JP2001515058A5 - - Google Patents
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- Publication number
- JP2001515058A5 JP2001515058A5 JP2000509675A JP2000509675A JP2001515058A5 JP 2001515058 A5 JP2001515058 A5 JP 2001515058A5 JP 2000509675 A JP2000509675 A JP 2000509675A JP 2000509675 A JP2000509675 A JP 2000509675A JP 2001515058 A5 JP2001515058 A5 JP 2001515058A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexen
- methyl
- hexane
- ethyl acetate
- solution
- 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
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- 239000000243 solution Substances 0.000 description 66
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 238000000921 elemental analysis Methods 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 22
- -1 12-hydroxydodecyl Chemical group 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 8
- 108010025020 Nerve Growth Factor Proteins 0.000 description 7
- 102000015336 Nerve Growth Factor Human genes 0.000 description 7
- 210000004556 brain Anatomy 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229940053128 nerve growth factor Drugs 0.000 description 7
- YCGDYXSEXMQFIU-UHFFFAOYSA-N 3-(16-hydroxyhexadecyl)-2,4,4-trimethylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCCCCCO)C(C)(C)CCC1=O YCGDYXSEXMQFIU-UHFFFAOYSA-N 0.000 description 6
- 206010012289 Dementia Diseases 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 210000005036 nerve Anatomy 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 5
- LGZMUUBPTDRQQM-UHFFFAOYSA-N 10-Bromo-1-decanol Chemical compound OCCCCCCCCCCBr LGZMUUBPTDRQQM-UHFFFAOYSA-N 0.000 description 4
- LJZHMMCSXAOUMJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-8,8-dimethyl-1,4-dioxaspiro[4.5]decane Chemical compound C1C(S(=O)(=O)C=2C=CC=CC=2)C(C)(C)CCC21OCCO2 LJZHMMCSXAOUMJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000008499 blood brain barrier function Effects 0.000 description 4
- 210000001218 blood-brain barrier Anatomy 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- CCUJBDDWDSXJQT-UHFFFAOYSA-N 3-(10-hydroxydecyl)-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCO)CCCC1=O CCUJBDDWDSXJQT-UHFFFAOYSA-N 0.000 description 3
- RXWVWPVPAIVQPP-UHFFFAOYSA-N 3-(10-hydroxydecyl)-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1CCCCCCCCCCO RXWVWPVPAIVQPP-UHFFFAOYSA-N 0.000 description 3
- PHOPHUBOSWMCTL-UHFFFAOYSA-N 3-(10-hydroxydecyl)-4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1CCCCCCCCCCO PHOPHUBOSWMCTL-UHFFFAOYSA-N 0.000 description 3
- KZAHHZZXUVIIQI-UHFFFAOYSA-N 3-(10-hydroxydecyl)cyclohex-2-en-1-one Chemical compound OCCCCCCCCCCC1=CC(=O)CCC1 KZAHHZZXUVIIQI-UHFFFAOYSA-N 0.000 description 3
- LSOFWHHAFIIHAA-UHFFFAOYSA-N 3-(11-hydroxyundecyl)-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1CCCCCCCCCCCO LSOFWHHAFIIHAA-UHFFFAOYSA-N 0.000 description 3
- PPFPXSGCXDOEGH-UHFFFAOYSA-N 3-(12-hydroxydodecyl)-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1CCCCCCCCCCCCO PPFPXSGCXDOEGH-UHFFFAOYSA-N 0.000 description 3
