AU2013255437A1 - Substituted pyridine compounds as CRAC modulators - Google Patents
Substituted pyridine compounds as CRAC modulators Download PDFInfo
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- AU2013255437A1 AU2013255437A1 AU2013255437A AU2013255437A AU2013255437A1 AU 2013255437 A1 AU2013255437 A1 AU 2013255437A1 AU 2013255437 A AU2013255437 A AU 2013255437A AU 2013255437 A AU2013255437 A AU 2013255437A AU 2013255437 A1 AU2013255437 A1 AU 2013255437A1
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- Australia
- Prior art keywords
- methyl
- substituted
- oxadiazol
- oxo
- dihydro
- 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
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- 150000003222 pyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 106
- 201000010099 disease Diseases 0.000 claims abstract description 56
- 208000035475 disorder Diseases 0.000 claims abstract description 50
- 239000011575 calcium Substances 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 16
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 150000001669 calcium Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 99
- -1 nitro, hydroxyl Chemical group 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 201000006417 multiple sclerosis Diseases 0.000 claims description 24
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 206010061218 Inflammation Diseases 0.000 claims description 14
- 230000004054 inflammatory process Effects 0.000 claims description 14
- 208000023275 Autoimmune disease Diseases 0.000 claims description 13
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 210000000056 organ Anatomy 0.000 claims description 12
- 208000010668 atopic eczema Diseases 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- 230000000172 allergic effect Effects 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 229910000080 stannane Inorganic materials 0.000 claims description 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- LVLPYHYMBJCKSE-UHFFFAOYSA-N n-[4-[3-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]-2,6-difluorobenzamide Chemical compound CCC1=CC(C=2OC(=O)N(C)N=2)=CN=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F LVLPYHYMBJCKSE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DCZPOJMZCYLMIF-UHFFFAOYSA-N 2-chloro-n-[5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]-6-fluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1Cl DCZPOJMZCYLMIF-UHFFFAOYSA-N 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- OSAVUEOWPODIFQ-UHFFFAOYSA-N n-(2-chloro-6-fluorophenyl)-5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]thiophene-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)Cl)=CN=C1C1CC1 OSAVUEOWPODIFQ-UHFFFAOYSA-N 0.000 claims description 2
- RDKOCVXBVXKVHW-UHFFFAOYSA-N n-[4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-3,5-difluoropyridine-4-carboxamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F RDKOCVXBVXKVHW-UHFFFAOYSA-N 0.000 claims description 2
- LQAOMDQYQDFHAP-UHFFFAOYSA-N n-[4-[4-ethyl-6-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]-2,6-difluorobenzamide Chemical compound C=1C(CC)=CC(C=2OC(=O)N(C)N=2)=NC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F LQAOMDQYQDFHAP-UHFFFAOYSA-N 0.000 claims description 2
- WEVBLLUPMIKSEP-UHFFFAOYSA-N n-[4-[6-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-2,6-difluorobenzamide Chemical compound CCC1=NC=C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C=C1C1=NN(C)C(=O)O1 WEVBLLUPMIKSEP-UHFFFAOYSA-N 0.000 claims description 2
- KHPTZGQSKDNFRS-UHFFFAOYSA-N n-[5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F KHPTZGQSKDNFRS-UHFFFAOYSA-N 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- ZZVSSHQTNNGXAU-UHFFFAOYSA-N 2,6-difluoro-n-[3-methyl-4-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound C=1C=C(C=2C=C(C=NC=2)C=2OC(=O)N(C)N=2)C(C)=CC=1NC(=O)C1=C(F)C=CC=C1F ZZVSSHQTNNGXAU-UHFFFAOYSA-N 0.000 claims 1
