JP2008542359A5 - - Google Patents
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- Publication number
- JP2008542359A5 JP2008542359A5 JP2008514302A JP2008514302A JP2008542359A5 JP 2008542359 A5 JP2008542359 A5 JP 2008542359A5 JP 2008514302 A JP2008514302 A JP 2008514302A JP 2008514302 A JP2008514302 A JP 2008514302A JP 2008542359 A5 JP2008542359 A5 JP 2008542359A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethylheptyl
- hexahydro
- dibenzofuran
- group
- dimethylpentyl
- 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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- -1 1,1-dimethylpentyl Chemical group 0.000 claims 194
- 229910052739 hydrogen Inorganic materials 0.000 claims 63
- 239000001257 hydrogen Substances 0.000 claims 62
- 150000001875 compounds Chemical class 0.000 claims 46
- 229920006395 saturated elastomer Polymers 0.000 claims 45
- 150000002431 hydrogen Chemical class 0.000 claims 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 34
- 229910052799 carbon Inorganic materials 0.000 claims 34
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 26
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 25
- 150000002148 esters Chemical class 0.000 claims 22
- 239000008194 pharmaceutical composition Substances 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 150000002923 oximes Chemical class 0.000 claims 16
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 15
- 125000004122 cyclic group Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 13
- IKTRNOZMSJUISH-UHFFFAOYSA-N azulen-4-ol Chemical compound OC1=CC=CC=C2C=CC=C12 IKTRNOZMSJUISH-UHFFFAOYSA-N 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- TZEIAPXWECOJGT-UHFFFAOYSA-N 1h-inden-4-ol Chemical compound OC1=CC=CC2=C1C=CC2 TZEIAPXWECOJGT-UHFFFAOYSA-N 0.000 claims 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 239000011630 iodine Substances 0.000 claims 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 7
- 239000004480 active ingredient Substances 0.000 claims 7
- 125000003324 azulen-4-yl group Chemical group [H]C1=C([H])C2=C(*)C([H])=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 7
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 6
- 206010047700 Vomiting Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 230000036407 pain Effects 0.000 claims 6
- 230000008673 vomiting Effects 0.000 claims 6
- 206010061218 Inflammation Diseases 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 230000004054 inflammatory process Effects 0.000 claims 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 5
- 208000027559 Appetite disease Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 4
- 206010020751 Hypersensitivity Diseases 0.000 claims 4
- DITZKPGGPGEQCE-UHFFFAOYSA-N azulene-5-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC=CC2=C1 DITZKPGGPGEQCE-UHFFFAOYSA-N 0.000 claims 4
- 230000000747 cardiac effect Effects 0.000 claims 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 201000001119 neuropathy Diseases 0.000 claims 4
