JP2013544893A5 - - Google Patents
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- Publication number
- JP2013544893A5 JP2013544893A5 JP2013543335A JP2013543335A JP2013544893A5 JP 2013544893 A5 JP2013544893 A5 JP 2013544893A5 JP 2013543335 A JP2013543335 A JP 2013543335A JP 2013543335 A JP2013543335 A JP 2013543335A JP 2013544893 A5 JP2013544893 A5 JP 2013544893A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- pyrimidine
- difluoromethyl
- alkyl
- dihydropyrazolo
- 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.)
- Granted
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- -1 cyano, nitro, amino Chemical group 0.000 claims 47
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 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 5
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims 2
- SNXQLBHDNMAMCD-UHFFFAOYSA-N 7-(3,5-dimethylmorpholin-4-yl)-n-(4-ethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C=C(N3C(COCC3C)C)N2N=C1 SNXQLBHDNMAMCD-UHFFFAOYSA-N 0.000 claims 2
- OESWFRMZSUAEDJ-UHFFFAOYSA-N 7-(3,5-dimethylpiperazin-1-yl)-n-(4-ethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C=C(N3CC(C)NC(C)C3)N2N=C1 OESWFRMZSUAEDJ-UHFFFAOYSA-N 0.000 claims 2
- YFKXHYCAXKALMF-UHFFFAOYSA-N 7-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]-n-(4-ethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C=C(N3CCN(CCN(C)C)CC3)N2N=C1 YFKXHYCAXKALMF-UHFFFAOYSA-N 0.000 claims 2
- 241000282376 Panthera tigris Species 0.000 claims 2
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- NBVXSTLIUNQXBT-UHFFFAOYSA-N chembl3185251 Chemical compound CCOC1=CC=CC=C1NC(=O)C1=C(NC(=C)C=C2C(F)F)N2N=C1 NBVXSTLIUNQXBT-UHFFFAOYSA-N 0.000 claims 2
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- YHCDLYUQTOQNLN-UHFFFAOYSA-N n-(4-ethylphenyl)-5-methyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C=C(N3CCN(C)CC3)N2N=C1 YHCDLYUQTOQNLN-UHFFFAOYSA-N 0.000 claims 2
- CHFXTFMIFBNPSJ-UHFFFAOYSA-N n-(4-ethylphenyl)-5-methyl-7-[4-(2-methylpropyl)piperazin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C=C(N3CCN(CC(C)C)CC3)N2N=C1 CHFXTFMIFBNPSJ-UHFFFAOYSA-N 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- KLFXDMIVOKQLJQ-UHFFFAOYSA-N (5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-[4-(4-nitrophenyl)piperazin-1-yl]methanone Chemical compound C=12N=C(C)C=C(C)N2N=CC=1C(=O)N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1 KLFXDMIVOKQLJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- ONGSAYSLHZBWEP-UHFFFAOYSA-N 5,7-dimethyl-n-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=12N=C(C)C=C(C)N2N=CC=1C(=O)NC1=CC=CC(C(F)(F)F)=C1 ONGSAYSLHZBWEP-UHFFFAOYSA-N 0.000 claims 1
- YBKYTNNBXFZNFF-UHFFFAOYSA-N 5,7-dimethyl-n-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=12N=C(C)C=C(C)N2N=CC=1C(=O)NC1=CC=C(C(F)(F)F)C=C1 YBKYTNNBXFZNFF-UHFFFAOYSA-N 0.000 claims 1
- CYEFRDZGYTWHFV-UHFFFAOYSA-N 5-cyclopropylidene-7-(difluoromethyl)-N-(3,4-difluorophenyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(F)C(F)=C1 CYEFRDZGYTWHFV-UHFFFAOYSA-N 0.000 claims 1
