JPWO2021007662A5 - - Google Patents
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- JPWO2021007662A5 JPWO2021007662A5 JP2022500797A JP2022500797A JPWO2021007662A5 JP WO2021007662 A5 JPWO2021007662 A5 JP WO2021007662A5 JP 2022500797 A JP2022500797 A JP 2022500797A JP 2022500797 A JP2022500797 A JP 2022500797A JP WO2021007662 A5 JPWO2021007662 A5 JP WO2021007662A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxy
- biphenyl
- pentyl
- alkyl
- 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.)
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- -1 C 1 -C 4 alkyl Chemical group 0.000 claims 189
- 125000000217 alkyl group Chemical group 0.000 claims 100
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 92
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 69
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 62
- 235000010290 biphenyl Nutrition 0.000 claims 55
- 150000001875 compounds Chemical class 0.000 claims 47
- 229910052739 hydrogen Inorganic materials 0.000 claims 44
- 239000001257 hydrogen Substances 0.000 claims 42
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 28
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 16
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 16
- 229910019142 PO4 Inorganic materials 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 15
- 239000010452 phosphate Substances 0.000 claims 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 claims 11
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- VOWPVJACXJNHBC-UHFFFAOYSA-N methyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC)OC1=CC=CC=C1 VOWPVJACXJNHBC-UHFFFAOYSA-N 0.000 claims 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 229910052698 phosphorus Inorganic materials 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004437 phosphorous atom Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 4
- 239000002207 metabolite Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- HBYXSLLRTLMMNK-UHFFFAOYSA-N cyclopentylphosphonic acid Chemical compound OP(O)(=O)C1CCCC1 HBYXSLLRTLMMNK-UHFFFAOYSA-N 0.000 claims 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 3
- 229940090181 propyl acetate Drugs 0.000 claims 3
- 229920006395 saturated elastomer Polymers 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
- KVBKSTUZBCAXQG-UHFFFAOYSA-N 1,3-bis[[benzyl(methoxy)phosphoryl]oxy]-5-(2-methyloctan-2-yl)-2-(5-methyl-2-prop-1-en-2-ylphenyl)benzene Chemical compound C(C1=CC=CC=C1)P(OC)(OC1=C(C(=CC(=C1)C(C)(CCCCCC)C)OP(OC)(=O)CC1=CC=CC=C1)C1=C(C=CC(=C1)C)C(=C)C)=O KVBKSTUZBCAXQG-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- JJQBGFUZRWYZGF-UHFFFAOYSA-N COP(=O)(OC)C(C)(O)P(O)(O)=O Chemical compound COP(=O)(OC)C(C)(O)P(O)(O)=O JJQBGFUZRWYZGF-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
- VVUHUDLLBPXWMP-UHFFFAOYSA-N O=P1CCCCO1 Chemical compound O=P1CCCCO1 VVUHUDLLBPXWMP-UHFFFAOYSA-N 0.000 claims 2