- 230000007823 neuropathy Effects 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- FNBDPHKBUBKFCO-UHFFFAOYSA-N 2-(2-phenylethyl)-1,3-dithiolane Chemical compound S1CCSC1CCC1=CC=CC=C1 FNBDPHKBUBKFCO-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 239000000839 emulsion Substances 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 230000002314 neuroinflammatory effect Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- FXYAHUSLDJDRLO-UHFFFAOYSA-N 1-(1-hydroxy-5a,6,7,8,9,9a-hexahydrodibenzofuran-3-yl)ethanone Chemical compound O1C2CCCCC2C2=C1C=C(C(=O)C)C=C2O FXYAHUSLDJDRLO-UHFFFAOYSA-N 0.000 claims 2
- YHBWXWLDOKIVCJ-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]acetic acid Chemical compound COCCOCCOCC(O)=O YHBWXWLDOKIVCJ-UHFFFAOYSA-N 0.000 claims 2
- HXIYMEWSKLDQCQ-UHFFFAOYSA-N 2-[[3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl]oxy]acetic acid Chemical compound O1C2CCCCC2C2=C1C=C(C(C)(C)CCCC)C=C2OCC(O)=O HXIYMEWSKLDQCQ-UHFFFAOYSA-N 0.000 claims 2
- FRUBTCCEEBSTQZ-UHFFFAOYSA-N 2-[[7,7-dimethyl-3-(2-methyloctan-2-yl)-6,8,9,9a-tetrahydro-5ah-dibenzofuran-1-yl]oxy]acetic acid Chemical compound O1C2CC(C)(C)CCC2C2=C1C=C(C(C)(C)CCCCCC)C=C2OCC(O)=O FRUBTCCEEBSTQZ-UHFFFAOYSA-N 0.000 claims 2
- MLQIEDVHZPQCEP-UHFFFAOYSA-N 3,3-dimethyl-7-(2-methylhexan-2-yl)-9-(methylsulfanylmethoxy)-1,2,4a,9b-tetrahydrodibenzofuran-4-one Chemical compound C1=2C(OCSC)=CC(C(C)(C)CCCC)=CC=2OC2C1CCC(C)(C)C2=O MLQIEDVHZPQCEP-UHFFFAOYSA-N 0.000 claims 2
- YOENXHCCKWLYKJ-UHFFFAOYSA-N 3-(2-methyl-1,3-dithiolan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound C=1C=2OC3CCCCC3C=2C(O)=CC=1C1(C)SCCS1 YOENXHCCKWLYKJ-UHFFFAOYSA-N 0.000 claims 2
- QRXPBEJPKKERTR-UHFFFAOYSA-N 3-(2-methylhexan-2-yl)-2,4-dinitro-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound O1C2CCCCC2C2=C1C([N+]([O-])=O)=C(C(C)(C)CCCC)C([N+]([O-])=O)=C2O QRXPBEJPKKERTR-UHFFFAOYSA-N 0.000 claims 2
- HMCRBYBBZWZUPI-UHFFFAOYSA-N 3-(2-methylhexan-2-yl)-2-nitro-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound O1C2CCCCC2C2=C1C=C(C(C)(C)CCCC)C([N+]([O-])=O)=C2O HMCRBYBBZWZUPI-UHFFFAOYSA-N 0.000 claims 2
- ZFASOOHAQPBBDY-UHFFFAOYSA-N 3-(2-methylhexan-2-yl)-4-nitro-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound C1CCCC2OC3=C([N+]([O-])=O)C(C(C)(C)CCCC)=CC(O)=C3C21 ZFASOOHAQPBBDY-UHFFFAOYSA-N 0.000 claims 2
- MXCHDXLYSWFKRQ-UHFFFAOYSA-N 3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1,6-diol Chemical compound C1=2C(O)=CC(C(C)(C)CCCC)=CC=2OC2C1CCCC2O MXCHDXLYSWFKRQ-UHFFFAOYSA-N 0.000 claims 2
- GJTRJNGKVFBAHL-UHFFFAOYSA-N 3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound O1C2CCCCC2C2=C1C=C(C(C)(C)CCCC)C=C2O GJTRJNGKVFBAHL-UHFFFAOYSA-N 0.000 claims 2
- HZKGSULKXZIPAH-UHFFFAOYSA-N 3-(2-methyloctan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1,6-diol Chemical compound C1=2C(O)=CC(C(C)(C)CCCCCC)=CC=2OC2C1CCCC2O HZKGSULKXZIPAH-UHFFFAOYSA-N 0.000 claims 2
- FKFKFBBFGYLPPO-UHFFFAOYSA-N 3-(2-methyloctan-2-yl)-5a,8,9,9a-tetrahydrodibenzofuran-1-ol Chemical compound O1C2C=CCCC2C2=C1C=C(C(C)(C)CCCCCC)C=C2O FKFKFBBFGYLPPO-UHFFFAOYSA-N 0.000 claims 2
- XLUZQAUWZLSCHC-UHFFFAOYSA-N 3-(2-methyloctan-2-yl)-6,7,8,9-tetrahydrodibenzofuran-1-ol Chemical compound C1CCCC2=C1C1=C(O)C=C(C(C)(C)CCCCCC)C=C1O2 XLUZQAUWZLSCHC-UHFFFAOYSA-N 0.000 claims 2
- DPDJOSWZRZBGKE-UHFFFAOYSA-N 3-[[3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl]oxy]propane-1,2-diol Chemical compound O1C2CCCCC2C2=C1C=C(C(C)(C)CCCC)C=C2OCC(O)CO DPDJOSWZRZBGKE-UHFFFAOYSA-N 0.000 claims 2
- VOCRUTUQBPZTBX-UHFFFAOYSA-N 4-[2-[[3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl]oxy]ethyl]morpholine Chemical compound C=1C(C(C)(C)CCCC)=CC=2OC3CCCCC3C=2C=1OCCN1CCOCC1 VOCRUTUQBPZTBX-UHFFFAOYSA-N 0.000 claims 2