- AWDMEPYOBMQXRW-UHFFFAOYSA-N 5-cyclopropylidene-7-(difluoromethyl)-N-(4-sulfamoylphenyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=C(NC(C=C2C(F)F)=C3CC3)N2N=C1 AWDMEPYOBMQXRW-UHFFFAOYSA-N 0.000 claims 1
- GTZRFXVCWJKLEH-UHFFFAOYSA-N 5-cyclopropylidene-7-(difluoromethyl)-N-(6-methylpyridin-2-yl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C2=C3N(C(=CC(N3)=C3CC3)C(F)F)N=C2)=N1 GTZRFXVCWJKLEH-UHFFFAOYSA-N 0.000 claims 1
- PFBZJDASYDABLN-UHFFFAOYSA-N 5-cyclopropylidene-N-(3,5-dichlorophenyl)-7-(difluoromethyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 PFBZJDASYDABLN-UHFFFAOYSA-N 0.000 claims 1
- VCRFPNNYMJNLSQ-UHFFFAOYSA-N 7-(difluoromethyl)-5-methyl-n-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=12N=C(C)C=C(C(F)F)N2N=CC=1C(=O)NC1=CC=C(C(F)(F)F)C=C1 VCRFPNNYMJNLSQ-UHFFFAOYSA-N 0.000 claims 1
- WICPNVMYTPNMIV-UHFFFAOYSA-N 7-(difluoromethyl)-n-(4-ethynylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=12N=C(C)C=C(C(F)F)N2N=CC=1C(=O)NC1=CC=C(C#C)C=C1 WICPNVMYTPNMIV-UHFFFAOYSA-N 0.000 claims 1
- PMWQSQNHUBGLLI-UHFFFAOYSA-N 7-methyl-N-[4-(trifluoromethyl)phenyl]-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound C1=NN2C=3CCCC=3C(C)=NC2=C1C(=O)NC1=CC=C(C(F)(F)F)C=C1 PMWQSQNHUBGLLI-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101150028412 GBA gene Proteins 0.000 claims 1
- 208000015872 Gaucher disease Diseases 0.000 claims 1
- 206010064571 Gene mutation Diseases 0.000 claims 1
- 108010017544 Glucosylceramidase Proteins 0.000 claims 1
- 102100033342 Lysosomal acid glucosylceramidase Human genes 0.000 claims 1
- IJHKKHPENYDANX-UHFFFAOYSA-N N-(2,3-dihydro-1H-inden-5-yl)-5,7-dimethyl-3-pyrazolo[1,5-a]pyrimidinecarboxamide Chemical compound C1=C2CCCC2=CC(NC(=O)C=2C=NN3C(C)=CC(=NC3=2)C)=C1 IJHKKHPENYDANX-UHFFFAOYSA-N 0.000 claims 1
- XUPMMFBGZQUWOI-UHFFFAOYSA-N N-(3,4-dichlorophenyl)-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound C1=NN2C=3CCCC=3C(C)=NC2=C1C(=O)NC1=CC=C(Cl)C(Cl)=C1 XUPMMFBGZQUWOI-UHFFFAOYSA-N 0.000 claims 1
- OEPHUHZIEWQNMV-UHFFFAOYSA-N N-(4-bromo-2-chlorophenyl)-5-cyclopropylidene-7-(difluoromethyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Br)C=C1Cl OEPHUHZIEWQNMV-UHFFFAOYSA-N 0.000 claims 1
- YLOVOAWHCHJWRE-UHFFFAOYSA-N N-(4-bromophenyl)-5-cyclopropylidene-7-(difluoromethyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Br)C=C1 YLOVOAWHCHJWRE-UHFFFAOYSA-N 0.000 claims 1
- ZVARWXBKZUMXPQ-UHFFFAOYSA-N N-(4-ethylphenyl)-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)C1=C2N=C(C)C(CCC3)=C3N2N=C1 ZVARWXBKZUMXPQ-UHFFFAOYSA-N 0.000 claims 1
- OHQBGXMWKGOOAQ-UHFFFAOYSA-N N-(4-ethynylphenyl)-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound C1=NN2C=3CCCC=3C(C)=NC2=C1C(=O)NC1=CC=C(C#C)C=C1 OHQBGXMWKGOOAQ-UHFFFAOYSA-N 0.000 claims 1
- LSYHYTOVOAOWMT-UHFFFAOYSA-N N-(4-tert-butylcyclohexyl)-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound C1=NN2C=3CCCC=3C(C)=NC2=C1C(=O)NC1CCC(C(C)(C)C)CC1 LSYHYTOVOAOWMT-UHFFFAOYSA-N 0.000 claims 1
