JPWO2021102567A5 - - Google Patents
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- Publication number
- JPWO2021102567A5 JPWO2021102567A5 JP2022530210A JP2022530210A JPWO2021102567A5 JP WO2021102567 A5 JPWO2021102567 A5 JP WO2021102567A5 JP 2022530210 A JP2022530210 A JP 2022530210A JP 2022530210 A JP2022530210 A JP 2022530210A JP WO2021102567 A5 JPWO2021102567 A5 JP WO2021102567A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dimethyloct
- dien
- dihydroxy
- sulfonyl
- 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 36
- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 23
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000002207 metabolite Substances 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 4
- 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
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004043 oxo group Chemical group 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 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
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl 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
- ARJFEASRVVKOER-UHFFFAOYSA-N C(C)(C)(C)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C(C)(C)(C)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O ARJFEASRVVKOER-UHFFFAOYSA-N 0.000 claims 1
- JHMJDKXJWWQMBO-UHFFFAOYSA-N C(C1=CC=CC=C1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C(C1=CC=CC=C1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O JHMJDKXJWWQMBO-UHFFFAOYSA-N 0.000 claims 1
- UZJQKWWDOJWSRQ-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O UZJQKWWDOJWSRQ-UHFFFAOYSA-N 0.000 claims 1
- FPVZDVLXXDGHFZ-UHFFFAOYSA-N C1(CC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C1(CC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O FPVZDVLXXDGHFZ-UHFFFAOYSA-N 0.000 claims 1
- ATURLMUNMQUYBE-UHFFFAOYSA-N C1(CC1)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C1(CC1)S(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O ATURLMUNMQUYBE-UHFFFAOYSA-N 0.000 claims 1
- MZLMWAIHYRKASH-UHFFFAOYSA-N C1(CCC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C1(CCC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O MZLMWAIHYRKASH-UHFFFAOYSA-N 0.000 claims 1
- AXZCEMWZRPQEKO-UHFFFAOYSA-N C1(CCCCC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O Chemical compound C1(CCCCC1)NS(=O)(=O)C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O AXZCEMWZRPQEKO-UHFFFAOYSA-N 0.000 claims 1
- VBXGPJLXYKOKDM-UHFFFAOYSA-N C1(CCCCC1)S(=O)(=O)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O Chemical compound C1(CCCCC1)S(=O)(=O)NC(C1=C(C(=C(C=C1CCCCC)O)CC=C(CCC=C(C)C)C)O)=O VBXGPJLXYKOKDM-UHFFFAOYSA-N 0.000 claims 1
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