- BPYNQBOVOFXWFN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BPYNQBOVOFXWFN-UHFFFAOYSA-N 0.000 claims 1
- QANOPYAOAXAPFN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methoxy-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound COC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F QANOPYAOAXAPFN-UHFFFAOYSA-N 0.000 claims 1
- YRFOJUUSTKSSDD-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F YRFOJUUSTKSSDD-UHFFFAOYSA-N 0.000 claims 1
- IXHVNPQABNHDJZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[3-methyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]benzamide Chemical compound CC1=C(C=2OC(=O)N(C)N=2)C=CN=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F IXHVNPQABNHDJZ-UHFFFAOYSA-N 0.000 claims 1
- BXQOUXBFUWOMQH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-6-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CC1=CC(C=2OC(=O)N(C)N=2)=NC=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BXQOUXBFUWOMQH-UHFFFAOYSA-N 0.000 claims 1
- KQBBFGMNEYJWTC-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 KQBBFGMNEYJWTC-UHFFFAOYSA-N 0.000 claims 1
- NJZXRQZXVFOFKH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[6-methyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]benzamide Chemical compound N=1C(C)=CC(C=2OC(=O)N(C)N=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F NJZXRQZXVFOFKH-UHFFFAOYSA-N 0.000 claims 1
- ZVZIYLLKDARKMS-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F ZVZIYLLKDARKMS-UHFFFAOYSA-N 0.000 claims 1
- MEXWYXRQNRGPHL-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F MEXWYXRQNRGPHL-UHFFFAOYSA-N 0.000 claims 1
- KYKOOENIONYICB-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 KYKOOENIONYICB-UHFFFAOYSA-N 0.000 claims 1
- KKXVOLVZGIWQCP-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 KKXVOLVZGIWQCP-UHFFFAOYSA-N 0.000 claims 1
- QITGKAOYCSIFCM-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[4-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]phenyl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=CC=2)=C1 QITGKAOYCSIFCM-UHFFFAOYSA-N 0.000 claims 1
- QSUHEZAOJVTNKR-UHFFFAOYSA-N 2-chloro-n-[4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-6-fluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1Cl QSUHEZAOJVTNKR-UHFFFAOYSA-N 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- YDIKJVJDOQLUNR-UHFFFAOYSA-N n-(2,6-difluorophenyl)-1-methyl-5-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrrole-2-carboxamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N1C)=CC=C1C(=O)NC1=C(F)C=CC=C1F YDIKJVJDOQLUNR-UHFFFAOYSA-N 0.000 claims 1
- UAUJRKSKWQZDFO-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[3-ethyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]benzamide Chemical compound CCC1=C(C=2OC(=O)N(C)N=2)C=CN=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UAUJRKSKWQZDFO-UHFFFAOYSA-N 0.000 claims 1
- LZJUGNCGBRHAGD-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[4-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]benzamide Chemical compound CCC1=C(C=2OC(=O)N(C)N=2)C=NC=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F LZJUGNCGBRHAGD-UHFFFAOYSA-N 0.000 claims 1
- UUVVTEOEHRECCA-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[5-ethyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]benzamide Chemical compound CCC1=CN=C(C=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)C=C1C1=NN(C)C(=O)O1 UUVVTEOEHRECCA-UHFFFAOYSA-N 0.000 claims 1
- UXPICKRHSZKBNE-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(S1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UXPICKRHSZKBNE-UHFFFAOYSA-N 0.000 claims 1
- LGBJWYSUSYETHI-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]furan-2-carboxamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(O1)=CC=C1C(=O)NC1=C(F)C=CC=C1F LGBJWYSUSYETHI-UHFFFAOYSA-N 0.000 claims 1
- ZMKDYABEGJGMPY-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]thiophene-2-carboxamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(S1)=CC=C1C(=O)NC1=C(F)C=CC=C1F ZMKDYABEGJGMPY-UHFFFAOYSA-N 0.000 claims 1
