JP5749261B2 - 3,3,5,5−テトラメチルシクロヘキサノンを調製する方法 - Google Patents
3,3,5,5−テトラメチルシクロヘキサノンを調製する方法 Download PDFInfo
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- JP5749261B2 JP5749261B2 JP2012516587A JP2012516587A JP5749261B2 JP 5749261 B2 JP5749261 B2 JP 5749261B2 JP 2012516587 A JP2012516587 A JP 2012516587A JP 2012516587 A JP2012516587 A JP 2012516587A JP 5749261 B2 JP5749261 B2 JP 5749261B2
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- JP
- Japan
- Prior art keywords
- chloride
- copper
- tetramethylcyclohexanone
- isophorone
- lithium
- 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.)
- Expired - Fee Related
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
ステップ(i):塩化メチルマグネシウム存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。
ステップ(i):塩化メチルマグネシウムを用いてイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。
ステップ(i):塩化メチルマグネシウム存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。
ステップ(i):塩化メチルマグネシウム存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。
Claims (12)
- 下記ステップ(i)を含む、3,3,5,5-テトラメチルシクロヘキサノンを調製する方法。:
ステップ(i):塩化メチルマグネシウム、ハロゲン化銅(I)及びハロゲン化リチウムの存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。 - 前記ハロゲン化銅(I)がヨウ化銅(I)である請求項1に記載の方法。
- 前記ハロゲン化リチウムが塩化リチウムである請求項1または2に記載の方法。
- ハロゲン化銅(I)とハロゲン化リチウムとのモル比が1:1.5〜1:2.5の範囲内である請求項1〜3のいずれかに記載の方法。
- エーテルを含有する溶媒中でステップ(i)を実施する請求項1〜3のいずれかに記載の方法。
- 前記エーテルがテトラヒドロフランである請求項5に記載の方法。
- ステップ(i)においてはテトラヒドロフラン中で塩化メチルマグネシウムとヨウ化銅(I)と塩化リチウムとの存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する請求項1〜5のいずれかに記載の方法。
- イソホロンとヨウ化銅(I)と塩化リチウムとを含有する溶液に、塩化メチルマグネシウムを含有するテトラヒドロフラン溶液を添加する請求項7に記載の方法。
- 下記ステップ(i)を含む1-アミノ-1,3,3,5,5-ペンタメチルシクロヘキサンまたはその薬剤学的に許容可能な塩を調製する方法。:
ステップ(i):塩化メチルマグネシウム、ハロゲン化銅(I)及びハロゲン化リチウムの存在下でイソホロンを3,3,5,5-テトラメチルシクロヘキサノンに変換する。 - 請求項2〜8のいずれかに記載の方法にしたがってステップ(i)を実施する請求項9に記載の方法。
- 薬剤学的に許容可能な塩が、塩酸塩またはメシラートであることを特徴とする請求項9または10に記載の方法。
- 前記塩化メチルマグネシウムが塩化エチルマグネシウムを含有しない請求項1〜11のいずれかに記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26977109P | 2009-06-29 | 2009-06-29 | |
EP09008464.1 | 2009-06-29 | ||
EP09008464 | 2009-06-29 | ||
US61/269,771 | 2009-06-29 | ||
PCT/EP2010/003923 WO2011000540A1 (en) | 2009-06-29 | 2010-06-28 | Method of preparing 3,3,5,5-tetramethylcyclohexanone |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012531389A JP2012531389A (ja) | 2012-12-10 |
JP5749261B2 true JP5749261B2 (ja) | 2015-07-15 |
Family
ID=41172330
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012516587A Expired - Fee Related JP5749261B2 (ja) | 2009-06-29 | 2010-06-28 | 3,3,5,5−テトラメチルシクロヘキサノンを調製する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20130123541A1 (ja) |
EP (1) | EP2448901A1 (ja) |
JP (1) | JP5749261B2 (ja) |
AR (1) | AR078138A1 (ja) |
BR (1) | BRPI1012669A2 (ja) |
CA (1) | CA2765610A1 (ja) |
TW (1) | TW201105614A (ja) |
WO (1) | WO2011000540A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011000539A1 (en) * | 2009-06-29 | 2011-01-06 | Merz Pharma Gmbh & Co. Kgaa | Method of preparing neramexane |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2838508A (en) * | 1956-09-18 | 1958-06-10 | Metal & Thermit Corp | Chemical process and product |
