CA2871270A1 - Substituted pyridine compounds as crac modulators - Google Patents

Substituted pyridine compounds as crac modulators Download PDF

Info

Publication number: CA2871270A1
Authority: CA; Canada
Prior art keywords: methyl; substituted; oxadiazol; oxo; dihydro
Prior art date: 2012-05-02
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

Application number

CA2871270A

Other languages

English (en)

French (fr)

Inventor

Nageswara Rao Irlapati

Zubair Abdul Wajid Shaikh

Vijay Pandurang Karche

Gokul Keruji Deshmukh

Neelima Sinha

Venkata P. Palle

Rajender Kumar Kamboj

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.)

Lupin Ltd

Original Assignee

Lupin Ltd

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.)

2012-05-02

Filing date

2013-05-01

Publication date

2013-11-07

2013-05-01 Application filed by Lupin Ltd filed Critical Lupin Ltd

2013-11-07 Publication of CA2871270A1 publication Critical patent/CA2871270A1/en

Status Abandoned legal-status Critical Current

Links

150000003222 pyridines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 205
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 104
201000010099 disease Diseases 0.000 claims abstract description 56
208000035475 disorder Diseases 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 23
239000011575 calcium Substances 0.000 claims abstract description 17
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 14
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
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 83
125000000217 alkyl group Chemical group 0.000 claims description 65
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 41
125000003118 aryl group Chemical group 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
229910052736 halogen Inorganic materials 0.000 claims description 33
125000001188 haloalkyl group Chemical group 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000000623 heterocyclic group Chemical group 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
201000006417 multiple sclerosis Diseases 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 20
206010028980 Neoplasm Diseases 0.000 claims description 18
238000005859 coupling reaction Methods 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000004438 haloalkoxy group Chemical group 0.000 claims description 15
208000024172 Cardiovascular disease Diseases 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
201000011510 cancer Diseases 0.000 claims description 13
210000000056 organ Anatomy 0.000 claims description 12
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 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
230000000172 allergic effect Effects 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 9
238000010168 coupling process Methods 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 8
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 8
230000008878 coupling Effects 0.000 claims description 8
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
206010033645 Pancreatitis Diseases 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 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
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
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
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 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
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
150000002431 hydrogen Chemical class 0.000 claims 9
PPRZCLXXYKZUSI-UHFFFAOYSA-N 2,6-difluoro-n-[3-methyl-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)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F PPRZCLXXYKZUSI-UHFFFAOYSA-N 0.000 claims 1
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
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
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
VQWJUCBLOQUNKC-UHFFFAOYSA-N 2,6-difluoro-n-[6-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyridin-3-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)=CC=2)=C1 VQWJUCBLOQUNKC-UHFFFAOYSA-N 0.000 claims 1
QCABWHXPLIOOOC-UHFFFAOYSA-N 2-chloro-6-fluoro-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=C1Cl QCABWHXPLIOOOC-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
MIADLJOXYXVUOJ-UHFFFAOYSA-N 2-chloro-n-[5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]-6-fluorobenzamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2N=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=NC=2)=CN=C1C1CC1 MIADLJOXYXVUOJ-UHFFFAOYSA-N 0.000 claims 1
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 1
XEWYMSHQKLWAPB-UHFFFAOYSA-N 2-fluoro-6-methyl-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(C)C=CC=C1F XEWYMSHQKLWAPB-UHFFFAOYSA-N 0.000 claims 1
BLZSFZSANKKGPF-UHFFFAOYSA-N 4-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)benzamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 BLZSFZSANKKGPF-UHFFFAOYSA-N 0.000 claims 1
QAOPDAXPTZSLLB-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)furan-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2OC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 QAOPDAXPTZSLLB-UHFFFAOYSA-N 0.000 claims 1
VTNZPMJAXJQINO-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 VTNZPMJAXJQINO-UHFFFAOYSA-N 0.000 claims 1
XFRUEBWRBSPKPX-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CN=CC=C1NC(=O)C1=CC=C(C=2C(=NC=C(C=2)C=2OC(=O)N(C)N=2)C2CC2)S1 XFRUEBWRBSPKPX-UHFFFAOYSA-N 0.000 claims 1
XNKQRDJADVUOGX-UHFFFAOYSA-N 5-[5-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-6-ethylpyridin-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CC=C1NCC1=C(F)C=CC=C1F XNKQRDJADVUOGX-UHFFFAOYSA-N 0.000 claims 1
JGEVQLZYMJHDLP-UHFFFAOYSA-N 5-[5-[6-[(2,6-difluorophenyl)methylamino]pyridin-3-yl]-6-ethylpyridin-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=N1)=CC=C1NCC1=C(F)C=CC=C1F JGEVQLZYMJHDLP-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
UQKOVHQHWZMKST-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]benzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UQKOVHQHWZMKST-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
UDVOMFANSRHYON-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-1-methylpyrrole-2-carboxamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N1C)=CC=C1C(=O)NC1=C(F)C=CC=C1F UDVOMFANSRHYON-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- 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