- OBCCIBATJJVBID-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]thiophene-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 OBCCIBATJJVBID-UHFFFAOYSA-N 0.000 claims 1
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- FSOZFNZCNXKUIT-UHFFFAOYSA-N n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CN=CC=C1NC(=O)C1=CC=CS1 FSOZFNZCNXKUIT-UHFFFAOYSA-N 0.000 claims 1
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- DLPGDSFPGNIVMW-UHFFFAOYSA-N n-[4-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-2,6-difluorobenzamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=CN=C1C1CC1 DLPGDSFPGNIVMW-UHFFFAOYSA-N 0.000 claims 1
- RJPPZWNROPRPEM-UHFFFAOYSA-N n-[4-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=NC=C(C=2)C=2OC(=O)N(C)N=2)C2CC2)=C1C RJPPZWNROPRPEM-UHFFFAOYSA-N 0.000 claims 1
- KQXHGPOZNNDDEA-UHFFFAOYSA-N n-[4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-3-methylphenyl]-2,6-difluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C(=C1)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F KQXHGPOZNNDDEA-UHFFFAOYSA-N 0.000 claims 1
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| IN6KO2012 | 2012-05-02 | ||
| IN6/KOL/2012 | 2012-05-02 | ||
| PCT/IB2013/053440 WO2013164769A1 (en) | 2012-05-02 | 2013-05-01 | Substituted pyridine compounds as crac modulators |
Publications (1)
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| AU2013255437A1 true AU2013255437A1 (en) | 2014-11-13 |
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| US (2) | US9399638B2 (enExample) |
| EP (1) | EP2844655A1 (enExample) |
| AU (1) | AU2013255437A1 (enExample) |
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| IN (1) | IN2014MN02126A (enExample) |
| WO (1) | WO2013164769A1 (enExample) |
| ZA (1) | ZA201407685B (enExample) |
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| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| WO2014203217A1 (en) | 2013-06-21 | 2014-12-24 | Lupin Limited | Substituted heterocyclic compounds as crac modulators |
| WO2014207648A1 (en) | 2013-06-24 | 2014-12-31 | Lupin Limited | Chromane and chromene derivatives and their use as crac modulators |
| WO2015090579A1 (en) * | 2013-12-18 | 2015-06-25 | Grünenthal GmbH | Pyrazolyl-based carboxamides iv |
| CN105367547B (zh) * | 2014-08-19 | 2019-04-23 | 北京桦冠生物技术有限公司 | 一种噁唑啉酮抗生素的新合成工艺 |
| UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
| US10525021B2 (en) | 2014-11-18 | 2020-01-07 | Rutgers, The State University Of New Jersey | Mitochondrial uncouplers for treatment of metabolic diseases and cancer |
| EP3261641B1 (en) * | 2015-02-27 | 2023-07-12 | Calcimedica, Inc. | Pancreatitis treatment |
| CN107847548B (zh) | 2015-05-18 | 2022-06-14 | 贝思以色列女会吏医学中心公司 | P物质、肥大细胞脱颗粒抑制剂和周围神经病 |
| EA034912B1 (ru) * | 2015-06-03 | 2020-04-06 | Бристол-Маерс Сквибб Компани | 4-гидрокси-3-(гетероарил)пиридин-2-оновые агонисты apj для применения в лечении сердечно-сосудистых заболеваний |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| WO2017201313A1 (en) | 2016-05-18 | 2017-11-23 | Shengkan Jin | Novel mitochondrial uncouplers for treatment of metabolic diseases and cancer |
| CA3037456A1 (en) | 2016-09-19 | 2018-03-22 | Novartis Ag | Therapeutic combinations comprising a raf inhibitor and a erk inhibitor |
| IL270224B1 (en) | 2017-05-02 | 2024-04-01 | Novartis Ag | Combination therapy employing trametinib and a defined raf inhibitor |
| EP3728230A1 (en) * | 2017-12-22 | 2020-10-28 | Ravenna Pharmaceuticals, Inc. | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| EP3849552A1 (en) | 2018-09-14 | 2021-07-21 | Rhizen Pharmaceuticals AG | Compositions comprising a crac inhibitor and a corticosteroid and methods of use thereof |
| EP4563150A3 (en) | 2019-05-13 | 2025-07-23 | Novartis AG | New crystalline forms of n-(3-(2-(2-hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methvlphenyl)-2(trifluoromethyl) isonicotinamide as raf inhibitors for the treatment of cancer |