US4084009A (en) * | 1977-03-03 | 1978-04-11 | International Flavors & Fragrances Inc. | Flavoring with a hydroxy cyclohexenone derivative |
DE3366927D1 (en) * | 1982-08-13 | 1986-11-20 | Secr Defence Brit | Preparation of organometallic indium and gallium compounds |
EA002254B1 (ru) * | 1997-06-30 | 2002-02-28 | Мерц + Ко. Гмбх Унд Ко. | 1-аминоалкилциклогексановые антагонисты рецепторов nmda |
US6071966A (en) * | 1997-06-30 | 2000-06-06 | Merz + Co. Gmbh & Co. | 1-amino-alkylcyclohexane NMDA receptor antagonists |
US6602862B1 (en) * | 2000-09-19 | 2003-08-05 | Merz Pharma Gmbh & Co., Kgaa | 1-Amino-alkylcyclohexanes as trypanocidal agents |
TWI322813B (en) * | 2002-01-21 | 2010-04-01 | Organon Nv | Process for the preparation of 7alpha-methylsteroids |
GB0304927D0 (en) * | 2003-03-04 | 2003-04-09 | Resolution Chemicals Ltd | Process for the production of tibolone |
UA89964C2 (ru) * | 2004-09-08 | 2010-03-25 | Н.В. Органон | 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ, КОТОРЫЕ ИМЕЮТ СЕЛЕКТИВНУЮ ЭСТРОГЕННУЮ АКТИВНОСТЬ |
CA2587162A1 (en) * | 2004-11-11 | 2006-05-18 | Takasago International Corporation | Method of producing macrocyclic ketone, and intermediate thereof |
JP2007308463A (ja) * | 2006-05-22 | 2007-11-29 | Mitsubishi Chemicals Corp | 2−メチル−2−アダマンチル(メタ)アクリレートの製造方法 |
JP2007308460A (ja) * | 2006-05-22 | 2007-11-29 | Mitsubishi Chemicals Corp | 2−メチル−2−アダマンタノールおよびそのマグネシウムクロリド塩の製造方法 |
NZ584161A (en) * | 2007-10-26 | 2011-12-22 | Japan Tobacco Inc | Spiro-ring compound and use thereof for medical purposes |
TWI432188B (zh) * | 2008-12-19 | 2014-04-01 | Merz Pharma Gmbh & Co Kgaa | 供治療發炎性皮膚疾病之1-胺基-烷基環己烷衍生物類 |
EP2373304B1 (en) * | 2008-12-19 | 2014-07-30 | Merz Pharma GmbH & Co. KGaA | Neramexane for the treatment of mast cell mediated diseases |
WO2011000539A1 (en) * | 2009-06-29 | 2011-01-06 | Merz Pharma Gmbh & Co. Kgaa | Method of preparing neramexane |
-
2010
- 2010-06-28 JP JP2012516587A patent/JP5749261B2/ja not_active Expired - Fee Related
- 2010-06-28 CA CA2765610A patent/CA2765610A1/en not_active Abandoned
- 2010-06-28 BR BRPI1012669A patent/BRPI1012669A2/pt not_active IP Right Cessation
- 2010-06-28 WO PCT/EP2010/003923 patent/WO2011000540A1/en active Application Filing
- 2010-06-28 EP EP10737261A patent/EP2448901A1/en not_active Withdrawn
- 2010-06-28 US US13/378,773 patent/US20130123541A1/en not_active Abandoned
- 2010-06-29 TW TW099121158A patent/TW201105614A/zh unknown
- 2010-06-29 AR ARP100102319A patent/AR078138A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
TW201105614A (en) | 2011-02-16 |
US20130123541A1 (en) | 2013-05-16 |
AR078138A1 (es) | 2011-10-19 |
CA2765610A1 (en) | 2011-01-06 |
EP2448901A1 (en) | 2012-05-09 |
WO2011000540A1 (en) | 2011-01-06 |
JP2012531389A (ja) | 2012-12-10 |
BRPI1012669A2 (pt) | 2016-04-05 |
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