- LXAUSFLJFJIATN-UHFFFAOYSA-N O=P1OCCC(O1)C1=CC=CC=C1 Chemical compound O=P1OCCC(O1)C1=CC=CC=C1 LXAUSFLJFJIATN-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-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
- 125000004429 atom 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
- KGQCLZJFUIPDGS-UHFFFAOYSA-N dioxaphospholane Chemical compound C1CPOO1 KGQCLZJFUIPDGS-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- MDSHYOZGQVBLDM-UHFFFAOYSA-N ethyl 3-[[3-[(3-ethoxy-3-oxopropyl)-methoxyphosphoryl]oxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]propanoate Chemical compound C(C)OC(CCP(=O)(OC)OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP(=O)(OC)CCC(=O)OCC)CCCCC)=O MDSHYOZGQVBLDM-UHFFFAOYSA-N 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- IRTWXRWGKPXWAV-UHFFFAOYSA-N oxaphosphinane Chemical compound C1CCPOC1 IRTWXRWGKPXWAV-UHFFFAOYSA-N 0.000 claims 2
- FXPDGSSSQUFIPW-UHFFFAOYSA-N oxaphospholane Chemical compound C1COPC1 FXPDGSSSQUFIPW-UHFFFAOYSA-N 0.000 claims 2
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical compound C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- RZNBJYVVASTWHR-UHFFFAOYSA-N 1,3-bis[[benzyl(ethoxy)phosphoryl]oxy]-5-(2-methyloctan-2-yl)-2-(5-methyl-2-prop-1-en-2-ylphenyl)benzene Chemical compound C(C1=CC=CC=C1)P(OCC)(OC1=C(C(=CC(=C1)C(C)(CCCCCC)C)OP(OCC)(=O)CC1=CC=CC=C1)C1=C(C=CC(=C1)C)C(=C)C)=O RZNBJYVVASTWHR-UHFFFAOYSA-N 0.000 claims 1
- UTRCWDKAUDRKID-UHFFFAOYSA-N 1,3-bis[[methoxy(methyl)phosphoryl]oxy]-5-(2-methyloctan-2-yl)-2-(5-methyl-2-prop-1-en-2-ylphenyl)benzene Chemical compound CP(OC)(OC1=C(C(=CC(=C1)C(C)(CCCCCC)C)OP(OC)(=O)C)C1=C(C=CC(=C1)C)C(=C)C)=O UTRCWDKAUDRKID-UHFFFAOYSA-N 0.000 claims 1
- CRYZAZWXPNPKFD-UHFFFAOYSA-N 1,3-bis[[methoxy(phenyl)phosphoryl]oxy]-5-(2-methyloctan-2-yl)-2-(5-methyl-2-prop-1-en-2-ylphenyl)benzene Chemical compound C1(=CC=CC=C1)P(OC)(OC1=C(C(=CC(=C1)C(C)(CCCCCC)C)OP(OC)(=O)C1=CC=CC=C1)C1=C(C=CC(=C1)C)C(=C)C)=O CRYZAZWXPNPKFD-UHFFFAOYSA-N 0.000 claims 1
- IWCLEJYKMYSCSU-UHFFFAOYSA-N 1-[[3-[1-acetyloxyethoxy(propyl)phosphoryl]oxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-propylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)OP(=O)(CCC)OC(C)OC(C)=O)C1C(CCC(=C1)C)C(=C)C IWCLEJYKMYSCSU-UHFFFAOYSA-N 0.000 claims 1
- XOIJPBYSMGWPCS-UHFFFAOYSA-N 1-[[3-[1-acetyloxyethoxy(propyl)phosphoryl]oxy-2-(3-methylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)OP(=O)(C)OC(C)OC(C)=O)C1CCCC(=C1)C XOIJPBYSMGWPCS-UHFFFAOYSA-N 0.000 claims 1
- IJIGIIZRMJHRBV-UHFFFAOYSA-N 1-[[3-[1-acetyloxyethoxy(propyl)phosphoryl]oxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-propylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)OP(=O)(CCC)OC(C)OC(C)=O)C1=C(C=CC(=C1)C)C(=C)C IJIGIIZRMJHRBV-UHFFFAOYSA-N 0.000 claims 1
- VZBPZKWXRJGRFU-UHFFFAOYSA-N 1-[[3-hydroxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-propylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)O)C1C(CCC(=C1)C)C(=C)C VZBPZKWXRJGRFU-UHFFFAOYSA-N 0.000 claims 1