Landscapes

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)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA2871270A 2012-05-02 2013-05-01 Substituted pyridine compounds as crac modulators Abandoned CA2871270A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
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

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Publication Number	Publication Date
CA2871270A1 true CA2871270A1 (en)	2013-11-07

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CA2871270A Abandoned CA2871270A1 (en)	2012-05-02	2013-05-01	Substituted pyridine compounds as crac modulators

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US (2)	US9399638B2 (2)
EP (1)	EP2844655A1 (2)
AU (1)	AU2013255437A1 (2)
CA (1)	CA2871270A1 (2)
IN (1)	IN2014MN02126A (2)
WO (1)	WO2013164769A1 (2)
ZA (1)	ZA201407685B (2)

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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
CA2968299A1 (en)	2014-11-18	2016-05-26	Rutgers, The State University Of New Jersey	Novel mitochondrial uncouplers for treatment of metabolic diseases and cancer
EP3778595B1 (en) *	2015-02-27	2021-08-25	Calcimedica, Inc.	Pancreatitis treatment
US20180161388A1 (en)	2015-05-18	2018-06-14	Beth Israel Deaconess Medical Center, Inc.	Substance p, mast cell degranulation inhibitors, and peripheral neuropathy
PL3303330T3 (pl) *	2015-06-03	2019-10-31	Bristol Myers Squibb Co	Agoniści 4 - hydroksy - 3 - ( heteroarylo ) pirydyno - 2 - onowi receptora apj do stosowania w leczeniu zaburzeń sercowo-naczyniowych
CA2995094A1 (en)	2015-08-07	2017-02-16	Calcimedica, Inc.	Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury
US10227315B2 (en)	2016-05-18	2019-03-12	Rutgers, The State University Of New Jersey	Mitochondrial uncouplers for treatment of metabolic diseases and cancer
AU2017329090B9 (en)	2016-09-19	2019-09-05	Novartis Ag	Therapeutic combinations comprising a RAF inhibitor and a ERK inhibitor
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2013
- 2013-05-01 CA CA2871270A patent/CA2871270A1/en not_active Abandoned
- 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
- 2013-05-01 WO PCT/IB2013/053440 patent/WO2013164769A1/en not_active Ceased
- 2013-05-01 EP EP13722111.5A patent/EP2844655A1/en not_active Withdrawn
- 2013-05-01 IN IN2126MUN2014 patent/IN2014MN02126A/en unknown
2014
- 2014-10-22 ZA ZA2014/07685A patent/ZA201407685B/en unknown
2016
- 2016-06-20 US US15/186,882 patent/US20160304506A1/en not_active Abandoned

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WO2013164769A1 (en)	2013-11-07
AU2013255437A1 (en)	2014-11-13
US20150111900A1 (en)	2015-04-23
EP2844655A1 (en)	2015-03-11
US9399638B2 (en)	2016-07-26
ZA201407685B (en)	2015-11-25
US20160304506A1 (en)	2016-10-20
IN2014MN02126A (2)	2015-09-11

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Date	Code	Title	Description
2019-06-12	FZDE	Dead	Effective date: 20190501

Publication	Publication Date	Title
CA2871270A1 (en)	2013-11-07	Substituted pyridine compounds as crac modulators
US9725463B2 (en)	2017-08-08	Substituted heterocyclic compounds as CRAC modulators
AU2013255441B2 (en)	2017-11-09	Substituted pyrazole compounds as CRAC modulators
DK2632906T3 (en)	2016-05-30	Oxazoline and isoxazolines AS CRACMODULATORER
US9790231B2 (en)	2017-10-17	Chromane and chromene derivatives and their use as CRAC modulators
JP6692113B2 (ja)	2020-05-13	６員複素環誘導体を含有する医薬組成物
HK1227858A1 (en)	2017-10-27	Oxazoline and isoxazoline derivatives as crac modulators
HK1187918B (en)	2016-12-23	Oxazoline and isoxazoline derivatives as crac modulators