JPWO2022211060A5 - - Google Patents
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- Publication number
- JPWO2022211060A5 JPWO2022211060A5 JP2023511731A JP2023511731A JPWO2022211060A5 JP WO2022211060 A5 JPWO2022211060 A5 JP WO2022211060A5 JP 2023511731 A JP2023511731 A JP 2023511731A JP 2023511731 A JP2023511731 A JP 2023511731A JP WO2022211060 A5 JPWO2022211060 A5 JP WO2022211060A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- alkyl group
- membered cyclic
- pharmaceutically acceptable
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 24
- HEMMPBFUIREAEA-YNEHKIRRSA-N CC1=CC=C(C(N(C[C@@H]2CC3)C[C@H]2[C@@H]3NC(N=N2)=CC=C2Br)=O)S1 Chemical compound CC1=CC=C(C(N(C[C@@H]2CC3)C[C@H]2[C@@H]3NC(N=N2)=CC=C2Br)=O)S1 HEMMPBFUIREAEA-YNEHKIRRSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 42
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 33
- 125000004122 cyclic group Chemical group 0.000 description 30
- 125000005843 halogen group Chemical group 0.000 description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 20
- 101000929834 Homo sapiens Monoacylglycerol lipase ABHD6 Proteins 0.000 description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 18
- 210000003141 lower extremity Anatomy 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 102100035912 Monoacylglycerol lipase ABHD6 Human genes 0.000 description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 15
- 208000002193 Pain Diseases 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 230000036407 pain Effects 0.000 description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 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 description 12
- 238000012360 testing method Methods 0.000 description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- -1 {(3aS,4R,6aR)-4-[(6-chloro-3-pyridazinyl)amino]hexahydrocyclopenta[c]pyrrol-2(1H)-yl}(5-methyl-2-thienyl ) methanone Chemical compound 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 208000035217 Ring chromosome 1 syndrome Diseases 0.000 description 9
- 125000000262 haloalkenyl group Chemical group 0.000 description 9
- 125000000232 haloalkynyl group Chemical group 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 6
- 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 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000006911 enzymatic reaction Methods 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229960004380 tramadol Drugs 0.000 description 6
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 description 3
- 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 description 3
- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101710116393 Monoglyceride lipase Proteins 0.000 description 3
- 102100029814 Monoglyceride lipase Human genes 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 208000008930 Low Back Pain Diseases 0.000 description 2
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical group CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 2
- JFSHCJDJMQSJBI-IACUBPJLSA-N O=C(C1=CC(COCC2)=C2S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Cl Chemical compound O=C(C1=CC(COCC2)=C2S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Cl JFSHCJDJMQSJBI-IACUBPJLSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- YZXBAPSDXZZRGB-FBFLGLDDSA-N arachidonic acid-d8 Chemical compound CCCCCC(/[2H])=C(/[2H])C\C([2H])=C(\[2H])C\C([2H])=C(\[2H])C\C([2H])=C(\[2H])CCCC(O)=O YZXBAPSDXZZRGB-FBFLGLDDSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 102000052890 human ABHD6 Human genes 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000011552 rat model Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- DCPCOKIYJYGMDN-HUDVFFLJSA-N 1-arachidonoyl-sn-glycerol Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@@H](O)CO DCPCOKIYJYGMDN-HUDVFFLJSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 1
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 1
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- CIUUIPMOFZIWIZ-UHFFFAOYSA-N Bropirimine Chemical compound NC1=NC(O)=C(Br)C(C=2C=CC=CC=2)=N1 CIUUIPMOFZIWIZ-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 206010072132 Fracture pain Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 208000005615 Interstitial Cystitis Diseases 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- NBJZETZOSUFBNB-IACUBPJLSA-N O=C(C1=CC(COCC2)=C2S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Br Chemical compound O=C(C1=CC(COCC2)=C2S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Br NBJZETZOSUFBNB-IACUBPJLSA-N 0.000 description 1
