JP2017503024A5 - - Google Patents
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- JP2017503024A5 JP2017503024A5 JP2016562455A JP2016562455A JP2017503024A5 JP 2017503024 A5 JP2017503024 A5 JP 2017503024A5 JP 2016562455 A JP2016562455 A JP 2016562455A JP 2016562455 A JP2016562455 A JP 2016562455A JP 2017503024 A5 JP2017503024 A5 JP 2017503024A5
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- Japan
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- cyano
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- 150000001875 compounds Chemical class 0.000 claims description 80
- -1 cyano, carboxyl Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 208000002193 Pain Diseases 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000001990 intravenous administration Methods 0.000 claims description 8
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- 239000000952 serotonin receptor agonist Substances 0.000 claims description 8
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical group CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
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- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 claims description 4
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- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
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- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001802 infusion Methods 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 238000007912 intraperitoneal administration Methods 0.000 claims description 4
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- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- 239000003706 n methyl dextro aspartic acid receptor stimulating agent Substances 0.000 claims description 4
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- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 4
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 4
- 239000003401 opiate antagonist Substances 0.000 claims description 4
- 102000017953 prostanoid receptors Human genes 0.000 claims description 4
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- 239000000018 receptor agonist Substances 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical group C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229940126033 PPAR agonist Drugs 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 2
- WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 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 2
- 206010065390 Inflammatory pain Diseases 0.000 claims description 2
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 2
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 2
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- 208000001294 Nociceptive Pain Diseases 0.000 claims description 2
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 229960002133 almotriptan Drugs 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229960000590 celecoxib Drugs 0.000 claims description 2
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229960004126 codeine Drugs 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229960001259 diclofenac Drugs 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229960000616 diflunisal Drugs 0.000 claims description 2
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims description 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229960002472 eletriptan Drugs 0.000 claims description 2
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960005293 etodolac Drugs 0.000 claims description 2
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims description 2
- CAHCBJPUTCKATP-FAWZKKEFSA-N etorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O CAHCBJPUTCKATP-FAWZKKEFSA-N 0.000 claims description 2
- 229950004155 etorphine Drugs 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229960002428 fentanyl Drugs 0.000 claims description 2
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims description 2
- 229960002390 flurbiprofen Drugs 0.000 claims description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 2
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
- 229960000991 ketoprofen Drugs 0.000 claims description 2
- 229960004752 ketorolac Drugs 0.000 claims description 2
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims description 2
- 229960002373 loxoprofen Drugs 0.000 claims description 2
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 claims description 2
- 229960001929 meloxicam Drugs 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims description 2
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- UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 2
- 229960002748 norepinephrine Drugs 0.000 claims description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 2
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 claims description 2
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- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims description 2
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 2
- 229960002702 piroxicam Drugs 0.000 claims description 2
- 229960000425 rizatriptan Drugs 0.000 claims description 2
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 claims description 2
- 229960000371 rofecoxib Drugs 0.000 claims description 2
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 2
- GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical compound C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000725 suspension Substances 0.000 claims description 2
- 229960004380 tramadol Drugs 0.000 claims description 2