- XVIDJCQIHYEMAW-UHFFFAOYSA-N 3-(12-hydroxydodecyl)-4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1CCCCCCCCCCCCO XVIDJCQIHYEMAW-UHFFFAOYSA-N 0.000 description 3
- QGXUYVLGLZMWPS-UHFFFAOYSA-N 3-(13-hydroxytridecyl)-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCCO)CCCC1=O QGXUYVLGLZMWPS-UHFFFAOYSA-N 0.000 description 3
- DIMCJRWLDZRVIM-UHFFFAOYSA-N 3-(13-hydroxytridecyl)-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1CCCCCCCCCCCCCO DIMCJRWLDZRVIM-UHFFFAOYSA-N 0.000 description 3
- MTUBSIHZXDACDT-UHFFFAOYSA-N 3-(13-hydroxytridecyl)-4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1CCCCCCCCCCCCCO MTUBSIHZXDACDT-UHFFFAOYSA-N 0.000 description 3
- HSOSVMPNTJVFTO-UHFFFAOYSA-N 3-(14-hydroxytetradecyl)-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCCCO)CCCC1=O HSOSVMPNTJVFTO-UHFFFAOYSA-N 0.000 description 3
- BZFFVDZXALQDDP-UHFFFAOYSA-N 3-(14-hydroxytetradecyl)-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1CCCCCCCCCCCCCCO BZFFVDZXALQDDP-UHFFFAOYSA-N 0.000 description 3
- LKOHCUYBNLXSCN-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylcyclohexan-1-one Chemical compound C1CCC(=O)C(C)C1S(=O)(=O)C1=CC=CC=C1 LKOHCUYBNLXSCN-UHFFFAOYSA-N 0.000 description 3
- GNLHTHKIAWHDLB-UHFFFAOYSA-N 3-(benzenesulfonyl)-4,4-dimethylcyclohexan-1-one Chemical compound CC1(C)CCC(=O)CC1S(=O)(=O)C1=CC=CC=C1 GNLHTHKIAWHDLB-UHFFFAOYSA-N 0.000 description 3
- KYXYUBRSMMVUBO-UHFFFAOYSA-N 3-(benzenesulfonyl)-4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1S(=O)(=O)C1=CC=CC=C1 KYXYUBRSMMVUBO-UHFFFAOYSA-N 0.000 description 3
- BXKSAMBHWAXWHU-UHFFFAOYSA-N 3-(benzenesulfonyl)cyclohexan-1-one Chemical compound C1C(=O)CCCC1S(=O)(=O)C1=CC=CC=C1 BXKSAMBHWAXWHU-UHFFFAOYSA-N 0.000 description 3
- RKSNPTXBQXBXDJ-UHFFFAOYSA-N 4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1 RKSNPTXBQXBXDJ-UHFFFAOYSA-N 0.000 description 3
- KZRWSVHOYCUWNM-UHFFFAOYSA-N 7-(benzenesulfonyl)-1,4-dioxaspiro[4.5]decane Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1)CCCC21OCCO2 KZRWSVHOYCUWNM-UHFFFAOYSA-N 0.000 description 3
- ZYAODYITFKMKJC-UHFFFAOYSA-N 7-(benzenesulfonyl)-6-methyl-1,4-dioxaspiro[4.5]decane Chemical compound CC1C(S(=O)(=O)C=2C=CC=CC=2)CCCC11OCCO1 ZYAODYITFKMKJC-UHFFFAOYSA-N 0.000 description 3
- XOBVEZYLDYRXKM-UHFFFAOYSA-N 7-(benzenesulfonyl)-8-methyl-1,4-dioxaspiro[4.5]decane Chemical compound C1C(S(=O)(=O)C=2C=CC=CC=2)C(C)CCC21OCCO2 XOBVEZYLDYRXKM-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 210000002241 neurite Anatomy 0.000 description 3
- 230000014511 neuron projection development Effects 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- RXHONFUPUZJGQP-UHFFFAOYSA-N trimethyl-(4-methylcyclohexen-1-yl)oxysilane Chemical compound CC1CCC(O[Si](C)(C)C)=CC1 RXHONFUPUZJGQP-UHFFFAOYSA-N 0.000 description 3
- VUUAVAQNQQXQSU-UHFFFAOYSA-N 10-[7-(benzenesulfonyl)-1,4-dioxaspiro[4.5]decan-7-yl]decan-1-ol Chemical compound C1C(CCCCCCCCCCO)(S(=O)(=O)C=2C=CC=CC=2)CCCC21OCCO2 VUUAVAQNQQXQSU-UHFFFAOYSA-N 0.000 description 2