- GGBNAHMOTCFJHS-UHFFFAOYSA-N N-(5-bromopyridin-2-yl)-5-cyclopropylidene-7-(difluoromethyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Br)C=N1 GGBNAHMOTCFJHS-UHFFFAOYSA-N 0.000 claims 1
- XLUAAOIBRIUDQP-UHFFFAOYSA-N N-[(2-chlorophenyl)methyl]-7-(difluoromethyl)-5-methylidene-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)NCC1=CC=CC=C1Cl XLUAAOIBRIUDQP-UHFFFAOYSA-N 0.000 claims 1
- QGCNZLGLSRHLQF-LUIVOBPISA-N N-[(2E,4E)-hexa-2,4-dien-2-yl]-7-methyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-10-carboxamide Chemical compound CC1=NC2=C(C(=O)NC(/C)=C/C=C/C)C=NN2C2=C1CCC2 QGCNZLGLSRHLQF-LUIVOBPISA-N 0.000 claims 1
- ZFIIFXLGSQPYGE-UHFFFAOYSA-N N-[(4-chlorophenyl)methyl]-7-(difluoromethyl)-5-methylidene-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)NCC1=CC=C(Cl)C=C1 ZFIIFXLGSQPYGE-UHFFFAOYSA-N 0.000 claims 1
- UGTVODMYDKHASE-UHFFFAOYSA-N N-butan-2-yl-7-(difluoromethyl)-5-methylidene-4H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1C(=C)C=C(C(F)F)N2C1=C(C(=O)NC(C)CC)C=N2 UGTVODMYDKHASE-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- PWYSFEDEWYZHQH-UHFFFAOYSA-N [7-(difluoromethyl)-5-methylidene-4H-pyrazolo[1,5-a]pyrimidin-3-yl]-(4-pyridin-2-ylpiperazin-1-yl)methanone Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)N(CC1)CCN1C1=CC=CC=N1 PWYSFEDEWYZHQH-UHFFFAOYSA-N 0.000 claims 1
- XMBVLXDWUPESNP-UHFFFAOYSA-N [7-(difluoromethyl)-5-methylidene-4H-pyrazolo[1,5-a]pyrimidin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)N1CCCCC1 XMBVLXDWUPESNP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- BLWPNCPHSRWMOK-UHFFFAOYSA-N chembl1714232 Chemical compound N1C2=C(C(=O)NC=3C=C4CCCC4=CC=3)C=NN2C(C(F)F)=CC1=C1CC1 BLWPNCPHSRWMOK-UHFFFAOYSA-N 0.000 claims 1
- XPZTZQKJXDOKPR-UHFFFAOYSA-N chembl1716885 Chemical compound C1=NN2C(C(F)(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=CC=C1SC1=CC=CC=C1 XPZTZQKJXDOKPR-UHFFFAOYSA-N 0.000 claims 1
- IUJQOWDONOIJRD-UHFFFAOYSA-N chembl1723999 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1CCCCC1 IUJQOWDONOIJRD-UHFFFAOYSA-N 0.000 claims 1
- YHAVWNXZFBVYOJ-UHFFFAOYSA-N chembl1725455 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=CC=C1SC1=CC=CC=C1 YHAVWNXZFBVYOJ-UHFFFAOYSA-N 0.000 claims 1
- ZJTWTDPHRBJXQN-UHFFFAOYSA-N chembl1867541 Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)C1=C(NC(C=C2C(F)F)=C3CC3)N2N=C1 ZJTWTDPHRBJXQN-UHFFFAOYSA-N 0.000 claims 1
- AAWGXKDFFFEINN-UHFFFAOYSA-N chembl1870221 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=CN=C1Cl AAWGXKDFFFEINN-UHFFFAOYSA-N 0.000 claims 1
- FZGYHQIVTONTQY-UHFFFAOYSA-N chembl1873702 Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)NC1=CC=C(Br)C=C1C(F)(F)F FZGYHQIVTONTQY-UHFFFAOYSA-N 0.000 claims 1
- WFCTUWCTLULDLZ-UHFFFAOYSA-N chembl1874145 Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=C(NC(C=C2C(F)F)=C3CC3)N2N=C1 WFCTUWCTLULDLZ-UHFFFAOYSA-N 0.000 claims 1