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 2
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims description 2
- 229960002004 valdecoxib Drugs 0.000 claims description 2
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 2
- 229960001360 zolmitriptan Drugs 0.000 claims description 2
- UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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- 238000007792 addition Methods 0.000 claims 1
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- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461924119P | 2014-01-06 | 2014-01-06 | |
| US61/924,119 | 2014-01-06 | ||
| PCT/US2014/072291 WO2015103060A1 (en) | 2014-01-06 | 2014-12-23 | Trpa1 modulators |
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| SG11201605559VA (en) | 2014-01-06 | 2016-08-30 | Algomedix Inc | Trpa1 modulators |
| WO2017090756A1 (ja) | 2015-11-27 | 2017-06-01 | 大鵬薬品工業株式会社 | 新規なビフェニル化合物又はその塩 |
| JP2019521189A (ja) * | 2016-07-06 | 2019-07-25 | アルゴメディックス，インク． | ドライアイ、眼痛および炎症の処置のためのｔｒｐａ１アンタゴニスト |
| CN106580984A (zh) * | 2016-12-12 | 2017-04-26 | 高群 | 一种治疗高血脂症的药物组合物 |
| CN110461838B (zh) * | 2017-03-07 | 2022-05-06 | 豪夫迈·罗氏有限公司 | 噁二唑瞬时受体电位通道抑制剂 |
| KR102361918B1 (ko) | 2017-05-26 | 2022-02-14 | 다이호야쿠힌고교 가부시키가이샤 | 신규 비페닐 화합물 또는 그의 염 |
| JP6738962B2 (ja) * | 2017-05-26 | 2020-08-12 | 大鵬薬品工業株式会社 | 新規なビフェニル化合物を用いた抗腫瘍効果増強剤 |
| WO2018221555A1 (ja) | 2017-05-31 | 2018-12-06 | 大鵬薬品工業株式会社 | Ｉｎｓｍ１の発現に基づくｌｓｄ１阻害剤の治療効果の予測方法 |
| CN109596818B (zh) * | 2018-12-13 | 2024-03-19 | 丁蓉 | 一种基于电生理学分析当归四逆汤预防奥沙利铂神经毒性机制的研究方法 |
| EP4058151B1 (en) | 2019-11-13 | 2025-05-21 | Taiho Pharmaceutical Co., Ltd. | Novel salt of terphenyl compound |
| JP7688339B2 (ja) * | 2020-01-22 | 2025-06-04 | 国立研究開発法人理化学研究所 | 新規化合物、およびその利用 |
| FR3114235A1 (fr) | 2020-09-18 | 2022-03-25 | Université Grenoble Alpes | Inhibition du canal trpa1 astrocytaire comme nouvelle cible therapeutique neuroprotectrice dans les phases prodromales de la maladie d’alzheimer |
| CN112694436B (zh) * | 2020-12-30 | 2022-07-08 | 济南周行医药科技有限公司 | 一种槟榔碱的合成方法 |
| IT202100015098A1 (it) | 2021-06-09 | 2022-12-09 | Flonext S R L | Composto antagonista del canale trpa1 per uso in patologie degenerative della retina |
| WO2024099404A1 (zh) * | 2022-11-10 | 2024-05-16 | 北京普祺医药科技股份有限公司 | 一种含氮螺环类化合物、药物组合物以及其用途 |
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| GB8429128D0 (en) * | 1984-11-17 | 1984-12-27 | Fisons Plc | Heterocyclic compounds |
| ATE49198T1 (de) * | 1984-05-12 | 1990-01-15 | Fisons Plc | Antiinflammatorische 1,n-diarylpyrazol-3-amine, deren zusammensetzungen und verfahren zu deren herstellung. |
| WO1998052941A1 (en) * | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | PYRAZOLE DERIVATIVES AS p38 KINASE INHIBITORS |
| CA2331878A1 (en) * | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
| AU2004200420A1 (en) * | 2003-03-11 | 2004-09-30 | Astellas Pharma Inc. | Inhibitor of cyclooxygenase |
| EP1620095A4 (en) * | 2003-04-24 | 2009-04-01 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
| JP4490434B2 (ja) | 2003-10-23 | 2010-06-23 | エフ．ホフマン−ラ ロシュ アーゲー | 神経及び神経精神疾患の処置においてＧｌｙＴ−１阻害剤として使用するためのトリアザ−スピロピペリジン誘導体 |
| CN1902191A (zh) * | 2003-12-26 | 2007-01-24 | 第一制药株式会社 | 酰胺基吡唑衍生物 |
| TW200526641A (en) * | 2003-12-26 | 2005-08-16 | Daiichi Seiyaku Co | Amidopyrazole derivatives |
| GB0417910D0 (en) * | 2004-08-11 | 2004-09-15 | Novartis Ag | Organic compounds |
| NZ564916A (en) | 2005-06-27 | 2011-03-31 | Exelixis Inc | Imidazole based LXR modulators |
| TW201900217A (zh) | 2005-12-22 | 2019-01-01 | 美商海卓勒生物科學公司 | 用於調節ｔｒｐａ１功能之化合物 |
| US7977358B2 (en) | 2007-07-26 | 2011-07-12 | Hoffmann-La Roche Inc. | Pyrazol derivatives |
| CA2711159A1 (en) | 2008-01-04 | 2009-07-16 | Abbott Laboratories | Trpa1 antagonists |
| US20110124666A1 (en) | 2008-06-02 | 2011-05-26 | Janssen Pharmaceutica NV a corporation | 3,4-dihydropyrimidine trpa1 antagonists |
| WO2010125469A1 (en) * | 2009-04-29 | 2010-11-04 | Glenmark Pharmaceuticals, S.A. | Pyrimidinedione-fused heterocyclic compounds as trpa1 modulators |
| EP2485737B1 (en) | 2009-10-07 | 2014-06-25 | Merck Sharp & Dohme Corp. | Novel trpa1 antagonists |
| US9133128B2 (en) | 2011-06-17 | 2015-09-15 | Research Triangle Institute | Pyrazole derivatives as cannabinoid receptor 1 antagonists |
| DE102011055815A1 (de) | 2011-11-29 | 2013-05-29 | Aicuris Gmbh & Co. Kg | Carboxamid-substituierte Heteroaryl-Pyrazole und ihre Verwendung |
| WO2014053694A1 (en) | 2012-10-01 | 2014-04-10 | Orion Corporation | N-prop-2-ynyl carboxamide derivatives and their use as trpa1 antagonists |
| SG11201605559VA (en) | 2014-01-06 | 2016-08-30 | Algomedix Inc | Trpa1 modulators |
| JP2019521189A (ja) | 2016-07-06 | 2019-07-25 | アルゴメディックス，インク． | ドライアイ、眼痛および炎症の処置のためのｔｒｐａ１アンタゴニスト |
-
2014
- 2014-12-23 SG SG11201605559VA patent/SG11201605559VA/en unknown
- 2014-12-23 AU AU2014374043A patent/AU2014374043B2/en not_active Ceased
- 2014-12-23 WO PCT/US2014/072291 patent/WO2015103060A1/en not_active Ceased
- 2014-12-23 CN CN201480076547.8A patent/CN106061969B/zh not_active Expired - Fee Related
- 2014-12-23 JP JP2016562455A patent/JP6626454B2/ja active Active
- 2014-12-23 EP EP14876732.0A patent/EP3092228A4/en not_active Withdrawn
- 2014-12-23 CA CA2936111A patent/CA2936111C/en active Active
-
2016
- 2016-07-06 IL IL246625A patent/IL246625B/en active IP Right Grant
- 2016-07-06 US US15/203,774 patent/US9951046B2/en not_active Expired - Fee Related
- 2016-08-02 ZA ZA2016/05332A patent/ZA201605332B/en unknown
-
2018
- 2018-03-01 US US15/909,652 patent/US10428049B2/en not_active Expired - Fee Related
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