- IMUKUASQDQPYGV-UHFFFAOYSA-N 10-[7-(benzenesulfonyl)-6-methyl-1,4-dioxaspiro[4.5]decan-7-yl]decan-1-ol Chemical compound C1CCC(S(=O)(=O)C=2C=CC=CC=2)(CCCCCCCCCCO)C(C)C21OCCO2 IMUKUASQDQPYGV-UHFFFAOYSA-N 0.000 description 2
- NZGSTCKVQKBABW-UHFFFAOYSA-N 10-[7-(benzenesulfonyl)-8-methyl-1,4-dioxaspiro[4.5]decan-7-yl]decan-1-ol Chemical compound C1C(S(=O)(=O)C=2C=CC=CC=2)(CCCCCCCCCCO)C(C)CCC21OCCO2 NZGSTCKVQKBABW-UHFFFAOYSA-N 0.000 description 2
- UMDOBZGVKMUFLF-UHFFFAOYSA-N 12-(2,6,6-trimethylcyclohexen-1-yl)dodecyl acetate Chemical compound CC(=O)OCCCCCCCCCCCCC1=C(C)CCCC1(C)C UMDOBZGVKMUFLF-UHFFFAOYSA-N 0.000 description 2
- REKKCYFYHBLAQD-UHFFFAOYSA-N 3-(11-hydroxyundecyl)-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCO)CCCC1=O REKKCYFYHBLAQD-UHFFFAOYSA-N 0.000 description 2
- YXTZSJUYMJMXDR-UHFFFAOYSA-N 3-(11-hydroxyundecyl)-4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1CCCCCCCCCCCO YXTZSJUYMJMXDR-UHFFFAOYSA-N 0.000 description 2
- PJSTXVKOYOYIFH-UHFFFAOYSA-N 3-(11-hydroxyundecyl)cyclohex-2-en-1-one Chemical compound OCCCCCCCCCCCC1=CC(=O)CCC1 PJSTXVKOYOYIFH-UHFFFAOYSA-N 0.000 description 2
- UNNNLVVXTUETAT-UHFFFAOYSA-N 3-(12-hydroxydodecyl)-2,4,4-trimethylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCO)C(C)(C)CCC1=O UNNNLVVXTUETAT-UHFFFAOYSA-N 0.000 description 2
- QXFYDQMUZMAMAL-UHFFFAOYSA-N 3-(12-hydroxydodecyl)-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCO)CCCC1=O QXFYDQMUZMAMAL-UHFFFAOYSA-N 0.000 description 2
- OSHCSGKZRIPLMT-UHFFFAOYSA-N 3-(12-hydroxydodecyl)cyclohex-2-en-1-one Chemical compound OCCCCCCCCCCCCC1=CC(=O)CCC1 OSHCSGKZRIPLMT-UHFFFAOYSA-N 0.000 description 2
- LQCWFSYOTDYPJU-UHFFFAOYSA-N 3-(13-hydroxytridecyl)cyclohex-2-en-1-one Chemical compound OCCCCCCCCCCCCCC1=CC(=O)CCC1 LQCWFSYOTDYPJU-UHFFFAOYSA-N 0.000 description 2
- GOFNAJYJBAOKOD-UHFFFAOYSA-N 3-(14-hydroxytetradecyl)cyclohex-2-en-1-one Chemical compound OCCCCCCCCCCCCCCC1=CC(=O)CCC1 GOFNAJYJBAOKOD-UHFFFAOYSA-N 0.000 description 2
- FGMAOXGOTRUOKJ-UHFFFAOYSA-N 3-(15-hydroxypentadecyl)-2,4,4-trimethylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCCCCO)C(C)(C)CCC1=O FGMAOXGOTRUOKJ-UHFFFAOYSA-N 0.000 description 2
- 208000014644 Brain disease Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000002932 cholinergic neuron Anatomy 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- GCNSHAQTYKVLHX-UHFFFAOYSA-N cyclohexylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C1CCCCC1 GCNSHAQTYKVLHX-UHFFFAOYSA-N 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
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| JP4490536B2 (ja) * | 2000-01-31 | 2010-06-30 | 明治乳業株式会社 | 脳血管障害に基づく疾患の予防又は治療薬 |
| JP2002068973A (ja) * | 2000-06-16 | 2002-03-08 | Meiji Milk Prod Co Ltd | 幹細胞分化誘導促進剤 |
| US20040115810A1 (en) * | 2000-10-04 | 2004-06-17 | Bang Luu | Stem cell differentiation-inducing promoter |
| JP4250882B2 (ja) * | 2000-10-18 | 2009-04-08 | 住友化学株式会社 | スルホン誘導体およびその製造方法 |
| JP4861560B2 (ja) * | 2001-02-19 | 2012-01-25 | 株式会社明治 | 糖尿病合併症治療剤 |
| JP3836684B2 (ja) * | 2001-02-19 | 2006-10-25 | 明治乳業株式会社 | 排尿障害治療剤 |
