as pi3 inhibitors |
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| WO2008032162A1 (en) * | 2006-09-15 | 2008-03-20 | Pfizer Products Inc. | Pyrido (2, 3-d) pyrimidin0ne compounds and their use as pi3 inhibitors |
| RS52939B (sr) * | 2007-04-10 | 2014-02-28 | Exelixis Inc. | Postupci za lečenje kancera upotrebom piridopirimidinonskih inhibitora pi3k alfa |
| CN101711249A (zh) * | 2007-04-11 | 2010-05-19 | 埃克塞里艾克西斯公司 | 作为PI3K-α的抑制剂用于治疗癌症的吡啶并[2,3-D]嘧啶-7-酮化合物 |
| MX2011000440A (es) | 2008-07-11 | 2011-02-24 | Novartis Ag | Combinacion de (a) un inhibidor de fosfoinositido 3-cinasa y (b) un modulador de la ruta de ras/raf/mek. |
| JP5674661B2 (ja) | 2008-08-20 | 2015-02-25 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | エチニル置換ピリジンおよびピリミジン誘導体ならびにそれらのウイルス感染の治療における使用 |
| AU2009282574B2 (en) * | 2008-08-20 | 2014-08-21 | Merck Sharp & Dohme Corp. | Ethenyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| US8697694B2 (en) | 2008-08-20 | 2014-04-15 | Merck Sharp & Dohme Corp. | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| WO2010022126A1 (en) | 2008-08-20 | 2010-02-25 | Schering Corporation | Azo-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| WO2010039740A1 (en) * | 2008-09-30 | 2010-04-08 | Exelixis, Inc. | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kα AND MTOR |
| US10010439B2 (en) | 2010-06-13 | 2018-07-03 | Synerz Medical, Inc. | Intragastric device for treating obesity |
| US8628554B2 (en) | 2010-06-13 | 2014-01-14 | Virender K. Sharma | Intragastric device for treating obesity |
| US9526648B2 (en) | 2010-06-13 | 2016-12-27 | Synerz Medical, Inc. | Intragastric device for treating obesity |
| US10420665B2 (en) | 2010-06-13 | 2019-09-24 | W. L. Gore & Associates, Inc. | Intragastric device for treating obesity |
| BR112013014914B8 (pt) | 2010-12-16 | 2020-08-04 | Hoffmann La Roche | composto, composição farmacêutica e uso de um composto |
| US8664230B2 (en) * | 2011-03-17 | 2014-03-04 | The Asan Foundation | Pyridopyrimidine derivatives and use thereof |
| TW201306842A (zh) * | 2011-06-15 | 2013-02-16 | Exelixis Inc | 使用ｐｉ３ｋ／ｍｔｏｒ吡啶並嘧啶酮抑制劑及苯達莫司汀及／或利妥昔單抗治療惡性血液疾病之組合療法 |
| US9675595B2 (en) | 2011-08-31 | 2017-06-13 | Novartis Ag | Synergistic combinations of PI3K- and MEK-inhibitors |
| CN104829609B (zh) * | 2014-02-11 | 2016-08-03 | 北大方正集团有限公司 | 取代的吡啶并嘧啶化合物及其制备方法和应用 |
| CN105294681B (zh) | 2014-07-26 | 2017-07-07 | 广东东阳光药业有限公司 | Cdk类小分子抑制剂的化合物及其用途 |
| CN105330699B (zh) * | 2014-08-13 | 2018-12-04 | 山东汇睿迪生物技术有限公司 | 一种含磷吡啶并[2,3-d]嘧啶-7-酮类化合物或其药学上可接受的盐、药物组合物及其应用 |
| WO2016055907A1 (en) | 2014-10-10 | 2016-04-14 | Pfizer Inc. | Synergistic auristatin combinations |
| WO2016193860A1 (en) | 2015-06-04 | 2016-12-08 | Pfizer Inc. | Solid dosage forms of palbociclib |
| US10779980B2 (en) | 2016-04-27 | 2020-09-22 | Synerz Medical, Inc. | Intragastric device for treating obesity |
| JP2019519593A (ja) | 2016-07-06 | 2019-07-11 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガンＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍｉｃｈｉｇａｎ | ＭＥＫ／ＰＩ３Ｋ及びｍＴＯＲ／ＭＥＫ／ＰＩ３Ｋ生物学的経路の多官能性阻害剤、並びに同多官能性阻害剤を用いた治療方法 |
| ES2876411T3 (es) | 2016-08-15 | 2021-11-12 | Pfizer | Inhibidores de piridopirimdinona CDK2/4/6 |
| JP2020503289A (ja) * | 2016-12-14 | 2020-01-30 | ターベダ セラピューティクス インコーポレイテッドＴａｒｖｅｄａ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． | Ｈｓｐ９０標的化コンジュゲート及びその製剤 |
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| EA202092692A1 (ru) | 2018-06-15 | 2021-04-21 | Навитор Фармасьютикалз, Инк. | Аналоги рапамицина и их применения |
| US20220220103A1 (en) * | 2018-12-28 | 2022-07-14 | Spv Therapeutics Inc. | Cyclin-dependent kinase inhibitors |
| WO2020140055A1 (en) * | 2018-12-28 | 2020-07-02 | Spv Therapeutics Inc. | Cyclin-dependent kinase inhibitors |
| US11583538B2 (en) | 2019-04-08 | 2023-02-21 | Venenum Biodesign, LLC | Substituted pyrrolo[1,2-a]pyrazines and pyrrolo[1,2-a][1,4]diazepines as TREX1 inhibitors |
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| CN114901664B (zh) * | 2020-01-10 | 2024-07-02 | 南京再明医药有限公司 | 吡啶酮化合物及应用 |
| WO2022075974A1 (en) * | 2020-10-06 | 2022-04-14 | Venenum Biodesign, LLC | Cyclic trex1 inhibitors |
| JP2023549540A (ja) | 2020-11-18 | 2023-11-27 | デシフェラ・ファーマシューティカルズ，エルエルシー | Ｇｃｎ２およびｐｅｒｋキナーゼ阻害剤およびその使用方法 |
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