| CN110407740A (zh) * | 2019-09-04 | 2019-11-05 | 上海毕得医药科技有限公司 | 一种3-溴-2-乙基吡啶的合成方法 |
| CN119421876A (zh) | 2022-04-25 | 2025-02-11 | 日本新药株式会社 | 作为ddr1激酶抑制剂的化合物和药物 |
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| BRPI0412805A (pt) | 2003-07-23 | 2006-09-26 | Synta Pharmaceuticals Corp | método para modular canais de ìon de cálcio ativado por liberação de ìon de cálcio |
| KR20070057965A (ko) | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| KR20070107022A (ko) | 2005-01-07 | 2007-11-06 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| KR101436161B1 (ko) | 2005-01-25 | 2014-09-01 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| US8802721B2 (en) | 2005-01-25 | 2014-08-12 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
| US8741960B2 (en) | 2006-01-25 | 2014-06-03 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| AU2007208240B2 (en) | 2006-01-25 | 2013-04-11 | Synta Pharmaceuticals Corp. | Substituted biaryl compounds for inflammation and immune-related uses |
| TWI417096B (zh) | 2006-01-25 | 2013-12-01 | Synta Pharmaceuticals Corp | 用於發炎及免疫相關用途之苯基及吡啶基化合物 |
| WO2007089904A2 (en) | 2006-01-31 | 2007-08-09 | Synta Pharmaceuticals Corp. | Pyridylphenyl compounds for inflammation and immune-related uses |
| CA2660963A1 (en) | 2006-08-21 | 2008-02-28 | Genentech, Inc. | Aza-benzothiophenyl compounds and methods of use |
| TW200911800A (en) | 2007-08-01 | 2009-03-16 | Synta Pharmaceuticals Corp | Pyridine compounds for inflammation and immune-related uses |
| HRP20110449T1 (hr) | 2007-08-17 | 2011-07-31 | Actelion Pharmaceuticals Ltd. | Derivati piridina kao modulatori receptora s1p1/edg1 |
| CA2699157A1 (en) | 2007-09-10 | 2009-03-19 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2009076454A2 (en) | 2007-12-12 | 2009-06-18 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| ES2455496T3 (es) | 2008-05-23 | 2014-04-15 | Glaxo Group Limited | Compuestos tricíclicos que contienen nitrógeno y su uso como agentes antibacterianos |
| DE102008031299B4 (de) | 2008-07-02 | 2014-10-30 | Acandis Gmbh & Co. Kg | Filter für ein Blutgefäß |
| KR101724161B1 (ko) | 2008-08-27 | 2017-04-06 | 칼시메디카, 인크 | 세포내 칼슘을 조절하는 화합물 |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US20100130522A1 (en) | 2008-10-01 | 2010-05-27 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| WO2011024004A1 (en) | 2009-08-26 | 2011-03-03 | Astrazeneca Ab | Heterocyclic urea derivatives useful for treatment of bacterial infection |
| US8618307B2 (en) | 2009-09-16 | 2013-12-31 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| NZ609572A (en) | 2010-10-30 | 2015-05-29 | Lupin Ltd | Oxazoline and isoxazoline derivatives as crac modulators |
| JP5985611B2 (ja) | 2011-05-03 | 2016-09-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途のための化合物 |
| WO2013059666A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
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2013
- 2013-05-01 EP EP13722111.5A patent/EP2844655A1/en not_active Withdrawn
- 2013-05-01 US US14/398,154 patent/US9399638B2/en not_active Expired - Fee Related
- 2013-05-01 AU AU2013255437A patent/AU2013255437A1/en not_active Abandoned
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- 2013-05-01 CA CA2871270A patent/CA2871270A1/en not_active Abandoned
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2014
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2016
- 2016-06-20 US US15/186,882 patent/US20160304506A1/en not_active Abandoned
Also Published As
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| US20160304506A1 (en) | 2016-10-20 |
| US9399638B2 (en) | 2016-07-26 |
| CA2871270A1 (en) | 2013-11-07 |
| EP2844655A1 (en) | 2015-03-11 |
| WO2013164769A1 (en) | 2013-11-07 |
| ZA201407685B (en) | 2015-11-25 |
| US20150111900A1 (en) | 2015-04-23 |
| IN2014MN02126A (enExample) | 2015-09-11 |
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| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |