CA2846369A1 - N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl-sulfonamides et leurs utilisation comme produits pharmaceutiques - Google Patents

N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl-sulfonamides et leurs utilisation comme produits pharmaceutiques Download PDF

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Publication number: CA2846369A1
Authority: CA; Canada
Prior art keywords: phenyl; alkyl; series consisting; pyrazin; pyrazolo
Prior art date: 2011-09-19
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

Application number

CA2846369A

Other languages

English (en)

Other versions

CA2846369C (fr

Inventor

Marc Nazare

Nis Halland

Friedemann Schmidt

Tilo Weiss

Uwe Dietz

Armin Hofmeister

Jean-Christophe Carry

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi SA

Original Assignee

Sanofi SA

Priority date (The priority date 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 date listed.)

2011-09-19

Filing date

2011-09-19

Publication date

2013-03-28

2011-09-19 Application filed by Sanofi SA filed Critical Sanofi SA

2013-03-28 Publication of CA2846369A1 publication Critical patent/CA2846369A1/fr

2018-11-13 Application granted granted Critical

2018-11-13 Publication of CA2846369C publication Critical patent/CA2846369C/fr

Status Active legal-status Critical Current

2031-09-19 Anticipated expiration legal-status Critical

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239000003814 drug Substances 0.000 title claims abstract description 19
QALHRKSMKVLJQH-UHFFFAOYSA-N C1=CC(NS(=O)=O)=CC=C1C1=CN=C(C=NN2)C2=N1 Chemical class C1=CC(NS(=O)=O)=CC=C1C1=CN=C(C=NN2)C2=N1 QALHRKSMKVLJQH-UHFFFAOYSA-N 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 309
238000000034 method Methods 0.000 claims abstract description 80
108010022404 serum-glucocorticoid regulated kinase Proteins 0.000 claims abstract description 62
238000011282 treatment Methods 0.000 claims abstract description 35
230000003412 degenerative effect Effects 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
230000004054 inflammatory process Effects 0.000 claims abstract description 12
230000008569 process Effects 0.000 claims abstract description 12
208000012659 Joint disease Diseases 0.000 claims abstract description 11
-1 2,3-dichloro-phenyl Chemical group 0.000 claims description 227
239000001257 hydrogen Substances 0.000 claims description 151
229910052739 hydrogen Inorganic materials 0.000 claims description 151
229910052757 nitrogen Inorganic materials 0.000 claims description 138
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 136
125000001424 substituent group Chemical group 0.000 claims description 129
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 110
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
150000003839 salts Chemical class 0.000 claims description 86
150000002367 halogens Chemical class 0.000 claims description 84
229910052736 halogen Inorganic materials 0.000 claims description 83
125000004433 nitrogen atom Chemical group N* 0.000 claims description 74
125000005842 heteroatom Chemical group 0.000 claims description 71
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 69
125000004432 carbon atom Chemical group C* 0.000 claims description 68
125000000623 heterocyclic group Chemical group 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 60
125000004093 cyano group Chemical group *C#N 0.000 claims description 57
229910052717 sulfur Inorganic materials 0.000 claims description 53
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 52