- NCMRJVKCUUVYBX-FRRDWIJNSA-N O=C(C1=CC(COCC2)=C2S1)N(C[C@H]1[C@@H](C2)NC(N=N3)=CC=C3Br)C[C@@H]1C2(F)F Chemical compound O=C(C1=CC(COCC2)=C2S1)N(C[C@H]1[C@@H](C2)NC(N=N3)=CC=C3Br)C[C@@H]1C2(F)F NCMRJVKCUUVYBX-FRRDWIJNSA-N 0.000 description 1
- DSQCODBHEIAIQK-HBNTYKKESA-N O=C(C1=CC=C(C(F)F)S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Cl Chemical compound O=C(C1=CC=C(C(F)F)S1)N(C[C@@H]1CC2)C[C@H]1[C@@H]2NC(N=N1)=CC=C1Cl DSQCODBHEIAIQK-HBNTYKKESA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 201000004328 Pulpitis Diseases 0.000 description 1
- 206010037464 Pulpitis dental Diseases 0.000 description 1
- 101150007742 RING1 gene Proteins 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 208000016097 disease of metabolism Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 239000012160 loading buffer Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229940124636 opioid drug Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AGDSCTQQXMDDCV-UHFFFAOYSA-M sodium;2-iodoacetate Chemical compound [Na+].[O-]C(=O)CI AGDSCTQQXMDDCV-UHFFFAOYSA-M 0.000 description 1
- YYEADNLMHYZIQS-UHFFFAOYSA-M sodium;acetate;hydroiodide Chemical compound [Na+].[I-].CC(O)=O YYEADNLMHYZIQS-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024109044A JP7750341B2 (ja) | 2021-04-01 | 2024-07-05 | Ａｂｈｄ６アンタゴニスト |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021062790 | 2021-04-01 | ||
| JP2021062790 | 2021-04-01 | ||
| PCT/JP2022/016679 WO2022211060A1 (ja) | 2021-04-01 | 2022-03-31 | Ａｂｈｄ６アンタゴニスト |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024109044A Division JP7750341B2 (ja) | 2021-04-01 | 2024-07-05 | Ａｂｈｄ６アンタゴニスト |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2022211060A1 JPWO2022211060A1 (https=) | 2022-10-06 |
| JPWO2022211060A5 true JPWO2022211060A5 (https=) | 2023-09-08 |
| JP7525058B2 JP7525058B2 (ja) | 2024-07-30 |
Family
ID=83459597
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023511731A Active JP7525058B2 (ja) | 2021-04-01 | 2022-03-31 | Ａｂｈｄ６アンタゴニスト |
| JP2024109044A Active JP7750341B2 (ja) | 2021-04-01 | 2024-07-05 | Ａｂｈｄ６アンタゴニスト |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024109044A Active JP7750341B2 (ja) | 2021-04-01 | 2024-07-05 | Ａｂｈｄ６アンタゴニスト |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US11981682B2 (https=) |
| EP (1) | EP4317153A4 (https=) |
| JP (2) | JP7525058B2 (https=) |
| KR (1) | KR20230166084A (https=) |
| CN (1) | CN117120435A (https=) |
| AU (1) | AU2022251752A1 (https=) |
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| TW202304932A (zh) * | 2021-04-01 | 2023-02-01 | 日商小野藥品工業股份有限公司 | Abhd6拮抗劑 |
| TW202421635A (zh) * | 2022-09-30 | 2024-06-01 | 日商小野藥品工業股份有限公司 | Abhd6拮抗劑 |
| CN119798162A (zh) * | 2024-12-13 | 2025-04-11 | 浙江瑞博制药有限公司 | 一种5,6-二氢环戊并吡啶-7-酮类化合物上三元环的制备方法 |
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| JP5017103B2 (ja) | 2004-06-17 | 2012-09-05 | トランスフオーム・フアーマシユーチカルズ・インコーポレーテツド | 薬剤共結晶組成物および関連した使用方法 |
| JP2010062927A (ja) | 2008-09-04 | 2010-03-18 | Sharp Corp | 表示装置、作動特性制御方法、制御プログラム及び記録媒体 |
| WO2010056309A2 (en) * | 2008-11-14 | 2010-05-20 | The Scripps Research Institute | Methods and compositions related to targeting monoacylglycerol lipase |
| KR20110091784A (ko) | 2008-11-26 | 2011-08-12 | 아보트 러보러터리즈 | 칼슘 채널 차단제로서의 치환된 옥타하이드로사이클로펜타［ｃ］피롤4아민 |
| JP2010130944A (ja) | 2008-12-04 | 2010-06-17 | Yamamori Kk | 含気形態のレトルトパウチ食品 |
| FR2945534B1 (fr) | 2009-05-12 | 2012-11-16 | Sanofi Aventis | DERIVES DE CYCLOPENTAL[c]PYRROLE-2-CARBOXYLATES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| WO2013016807A1 (en) * | 2011-08-03 | 2013-02-07 | Centre Hospitalier De L'universite De Montreal | Insulin secretion promoting agents |
| CA2917050A1 (en) | 2013-07-03 | 2015-01-08 | Todd K. Jones | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
| IL273924B2 (en) | 2017-10-20 | 2024-07-01 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| WO2019089676A1 (en) | 2017-10-31 | 2019-05-09 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| JP6870587B2 (ja) | 2017-11-16 | 2021-05-12 | 株式会社Sumco | シリコン単結晶の評価方法およびシリコンウェーハの製造方法 |
| US10662159B2 (en) * | 2017-11-22 | 2020-05-26 | Makscientific, Llc | ABHD6 and dual ABHD6/MGL inhibitors and their uses |
| TW202304932A (zh) * | 2021-04-01 | 2023-02-01 | 日商小野藥品工業股份有限公司 | Abhd6拮抗劑 |
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