- RFNZEXMNUWPZRX-UHFFFAOYSA-N 1-[[3-hydroxy-2-(3-methylphenyl)-5-pentylphenoxy]-propylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)O)C1=CC(=CC=C1)C RFNZEXMNUWPZRX-UHFFFAOYSA-N 0.000 claims 1
- XWICSWPDEQRBCM-UHFFFAOYSA-N 1-[[3-hydroxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-propylphosphoryl]oxyethyl acetate Chemical compound C(C)(=O)OC(C)OP(=O)(CCC)OC1=C(C(=CC(=C1)CCCCC)O)C1=C(C=CC(=C1)C)C(=C)C XWICSWPDEQRBCM-UHFFFAOYSA-N 0.000 claims 1
- YAHMCUMHNLZAAJ-UHFFFAOYSA-N 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-3-[(2-oxo-4-phenyl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP1(OCCC(O1)C1=CC=CC=C1)=O)CCCCC YAHMCUMHNLZAAJ-UHFFFAOYSA-N 0.000 claims 1
- QRNBGQJHQQEWBE-UHFFFAOYSA-N 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-3-[(2-oxo-4-pyridin-4-yl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP1(OCCC(O1)C1=CC=NC=C1)=O)CCCCC QRNBGQJHQQEWBE-UHFFFAOYSA-N 0.000 claims 1
- QVJLNCUGRBJVMM-UHFFFAOYSA-N 2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-3-[(2-oxo-4-thiophen-2-yl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP1(OCCC(O1)C=1SC=CC=1)=O)CCCCC QVJLNCUGRBJVMM-UHFFFAOYSA-N 0.000 claims 1
- BTKQFAUDHFKSFK-UHFFFAOYSA-N 2-(3-methylcyclohex-2-en-1-yl)-3-[(2-oxo-4-phenyl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1CCCC(=C1)C)OP1(OCCC(O1)C1=CC=CC=C1)=O)CCCCC BTKQFAUDHFKSFK-UHFFFAOYSA-N 0.000 claims 1
- IBCBXSGKMNDDQG-UHFFFAOYSA-N 2-(3-methylcyclohex-2-en-1-yl)-3-[(2-oxo-4-pyridin-4-yl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1CCCC(=C1)C)OP1(OCCC(O1)C1=CC=NC=C1)=O)CCCCC IBCBXSGKMNDDQG-UHFFFAOYSA-N 0.000 claims 1
- ULYJQYFMLDIJJU-UHFFFAOYSA-N 2-(3-methylcyclohex-2-en-1-yl)-3-[(2-oxo-4-thiophen-2-yl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1CCCC(=C1)C)OP1(OCCC(O1)C=1SC=CC=1)=O)CCCCC ULYJQYFMLDIJJU-UHFFFAOYSA-N 0.000 claims 1
- LDQQOQNIZIMPCO-UHFFFAOYSA-N 2-(3-methylphenyl)-3-[(2-oxo-4-phenyl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1=CC(=CC=C1)C)OP1(OCCC(O1)C1=CC=CC=C1)=O)CCCCC LDQQOQNIZIMPCO-UHFFFAOYSA-N 0.000 claims 1
- ADLWYUOPJSMPES-UHFFFAOYSA-N 2-(5-methyl-2-prop-1-en-2-ylphenyl)-3-[(2-oxo-4-phenyl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP1(OCCC(O1)C1=CC=CC=C1)=O)CCCCC ADLWYUOPJSMPES-UHFFFAOYSA-N 0.000 claims 1
- PNHQRNVBKWQQPZ-UHFFFAOYSA-N 2-(5-methyl-2-prop-1-en-2-ylphenyl)-3-[(2-oxo-4-pyridin-4-yl-1,3,2lambda5-dioxaphosphinan-2-yl)oxy]-5-pentylphenol Chemical compound OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP1(OCCC(O1)C1=CC=NC=C1)=O)CCCCC PNHQRNVBKWQQPZ-UHFFFAOYSA-N 0.000 claims 1
- RETRZGQWBXRMJV-UHFFFAOYSA-N 2-[3-hydroxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]propan-2-yl dimethyl phosphate Chemical compound P(=O)(OC(C)(C)OC1=C(C(=CC(=C1)CCCCC)O)C1C(CCC(=C1)C)C(=C)C)(OC)OC RETRZGQWBXRMJV-UHFFFAOYSA-N 0.000 claims 1