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 52
229910052760 oxygen Inorganic materials 0.000 claims description 52
239000001301 oxygen Substances 0.000 claims description 52
239000011593 sulfur Substances 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 41
239000011737 fluorine Substances 0.000 claims description 38
229910052731 fluorine Inorganic materials 0.000 claims description 38
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 37
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 37
208000002193 Pain Diseases 0.000 claims description 36
125000001153 fluoro group Chemical group F* 0.000 claims description 36
125000002950 monocyclic group Chemical group 0.000 claims description 34
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 34
230000036407 pain Effects 0.000 claims description 30
210000000845 cartilage Anatomy 0.000 claims description 28
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
230000005764 inhibitory process Effects 0.000 claims description 17
239000003112 inhibitor Substances 0.000 claims description 16
229910052740 iodine Inorganic materials 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 12
206010028980 Neoplasm Diseases 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
206010012601 diabetes mellitus Diseases 0.000 claims description 10
125000000524 functional group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
239000002243 precursor Substances 0.000 claims description 9
208000024172 Cardiovascular disease Diseases 0.000 claims description 8
206010016654 Fibrosis Diseases 0.000 claims description 7
206010008118 cerebral infarction Diseases 0.000 claims description 7
230000004761 fibrosis Effects 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
XPTVVTRLVZNJAA-UHFFFAOYSA-N 2,5-dichloro-n-[2-fluoro-4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound FC1=CC(C=2N=C3NN=CC3=NC=2)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl XPTVVTRLVZNJAA-UHFFFAOYSA-N 0.000 claims description 4
NFEGNNZUUDFMLA-UHFFFAOYSA-N 2,5-dichloro-n-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=CC3=NC=2)=C1 NFEGNNZUUDFMLA-UHFFFAOYSA-N 0.000 claims description 4
125000005620 boronic acid group Chemical group 0.000 claims description 4
OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 claims description 4
DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims description 4
DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims description 4
APEZSRSLDCCOAT-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NC3=CC=C(C=C3)C=3N=C4NN=C(C4=NC=3)N)=CC=CC2=C1 APEZSRSLDCCOAT-UHFFFAOYSA-N 0.000 claims description 3
SADZGULVBNJDKE-UHFFFAOYSA-N 2,5-dichloro-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl SADZGULVBNJDKE-UHFFFAOYSA-N 0.000 claims description 2
LQOIAHRPEWFITJ-UHFFFAOYSA-N 2-chloro-5-methoxy-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(C)C3=NC=2)=C1 LQOIAHRPEWFITJ-UHFFFAOYSA-N 0.000 claims description 2
BJRYMGKNXLWDQJ-UHFFFAOYSA-N 2-cyano-5-methyl-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(C)=CC=C1C#N BJRYMGKNXLWDQJ-UHFFFAOYSA-N 0.000 claims description 2
DGQPIYWVZMLYAW-UHFFFAOYSA-N 2-fluoro-5-methyl-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(C)=CC=C1F DGQPIYWVZMLYAW-UHFFFAOYSA-N 0.000 claims description 2
MXDZOWTTWZNIAF-UHFFFAOYSA-N 5-chloro-2-cyano-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1C#N MXDZOWTTWZNIAF-UHFFFAOYSA-N 0.000 claims description 2
JTEZPYCVHLQJEA-UHFFFAOYSA-N 5-chloro-2-fluoro-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1F JTEZPYCVHLQJEA-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 74