- KBAUUTYIXSQGFU-UHFFFAOYSA-N 5-[[3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl]oxymethyl]-2h-tetrazole Chemical compound C=1C(C(C)(C)CCCC)=CC=2OC3CCCCC3C=2C=1OCC1=NN=NN1 KBAUUTYIXSQGFU-UHFFFAOYSA-N 0.000 claims 2
- ZYZKQOMUFDURCI-UHFFFAOYSA-N 6-hydroxyimino-3-(2-methylhexan-2-yl)-7,8,9,9a-tetrahydro-5ah-dibenzofuran-1-ol Chemical compound C1=2C(O)=CC(C(C)(C)CCCC)=CC=2OC2C1CCCC2=NO ZYZKQOMUFDURCI-UHFFFAOYSA-N 0.000 claims 2
- ONOWVHRKFZJKAX-UHFFFAOYSA-N 6-hydroxyimino-3-(2-methyloctan-2-yl)-7,8,9,9a-tetrahydro-5ah-dibenzofuran-1-ol Chemical compound C1=2C(O)=CC(C(C)(C)CCCCCC)=CC=2OC2C1CCCC2=NO ONOWVHRKFZJKAX-UHFFFAOYSA-N 0.000 claims 2
- ZWOIUTOBWYNGGM-UHFFFAOYSA-N 6-iodo-3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-ol Chemical compound C1=2C(O)=CC(C(C)(C)CCCC)=CC=2OC2C1CCCC2I ZWOIUTOBWYNGGM-UHFFFAOYSA-N 0.000 claims 2
- DKTMEQYYBKBYJZ-UHFFFAOYSA-N 7,7-dimethyl-3-(2-methylhexan-2-yl)-6,8,9,9a-tetrahydro-5ah-dibenzofuran-1,6-diol Chemical compound C1=2C(O)=CC(C(C)(C)CCCC)=CC=2OC2C1CCC(C)(C)C2O DKTMEQYYBKBYJZ-UHFFFAOYSA-N 0.000 claims 2
- GJHWFJYVNZFZHR-UHFFFAOYSA-N 7,7-dimethyl-3-(2-methyloctan-2-yl)-6,8,9,9a-tetrahydro-5ah-dibenzofuran-1-ol Chemical compound O1C2CC(C)(C)CCC2C2=C1C=C(C(C)(C)CCCCCC)C=C2O GJHWFJYVNZFZHR-UHFFFAOYSA-N 0.000 claims 2
- JVISSGBRRMADQX-UHFFFAOYSA-N 7-(2-methylhexan-2-yl)-9-(methylsulfanylmethoxy)-2,3,4a,9b-tetrahydro-1h-dibenzofuran-4-one Chemical compound C1=2C(OCSC)=CC(C(C)(C)CCCC)=CC=2OC2C1CCCC2=O JVISSGBRRMADQX-UHFFFAOYSA-N 0.000 claims 2
- AKVHXCVQKNWDLI-UHFFFAOYSA-N 7-methoxy-1,1-dimethyl-9-(2-methyloctan-2-yl)-2,3-dihydrodibenzofuran-4-one Chemical compound O1C(C(CCC2(C)C)=O)=C2C2=C1C=C(OC)C=C2C(C)(C)CCCCCC AKVHXCVQKNWDLI-UHFFFAOYSA-N 0.000 claims 2
- GWHDHCXQOCCDEK-UHFFFAOYSA-N 9-hydroxy-1,1-dimethyl-7-(2-methyloctan-2-yl)-2,3-dihydrodibenzofuran-4-one Chemical compound O=C1CCC(C)(C)C2=C1OC1=CC(C(C)(C)CCCCCC)=CC(O)=C12 GWHDHCXQOCCDEK-UHFFFAOYSA-N 0.000 claims 2
- DJSAUXRCBZHTAX-UHFFFAOYSA-N 9-hydroxy-3,3-dimethyl-7-(2-methylhexan-2-yl)-1,2,4a,9b-tetrahydrodibenzofuran-4-one Chemical compound C1=2C(O)=CC(C(C)(C)CCCC)=CC=2OC2C1CCC(C)(C)C2=O DJSAUXRCBZHTAX-UHFFFAOYSA-N 0.000 claims 2
- BAHPWWQOQMVTDQ-UHFFFAOYSA-N 9-hydroxy-3,3-dimethyl-7-(2-methyloctan-2-yl)-1,2,4a,9b-tetrahydrodibenzofuran-4-one Chemical compound C1=2C(O)=CC(C(C)(C)CCCCCC)=CC=2OC2C1CCC(C)(C)C2=O BAHPWWQOQMVTDQ-UHFFFAOYSA-N 0.000 claims 2
- HNFUQJZHJZSOHA-UHFFFAOYSA-N 9-hydroxy-7-(2-methyloctan-2-yl)-2,3,4a,9b-tetrahydro-1h-dibenzofuran-4-one Chemical compound C1=2C(O)=CC(C(C)(C)CCCCCC)=CC=2OC2C1CCCC2=O HNFUQJZHJZSOHA-UHFFFAOYSA-N 0.000 claims 2
- FDPNDIVKTJUAIQ-UHFFFAOYSA-N 9-methoxy-1,1-dimethyl-7-(2-methyloctan-2-yl)-2,3-dihydrodibenzofuran-4-one Chemical compound O=C1CCC(C)(C)C2=C1OC1=CC(C(C)(C)CCCCCC)=CC(OC)=C12 FDPNDIVKTJUAIQ-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000020084 Bone disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000006561 Cluster Headache Diseases 0.000 claims 2
- 208000015943 Coeliac disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 206010025476 Malabsorption Diseases 0.000 claims 2
- 208000004155 Malabsorption Syndromes Diseases 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 208000009525 Myocarditis Diseases 0.000 claims 2
