CA2711408A1

CA2711408A1 - Trpa1 antagonists

Trpa1 antagonists Download PDF

Info

Publication number: CA2711408A1
Authority: CA; Canada
Prior art keywords: alkyl; oxime; fluorophenyl; pain; haloalkyl
Prior art date: 2008-01-04
Legal status : Abandoned

Application number

CA2711408A

Other languages

English (en)

French (fr)

Inventor

Richard J. Perner

Michael E. Kort

Stanley Didomenico, Jr.

Jun Chen

Anil Vasudevan

Current Assignee

Abbott Laboratories

Original Assignee

Individual

Priority date

2008-01-04

Filing date

2009-01-02

Publication date

2009-07-16

2009-01-02 Application filed by Individual filed Critical Individual

2009-07-16 Publication of CA2711408A1 publication Critical patent/CA2711408A1/en

Status Abandoned legal-status Critical Current

Links

239000005557 antagonist Substances 0.000 title abstract description 16
101150092793 Trpa1 gene Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 142
238000000034 method Methods 0.000 claims abstract description 77
101000764872 Homo sapiens Transient receptor potential cation channel subfamily A member 1 Proteins 0.000 claims abstract description 30
102100026186 Transient receptor potential cation channel subfamily A member 1 Human genes 0.000 claims abstract description 28
-1 -OR a Chemical group 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 45
208000002193 Pain Diseases 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 42
230000036407 pain Effects 0.000 claims description 40
239000000651 prodrug Substances 0.000 claims description 34
229940002612 prodrug Drugs 0.000 claims description 34
125000001188 haloalkyl group Chemical group 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
239000003638 chemical reducing agent Substances 0.000 claims description 16
239000012453 solvate Substances 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical group 0.000 claims description 13
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 12
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
208000004296 neuralgia Diseases 0.000 claims description 9
230000003349 osteoarthritic effect Effects 0.000 claims description 9
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 8
206010065390 Inflammatory pain Diseases 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
208000001294 Nociceptive Pain Diseases 0.000 claims description 6
208000026935 allergic disease Diseases 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
208000021722 neuropathic pain Diseases 0.000 claims description 6
201000001119 neuropathy Diseases 0.000 claims description 6
230000007823 neuropathy Effects 0.000 claims description 6
201000006474 Brain Ischemia Diseases 0.000 claims description 5
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125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
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208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
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HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 4
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ALEGZXFLOSZQFJ-OIPGSKEASA-N (ne)-n-[(e)-1-(4-fluorophenyl)-2-methylhept-1-en-3-ylidene]hydroxylamine Chemical compound CCCC\C(=N/O)\C(\C)=C\C1=CC=C(F)C=C1 ALEGZXFLOSZQFJ-OIPGSKEASA-N 0.000 claims 2
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