CA2842190A1 - Heterocyclic compounds and uses thereof - Google Patents
Heterocyclic compounds and uses thereof Download PDFInfo
- Publication number
- CA2842190A1 CA2842190A1 CA2842190A CA2842190A CA2842190A1 CA 2842190 A1 CA2842190 A1 CA 2842190A1 CA 2842190 A CA2842190 A CA 2842190A CA 2842190 A CA2842190 A CA 2842190A CA 2842190 A1 CA2842190 A1 CA 2842190A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- substituted
- heteroaryl
- cycloalkyl
- 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.)
- Abandoned
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 325
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 55
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 241
- 125000000217 alkyl group Chemical group 0.000 claims description 235
- 125000003118 aryl group Chemical group 0.000 claims description 219
- -1 cyano, hydroxyl Chemical group 0.000 claims description 214
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 187
- 125000000623 heterocyclic group Chemical group 0.000 claims description 177
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 149
- 125000003342 alkenyl group Chemical group 0.000 claims description 139
- 125000000304 alkynyl group Chemical group 0.000 claims description 135
- 125000005843 halogen group Chemical group 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
- 239000001257 hydrogen Substances 0.000 claims description 114
- 125000003545 alkoxy group Chemical group 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 107
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 99
- 125000003368 amide group Chemical group 0.000 claims description 97
- 125000002252 acyl group Chemical group 0.000 claims description 95
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 85
- 125000004423 acyloxy group Chemical group 0.000 claims description 82
- 125000001424 substituent group Chemical group 0.000 claims description 80
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 78
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 78
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 78
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 229910019142 PO4 Inorganic materials 0.000 claims description 44
- 239000010452 phosphate Chemical group 0.000 claims description 44
- 239000004202 carbamide Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 42
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 41
- 125000004043 oxo group Chemical group O=* 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 18
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 150000003462 sulfoxides Chemical group 0.000 claims description 9
- 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims description 8
- 108091007960 PI3Ks Proteins 0.000 claims description 8
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 7
- 150000003457 sulfones Chemical group 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 150000002829 nitrogen Chemical class 0.000 claims description 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract description 35
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract description 35
- 201000010099 disease Diseases 0.000 abstract description 20
- 238000011282 treatment Methods 0.000 abstract description 10
- 150000002431 hydrogen Chemical group 0.000 description 79
- 229910052799 carbon Inorganic materials 0.000 description 75
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 72
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 63
- 125000004432 carbon atom Chemical group C* 0.000 description 44
- 125000005842 heteroatom Chemical group 0.000 description 44
- 150000003254 radicals Chemical class 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 33
- 125000004429 atom Chemical group 0.000 description 32
- 229940002612 prodrug Drugs 0.000 description 29
- 239000000651 prodrug Substances 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 25
- 229930195729 fatty acid Natural products 0.000 description 25
- 235000014113 dietary fatty acids Nutrition 0.000 description 24
- 239000000194 fatty acid Substances 0.000 description 24
- 125000006413 ring segment Chemical group 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 108010029485 Protein Isoforms Proteins 0.000 description 21
- 102000001708 Protein Isoforms Human genes 0.000 description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
- 125000004452 carbocyclyl group Chemical group 0.000 description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000004094 surface-active agent Substances 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 229920001223 polyethylene glycol Polymers 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 18
- 125000002877 alkyl aryl group Chemical group 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 125000004438 haloalkoxy group Chemical group 0.000 description 18
- 239000001301 oxygen Chemical group 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 125000004414 alkyl thio group Chemical group 0.000 description 17
- 125000005110 aryl thio group Chemical group 0.000 description 17
- 125000005884 carbocyclylalkyl group Chemical group 0.000 description 17
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 17
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 17