- ZFJQPUVLCSTHLP-UHFFFAOYSA-N 2-[3-hydroxy-2-(3-methylcyclohex-2-en-1-yl)-5-pentylphenoxy]propan-2-yl dimethyl phosphate Chemical compound P(=O)(OC(C)(C)OC1=C(C(=CC(=C1)CCCCC)O)C1CCCC(=C1)C)(OC)OC ZFJQPUVLCSTHLP-UHFFFAOYSA-N 0.000 claims 1
- OJKXSRYRKUKNJV-UHFFFAOYSA-N 2-[3-hydroxy-2-(3-methylphenyl)-5-pentylphenoxy]propan-2-yl dimethyl phosphate Chemical compound P(=O)(OC(C)(C)OC1=C(C(=CC(=C1)CCCCC)O)C1=CC(=CC=C1)C)(OC)OC OJKXSRYRKUKNJV-UHFFFAOYSA-N 0.000 claims 1
- SNQXTQNOKAHDGB-UHFFFAOYSA-N 2-[3-hydroxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]propan-2-yl dimethyl phosphate Chemical compound P(=O)(OC(C)(C)OC1=C(C(=CC(=C1)CCCCC)O)C1=C(C=CC(=C1)C)C(=C)C)(OC)OC SNQXTQNOKAHDGB-UHFFFAOYSA-N 0.000 claims 1
- CLZATGVMGCAZMH-UHFFFAOYSA-N 2-[[3-hydroxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methylphosphoryl]oxypropan-2-yl acetate Chemical compound C(C)(=O)OC(C)(C)OP(=O)(C)OC1=C(C(=CC(=C1)CCCCC)O)C1C(CCC(=C1)C)C(=C)C CLZATGVMGCAZMH-UHFFFAOYSA-N 0.000 claims 1
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- WLSWWCDBKJLDGB-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methoxyphosphoryl]propanoate Chemical compound OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP(=O)(OC)CCC(=O)OCC)CCCCC WLSWWCDBKJLDGB-UHFFFAOYSA-N 0.000 claims 1
- DEIRNLFXLFZRKP-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(3-methylcyclohex-2-en-1-yl)-5-pentylphenoxy]-(methylamino)phosphoryl]propanoate Chemical compound OC1=CC(=CC(=C1C1CCCC(=C1)C)OP(=O)(NC)CCC(=O)OCC)CCCCC DEIRNLFXLFZRKP-UHFFFAOYSA-N 0.000 claims 1
- MZXSRENRRCDTSH-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(3-methylphenyl)-5-pentylphenoxy]-(methylamino)phosphoryl]propanoate Chemical compound CCCCCC1=CC(=C(C(=C1)OP(=O)(CCC(=O)OCC)NC)C2=CC=CC(=C2)C)O MZXSRENRRCDTSH-UHFFFAOYSA-N 0.000 claims 1
- WCQJKWYAGCJFMC-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(3-methylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]propanoate Chemical compound CCCCCC1=CC(=C(C(=C1)OP(=O)(CCC(=O)OCC)OC)C2=CC=CC(=C2)C)O WCQJKWYAGCJFMC-UHFFFAOYSA-N 0.000 claims 1
- NGGRHBUXEAZNDN-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-(methylamino)phosphoryl]propanoate Chemical compound OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP(=O)(NC)CCC(=O)OCC)CCCCC NGGRHBUXEAZNDN-UHFFFAOYSA-N 0.000 claims 1
- QZMILAWCSSXNLN-UHFFFAOYSA-N ethyl 3-[[3-hydroxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]propanoate Chemical compound OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP(=O)(OC)CCC(=O)OCC)CCCCC QZMILAWCSSXNLN-UHFFFAOYSA-N 0.000 claims 1
- CHHQSVBAWVDZPY-UHFFFAOYSA-N ethyl 4-[[3-[(4-ethoxy-4-oxobutyl)-methoxyphosphoryl]oxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound C(C)OC(CCCP(=O)(OC)OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP(=O)(OC)CCCC(=O)OCC)CCCCC)=O CHHQSVBAWVDZPY-UHFFFAOYSA-N 0.000 claims 1
- ZOIFBZVQRSJXMC-UHFFFAOYSA-N ethyl 4-[[3-[(4-ethoxy-4-oxobutyl)-methoxyphosphoryl]oxy-2-(3-methylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound C(C)OC(CCCP(=O)(OC)OC1=CC(=CC(=C1C1CCCC(=C1)C)OP(=O)(OC)CCCC(=O)OCC)CCCCC)=O ZOIFBZVQRSJXMC-UHFFFAOYSA-N 0.000 claims 1
