JP2013529223A - ピタバスタチンまたはその塩の中間体の製造方法 - Google Patents
ピタバスタチンまたはその塩の中間体の製造方法 Download PDFInfo
- Publication number
- JP2013529223A JP2013529223A JP2013514094A JP2013514094A JP2013529223A JP 2013529223 A JP2013529223 A JP 2013529223A JP 2013514094 A JP2013514094 A JP 2013514094A JP 2013514094 A JP2013514094 A JP 2013514094A JP 2013529223 A JP2013529223 A JP 2013529223A
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- formula
- compound
- dimethyl sulfoxide
- pitavastatin
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- 0 CC(C)(O[C@@](CC(O*)=O)C1)O[C@@]1C=Cc1c(-c(cc2)ccc2F)c(cccc2)c2nc1C1CC1 Chemical compound CC(C)(O[C@@](CC(O*)=O)C1)O[C@@]1C=Cc1c(-c(cc2)ccc2F)c(cccc2)c2nc1C1CC1 0.000 description 2
- JEFQIIXBSQLRTF-ZJUUUORDSA-N CC(C)(C)OC(C[C@@H](C1)OC(C)(C)O[C@@H]1C=O)=O Chemical compound CC(C)(C)OC(C[C@@H](C1)OC(C)(C)O[C@@H]1C=O)=O JEFQIIXBSQLRTF-ZJUUUORDSA-N 0.000 description 1
- CYXZPGJPODMCPR-JKIPGYCUSA-N C[C@H](C[C@@H](/C=C/c1c(-c(cc2)ccc2F)c(cccc2)c2nc1C1CC1)OC(C)(C)O)CC(OC(C)(C)C)=O Chemical compound C[C@H](C[C@@H](/C=C/c1c(-c(cc2)ccc2F)c(cccc2)c2nc1C1CC1)OC(C)(C)O)CC(OC(C)(C)C)=O CYXZPGJPODMCPR-JKIPGYCUSA-N 0.000 description 1
- UTDVDLSRTUDNTR-UHFFFAOYSA-N Fc(cc1)ccc1-c1c(CP(c2ccccc2)c2ccccc2)c(C2CC2)nc2c1cccc2 Chemical compound Fc(cc1)ccc1-c1c(CP(c2ccccc2)c2ccccc2)c(C2CC2)nc2c1cccc2 UTDVDLSRTUDNTR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
Abstract
Description
融点: 113 ℃ - 116 ℃
HPLC%面積: 99.396%
1H-NMR (CDCl3): 0.9〜1.0(m, 2H), 1.0〜1.03(m, 1H), 1.2〜1.3(m, 2H), 1.3〜1.38(s, 6H), 1.38〜1.4(m, 1H), 1.45(s, 9H), 2.2〜2.3(dd, 1H, J=0.015, J=0.038), 2.3〜2.4 (m, 2H), 4.1〜4.2(m, 1H), 4.3〜4.4(m, 1H), 5.5〜5.6(dd, 1H, J=0.015, J=0.04), 6.5(d, 1H, J=0.04), 7.0〜7.3(m, 6H), 7.5(t, 1H), 7.9(d, 1H, J=0.021)
融点: 97 ℃ - 103 ℃
HPLC%面積: 99.221%
1H-NMR (CDCl3): 0.9〜1.0(m, 2H), 1.0〜1.03(m, 1H), 1.2〜1.3(m, 2H), 1.3〜1.38(s, 6H), 1.38〜1.4(m, 1H), 1.45(s, 9H), 2.2〜2.3(dd, 1H, J=0.015, J=0.038), 2.3〜2.4 (m, 2H), 2.5〜2.7(m, 12H), 4.1〜4.2(m, 1H), 4.3〜4.4(m, 1H), 5.5〜5.6(dd, 1H, J=0.015, J=0.04), 6.5(d, 1H, J=0.04), 7.0〜7.3(m, 6H), 7.5(t, 1H), 7.9(d, 1H, J=0.021)
HPLC%面積: 98.555%
HPLC%面積: 98.615%
HPLC%面積: 99.826%
HPLC%面積: 99.776%
Claims (7)
- 前記塩基が、アルカリ金属塩であることを特徴とする請求項1または請求項2に記載の製造方法。
- 前記C1−C4アルコールが、メタノール、エタノール及び2−プロパノールからなる群から選択される1種以上であることを特徴とする請求項1に記載の製造方法。
- 前記沈殿物を形成させる工程が、前記化学式2の化合物と化学式3の化合物との反応混合物に、40ないし45℃でC1−C4アルコールを加えた後、得られた反応混合物を5ないし15℃に冷却することによって遂行されることを特徴とする請求項1に記載の製造方法。
- (e)請求項1ないし請求項5のいずれか1項に記載の製造方法によって、結晶型固体状の化学式4の化合物(式中、Rはカルボン酸保護基である)またはそのジメチルスルホキシド溶媒和物を製造する段階、
(h)任意で実施してもよい、前記遊離塩基形態のピタバスタチンをその薬学的に許容可能な塩に転換する段階
を含む、ピタバスタチンまたはその薬学的に許容可能な塩の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020100053631A KR100995882B1 (ko) | 2010-06-08 | 2010-06-08 | 피타바스타틴 또는 그의 염의 중간체의 제조방법 |
KR10-2010-0053631 | 2010-06-08 | ||
PCT/KR2011/001704 WO2011155689A2 (ko) | 2010-06-08 | 2011-03-11 | 피타바스타틴 또는 그의 염의 중간체의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013529223A true JP2013529223A (ja) | 2013-07-18 |
