JP2002241270A5 - - Google Patents
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- Publication number
- JP2002241270A5 JP2002241270A5 JP2001041586A JP2001041586A JP2002241270A5 JP 2002241270 A5 JP2002241270 A5 JP 2002241270A5 JP 2001041586 A JP2001041586 A JP 2001041586A JP 2001041586 A JP2001041586 A JP 2001041586A JP 2002241270 A5 JP2002241270 A5 JP 2002241270A5
- Authority
- JP
- Japan
- Prior art keywords
- solution
- methyl
- cyclohexen
- trimethyl
- production example
- 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
Links
- 238000004519 manufacturing process Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
- 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 3
- 208000002249 Diabetes Complications Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- -1 15-hydroxypentadecyl Chemical group 0.000 description 2
- FLPBIOUJTQLUAU-UHFFFAOYSA-N 3-(18-hydroxyoctadecyl)-2,4,4-trimethylcyclohex-2-en-1-one Chemical compound CC1=C(CCCCCCCCCCCCCCCCCCO)C(C)(C)CCC1=O FLPBIOUJTQLUAU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QJUIMZKRLGOMDK-UHFFFAOYSA-N 14-[7-(benzenesulfonyl)-8-methyl-1,4-dioxaspiro[4.5]decan-7-yl]tetradecan-1-ol Chemical compound C1C(S(=O)(=O)C=2C=CC=CC=2)(CCCCCCCCCCCCCCO)C(C)CCC21OCCO2 QJUIMZKRLGOMDK-UHFFFAOYSA-N 0.000 description 1
- VKXZRJZWAYBBAE-UHFFFAOYSA-N 14-bromotetradecan-1-ol Chemical compound OCCCCCCCCCCCCCCBr VKXZRJZWAYBBAE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PKWPHLCCQVCBLJ-UHFFFAOYSA-N 3-(14-hydroxytetradecyl)-4-methylcyclohex-2-en-1-one Chemical group CC1CCC(=O)C=C1CCCCCCCCCCCCCCO PKWPHLCCQVCBLJ-UHFFFAOYSA-N 0.000 description 1
- CWZACLGIXULVCV-UHFFFAOYSA-N 3-(15-hydroxypentadecyl)-4-methylcyclohex-2-en-1-one Chemical compound CC1CCC(=O)C=C1CCCCCCCCCCCCCCCO CWZACLGIXULVCV-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- RXHONFUPUZJGQP-UHFFFAOYSA-N trimethyl-(4-methylcyclohexen-1-yl)oxysilane Chemical compound CC1CCC(O[Si](C)(C)C)=CC1 RXHONFUPUZJGQP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001041586A JP4861560B2 (ja) | 2001-02-19 | 2001-02-19 | 糖尿病合併症治療剤 |
| PCT/JP2002/001291 WO2002066023A1 (en) | 2001-02-19 | 2002-02-15 | Use of a cyclohexenone derivatives in the manufacture of a medicament for treating diabetic complications |
| ES02712380T ES2355891T3 (es) | 2001-02-19 | 2002-02-15 | Derivado de ciclohexanona para el tratamiento de la neuropatía diabética. |
| US10/467,063 US7838565B2 (en) | 2001-02-19 | 2002-02-15 | Use of cyclohexenone derivatives in the manufacture of a medicament for treating diabetic complications |
| DE60238666T DE60238666D1 (de) | 2001-02-19 | 2002-02-15 | Cyclohexenon derivate zur behandlung der diabetischen neuropathie |
| CA2438506A CA2438506C (en) | 2001-02-19 | 2002-02-15 | Use of a cyclohexenone derivatives in the manufacture of a medicament for treating diabetic complications |
| EP02712380A EP1368013B1 (en) | 2001-02-19 | 2002-02-15 | Cyclohexenone derivative for treating diabetic neuropathy |
| AT02712380T ATE492274T1 (de) | 2001-02-19 | 2002-02-15 | Cyclohexenon derivate zur behandlung der diabetischen neuropathie |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001041586A JP4861560B2 (ja) | 2001-02-19 | 2001-02-19 | 糖尿病合併症治療剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002241270A JP2002241270A (ja) | 2002-08-28 |