- 206010028813 Nausea Diseases 0.000 claims 2
- 208000010191 Osteitis Deformans Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000027868 Paget disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000014675 Prion-associated disease Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010044565 Tremor Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- NPHHYASNFSKKRY-UHFFFAOYSA-N [3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl] piperidine-3-carboxylate Chemical compound C=1C(C(C)(C)CCCC)=CC=2OC3CCCCC3C=2C=1OC(=O)C1CCCNC1 NPHHYASNFSKKRY-UHFFFAOYSA-N 0.000 claims 2
- DRUSRLANLKWFMA-UHFFFAOYSA-N [7,7-dimethyl-3-(2-methyloctan-2-yl)-6,8,9,9a-tetrahydro-5ah-dibenzofuran-1-yl] 3-(methylamino)propanoate Chemical compound O1C2CC(C)(C)CCC2C2=C1C=C(C(C)(C)CCCCCC)C=C2OC(=O)CCNC DRUSRLANLKWFMA-UHFFFAOYSA-N 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 208000030961 allergic reaction Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 230000004097 bone metabolism Effects 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000018912 cluster headache syndrome Diseases 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- KQMLQXNQYNAAHP-UHFFFAOYSA-N diethyl [3-(2-methylhexan-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1-yl] phosphate Chemical compound O1C2CCCCC2C2=C1C=C(C(C)(C)CCCC)C=C2OP(=O)(OCC)OCC KQMLQXNQYNAAHP-UHFFFAOYSA-N 0.000 claims 2
- 229910001882 dioxygen Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 206010014599 encephalitis Diseases 0.000 claims 2
- 206010014665 endocarditis Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000037906 ischaemic injury Diseases 0.000 claims 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 2
- 208000027202 mammary Paget disease Diseases 0.000 claims 2
- HUDLUWKIZNYYFJ-UHFFFAOYSA-N methyl 1-hydroxy-5a,6,7,8,9,9a-hexahydrodibenzofuran-3-carboxylate Chemical compound O1C2CCCCC2C2=C1C=C(C(=O)OC)C=C2O HUDLUWKIZNYYFJ-UHFFFAOYSA-N 0.000 claims 2
- LJDMYRNJYQKQFD-UHFFFAOYSA-N methyl azulene-5-carboxylate Chemical compound COC(=O)C1=CC=CC2=CC=CC2=C1 LJDMYRNJYQKQFD-UHFFFAOYSA-N 0.000 claims 2
- 239000000693 micelle Substances 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 230000002107 myocardial effect Effects 0.000 claims 2
- 230000008693 nausea Effects 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 208000008494 pericarditis Diseases 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 210000001519 tissue Anatomy 0.000 claims 2
- 230000009278 visceral effect Effects 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
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- 239000007864 aqueous solution Substances 0.000 claims 1
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- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
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| US68537405P | 2005-05-31 | 2005-05-31 | |
| PCT/IL2006/000641 WO2006129318A2 (en) | 2005-05-31 | 2006-05-31 | Benzofuran derivatives with therapeutic activities |
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| JP2008542359A JP2008542359A (ja) | 2008-11-27 |
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| EP (1) | EP1885709A2 (cg-RX-API-DMAC10.html) |