- 125000005864 sulfonamidyl group Chemical group 0.000 description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 17
- 125000004962 sulfoxyl group Chemical group 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 16
- 125000004104 aryloxy group Chemical group 0.000 description 16
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 16
- 239000003755 preservative agent Substances 0.000 description 16
- 239000011593 sulfur Substances 0.000 description 16
- TVPVAGUBJCNUSJ-UHFFFAOYSA-N 1,1-diazidoguanidine Chemical group [N-]=[N+]=NN(C(=N)N)N=[N+]=[N-] TVPVAGUBJCNUSJ-UHFFFAOYSA-N 0.000 description 15
- 239000002202 Polyethylene glycol Substances 0.000 description 15
- 108091000080 Phosphotransferase Proteins 0.000 description 14
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 14
- 102000020233 phosphotransferase Human genes 0.000 description 14
- 108090000765 processed proteins & peptides Proteins 0.000 description 14
- 102000004169 proteins and genes Human genes 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- 239000012453 solvate Substances 0.000 description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- 229920001184 polypeptide Polymers 0.000 description 12
- 102000004196 processed proteins & peptides Human genes 0.000 description 12
- 238000003419 tautomerization reaction Methods 0.000 description 12
- 125000001544 thienyl group Chemical group 0.000 description 12
- 230000008901 benefit Effects 0.000 description 11
- 239000000969 carrier Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 235000011187 glycerol Nutrition 0.000 description 11
- 229960005150 glycerol Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000005829 chemical entities Chemical class 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 230000019491 signal transduction Effects 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 229930182558 Sterol Natural products 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 125000001786 isothiazolyl group Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 235000013772 propylene glycol Nutrition 0.000 description 9
- 150000003432 sterols Chemical class 0.000 description 9
- 235000003702 sterols Nutrition 0.000 description 9
- 125000000547 substituted alkyl group Chemical group 0.000 description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000004677 hydrates Chemical class 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 102000001253 Protein Kinase Human genes 0.000 description 7
- 235000010443 alginic acid Nutrition 0.000 description 7
- 229920000615 alginic acid Polymers 0.000 description 7
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- 229940024606 amino acid Drugs 0.000 description 7
- 239000000460 chlorine Chemical group 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000007884 disintegrant Substances 0.000 description 7
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
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- 125000006239 protecting group Chemical group 0.000 description 7
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- 125000000168 pyrrolyl group Chemical group 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
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- 229920002472 Starch Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 6
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- 239000003085 diluting agent Substances 0.000 description 6
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
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- 125000002950 monocyclic group Chemical group 0.000 description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 4
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
- 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)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
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|---|---|---|---|
| US201161509441P | 2011-07-19 | 2011-07-19 | |
| US61/509,441 | 2011-07-19 | ||
| US201261622251P | 2012-04-10 | 2012-04-10 | |
| US61/622,251 | 2012-04-10 | ||
| PCT/US2012/047190 WO2013012918A1 (en) | 2011-07-19 | 2012-07-18 | Heterocyclic compounds and uses thereof |
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| TW (1) | TWI565709B (enExample) |
| WO (1) | WO2013012918A1 (enExample) |
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| JP4903036B2 (ja) * | 2003-01-06 | 2012-03-21 | アンジオケム・インコーポレーテッド | 血液脳関門を通過する担体としてのアプロチニンおよび類似体 |
| PT1993360T (pt) | 2005-12-28 | 2017-05-25 | Vertex Pharma | Formas sólidas de n-[2,4-bis(1,1-dimetiletil)-5-hidroxifenil]-1,4-di-hidro-4-oxoquinolina-3-carboxamida |
| US9365634B2 (en) * | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| MX358640B (es) | 2008-01-04 | 2018-08-29 | Intellikine Llc | Isoquinolin-1 (2h) -onas y tieno [2,3-d]pirimidin-4(3h) -onas substituidas, y metodos de uso de las mismas. |
| WO2009127072A1 (en) | 2008-04-18 | 2009-10-22 | Angiochem Inc. | Pharmaceutical compositions of paclitaxel, paclitaxel analogs or paclitaxel conjugates and related methods of preparation and use |
| US8703778B2 (en) | 2008-09-26 | 2014-04-22 | Intellikine Llc | Heterocyclic kinase inhibitors |
| CA2740317A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Etoposide and doxorubicin conjugates for drug delivery |