- MUEZEYDZQXQLNT-UHFFFAOYSA-N chembl1876337 Chemical compound N1=CC=C2C(NC(=O)C3=C4NC(=C)C=C(N4N=C3)C)=CC=CC2=C1 MUEZEYDZQXQLNT-UHFFFAOYSA-N 0.000 claims 1
- YRUSMPLCKKPXOR-UHFFFAOYSA-N chembl1878874 Chemical compound C1=CC(N(CC)CC)=CC=C1NC(=O)C1=C(NC(=C)C=C2C(F)F)N2N=C1 YRUSMPLCKKPXOR-UHFFFAOYSA-N 0.000 claims 1
- BFGMJVMDZAXEHA-UHFFFAOYSA-N chembl1881090 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=CC=C1Br BFGMJVMDZAXEHA-UHFFFAOYSA-N 0.000 claims 1
- OHSZLQMKXVFEFE-UHFFFAOYSA-N chembl1881290 Chemical compound C1=NN2C(C(F)F)=CC(=C)NC2=C1C(=O)NCC1=CC=C(Cl)C=C1Cl OHSZLQMKXVFEFE-UHFFFAOYSA-N 0.000 claims 1
- RLJJHFBZZBETKS-UHFFFAOYSA-N chembl1885887 Chemical compound C1=NN2C(C)=CC(=C)NC2=C1C(=O)NC1=CC=CC=C1O RLJJHFBZZBETKS-UHFFFAOYSA-N 0.000 claims 1
- LGECWDNOBJRGIQ-UHFFFAOYSA-N chembl1886380 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Br)C=C1F LGECWDNOBJRGIQ-UHFFFAOYSA-N 0.000 claims 1
- OJSDGCOLPKPYAZ-UHFFFAOYSA-N chembl1887267 Chemical compound C1CC(C(C)(C)C)CCC1NC(=O)C1=C(NC(C=C2C(F)F)=C3CC3)N2N=C1 OJSDGCOLPKPYAZ-UHFFFAOYSA-N 0.000 claims 1
- IOKDCCFJHGEPMK-UHFFFAOYSA-N chembl1887655 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=CC=C1F IOKDCCFJHGEPMK-UHFFFAOYSA-N 0.000 claims 1
- GJUOWWGQGDXQBK-UHFFFAOYSA-N chembl1890316 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Cl)C=C1Cl GJUOWWGQGDXQBK-UHFFFAOYSA-N 0.000 claims 1
- KFBQUEJISGCYFS-UHFFFAOYSA-N chembl1893463 Chemical compound C1=NN2C(C(F)F)=CC(=C3CC3)NC2=C1C(=O)NC1=CC=C(Cl)C=N1 KFBQUEJISGCYFS-UHFFFAOYSA-N 0.000 claims 1
- ZOPRAITYHAXVHL-UHFFFAOYSA-N chembl1896615 Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=C(NC(C=C2C(F)(F)F)=C3CC3)N2N=C1 ZOPRAITYHAXVHL-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (55)
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| EP2723746A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| WO2012177997A1 (en) | 2011-06-22 | 2012-12-27 | The General Hospital Corporation | Treatment of proteinopathies |
| CA2839703A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| AP2013007331A0 (en) | 2011-06-24 | 2013-12-31 | Amgen Inc | TRPM8 antagonists and their use in treatments |
| JP6073343B2 (ja) * | 2011-10-20 | 2017-02-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| LT3486245T (lt) | 2012-12-07 | 2021-08-25 | Vertex Pharmaceuticals Incorporated | 2-amino-n-(piperidin-1-il-piridin-3-il)pirazolo[1,5alfa]pirimidin-3-karboksamidas, kaip atr kinazės inhibitorius |
| EP2970288A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| JP2016512815A (ja) | 2013-03-15 | 2016-05-09 | 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 | Ａｔｒキナーゼの阻害剤として有用な縮合ピラゾロピリミジン誘導体 |
| WO2014143241A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US9359365B2 (en) | 2013-10-04 | 2016-06-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CA2932757C (en) | 2013-12-06 | 2023-10-31 | Vertex Pharmaceuticals Incorporated | 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, its preparation, different solid forms and radiolabelled derivatives thereof |
