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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2649075B1 (en) | 2010-12-08 | 2018-04-25 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Substituted pyrazolopyrimidines as glucocerebrosidase activators |
| US9309250B2 (en) | 2011-06-22 | 2016-04-12 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-b]pyrazines as ATR kinase inhibitors |
| CN103764166B (zh) * | 2011-06-22 | 2017-10-24 | 通用医疗公司 | 蛋白质病的治疗 |
| AU2012272898A1 (en) | 2011-06-24 | 2013-04-11 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| EP2723717A2 (en) | 2011-06-24 | 2014-04-30 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| EP2768509B1 (en) * | 2011-10-20 | 2017-03-22 | Glaxosmithkline LLC | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
| 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 |
| WO2014089379A1 (en) | 2012-12-07 | 2014-06-12 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| EP2970288A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US9663519B2 (en) | 2013-03-15 | 2017-05-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| EP2970289A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| MX389256B (es) | 2013-10-04 | 2025-03-20 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos. |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2015085132A1 (en) | 2013-12-06 | 2015-06-11 | 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 |
| EP4066834A1 (en) | 2014-03-19 | 2022-10-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| HRP20200186T1 (hr) | 2014-06-05 | 2020-05-29 | Vertex Pharmaceuticals Inc. | Radioaktivno obilježeni derivati 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-karboksamid spojeva koji se koriste kao inhibitori atr kinaze, priprava navedenih spojeva i njihovi različiti čvrsti oblici |
| JP6936007B2 (ja) | 2014-06-17 | 2021-09-15 | 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 | Ｃｈｋ１阻害剤とａｔｒ阻害剤との組み合わせを使用してがんを処置する方法 |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| PE20170920A1 (es) | 2014-11-03 | 2017-07-12 | Bayer Pharma AG | Piperidinilpirazolopirimidinonas y utilizacion de las mismas |
| HRP20240644T1 (hr) | 2014-11-06 | 2024-08-02 | Bial-R&D Investments, S.A. | Supstituirani pirazolo(1,5-a)pirimidini i njihova uporaba u liječenju medicinskih poremećaja |
| 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 |
| 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 |
| EP3317282B1 (en) | 2015-07-01 | 2020-12-09 | Northwestern University | Substituted 4-methyl-pyrrolo[1.2-a]pyrimidine-8-carboxamide compounds and uses thereof for modulating glucocerebrosidase activity |
| US20190092789A1 (en) * | 2015-09-04 | 2019-03-28 | Lysosomal Therapeutics Inc. | Heterobicyclic pyrimidinone compounds and their use in the treatment of medical disorders |
| 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 |
| CN108349985A (zh) | 2015-09-14 | 2018-07-31 | 无限药品股份有限公司 | 异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法 |
| EP3355926B1 (en) | 2015-09-30 | 2025-12-24 | Vertex Pharmaceuticals Inc. | Combination of dna damaging agents and atr inhibitors for use in a method for treating cancer using |
| EP3429590A4 (en) * | 2016-03-16 | 2020-02-19 | Lysosomal Therapeutics Inc. | METHOD AND COMPOSITIONS FOR THE TREATMENT OF A NEURODEGENERATIVE DISEASE IN A SUBJECT CARRIING THE SPHINGOLIPIDOSIS GENE |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| JP7046827B2 (ja) * | 2016-04-06 | 2022-04-04 | リソソーマル・セラピューティクス・インコーポレイテッド | イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
| SG11201808830YA (en) * | 2016-04-06 | 2018-11-29 | Lysosomal Therapeutics Inc | Pyrazolo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| US11124516B2 (en) | 2016-04-06 | 2021-09-21 | BIAL-BioTech Investments, Inc. | Pyrrolo[1,2-A]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| JP7164774B2 (ja) | 2016-05-05 | 2022-11-02 | ビアル－アール・アンド・ディ・インベストメンツ・ソシエダーデ・アノニマ | 置換イミダゾ［１，２－ｂ］ピリダジン、置換イミダゾ［１，５－ｂ］ピリダジン、関連化合物、および医学的障害の治療におけるその使用 |
| WO2017192929A1 (en) * | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED PYRROLO[1,2-α]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 |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2018083085A1 (en) * | 2016-11-02 | 2018-05-11 | F. Hoffmann-La Roche Ag | PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS |
| JP7216705B2 (ja) * | 2017-07-28 | 2023-02-02 | ニンバス ラクシュミ， インコーポレイテッド | Ｔｙｋ２阻害剤およびその使用方法 |
| 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 |
| WO2019071073A1 (en) | 2017-10-06 | 2019-04-11 | Forma Therapeutics, Inc. | INHIBITION OF THE SPECIFIC PEPTIDASE OF UBIQUITIN |
| 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 |
| JP7179161B2 (ja) | 2018-09-10 | 2022-11-28 | イーライ リリー アンド カンパニー | 乾癬および全身性エリテマトーデスの処置に有用なピラゾロ［１，５－ａ］ピリミジン－３－カルボキサミド誘導体 |
| AU2019356011B2 (en) | 2018-10-05 | 2025-02-06 | Forma Therapeutics, Inc. | Fused pyrrolines which act as Ubiquitin-Specific Protease 30 (USP30) inhibitors |
