CA2871222A1 - Substituted pyrazole compounds as crac modulators - Google Patents

Substituted pyrazole compounds as crac modulators Download PDF

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Publication number: CA2871222A1
Authority: CA; Canada
Prior art keywords: substituted; pyrazol; methyl; unsubstituted; pyridin
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

CA 2871222

Other languages

English (en)

French (fr)

Inventor

Nageswara Rao Irlapati

Gokul Keruji Deshmukh

Nilesh Raghunath Khedkar

Kiran Chandrashekhar Kulkarni

Zubair Abdul Wajid Shaikh

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 CA2871222A1 publication Critical patent/CA2871222A1/en

Status Abandoned legal-status Critical Current

Links

NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 238
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 101
201000010099 disease Diseases 0.000 claims abstract description 55
208000035475 disorder Diseases 0.000 claims abstract description 46
150000003839 salts Chemical class 0.000 claims abstract description 24
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
125000000217 alkyl group Chemical group 0.000 claims description 62
238000000034 method Methods 0.000 claims description 62
-1 nitro, hydroxyl Chemical group 0.000 claims description 60
229910052736 halogen Inorganic materials 0.000 claims description 39
150000002367 halogens Chemical class 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
125000001188 haloalkyl group Chemical group 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 22
206010028980 Neoplasm Diseases 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 17
208000024172 Cardiovascular disease Diseases 0.000 claims description 16
230000015572 biosynthetic process Effects 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 15
208000023275 Autoimmune disease Diseases 0.000 claims description 14
206010061218 Inflammation Diseases 0.000 claims description 14
201000011510 cancer Diseases 0.000 claims description 14
230000004054 inflammatory process Effects 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
208000010668 atopic eczema Diseases 0.000 claims description 12
238000010168 coupling process Methods 0.000 claims description 12
125000004438 haloalkoxy group Chemical group 0.000 claims description 12
210000000056 organ Anatomy 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
238000007112 amidation reaction Methods 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 11
238000005859 coupling reaction Methods 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
230000000172 allergic effect Effects 0.000 claims description 10
230000009435 amidation Effects 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 10
230000008878 coupling Effects 0.000 claims description 10
125000004122 cyclic group Chemical group 0.000 claims description 10
201000006417 multiple sclerosis Diseases 0.000 claims description 10
230000002829 reductive effect Effects 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 8
125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 6
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
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
238000007363 ring formation reaction Methods 0.000 claims description 5
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
230000001684 chronic effect Effects 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 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
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
208000033808 peripheral neuropathy Diseases 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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
239000003638 chemical reducing agent Substances 0.000 claims description 2
201000008482 osteoarthritis Diseases 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 9
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
JSGMIUDHQQMUOD-UHFFFAOYSA-N 1-[5-[1-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone Chemical compound O1C(C)(C)N(C(=O)C)N=C1C1=NN(C=2N=CC(NCC=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 JSGMIUDHQQMUOD-UHFFFAOYSA-N 0.000 claims 1
RMVMTHZVTFCKCG-UHFFFAOYSA-N 2,3,4-trifluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=C(F)C(F)=CC=3)F)=CC=2)C(C(F)(F)F)=C1 RMVMTHZVTFCKCG-UHFFFAOYSA-N 0.000 claims 1
IMAYNKZXZYASJM-UHFFFAOYSA-N 2,3-difluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=C(F)C=CC=3)F)=CC=2)C(C(F)(F)F)=C1 IMAYNKZXZYASJM-UHFFFAOYSA-N 0.000 claims 1
PQNXHEPRHRBNMM-UHFFFAOYSA-N 2,3-dimethyl-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound CC1=CC=CC(C(=O)NC=2N=CC(=CC=2)N2C(=CC(=N2)C=2OC(=O)N(C)N=2)C(F)(F)F)=C1C PQNXHEPRHRBNMM-UHFFFAOYSA-N 0.000 claims 1
AYPAMJXATAOZSH-UHFFFAOYSA-N 2,4,5-trifluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC(F)=C(F)C=3)F)=CC=2)C(C(F)(F)F)=C1 AYPAMJXATAOZSH-UHFFFAOYSA-N 0.000 claims 1
ZHEFVZXPIAVBPS-UHFFFAOYSA-N 2,4-difluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC(F)=CC=3)F)=CC=2)C(C(F)(F)F)=C1 ZHEFVZXPIAVBPS-UHFFFAOYSA-N 0.000 claims 1
XQOGDJFYJQKXSA-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 XQOGDJFYJQKXSA-UHFFFAOYSA-N 0.000 claims 1
DUOBBXAAIXFNGC-UHFFFAOYSA-N 2,6-difluoro-n-[6-[3-(4-methyl-5-oxo-1,2,4-oxadiazol-3-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound O1C(=O)N(C)C(C2=NN(C(=C2)C(F)(F)F)C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=N1 DUOBBXAAIXFNGC-UHFFFAOYSA-N 0.000 claims 1
IZUDTMPPIYNGSB-UHFFFAOYSA-N 2,6-difluoro-n-[6-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 IZUDTMPPIYNGSB-UHFFFAOYSA-N 0.000 claims 1
QQNZLXYBTGFCFN-UHFFFAOYSA-N 2,6-difluoro-n-[6-[3-[5-(hydroxymethyl)-5-methyl-4h-1,2-oxazol-3-yl]-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound O1C(C)(CO)CC(C2=NN(C(=C2)C(F)(F)F)C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=N1 QQNZLXYBTGFCFN-UHFFFAOYSA-N 0.000 claims 1