| CN106456628A (zh) | 2014-03-19 | 2017-02-22 | 无限药品股份有限公司 | 用于治疗PI3K‑γ介导的障碍的杂环化合物 |
| AU2015271030B2 (en) | 2014-06-05 | 2019-05-16 | Vertex Pharmaceuticals Incorporated | Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo [1,5-a] pyrimidin-3-carboxamide compound useful as ATR kinase inhibitor, the preparation of said compound and different solid forms thereof |
| LT3157566T (lt) | 2014-06-17 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Vėžio gydymo būdas, panaudojant chk1 ir atr inhibitorių derinį |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| CN107108638A (zh) | 2014-11-03 | 2017-08-29 | 拜耳制药股份公司 | 哌啶基吡唑并嘧啶酮及其用途 |
| US20170333435A1 (en) | 2014-11-06 | 2017-11-23 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| IL252053B2 (en) | 2014-11-06 | 2024-04-01 | Lysosomal Therapeutics Inc | SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| CA2966581A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| JP2018522872A (ja) * | 2015-07-01 | 2018-08-16 | ノースウェスタン ユニバーシティ | 置換４−メチルピロロ［１，２−ａ］ピリミジン−８−カルボキサミド化合物及びグルコセレブロシダーゼ活性の調節のためのその使用 |
| EP3344625A4 (en) * | 2015-09-04 | 2019-03-27 | Lysosomal Therapeutics Inc. | THIAZOLO (3,2-A) PYRIMIDINONE AND OTHER HETEROBICYCLIC COMPOUNDS OF PYRIMIDINONE FOR THERAPEUTIC USE |
| EP3344632A4 (en) * | 2015-09-04 | 2019-03-20 | Lysosomal Therapeutics Inc. | Heterocyclic pyrimidine compounds and their use in the treatment of medical disorders |
| CA2998469C (en) | 2015-09-14 | 2025-12-09 | Twelve Therapeutics, Inc. | Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same |
| WO2017059357A1 (en) | 2015-09-30 | 2017-04-06 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of dna damaging agents and atr inhibitors |
| WO2017161137A1 (en) * | 2016-03-16 | 2017-09-21 | Lysosomal Therapeutics Inc. | Methods and compositions for treating a neurodegenerative disorder in a sphingotyped subject |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| MX2018012211A (es) | 2016-04-06 | 2019-03-28 | Lysosomal Therapeutics Inc | Compuestos de pirazol[1,5-a]pirimidinil carboxamida y su uso en el tratamiento de trastornos médicos. |
| CA3020305A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| EP3440081A4 (en) * | 2016-04-06 | 2019-09-18 | Lysosomal Therapeutics Inc. | PYRROLO [1,2-A] PYRIMIDINYL-CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDER |
| US20190389865A1 (en) * | 2016-05-05 | 2019-12-26 | Lysosomal Therapeutics Inc. | SUBSTITUTED PYRROLO[1,2-a]TRIAZINES AND RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| WO2017192931A1 (en) | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO[1,2-α]PYRIDINES, SUBSTITUTED IMIDAZO[1,2-α]PYRAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| EP3452481A4 (en) | 2016-05-05 | 2020-02-26 | Lysosomal Therapeutics Inc. | IMIDAZO [1,2-B] SUBSTITUTED PYRIDAZINES, IMIDAZO [1,5-B] SUBSTITUTED PYRIDAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL CONDITIONS |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN109890829B (zh) * | 2016-11-02 | 2022-07-15 | 豪夫迈·罗氏有限公司 | 作为IRAK4调节剂的吡唑并[1,5a]嘧啶衍生物 |