| US11414431B2 (en) * | 2018-10-15 | 2022-08-16 | Nimbus Lakshmi, Inc. | Substituted pyrazolo[1,5-a]pyrimidines as TYK2 inhibitors |
| AR117177A1 (es) | 2018-12-10 | 2021-07-14 | Lilly Co Eli | DERIVADOS DE 7-(METILAMINO)PIRAZOLO[1,5-A]PIRIMIDIN-3-CARBOXAMIDA COMO INHIBIDORES DE IL-23 E INFa |
| JP7414965B2 (ja) * | 2019-08-21 | 2024-01-16 | ザ スクリプス リサーチ インスティテュート | インターフェロン遺伝子の刺激因子ｓｔｉｎｇの二環式アゴニスト |
| WO2021055630A1 (en) | 2019-09-17 | 2021-03-25 | Bial- Biotech Investments, Inc. | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
| WO2021055627A1 (en) | 2019-09-17 | 2021-03-25 | Bial- Biotech Investments, Inc. | Substituted n-heterocyclic carboxamides as acid ceramidase inhibitors and their use as medicaments |
| CN114787135A (zh) | 2019-09-17 | 2022-07-22 | 比亚尔R&D投资股份公司 | 经取代的咪唑甲酰胺及其在治疗医学病症中的用途 |
| JP2023503470A (ja) * | 2019-11-25 | 2023-01-30 | ゲイン セラピューティクス エスアー | ガラクトセレブロシダーゼの活性の変質に関連する状態におけるアリールおよびヘテロアリール化合物、ならびにそれらの治療的使用 |
| WO2021162944A1 (en) | 2020-02-12 | 2021-08-19 | Eli Lilly And Company | Substituted 7-(methylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide derivatives |
| 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 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003284886A1 (en) | 2002-10-21 | 2004-05-13 | William E. Balch | CHEMICAL CHAPERONES AND THEIR EFFECT UPON THE CELLULAR ACTIVITY OF Beta-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 |
| WO2004089471A2 (en) * | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | NEW PYRAZOLO[1,5-a] PYRIMIDINES DERIVATIVES AND PHARMACEUTICAL USE THEREOF |
| BRPI0416216A (pt) | 2003-11-12 | 2006-12-26 | Amicus Therapeutics Inc | composto de glicoimidazol e polihidroxiciclohexenila e método para sintetizar composto de glicoimidazol e polihidroxiciclohexenila, métodos para inibir glicocerebrosidase, para aumentar a atividade de glicocerebrosidase e para estabilizar glicocerebrosidade, composição farmacêutica, métodos para inibir uma -glicosidade, e para tratar doença de gaucher, derivado de glicoimidazol e derivados de polihidroxiciclohexilamina |
| US7488721B2 (en) | 2004-05-13 | 2009-02-10 | Mcmaster University | Real time methylumbelliferone-based assay |
| WO2005113004A2 (en) | 2004-05-14 | 2005-12-01 | The Cleveland Clinic Founfation | Small molecule inhibitors for mrp1 and other multidrug transporters |
| PL1761541T3 (pl) | 2004-06-21 | 2008-06-30 | Hoffmann La Roche | Pochodne pirazolopirymidyny |
| DE102005007534A1 (de) * | 2005-02-17 | 2006-08-31 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| US20070155737A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| EA013525B1 (ru) | 2005-05-20 | 2010-06-30 | Алантос-Фармасьютикалз Холдинг, Инк. | Гетеробициклические ингибиторы металлопротеазы и их применение |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| ES2376642T3 (es) * | 2005-08-15 | 2012-03-15 | F. Hoffmann-La Roche Ag | Derivados de piperidina y de piperazina como antagonistas del p2x3. |
| JP5119157B2 (ja) * | 2005-10-21 | 2013-01-16 | エクセリクシス， インク． | カゼインキナーゼｉｉ（ｃｋ２）モジュレーターとしてのピラゾロ−ピリミジン類 |
| EP1945220A1 (en) * | 2005-10-21 | 2008-07-23 | Mitsubishi Tanabe Pharma Corporation | Pyrazolo[1,5-a]pyrimidine compounds as cannabinoid receptor antagonists |
| 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 |
| WO2008045664A2 (en) | 2006-10-06 | 2008-04-17 | Kalypsys, Inc. | Heterocyclic pde4 inhibitors as antiinflammatory agents |
| CA2670083A1 (en) | 2006-11-20 | 2008-05-29 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| AU2008240138B2 (en) | 2007-04-13 | 2013-03-07 | Amicus Therapeutics, Inc. | Treatment of Gaucher disease with specific pharmacological chaperones and monitoring treatment using surrogate markers |
| WO2008134036A1 (en) | 2007-04-27 | 2008-11-06 | Panacos Pharmaceuticals, Inc. | ALPHA-SUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-α]PYRIMIDINE AMIDE DERIVATIVES |
| ES2559859T3 (es) | 2007-05-16 | 2016-02-16 | The Brigham And Women's Hospital, Inc. | Tratamiento de sinucleinopatías |
| 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 |
| WO2009049421A1 (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 |
| US8642660B2 (en) * | 2007-12-21 | 2014-02-04 | The University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| AU2009257635A1 (en) * | 2008-06-10 | 2009-12-17 | Plexxikon, Inc. | 5H-Pyrrolo [2,3-b] pyrazine derivatives for kinase modulation, and indications therefor |
| 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 |
| EP2649075B1 (en) * | 2010-12-08 | 2018-04-25 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Substituted pyrazolopyrimidines as glucocerebrosidase activators |
| HRP20240644T1 (hr) * | 2014-11-06 | 2024-08-02 | Bial-R&D Investments, S.A. | Supstituirani pirazolo(1,5-a)pirimidini i njihova uporaba u liječenju medicinskih poremećaja |
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