| JP2002241270A5 true JP2002241270A5 (https=) | 2006-06-22 |
| JP4861560B2 JP4861560B2 (ja) | 2012-01-25 |
Family
ID=18904008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001041586A Expired - Lifetime JP4861560B2 (ja) | 2001-02-19 | 2001-02-19 | 糖尿病合併症治療剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7838565B2 (https=) |
| EP (1) | EP1368013B1 (https=) |
| JP (1) | JP4861560B2 (https=) |
| AT (1) | ATE492274T1 (https=) |
| CA (1) | CA2438506C (https=) |
| DE (1) | DE60238666D1 (https=) |
| ES (1) | ES2355891T3 (https=) |
| WO (1) | WO2002066023A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004087630A1 (en) * | 2003-03-28 | 2004-10-14 | Meiji Dairies Corporation | Process for producing cyclohexenone long-chain alcohols |
| EP1829536B1 (en) * | 2004-11-25 | 2011-03-30 | Meiji Dairies Corporation | Ameliorant for renal insufficiency |
| DE602006014799D1 (de) * | 2005-01-18 | 2010-07-22 | Meiji Dairies Corp | Heilmittel gegen sensorische erkrankungen |
| JP4986505B2 (ja) * | 2005-05-26 | 2012-07-25 | 株式会社明治 | 糖尿病性血管障害および呼吸障害予防および／または治療剤 |
| CA2609595C (en) * | 2005-05-26 | 2013-01-08 | Meiji Dairies Corporation | Preventive and/or therapeutic agents for diabetic vascular disorders and respiratory disorders |
| US8309611B2 (en) * | 2010-09-20 | 2012-11-13 | Golden Biotechnology Corporation | Methods and compositions for treating lung cancer |
| CA2800329A1 (en) * | 2011-12-30 | 2013-06-30 | Golden Biotechnology Corporation | Methods and compositions for treating diabetes |
| EP3406586B1 (en) | 2016-01-22 | 2020-12-30 | Taiho Pharmaceutical Co., Ltd. | Manufacturing method for high-purity cyclohexenone long-chain alcohol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0555149B1 (en) | 1992-02-07 | 1997-08-27 | Mitsubishi Gas Chemical Company, Inc. | Use of oxazopyrroloquinolines and pyrroloquinolinequinones for the manufacture of nerve growth factor production accelerators |
| US6113947A (en) * | 1997-06-13 | 2000-09-05 | Genentech, Inc. | Controlled release microencapsulated NGF formulation |
| EP1003706B1 (en) * | 1997-08-13 | 2003-03-05 | Meiji Milk Products Company Limited | Cyclohexenone long-chain alcohol and medicament containing same |
| JP4469441B2 (ja) | 1999-02-10 | 2010-05-26 | 明治乳業株式会社 | 神経変性疾患の予防又は治療薬 |
| ATE450602T1 (de) * | 2000-10-04 | 2009-12-15 | Meiji Dairies Corp | Stemzelldifferenzierung induzierende promoter |
| JP3836684B2 (ja) * | 2001-02-19 | 2006-10-25 | 明治乳業株式会社 | 排尿障害治療剤 |
| US20040152786A1 (en) * | 2001-05-24 | 2004-08-05 | Bang Luu | Preventive or remedy for diseases caused by cerebrovascular disturbances |
-
2001
- 2001-02-19 JP JP2001041586A patent/JP4861560B2/ja not_active Expired - Lifetime
-
2002
- 2002-02-15 DE DE60238666T patent/DE60238666D1/de not_active Expired - Lifetime
- 2002-02-15 ES ES02712380T patent/ES2355891T3/es not_active Expired - Lifetime
- 2002-02-15 AT AT02712380T patent/ATE492274T1/de not_active IP Right Cessation
- 2002-02-15 CA CA2438506A patent/CA2438506C/en not_active Expired - Fee Related
- 2002-02-15 WO PCT/JP2002/001291 patent/WO2002066023A1/en not_active Ceased
- 2002-02-15 US US10/467,063 patent/US7838565B2/en not_active Expired - Fee Related
- 2002-02-15 EP EP02712380A patent/EP1368013B1/en not_active Expired - Lifetime
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