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
BDSVBTSWYZHEPN-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[6-[4-[(2-fluoro-5-methylphenyl)sulfonylamino]phenyl]-1h-pyrazolo[3,4-b]pyrazin-3-yl]urea Chemical compound CC1=CC=C(F)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(NC(=O)NC=4C=CC(Cl)=CC=4)C3=NC=2)=C1 BDSVBTSWYZHEPN-UHFFFAOYSA-N 0.000 claims 1
BSPGTHRZNYXKAM-UHFFFAOYSA-N 1-[6-[4-[(2-fluoro-5-methylphenyl)sulfonylamino]phenyl]-1h-pyrazolo[3,4-b]pyrazin-3-yl]-3-pyridin-3-ylurea Chemical compound CC1=CC=C(F)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(NC(=O)NC=4C=NC=CC=4)C3=NC=2)=C1 BSPGTHRZNYXKAM-UHFFFAOYSA-N 0.000 claims 1
MBHQIISXEJXGPA-UHFFFAOYSA-N 2,3-dichloro-n-[2-fluoro-4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound FC1=CC(C=2N=C3NN=CC3=NC=2)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl MBHQIISXEJXGPA-UHFFFAOYSA-N 0.000 claims 1
QUBOLPJSCCUVLM-UHFFFAOYSA-N 2,3-dichloro-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl QUBOLPJSCCUVLM-UHFFFAOYSA-N 0.000 claims 1
VZFBDTSIYYNALZ-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[3-[(2,4,5-trifluorophenyl)sulfonylamino]-1h-pyrazolo[3,4-b]pyrazin-6-yl]phenyl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC1=NNC2=NC(C=3C=CC(NS(=O)(=O)C=4C(=CC(F)=C(F)C=4)F)=CC=3)=CN=C12 VZFBDTSIYYNALZ-UHFFFAOYSA-N 0.000 claims 1
ORPHVZMAFKVPGA-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[3-[(2,4,6-trichlorophenyl)sulfonylamino]-1h-pyrazolo[3,4-b]pyrazin-6-yl]phenyl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NNC2=NC(C=3C=CC(NS(=O)(=O)C=4C(=CC(Cl)=CC=4Cl)Cl)=CC=3)=CN=C12 ORPHVZMAFKVPGA-UHFFFAOYSA-N 0.000 claims 1
AMICJZVZWNPDRK-UHFFFAOYSA-N 2-chloro-n-[4-[3-[[2-chloro-4-(trifluoromethyl)phenyl]sulfonylamino]-1h-pyrazolo[3,4-b]pyrazin-6-yl]phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=NNC2=NC(C=3C=CC(NS(=O)(=O)C=4C(=CC(=CC=4)C(F)(F)F)Cl)=CC=3)=CN=C12 AMICJZVZWNPDRK-UHFFFAOYSA-N 0.000 claims 1
MTSVGFNCGCTFDK-UHFFFAOYSA-N 2-methyl-n-[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-5-nitrobenzenesulfonamide Chemical compound C=1N=C2C(C)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C MTSVGFNCGCTFDK-UHFFFAOYSA-N 0.000 claims 1
DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
IGPTXARXZZFPEN-UHFFFAOYSA-N 5-chloro-n-[4-[3-[(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylamino]-1h-pyrazolo[3,4-b]pyrazin-6-yl]phenyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NC1=NNC2=NC(C=3C=CC(NS(=O)(=O)C4=C(N(C)N=C4C)Cl)=CC=3)=CN=C12 IGPTXARXZZFPEN-UHFFFAOYSA-N 0.000 claims 1
GFFUAEKPDJYQRA-UHFFFAOYSA-N 5-chloro-n-[4-[3-[(5-chloro-2,4-difluorophenyl)sulfonylamino]-1h-pyrazolo[3,4-b]pyrazin-6-yl]phenyl]-2,4-difluorobenzenesulfonamide Chemical compound C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC1=NNC2=NC(C=3C=CC(NS(=O)(=O)C=4C(=CC(F)=C(Cl)C=4)F)=CC=3)=CN=C12 GFFUAEKPDJYQRA-UHFFFAOYSA-N 0.000 claims 1
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
RLUUEFQFGATIAJ-UHFFFAOYSA-N n-[3-methyl-4-[[4-(3-methyl-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]sulfamoyl]phenyl]acetamide Chemical compound CC1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(C=2N=C3NN=C(C)C3=NC=2)C=C1 RLUUEFQFGATIAJ-UHFFFAOYSA-N 0.000 claims 1
VZRWIHKCPQJCQE-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)-2-fluorophenyl]-2,3-dichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl VZRWIHKCPQJCQE-UHFFFAOYSA-N 0.000 claims 1
XULSDVPRNXYOBS-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)-2-fluorophenyl]-2,5-dichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl XULSDVPRNXYOBS-UHFFFAOYSA-N 0.000 claims 1