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Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DK2176208T3 (en) * | 2007-07-30 | 2015-04-27 | Zynerba Pharmaceuticals Inc | Prodrugs of cannabidiol, compositions containing prodrugs of cannabidiol and methods of use thereof |
| CN102300568A (zh) * | 2008-12-05 | 2011-12-28 | 赢泰医药科技发展有限公司 | Hif-1蛋白积聚的抑制剂 |
| WO2010091185A2 (en) * | 2009-02-05 | 2010-08-12 | Trustees Of Boston College | Inhibitors of fructose 1,6-bisphosphatase and methods of use thereof |
| US8476309B2 (en) | 2009-08-20 | 2013-07-02 | The University Of Tennessee Research Foundation | Benzofuran cannabinoid compounds and related methods of use |
| DE102011002934A1 (de) | 2011-01-20 | 2012-07-26 | Bayer Schering Pharma Ag | CB2 Agonisten zur Behandlung und Vorbeugung der Endometriose |
| WO2013025984A2 (en) * | 2011-08-18 | 2013-02-21 | Temple University | Cannabinoid receptor treatments |
| US9409872B1 (en) * | 2015-02-16 | 2016-08-09 | Mark Quang Nguyen | Fumarate compounds, pharmaceutical compositions thereof, and methods of use |
| RU2744758C2 (ru) * | 2018-10-19 | 2021-03-15 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова" | Производные оксимов дибензофуранов, обладающие противосудорожной и нейропротективной активностью |
| CN109223760B (zh) * | 2018-10-31 | 2021-02-02 | 广东药科大学 | 一种苯并呋喃衍生物的用途 |
| CN110251096A (zh) * | 2019-05-29 | 2019-09-20 | 佛山科学技术学院 | 一种母猪围产期体温评估方法及系统 |
| RU2747202C2 (ru) * | 2019-10-25 | 2021-04-29 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова" | Средство, улучшающее кровоснабжение ишемизированного мозга |
| EP4161903A4 (en) * | 2020-06-04 | 2024-05-22 | London Pharmaceuticals and Research Corporation | RIGID CANNABIDIOL ANALOGUES AS STRONG MODULATORS OF CANNABINOID RECEPTORS AND USES THEREOF |
| WO2023075339A1 (ko) * | 2021-10-27 | 2023-05-04 | 주식회사 휴켐바이오 | 신규한 트리사이클릭 유도체 화합물 및 이의 용도 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558667A (en) * | 1968-11-01 | 1971-01-26 | Sterling Drug Inc | Benzofurans from o-phenyl ketoximes |
| US3931288A (en) * | 1972-03-13 | 1976-01-06 | Hoffmann-La Roche Inc. | Alkyl esters of 4-chlorophenoxy-4-oxo-cycloalkyl-carboxylic acid |
| FR2482966A1 (fr) * | 1980-05-23 | 1981-11-27 | Cerm Cent Europ Rech Mauvernay | 1, 2, 3, 4, 4a, 9b, -hexahydro 4-amino dibenzofurannes, leur procede de preparation et leur application en therapeutique |
| US4837226A (en) * | 1988-04-27 | 1989-06-06 | Warner-Lambert Company | Polycyclic amine derivatives useful as cerebrovascular agents |
| US4960815A (en) * | 1988-09-22 | 1990-10-02 | Warner-Lambert Company | Isotopically-labeled polycyclic amine derivatives |
-
2006
- 2006-05-31 EP EP06756188A patent/EP1885709A2/en not_active Withdrawn
- 2006-05-31 WO PCT/IL2006/000641 patent/WO2006129318A2/en not_active Ceased
- 2006-05-31 AU AU2006253734A patent/AU2006253734A1/en not_active Abandoned
- 2006-05-31 CN CNA2006800272353A patent/CN101228146A/zh active Pending
- 2006-05-31 US US11/915,825 patent/US20090054376A1/en not_active Abandoned
- 2006-05-31 KR KR1020077030444A patent/KR20080019644A/ko not_active Ceased
- 2006-05-31 BR BRPI0610956-0A patent/BRPI0610956A2/pt not_active IP Right Cessation
- 2006-05-31 CA CA002610274A patent/CA2610274A1/en not_active Abandoned
- 2006-05-31 JP JP2008514302A patent/JP2008542359A/ja active Pending
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