| WO2010043047A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Conjugates of glp-1 agonists and uses thereof |
| US9914754B2 (en) | 2008-12-05 | 2018-03-13 | Angiochem Inc. | Conjugates of neurotensin or neurotensin analogs and uses thereof |
| AU2009327267A1 (en) | 2008-12-17 | 2011-07-14 | Angiochem, Inc. | Membrane type-1 matrix metalloprotein inhibitors and uses thereof |
| ES2729261T3 (es) | 2009-04-20 | 2019-10-31 | Angiochem Inc | Tratamiento del cáncer de ovario utilizando un agente anticancerígeno conjugado con un análogo de Angiopep-2 |
| JP5789252B2 (ja) | 2009-05-07 | 2015-10-07 | インテリカイン， エルエルシー | 複素環式化合物およびその使用 |
| WO2011000095A1 (en) | 2009-07-02 | 2011-01-06 | Angiochem Inc. | Multimeric peptide conjugates and uses thereof |
| EP2571357B1 (en) | 2010-05-21 | 2016-07-06 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| NZ604040A (en) | 2010-06-03 | 2015-02-27 | Pharmacyclics Inc | The use of inhibitors of bruton’s tyrosine kinase (btk) |
| CN103298474B (zh) | 2010-11-10 | 2016-06-29 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| TWI546305B (zh) | 2011-01-10 | 2016-08-21 | 英菲尼提製藥股份有限公司 | 製備異喹啉酮之方法及異喹啉酮之固體形式 |
| EP2481500A1 (de) | 2011-01-31 | 2012-08-01 | Stopinc Aktiengesellschaft | Verschlussplatte sowie ein Schiebenverschluss am Ausguss eines Metallschmelze enthaltenden Behälters |
| AU2012284088B2 (en) | 2011-07-19 | 2015-10-08 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2013012918A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| CA2846431A1 (en) | 2011-08-29 | 2013-03-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| US8940742B2 (en) * | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| KR20150032340A (ko) | 2012-07-24 | 2015-03-25 | 파마시클릭스, 인코포레이티드 | 브루톤 티로신 키나제(btk)의 억제제에 대한 내성과 관련된 돌연변이 |
| CN105102000B (zh) | 2012-11-01 | 2021-10-22 | 无限药品公司 | 使用pi3激酶亚型调节剂的癌症疗法 |
| CN104870017B (zh) | 2012-11-08 | 2020-08-14 | 理森制药股份公司 | 含有PDE4抑制剂和PI3δ或双重PI3δ-γ激酶抑制剂的药物组合物 |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| SG10201709926VA (en) | 2013-05-30 | 2017-12-28 | Infinity Pharmaceuticals Inc | Treatment of cancers using pi3 kinase isoform modulators |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| CA2918938C (en) | 2013-09-22 | 2021-05-18 | Calitor Sciences, Llc | Substituted aminopyrimidine compounds and methods of use |
| MX389256B (es) * | 2013-10-04 | 2025-03-20 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos. |
| US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
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| EA201691872A1 (ru) * | 2014-03-19 | 2017-04-28 | Инфинити Фармасьютикалз, Инк. | Гетероциклические соединения для применения в лечении pi3k-гамма-опосредованных расстройств |
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| JOP20150177B1 (ar) | 2014-08-01 | 2021-08-17 | Janssen Pharmaceutica Nv | مركبات 6 ، 7 ثاني هيدرو بيرازولو [ 1، 5 الفا ] بيرازين – 4 (5 يد) – اون واستخدامها كمنظمات الوسترية سلبية لمستقبلات ملجور 2 |
| JOP20150179B1 (ar) | 2014-08-01 | 2021-08-17 | Janssen Pharmaceutica Nv | مركبات 6 ، 7 ثاني هيدرو بيرازولو [ 1، 5 الفا ] بيرازين – 4 (5 يد) – اون واستخدامها كمنظمات الوسترية سلبية لمستقبلات ملجور 2 |
| TW201618773A (zh) | 2014-08-11 | 2016-06-01 | 艾森塔製藥公司 | Ｂｔｋ抑制劑、ｐｉ３ｋ抑制劑、ｊａｋ－２抑制劑、及／或ｃｄｋ４／６抑制劑的治療組合物 |
| SI3179992T1 (sl) | 2014-08-11 | 2022-09-30 | Acerta Pharma B.V. | Terapevtske kombinacije zaviralca BTK, zaviralca PD-1 in/ali zaviralca PD-L1 |
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-
2012
- 2012-07-18 WO PCT/US2012/047190 patent/WO2013012918A1/en not_active Ceased
- 2012-07-18 CA CA2842190A patent/CA2842190A1/en not_active Abandoned
- 2012-07-18 AR ARP120102605A patent/AR088218A1/es unknown
- 2012-07-18 JP JP2014521731A patent/JP6027611B2/ja not_active Expired - Fee Related
- 2012-07-18 HK HK14111976.9A patent/HK1198475A1/xx unknown
- 2012-07-18 EP EP12741197.3A patent/EP2734530A1/en not_active Withdrawn
- 2012-07-18 CN CN201280045608.5A patent/CN103946226A/zh active Pending
- 2012-07-18 US US13/552,473 patent/US9056877B2/en active Active
- 2012-07-18 KR KR1020147004100A patent/KR20140063605A/ko not_active Withdrawn
- 2012-07-18 MX MX2014000648A patent/MX2014000648A/es unknown
- 2012-07-18 TW TW101125905A patent/TWI565709B/zh not_active IP Right Cessation
- 2012-07-18 AU AU2012284091A patent/AU2012284091B2/en not_active Ceased
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- 2014-01-19 IL IL230536A patent/IL230536A0/en unknown
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|---|---|
| HK1198475A1 (en) | 2015-05-08 |
| KR20140063605A (ko) | 2014-05-27 |
| JP2014520888A (ja) | 2014-08-25 |
| IL230536A0 (en) | 2014-03-31 |
| EP2734530A1 (en) | 2014-05-28 |
| CN103946226A (zh) | 2014-07-23 |
| AU2012284091A1 (en) | 2013-03-21 |
| US20150246932A1 (en) | 2015-09-03 |
| TW201311700A (zh) | 2013-03-16 |
| US9605003B2 (en) | 2017-03-28 |
| TWI565709B (zh) | 2017-01-11 |
| JP6027611B2 (ja) | 2016-11-16 |
| AR088218A1 (es) | 2014-05-21 |
| AU2012284091B2 (en) | 2015-11-12 |
| US9056877B2 (en) | 2015-06-16 |
| WO2013012918A1 (en) | 2013-01-24 |
| US20130029984A1 (en) | 2013-01-31 |
| MX2014000648A (es) | 2014-09-25 |
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