UUXHNNPPTMJKAO-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)-2-fluorophenyl]-5-chloro-2-fluorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1F UUXHNNPPTMJKAO-UHFFFAOYSA-N 0.000 claims 1
GKNITJDAAUGNPY-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,3,4-trichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1Cl GKNITJDAAUGNPY-UHFFFAOYSA-N 0.000 claims 1
ZNPWMPYXWMQBKK-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,3,4-trifluorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1F ZNPWMPYXWMQBKK-UHFFFAOYSA-N 0.000 claims 1
MBNNXCKHRKSGSU-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,3-dichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl MBNNXCKHRKSGSU-UHFFFAOYSA-N 0.000 claims 1
RSXCSJDWIMTYOC-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,4,5-trichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl RSXCSJDWIMTYOC-UHFFFAOYSA-N 0.000 claims 1
PKHREDBGZXSZFR-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,4,5-trifluorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C=C1F PKHREDBGZXSZFR-UHFFFAOYSA-N 0.000 claims 1
NTNFIJOSYVUYFN-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,4,6-trichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl NTNFIJOSYVUYFN-UHFFFAOYSA-N 0.000 claims 1
RTERCHJCWXQPSS-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,5-dichlorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl RTERCHJCWXQPSS-UHFFFAOYSA-N 0.000 claims 1
ILVJCDROFKYCPX-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2,5-dichlorothiophene-3-sulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl ILVJCDROFKYCPX-UHFFFAOYSA-N 0.000 claims 1
ADFDYZAYSAIYHV-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl ADFDYZAYSAIYHV-UHFFFAOYSA-N 0.000 claims 1
NQAKQMPWEPLRDF-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2-chloro-5-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(N)C3=NC=2)=C1 NQAKQMPWEPLRDF-UHFFFAOYSA-N 0.000 claims 1
JCBHUXWCMRUNAL-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2-cyano-5-fluorobenzenesulfonamide Chemical compound C=1N=C2C(N)=NNC2=NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1C#N JCBHUXWCMRUNAL-UHFFFAOYSA-N 0.000 claims 1
WGDISKHJLCXFQH-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2-cyano-5-methoxybenzenesulfonamide Chemical compound COC1=CC=C(C#N)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(N)C3=NC=2)=C1 WGDISKHJLCXFQH-UHFFFAOYSA-N 0.000 claims 1
QWVORDHXWMYPGI-UHFFFAOYSA-N n-[4-(3-amino-2h-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-2-cyano-5-methylbenzenesulfonamide Chemical compound CC1=CC=C(C#N)C(S(=O)(=O)NC=2C=CC(=CC=2)C=2N=C3NN=C(N)C3=NC=2)=C1 QWVORDHXWMYPGI-UHFFFAOYSA-N 0.000 claims 1
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JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000001890 transfection Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000005945 translocation Effects 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000034512 ubiquitination Effects 0.000 description 1
238000010798 ubiquitination Methods 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000001325 yolk sac Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA2846369A 2011-09-19 2011-09-19 N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl-sulfonamides et leurs utilisation comme produits pharmaceutiques Active CA2846369C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/EP2011/066220 WO2013041119A1 (fr)	2011-09-19	2011-09-19	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phényl-sulfonamides et leurs utilisation comme produits pharmaceutiques

