JP2002241271A5 - - Google Patents
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- Publication number
- JP2002241271A5 JP2002241271A5 JP2001041587A JP2001041587A JP2002241271A5 JP 2002241271 A5 JP2002241271 A5 JP 2002241271A5 JP 2001041587 A JP2001041587 A JP 2001041587A JP 2001041587 A JP2001041587 A JP 2001041587A JP 2002241271 A5 JP2002241271 A5 JP 2002241271A5
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- -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
- 239000003814 drug Substances 0.000 description 2
- 206010013990 dysuria Diseases 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
- 229940124597 therapeutic agent Drugs 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
- 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
- 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 (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001041587A JP3836684B2 (ja) | 2001-02-19 | 2001-02-19 | 排尿障害治療剤 |
| US10/468,138 US6906107B2 (en) | 2001-02-19 | 2002-02-15 | Use of cyclohexenone derivatives for the manufacture of a medicament in the treatment of dysuria |
| PCT/JP2002/001292 WO2002066024A1 (en) | 2001-02-19 | 2002-02-15 | Use of cyclohexenone derivatives for the manufacture of a medicament in the treatment of dysuria |
| CA2438509A CA2438509C (en) | 2001-02-19 | 2002-02-15 | Use of cyclohexenone derivatives for the manufacture of a medicament in the treatment of dysuria |
| DE60216239T DE60216239T8 (de) | 2001-02-19 | 2002-02-15 | Verwendung von Cyclohexenon-Derivaten zur Herstellung eines Arzneimittels zur Behandlung von Dysurie |
| AT02712381T ATE345787T1 (de) | 2001-02-19 | 2002-02-15 | Verwendung von cyclohexenon derivaten zur herstellung eines medikaments für die behandlung von dysurie |
| EP02712381A EP1368014B1 (en) | 2001-02-19 | 2002-02-15 | Use of cyclohexenone derivatives for the manufacture of a medicament in the treatment of dysuria |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001041587A JP3836684B2 (ja) | 2001-02-19 | 2001-02-19 | 排尿障害治療剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002241271A JP2002241271A (ja) | 2002-08-28 |
| JP2002241271A5 true JP2002241271A5 (enExample) | 2006-06-22 |
| JP3836684B2 JP3836684B2 (ja) | 2006-10-25 |
Family
ID=18904009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001041587A Expired - Lifetime JP3836684B2 (ja) | 2001-02-19 | 2001-02-19 | 排尿障害治療剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6906107B2 (enExample) |
| EP (1) | EP1368014B1 (enExample) |
| JP (1) | JP3836684B2 (enExample) |
| AT (1) | ATE345787T1 (enExample) |
| CA (1) | CA2438509C (enExample) |
| DE (1) | DE60216239T8 (enExample) |
| WO (1) | WO2002066024A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4861560B2 (ja) * | 2001-02-19 | 2012-01-25 | 株式会社明治 | 糖尿病合併症治療剤 |
| CA2519178C (en) * | 2003-03-28 | 2010-01-12 | Meiji Dairies Corporation | Process for producing cyclohexenone long-chain alcohols |
| CN101065119B (zh) * | 2004-11-25 | 2010-08-25 | 明治乳业株式会社 | 肾功能不全的改良剂 |
| CN101180041B (zh) * | 2005-01-18 | 2011-04-13 | 明治乳业株式会社 | 感觉障碍治疗剂 |
| 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 |
| JP6894555B1 (ja) * | 2020-07-03 | 2021-06-30 | 大鵬薬品工業株式会社 | 排尿症状治療剤 |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6113947A (en) | 1997-06-13 | 2000-09-05 | Genentech, Inc. | Controlled release microencapsulated NGF formulation |
| DE69811905T2 (de) * | 1997-08-13 | 2003-11-06 | Meiji Milk Products Co. Ltd., Tokio/Tokyo | Cyclohexenon langketten alkohol und diese enthaltendes arzneimittel |
-
2001
- 2001-02-19 JP JP2001041587A patent/JP3836684B2/ja not_active Expired - Lifetime
-
2002
- 2002-02-15 DE DE60216239T patent/DE60216239T8/de active Active
- 2002-02-15 WO PCT/JP2002/001292 patent/WO2002066024A1/en not_active Ceased
- 2002-02-15 AT AT02712381T patent/ATE345787T1/de not_active IP Right Cessation
- 2002-02-15 US US10/468,138 patent/US6906107B2/en not_active Expired - Lifetime
- 2002-02-15 CA CA2438509A patent/CA2438509C/en not_active Expired - Lifetime
- 2002-02-15 EP EP02712381A patent/EP1368014B1/en not_active Expired - Lifetime
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