MYVWTGOYPVOLAM-UHFFFAOYSA-N 2,6-difluoro-n-[6-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CC(C(F)(F)F)=NN1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F MYVWTGOYPVOLAM-UHFFFAOYSA-N 0.000 claims 1
UILVOUAQWAKPBV-UHFFFAOYSA-N 2,6-difluoro-n-[6-[5-(trifluoromethyl)-3-(1,4,4-trimethyl-5-oxopyrazol-3-yl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound CC1(C)C(=O)N(C)N=C1C1=NN(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 UILVOUAQWAKPBV-UHFFFAOYSA-N 0.000 claims 1
GNPAFVPTPRRZLY-UHFFFAOYSA-N 2,6-difluoro-n-[6-[5-methyl-3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound CC1=CC(C=2OC(=O)N(C)N=2)=NN1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F GNPAFVPTPRRZLY-UHFFFAOYSA-N 0.000 claims 1
XMQCELZJEUYNPD-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 XMQCELZJEUYNPD-UHFFFAOYSA-N 0.000 claims 1
YNDZTORGEOHJMX-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[6-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 YNDZTORGEOHJMX-UHFFFAOYSA-N 0.000 claims 1
MZDPQHBQZDEWHF-UHFFFAOYSA-N 2-chloro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC=CC=3)Cl)=CC=2)C(C(F)(F)F)=C1 MZDPQHBQZDEWHF-UHFFFAOYSA-N 0.000 claims 1
ORKLJPPTJJDBHY-UHFFFAOYSA-N 2-chloro-n-[6-[3-(5,5-dimethyl-4-oxo-1,2-oxazol-3-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]-6-fluorobenzamide Chemical compound O=C1C(C)(C)ON=C1C1=NN(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 ORKLJPPTJJDBHY-UHFFFAOYSA-N 0.000 claims 1
XQDNMZTZVAEIBO-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound CC1=CC=CC(F)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C=2OC(=O)N(C)N=2)C(F)(F)F)C=N1 XQDNMZTZVAEIBO-UHFFFAOYSA-N 0.000 claims 1
ZHQMBDLIXOOORN-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[6-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound CC1=CC=CC(F)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C=2OC(=O)N(C)N=2)C(F)(F)F)N=C1 ZHQMBDLIXOOORN-UHFFFAOYSA-N 0.000 claims 1
XMWGYVBDUMYCAV-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[6-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]benzamide Chemical compound CC1=CC=CC(F)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C=2OC(=O)N(C)N=2)N=C1 XMWGYVBDUMYCAV-UHFFFAOYSA-N 0.000 claims 1
XUQDUFMXPOARND-UHFFFAOYSA-N 2-fluoro-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)C(C(F)(F)F)=C1 XUQDUFMXPOARND-UHFFFAOYSA-N 0.000 claims 1
JSNBTOKZNZSWED-UHFFFAOYSA-N 2-methyl-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C=2OC(=O)N(C)N=2)C(F)(F)F)C=N1 JSNBTOKZNZSWED-UHFFFAOYSA-N 0.000 claims 1
JAOWWZWFIITTSH-UHFFFAOYSA-N 3-[1-[5-[(2,6-difluorobenzoyl)amino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-5-methyl-4h-1,2-oxazole-5-carboxamide Chemical compound O1C(C)(C(N)=O)CC(C2=NN(C(=C2)C(F)(F)F)C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=N1 JAOWWZWFIITTSH-UHFFFAOYSA-N 0.000 claims 1
MFRAPLCCPFMEGR-UHFFFAOYSA-N 3-[1-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-4-methyl-1,2,4-oxadiazol-5-one Chemical compound O1C(=O)N(C)C(C2=NN(C(=C2)C(F)(F)F)C=2N=CC(NCC=3C(=CC=CC=3F)F)=CC=2)=N1 MFRAPLCCPFMEGR-UHFFFAOYSA-N 0.000 claims 1
YKXRTNHMWUNZKG-UHFFFAOYSA-N 4-ethyl-n-[5-[3-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]benzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C=2OC(=O)N(C)N=2)C(F)(F)F)C=N1 YKXRTNHMWUNZKG-UHFFFAOYSA-N 0.000 claims 1
UKPZLGWRKFEYLP-UHFFFAOYSA-N 5-[1-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-5-(fluoromethyl)pyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2N=CC(NCC=3C(=CC=CC=3F)F)=CC=2)C(CF)=C1 UKPZLGWRKFEYLP-UHFFFAOYSA-N 0.000 claims 1
ZVANEPHBQQBZKJ-UHFFFAOYSA-N 5-[1-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2N=CC(NCC=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 ZVANEPHBQQBZKJ-UHFFFAOYSA-N 0.000 claims 1
MCNDZJVJQRYGRE-UHFFFAOYSA-N 5-[1-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-5-methylpyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CC1=CC(C=2OC(=O)N(C)N=2)=NN1C(N=C1)=CC=C1NCC1=C(F)C=CC=C1F MCNDZJVJQRYGRE-UHFFFAOYSA-N 0.000 claims 1
PNRASTKJGQVKGW-UHFFFAOYSA-N 5-[1-[5-[(2-chloro-6-fluorophenyl)methylamino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-2,4,4-trimethylpyrazol-3-one Chemical compound CC1(C)C(=O)N(C)N=C1C1=NN(C=2N=CC(NCC=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 PNRASTKJGQVKGW-UHFFFAOYSA-N 0.000 claims 1
YKPQGGSMTQQEES-UHFFFAOYSA-N 5-[1-[5-[(2-chloro-6-fluorophenyl)methylamino]pyridin-2-yl]-5-(trifluoromethyl)pyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2N=CC(NCC=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 YKPQGGSMTQQEES-UHFFFAOYSA-N 0.000 claims 1
UGPUZBYDFZBPOL-UHFFFAOYSA-N 5-[1-[6-[(2,6-difluorophenyl)methylamino]pyridin-3-yl]-5-(trifluoromethyl)pyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NCC=3C(=CC=CC=3F)F)=CC=2)C(C(F)(F)F)=C1 UGPUZBYDFZBPOL-UHFFFAOYSA-N 0.000 claims 1
BKJBZDDHDCTQHT-UHFFFAOYSA-N 5-[1-[6-[(2-chloro-6-fluorophenyl)methylamino]pyridin-3-yl]-5-(trifluoromethyl)pyrazol-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound O1C(=O)N(C)N=C1C1=NN(C=2C=NC(NCC=3C(=CC=CC=3F)Cl)=CC=2)C(C(F)(F)F)=C1 BKJBZDDHDCTQHT-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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Dermatology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2871222 2012-05-02 2013-05-01 Substituted pyrazole compounds as crac modulators Abandoned CA2871222A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
IN6KO2012		2012-05-02
IN6/KOL/2012		2012-05-02
IN1474/KOL/2012		2012-12-28
IN1474KO2012		2012-12-28
PCT/IB2013/053446 WO2013164773A1 (en)	2012-05-02	2013-05-01	Substituted pyrazole compounds as crac modulators