Publications (2)

Publication Number	Publication Date
CA2846369A1 true CA2846369A1 (fr)	2013-03-28
CA2846369C CA2846369C (fr)	2018-11-13

Family

ID=44799999

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2846369A Active CA2846369C (fr)	2011-09-19	2011-09-19	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl-sulfonamides et leurs utilisation comme produits pharmaceutiques

Country Status (6)

Country	Link
KR (1)	KR20140064975A (fr)
AU (1)	AU2011377409B2 (fr)
CA (1)	CA2846369C (fr)
IL (1)	IL231097A0 (fr)
SG (1)	SG11201400551UA (fr)
WO (1)	WO2013041119A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20130072493A1 (en) *	2011-09-19	2013-03-21	Sanofi	N-[4-(1H-PYRAZOLO[3,4-b]PYRAZIN-6-YL)-PHENYL]-SULFONAMIDES AND THEIR USE AS PHARMACEUTICALS
DK2570415T3 (en)	2011-09-19	2015-11-23	Sanofi Sa	N- [4- (1H-pyrazolo [3,4-b] pyrazin-6-yl) phenyl] sulfonamides and their use as medicaments
TWI629275B (zh) *	2013-03-13	2018-07-11	賽諾菲公司	Ｎ－（４－（氮雜吲唑－６－基）－苯基）－磺醯胺及其作為醫藥之用途
ES2894333T3 (es)	2013-09-26	2022-02-14	Beth Israel Deaconess Medical Ct Inc	Inhibidores de SGK1 en el tratamiento del síndrome de QT Largo
EP3551613A4 (fr) *	2016-12-07	2020-07-22	New Era Pharma, Inc.	Composés et compositions pharmaceutiques pour moduler l'activité sgk, et leurs procédés

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6690240B2 (en)	2002-01-10	2004-02-10	Cirrus Logic, Inc.	Low-jitter loop filter for a phase-locked loop system
CA2537916A1 (fr)	2003-09-03	2005-03-31	Neurogen Corporation	5-aryl-pyrazolo[4,3-d]pyrimidines, pyridines, et pyrazines et composes associes
DE102005015255A1 (de) *	2005-04-04	2006-10-05	Merck Patent Gmbh	Acylhydrazide
DE102006043443A1 (de)	2006-09-15	2008-03-27	Bayer Healthcare Ag	Neue aza-bicyclische Verbindungen und ihre Verwendung
DE102007002717A1 (de) *	2007-01-18	2008-07-24	Merck Patent Gmbh	Heterocyclische Indazolderivate

2011
- 2011-09-19 CA CA2846369A patent/CA2846369C/fr active Active
- 2011-09-19 WO PCT/EP2011/066220 patent/WO2013041119A1/fr not_active Ceased
- 2011-09-19 KR KR1020147010212A patent/KR20140064975A/ko not_active Withdrawn
- 2011-09-19 SG SG11201400551UA patent/SG11201400551UA/en unknown
- 2011-09-19 AU AU2011377409A patent/AU2011377409B2/en active Active
2014
- 2014-02-23 IL IL231097A patent/IL231097A0/en unknown

Also Published As

Publication number	Publication date
IL231097A0 (en)	2014-03-31
KR20140064975A (ko)	2014-05-28
AU2011377409B2 (en)	2017-05-25
WO2013041119A1 (fr)	2013-03-28
SG11201400551UA (en)	2014-04-28
AU2011377409A1 (en)	2014-03-20
CA2846369C (fr)	2018-11-13

Publication	Publication Date	Title
EP2758399B1 (fr)	2017-11-15	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phényl]-sulfonamides et leur utilisation en tant que produits pharmaceutiques
CA2901534C (fr)	2021-04-27	N-(4-(azaindazol-6-yl)phenyl)sulfonamides et leur utilisation comme produits pharmaceutiques
JP5330430B2 (ja)	2013-10-30	プロテインキナーゼｂ阻害剤としてのピロロ［２，３−ｄ］ピリミジン誘導体
CA2846369C (fr)	2018-11-13	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl-sulfonamides et leurs utilisation comme produits pharmaceutiques
US9221828B2 (en)	2015-12-29	N-[4-(1H-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]sulfonamides as pharmaceuticals
JP5827849B2 (ja)	2015-12-02	Ｎ−［４−（１Ｈ−ピラゾロ［３，４−ｂ］ピラジン−６−イル）−フェニル］−スルホンアミド及び薬剤としてのその使用
CN103012407B (zh)	2016-06-29	N-[4-(1H-吡唑并[3,4-b]吡嗪-6-基)-苯基]-磺酰胺类及其作为药物的用途
HK1182388A (en)	2013-11-29	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]-sulfonamides and their use as pharmaceuticals
HK1182388B (en)	2018-05-11	N-[4-(1h-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]-sulfonamides and their use as pharmaceuticals

Legal Events

Date	Code	Title	Description
2016-09-15	EEER	Examination request	Effective date: 20160907