- CQDNCCLCTJSNHL-UHFFFAOYSA-N ethyl 4-[[3-[(4-ethoxy-4-oxobutyl)-methoxyphosphoryl]oxy-2-(3-methylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound C(C)OC(CCCP(=O)(OC)OC1=CC(=CC(=C1C1=CC(=CC=C1)C)OP(=O)(OC)CCCC(=O)OCC)CCCCC)=O CQDNCCLCTJSNHL-UHFFFAOYSA-N 0.000 claims 1
- OZSVPABZQZJSLY-UHFFFAOYSA-N ethyl 4-[[3-hydroxy-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound OC1=CC(=CC(=C1C1C(CCC(=C1)C)C(=C)C)OP(=O)(OC)CCCC(=O)OCC)CCCCC OZSVPABZQZJSLY-UHFFFAOYSA-N 0.000 claims 1
- FQUUMQXKVMOHSZ-UHFFFAOYSA-N ethyl 4-[[3-hydroxy-2-(3-methylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound CCCCCC1=CC(=C(C(=C1)OP(=O)(CCCC(=O)OCC)OC)C2=CC=CC(=C2)C)O FQUUMQXKVMOHSZ-UHFFFAOYSA-N 0.000 claims 1
- ZMAFBLWEXWDAQT-UHFFFAOYSA-N ethyl 4-[[3-hydroxy-2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylphenoxy]-methoxyphosphoryl]butanoate Chemical compound OC1=CC(=CC(=C1C1=C(C=CC(=C1)C)C(=C)C)OP(=O)(OC)CCCC(=O)OCC)CCCCC ZMAFBLWEXWDAQT-UHFFFAOYSA-N 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 208000029364 generalized anxiety disease Diseases 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 206010022437 insomnia Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- 210000001117 keloid Anatomy 0.000 claims 1
- 208000036546 leukodystrophy Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- DQYZCICODUZDMN-AZOIECFZSA-N methyl (2S)-2-[[1,1-difluoroethyl-[3-[1,1-difluoroethyl-[[(2S)-1-methoxy-1-oxopropan-2-yl]amino]phosphoryl]oxy-2-(3-methylphenyl)-5-pentylphenoxy]phosphoryl]amino]propanoate Chemical compound FC(C)(F)P(=O)(OC1=C(C(=CC(=C1)CCCCC)OP(=O)(N[C@H](C(=O)OC)C)C(C)(F)F)C1=CC(=CC=C1)C)N[C@H](C(=O)OC)C DQYZCICODUZDMN-AZOIECFZSA-N 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 102000051367 mu Opioid Receptors Human genes 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000008693 nausea Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
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- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
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- 201000000980 schizophrenia Diseases 0.000 claims 1
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- 230000009885 systemic effect Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
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| EP4065554A4 (en) | 2019-11-26 | 2024-01-10 | Canopy Growth Corporation | CANNABIGEROL DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS |
| WO2021228150A1 (zh) * | 2020-05-13 | 2021-11-18 | 成都百裕制药股份有限公司 | 大麻素衍生物及其制备方法和在医药上的应用 |
| KR20240096817A (ko) | 2020-05-19 | 2024-06-26 | 사이빈 아이알엘 리미티드 | 중수소화된 트립타민 유도체 및 사용 방법 |
| CN115315418B (zh) * | 2021-04-06 | 2023-03-21 | 山东绿叶制药有限公司 | 大麻二酚前药及其药物组合物和应用 |
| CN116253671B (zh) * | 2021-12-10 | 2025-07-04 | 德义制药有限公司 | 一种大麻二酚衍生物及其制备方法和应用 |