Publications (1)

Publication Number	Publication Date
CA2871222A1 true CA2871222A1 (en)	2013-11-07

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2871222 Abandoned CA2871222A1 (en)	2012-05-02	2013-05-01	Substituted pyrazole compounds as crac modulators

Country Status (7)

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US (2)	US9409898B2 (2)
EP (1)	EP2844656A1 (2)
AU (1)	AU2013255441B2 (2)
CA (1)	CA2871222A1 (2)
IN (1)	IN2014MN02127A (2)
WO (1)	WO2013164773A1 (2)
ZA (1)	ZA201407668B (2)

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WO2015197187A1 (en) *	2014-06-24	2015-12-30	Grünenthal GmbH	Pyrazolyl-based carboxamides v
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- 2013-05-01 US US14/398,161 patent/US9409898B2/en not_active Expired - Fee Related
- 2013-05-01 IN IN2127MUN2014 patent/IN2014MN02127A/en unknown
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2014
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2016
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US9409898B2 (en)	2016-08-09
WO2013164773A1 (en)	2013-11-07
AU2013255441A1 (en)	2014-11-13
EP2844656A1 (en)	2015-03-11
ZA201407668B (en)	2015-11-25
AU2013255441B2 (en)	2017-11-09
IN2014MN02127A (2)	2015-09-11
US20160304507A1 (en)	2016-10-20
US20150111925A1 (en)	2015-04-23

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