| DK3658557T3 (da) * | 2017-07-28 | 2024-07-29 | Takeda Pharmaceuticals Co | Tyk2-inhibitorer og anvendelser deraf |
| JP2020530000A (ja) | 2017-08-02 | 2020-10-15 | ノースウエスタン ユニバーシティ | 置換縮合ピリミジン化合物およびその使用 |
| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| US11459325B2 (en) | 2018-01-31 | 2022-10-04 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| ES2988920T3 (es) | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| US10882865B2 (en) | 2018-08-31 | 2021-01-05 | Northwestern University | Pyrrolopyrimidine compounds and uses thereof for modulating glucocerebrosidase activity |
| EP3849981B1 (en) | 2018-09-10 | 2023-02-01 | Eli Lilly and Company | Pyrazolo[1,5-a]pyrimidine-3-carboxamide derivatives useful in the treatment of psoriasis and systemic lupus erythematosus |
| HRP20230409T1 (hr) | 2018-10-05 | 2023-07-07 | Forma Therapeutics, Inc. | Fuzionirani pirolini koji djeluju kao inhibitori ubikvitin specifične proteaze 30 (usp30) |
| JP7619951B2 (ja) * | 2018-10-15 | 2025-01-22 | 武田薬品工業株式会社 | Ｔｙｋ２阻害剤およびその使用 |
| TWI800696B (zh) | 2018-12-10 | 2023-05-01 | 美商美國禮來大藥廠 | 7-(甲基胺基)吡唑并[1,5-a]嘧啶-3-甲醯胺衍生物 |
| KR102821711B1 (ko) * | 2019-08-21 | 2025-06-16 | 더 스크립스 리서치 인스티튜트 | 인터페론 유전자의 자극인자 sting의 비시클릭 효능제 |
| US20220380314A1 (en) | 2019-09-17 | 2022-12-01 | Bial - R&D Investments, S.A. | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
| KR20220100858A (ko) | 2019-09-17 | 2022-07-18 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 이미다졸 카르복사미드, 및 질병의 치료에서의 이의 용도 |
| AU2020349519A1 (en) | 2019-09-17 | 2022-03-17 | Bial-R&D Investments, S.A. | Substituted N-heterocyclic carboxamides as acid ceramidase inhibitors and their use as medicaments |
| BR112022010127A2 (pt) * | 2019-11-25 | 2022-09-06 | Gain Therapeutics Sa | Compostos de arila e heteroarila e usos terapêuticos dos mesmos em condições associadas à alteração da atividade de galatocerebrosidase |
| TWI810520B (zh) | 2020-02-12 | 2023-08-01 | 美商美國禮來大藥廠 | 7-(甲基胺基)吡唑并[1,5-a]嘧啶-3-甲醯胺化合物 |
| JP7375214B2 (ja) | 2020-02-12 | 2023-11-07 | イーライ リリー アンド カンパニー | 置換７－（メチルアミノ）ピラゾロ［１，５－ａ］ピリミジン－３－カルボキサミド誘導体 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037373A2 (en) | 2002-10-21 | 2004-05-06 | The Scripps Research Institute | CHEMICAL CHAPERONES AND THEIR EFFECT UPON THE CELLULAR ACTIVITY OF β-GLUCOSIDASE |
| JP2004277337A (ja) * | 2003-03-14 | 2004-10-07 | Sumitomo Pharmaceut Co Ltd | ピラゾロ［１，５−ａ］ピリミジン誘導体 |
| EP1615697A2 (en) * | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | New pyrazolo[1,5-a] pyrimidine derivatives and pharmaceutical use thereof |
| AU2004289327A1 (en) | 2003-11-12 | 2005-05-26 | Amicus Therapeutics Inc. | Glucoimidazole and polyhydroxycyclohexenyl amine derivatives to treat Gaucher disease |
| US7488721B2 (en) * | 2004-05-13 | 2009-02-10 | Mcmaster University | Real time methylumbelliferone-based assay |