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| SE431085B (sv) | 1977-09-13 | 1984-01-16 | Pfizer | 3-(2-hydroxi-4-(substituerade)fenyl)cykloalkanoner och -cykloalkanoder och vissa derivat derav till anvendning for farmakologiska och medicinska endamal |
| US4391827A (en) | 1980-09-08 | 1983-07-05 | Pfizer Inc. | 3-(2-Hydroxy-4-(substituted)phenyl)-cycloalkanone and cycloalkanol analgesic agents and intermediates therefor |
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| JP4716954B2 (ja) | 2006-08-17 | 2011-07-06 | 富士フイルム株式会社 | ｏ−ビフェニルジフェニルホスフェートおよびトリフェニルホスフェートの混合物の製造方法。 |
| PT2473475T (pt) * | 2009-08-31 | 2017-08-02 | Zynerba Pharmaceuticals Inc | Utilização de profármacos de canabidiol na administração tópica e transdérmica com microagulhas |
| JP6219414B2 (ja) * | 2013-03-08 | 2017-10-25 | ナンジン・サンホーム・ファーマシューティカル・カンパニー・リミテッドＮａｎｊｉｎｇ Ｓａｎｈｏｍｅ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． | 新規なヌクレオシドホスホロアミデート化合物およびその使用 |
| JP6589884B2 (ja) * | 2014-11-11 | 2019-10-16 | 宇部興産株式会社 | 非水電解液及びそれを用いた蓄電デバイス |
| EP3928776B1 (en) * | 2016-04-22 | 2025-11-12 | Spoke Sciences, Inc. | Fast-acting plant-based medicinal compounds and nutritional supplements |
| WO2018096504A1 (en) * | 2016-11-28 | 2018-05-31 | Kalytera Therapeutics, Inc | Cbd prodrugs, compositions, and methods of administering cbd and cbd prodrugs |
| CN107082789B (zh) | 2017-03-06 | 2020-08-28 | 湖南理工学院 | 一种以含p(o)-oh类化合物与酚高效酯化制备有机磷酸酯类化合物的方法 |
| CA3145109A1 (en) * | 2019-06-24 | 2020-12-30 | Diverse Biotech, Inc. | Cannabinoid conjugate molecules |
| EP3994129A4 (en) | 2019-07-04 | 2023-01-04 | Canopy Growth Corporation | CANNABINOID DERIVATIVES |
| JP2022539400A (ja) | 2019-07-04 | 2022-09-08 | キャノピー グロウス コーポレイション | カンナビノイド誘導体 |
| WO2021007663A1 (en) | 2019-07-12 | 2021-01-21 | Canopy Growth Corporation | Cannabinoid derivatives |
| US20220259221A1 (en) | 2019-07-12 | 2022-08-18 | Canopy Growth Corporation | Cannabinoid derivatives |
| WO2021007659A1 (en) | 2019-07-12 | 2021-01-21 | Canopy Growth Corporation | Cannabinoid derivatives |
| JP2022540586A (ja) | 2019-07-12 | 2022-09-16 | キャノピー グロウス コーポレイション | カンナビノイド誘導体 |
| EP4038058A4 (en) | 2019-10-02 | 2023-10-25 | Canopy Growth Corporation | Cannabinoid derivatives |
| WO2021062559A1 (en) | 2019-10-02 | 2021-04-08 | Canopy Growth Corporation | Cannabinoid derivatives |
| US20230122510A1 (en) | 2019-11-26 | 2023-04-20 | Canopy Growth Corporation | Cannabinoid derivatives |
| EP4065554A4 (en) | 2019-11-26 | 2024-01-10 | Canopy Growth Corporation | CANNABIGEROL DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS |
| WO2021113958A1 (en) | 2019-12-09 | 2021-06-17 | Canopy Growth Corporation | Cannabinoid derivatives |
| JP2023505517A (ja) | 2019-12-09 | 2023-02-09 | キャノピー グロウス コーポレイション | カンナビノイド誘導体 |
| CN113087741B (zh) * | 2020-01-08 | 2023-04-28 | 成都百裕制药股份有限公司 | 大麻二酚衍生物及其制备方法和在医药上的应用 |
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