| WO2002094252A1 (en) * | 2001-05-24 | 2002-11-28 | Meiji Dairies Corporation | Preventive or remedy for diseases caused by cerebrovascular disturbances |
| JP2005518403A (ja) * | 2002-01-09 | 2005-06-23 | トリデント サイエンシーズ エルエルシー | アンドロゲンレセプターをブロックする化合物 |
| JP4035332B2 (ja) * | 2002-01-22 | 2008-01-23 | 明治乳業株式会社 | シクロヘキセノン長鎖アルコールの製造法 |
| US7307098B2 (en) | 2002-07-19 | 2007-12-11 | Meiji Dairies Corporation | Indole derivatives and drugs containing the same |
| CA2519178C (en) | 2003-03-28 | 2010-01-12 | Meiji Dairies Corporation | Process for producing cyclohexenone long-chain alcohols |
| CA2583699C (en) * | 2004-10-13 | 2012-11-20 | Meiji Dairies Corporation | Stat3 phosphorylation inhibitor and notch1 expression inhibitor |
| CN101180041B (zh) * | 2005-01-18 | 2011-04-13 | 明治乳业株式会社 | 感觉障碍治疗剂 |
| EP1854777A4 (en) * | 2005-02-28 | 2010-07-07 | Meiji Dairies Corp | LONG-CHAINED HYDROCHINONE DERIVATIVE AND / OR LONG-CHAINED PHENOXY DERIVATIVE AND PHARMACEUTICAL PREPARATION CONTAINING THEREOF |
| US20080312336A1 (en) * | 2005-05-26 | 2008-12-18 | Keisuke Satoh | Preventive and/or Therapeutic Agent for Diabetic Vascular Disorder and Respiratory Disorder |
| WO2013147072A1 (ja) * | 2012-03-29 | 2013-10-03 | 大鵬薬品工業株式会社 | 3-(15-ヒドロキシペンタデシル)-2,4,4-トリメチル-2-シクロヘキセン-1-オンの共結晶 |
| JP5566521B1 (ja) | 2013-09-27 | 2014-08-06 | 大鵬薬品工業株式会社 | 膀胱・尿道協調不全改善剤 |
| US20170035705A1 (en) * | 2015-08-04 | 2017-02-09 | Taiho Pharmaceutical Co., Ltd. | Detrusor hyperactivity with impaired contractility ameliorating agent |
| BR112018014841B1 (pt) | 2016-01-22 | 2022-03-03 | Taiho Pharmaceutical Co., Ltd. | Álcoois de cadeia longa cicloexenona, seus usos e métodos para a produção dos mesmos com alta pureza |
| JP2022013721A (ja) | 2020-07-03 | 2022-01-18 | 大鵬薬品工業株式会社 | 排尿症状治療剤 |
| US20230295068A1 (en) * | 2020-08-07 | 2023-09-21 | Taiho Pharmaceutical Co., Ltd. | Novel cycloalkenone compound or salt thereof |
| US20250178998A1 (en) | 2022-02-09 | 2025-06-05 | Taiho Pharmaceutical Co., Ltd. | Crystal form of cyclohexenone compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448697B1 (fr) * | 1989-10-13 | 1996-04-10 | Neurofit | Analogues de la vitamine a, leurs applications, notamment en tant que molecules cytotrophiques et cytoprotectrices, et compositions pharmaceutiques les contenant |
| ATE105282T1 (de) * | 1992-11-18 | 1994-05-15 | Medafor | Langkettige fettalkohole mit neurotropischer und gedaechtnissfoerdernder wirkung. |
-
1998
- 1998-08-11 DE DE69811905T patent/DE69811905T2/de not_active Expired - Lifetime
- 1998-08-11 JP JP2000509675A patent/JP3766591B2/ja not_active Expired - Lifetime
- 1998-08-11 EP EP98936726A patent/EP1003706B1/en not_active Expired - Lifetime
- 1998-08-11 US US09/463,972 patent/US6228893B1/en not_active Expired - Lifetime
- 1998-08-11 AT AT98936726T patent/ATE233724T1/de not_active IP Right Cessation
- 1998-08-11 CA CA002299308A patent/CA2299308C/en not_active Expired - Lifetime
- 1998-08-11 WO PCT/JP1998/003560 patent/WO1999008987A1/en not_active Ceased
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