| EP1753422B1 (en) * | 2004-05-14 | 2008-05-28 | The Cleveland Clinic Foundation | Small molecule inhibitors for mrp1 and other multidrug transporters |
| WO2005123738A1 (en) * | 2004-06-21 | 2005-12-29 | F.Hoffmann-La Roche Ag | Pyrrazolo-pyrimidine derivatives |
| DE102005007534A1 (de) * | 2005-02-17 | 2006-08-31 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| EA013525B1 (ru) | 2005-05-20 | 2010-06-30 | Алантос-Фармасьютикалз Холдинг, Инк. | Гетеробициклические ингибиторы металлопротеазы и их применение |
| US20070155737A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| EP1917262B1 (en) * | 2005-08-15 | 2011-12-14 | F. Hoffmann-La Roche AG | Piperidine and piperazine derivatives as p2x3 antagonists |
| CA2626789A1 (en) * | 2005-10-21 | 2007-04-26 | Exelixis, Inc. | Pyrimidinones as casein kinase ii (ck2) modulators |
| US8188097B2 (en) * | 2005-10-21 | 2012-05-29 | Mitsubishi Tanabe Pharma Corporation | Pyrazolo[1,5-A]pyrimidine compounds |
| WO2008054947A2 (en) | 2006-10-02 | 2008-05-08 | The Brigham And Women's Hospital, Inc. | Structure of acid beta-glucosidase and methods for identifying therapeutic agents |
| US20090275586A1 (en) | 2006-10-06 | 2009-11-05 | Kalypsys, Inc. | Heterocyclic inhibitors of pde4 |
| US20080176870A1 (en) | 2006-11-20 | 2008-07-24 | Bert Nolte | Heterobicyclic metalloprotease inhibitors |
| JP5586453B2 (ja) | 2007-04-13 | 2014-09-10 | アミカス セラピューティックス インコーポレイテッド | 特異的薬理シャペロンによるゴーシェ病の治療および代理マーカーを用いた治療の監視 |
| WO2008134035A1 (en) | 2007-04-27 | 2008-11-06 | Panacos Pharmaceuticals, Inc. | Alpha-unsubstituted arylmethyl piperazine pyrazolo[1,5-a] pyrimidine amide derivatives |
| PL2154969T3 (pl) | 2007-05-16 | 2016-04-29 | Brigham & Womens Hospital Inc | Leczenie synukleinopatii |
| WO2008154207A1 (en) | 2007-06-08 | 2008-12-18 | The Burnham Institute For Medical Research | Methods and compounds for regulating apoptosis |
| JP5337405B2 (ja) | 2007-09-17 | 2013-11-06 | ザ・ホスピタル・フォー・シック・チルドレン | ゴーシェ病の治療方法 |
| WO2009049422A1 (en) | 2007-10-18 | 2009-04-23 | The Hospital For Sick Children | Compositions and methods for enhancing enzyme activity in gaucher, gm1 -gangliosidosis/morquio b disease. and parkinson's disease |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| JP5767965B2 (ja) * | 2008-06-10 | 2015-08-26 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼを調節する５ｈ−ピロロ［２，３−ｂ］ピラジン誘導体、およびその適応症 |
| EP2307440A4 (en) | 2008-07-01 | 2012-12-19 | Zacharon Pharmaceuticals Inc | HEPARAN SULFATE INHIBITORS |
| WO2010086040A1 (en) * | 2009-01-29 | 2010-08-05 | Biomarin Iga, Ltd. | Pyrazolo-pyrimidines for treatment of duchenne muscular dystrophy |
| EP3366688B1 (en) | 2010-12-08 | 2022-02-09 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Substituted pyrazolopyrimidines as glucocerebrosidase activators |
| IL252053B2 (en) * | 2014-11-06 | 2024-04-01 | Lysosomal Therapeutics Inc | SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
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