JPWO2021102568A5 - - Google Patents
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- Publication number
- JPWO2021102568A5 JPWO2021102568A5 JP2022530211A JP2022530211A JPWO2021102568A5 JP WO2021102568 A5 JPWO2021102568 A5 JP WO2021102568A5 JP 2022530211 A JP2022530211 A JP 2022530211A JP 2022530211 A JP2022530211 A JP 2022530211A JP WO2021102568 A5 JPWO2021102568 A5 JP WO2021102568A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dien
- dihydroxy
- dimethyloct
- pentylbenzamide
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 52
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 19
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 239000002207 metabolite Substances 0.000 claims 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- HROASLNNCRABBI-UHFFFAOYSA-N CC(=CCC=1C(=C(C(=O)NCC=2C=NC=CC=2)C(=CC=1O)CCCCC)O)CCC=C(C)C Chemical compound CC(=CCC=1C(=C(C(=O)NCC=2C=NC=CC=2)C(=CC=1O)CCCCC)O)CCC=C(C)C HROASLNNCRABBI-UHFFFAOYSA-N 0.000 claims 2
- LERRYDNPIGLAQH-UHFFFAOYSA-N CCCCCC1=CC(=C(C(=C1C(=O)N2CC2C)O)CC=C(C)CCC=C(C)C)O Chemical compound CCCCCC1=CC(=C(C(=C1C(=O)N2CC2C)O)CC=C(C)CCC=C(C)C)O LERRYDNPIGLAQH-UHFFFAOYSA-N 0.000 claims 2
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims 2
- 108050007331 Cannabinoid receptor Proteins 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 102000014461 Ataxins Human genes 0.000 claims 1
- 108010078286 Ataxins Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- UPFRKZIZZNJERW-UHFFFAOYSA-N BrC1=C(CNC(C2=C(C(=C(C=C2CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C=CC=C1 Chemical compound BrC1=C(CNC(C2=C(C(=C(C=C2CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C=CC=C1 UPFRKZIZZNJERW-UHFFFAOYSA-N 0.000 claims 1
- MMFOAQCFPJMDGK-UHFFFAOYSA-N C(#N)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C Chemical compound C(#N)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C MMFOAQCFPJMDGK-UHFFFAOYSA-N 0.000 claims 1
- ORYNEKKAJLMFGV-UHFFFAOYSA-N C(C)(=O)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O Chemical compound C(C)(=O)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O ORYNEKKAJLMFGV-UHFFFAOYSA-N 0.000 claims 1
- AIWBANYOAHDZEK-UHFFFAOYSA-N C(C1=CC=CC=C1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C Chemical compound C(C1=CC=CC=C1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C AIWBANYOAHDZEK-UHFFFAOYSA-N 0.000 claims 1
- SXVLTGVJCVYOGA-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O Chemical compound C(C1=CC=CC=C1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O SXVLTGVJCVYOGA-UHFFFAOYSA-N 0.000 claims 1
- FUQIXXBUDVMPRH-UHFFFAOYSA-N C(CCC)C1=CC(=C(C(=C1C(=O)N(C)CC1=NOC=C1)O)CC=C(CCC=C(C)C)C)O Chemical compound C(CCC)C1=CC(=C(C(=C1C(=O)N(C)CC1=NOC=C1)O)CC=C(CCC=C(C)C)C)O FUQIXXBUDVMPRH-UHFFFAOYSA-N 0.000 claims 1
- LXHYWJTZRJLTOF-UHFFFAOYSA-N C1(CC1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C Chemical compound C1(CC1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C LXHYWJTZRJLTOF-UHFFFAOYSA-N 0.000 claims 1
- CYOOUVGLFUAMDT-UHFFFAOYSA-N C1(CC1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O Chemical compound C1(CC1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O CYOOUVGLFUAMDT-UHFFFAOYSA-N 0.000 claims 1
- LKLUCJSNODWEHY-UHFFFAOYSA-N C1(CCCC1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O Chemical compound C1(CCCC1)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O LKLUCJSNODWEHY-UHFFFAOYSA-N 0.000 claims 1
- XQOZTAHESAGLAO-UHFFFAOYSA-N C1(CCCCC1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C Chemical compound C1(CCCCC1)N(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C XQOZTAHESAGLAO-UHFFFAOYSA-N 0.000 claims 1
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- ZCINGXBWXXIHAE-UHFFFAOYSA-N CN(CCN(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C)C Chemical compound CN(CCN(C(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O)C)C ZCINGXBWXXIHAE-UHFFFAOYSA-N 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 claims 1
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 1
- MMGBGUNAMKNRHA-UHFFFAOYSA-N FC1(CN(C1)C(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)F Chemical compound FC1(CN(C1)C(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)F MMGBGUNAMKNRHA-UHFFFAOYSA-N 0.000 claims 1
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