JP5796836B2 JP5796836B2 (ja) | 2015-10-21 |
Family
ID=43409987
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013514094A Active JP5796836B2 (ja) | 2010-06-08 | 2011-03-11 | ピタバスタチンまたはその塩の中間体の製造方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20130072688A1 (ja) |
JP (1) | JP5796836B2 (ja) |
KR (1) | KR100995882B1 (ja) |
CN (2) | CN103833737A (ja) |
WO (1) | WO2011155689A2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101292743B1 (ko) * | 2012-05-17 | 2013-08-02 | (주) 에프엔지리서치 | 신규한 스타틴 중간체 및 이를 이용한 피타바스타틴, 로수바스타틴, 세리바스타틴 및 플루바스타틴의 제조 방법 |
CN108976168B (zh) * | 2017-06-02 | 2020-09-25 | 浙江京新药业股份有限公司 | 一种匹伐他汀半钙盐晶型及其制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05310700A (ja) * | 1992-05-12 | 1993-11-22 | Sagami Chem Res Center | 縮合ピリジン系メバロノラクトン中間体及びその製法 |
JP2003238566A (ja) * | 2001-02-02 | 2003-08-27 | Takeda Chem Ind Ltd | 縮合複素環化合物 |
JP2004099540A (ja) * | 2002-09-10 | 2004-04-02 | Nippon Kasei Chem Co Ltd | ヘキサヒドロ−3h−ナフタレン−2−オン誘導体およびその製造方法ならびにヘキサヒドロ−3h−ナフタレン−2−オン誘導体のエナミン |
JP2006511618A (ja) * | 2002-12-12 | 2006-04-06 | テバ ファーマシューティカル インダストリーズ リミティド | ガチフロキサシンの結晶形態および調製の方法 |
WO2007132482A2 (en) * | 2006-05-17 | 2007-11-22 | Manne Satyanarayana Reddy | Novel process for the preparation of pitavastatin and its pharmaceutically acceptable salts |
WO2008152086A2 (en) * | 2007-06-15 | 2008-12-18 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-(1h)-pyrazole derivatives as cannabinoid cb1 receptor modulators |
KR20100052230A (ko) * | 2008-11-10 | 2010-05-19 | 미래파인켐 주식회사 | 피타바스타틴 중간체의 제조방법 및 이를 이용한 피타바스타틴 헤미 칼슘염의 제조방법 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2569746B2 (ja) * | 1987-08-20 | 1997-01-08 | 日産化学工業株式会社 | キノリン系メバロノラクトン類 |
JP4433156B2 (ja) * | 2001-11-14 | 2010-03-17 | 日産化学工業株式会社 | 光学活性オキソヘプテン酸エステルの製造方法 |
US8487105B2 (en) * | 2009-01-19 | 2013-07-16 | Msn Laboratories Limited | Process for preparing pitavastatin, intermediates and pharmaceuctically acceptable salts thereof |
-
2010
- 2010-06-08 KR KR1020100053631A patent/KR100995882B1/ko active IP Right Grant
-
2011
- 2011-03-11 WO PCT/KR2011/001704 patent/WO2011155689A2/ko active Application Filing
- 2011-03-11 CN CN201410048548.3A patent/CN103833737A/zh active Pending
- 2011-03-11 US US13/701,723 patent/US20130072688A1/en not_active Abandoned
- 2011-03-11 CN CN201180028329.3A patent/CN102971297B/zh active Active
- 2011-03-11 JP JP2013514094A patent/JP5796836B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05310700A (ja) * | 1992-05-12 | 1993-11-22 | Sagami Chem Res Center | 縮合ピリジン系メバロノラクトン中間体及びその製法 |
JP2003238566A (ja) * | 2001-02-02 | 2003-08-27 | Takeda Chem Ind Ltd | 縮合複素環化合物 |
JP2004099540A (ja) * | 2002-09-10 | 2004-04-02 | Nippon Kasei Chem Co Ltd | ヘキサヒドロ−3h−ナフタレン−2−オン誘導体およびその製造方法ならびにヘキサヒドロ−3h−ナフタレン−2−オン誘導体のエナミン |
JP2006511618A (ja) * | 2002-12-12 | 2006-04-06 | テバ ファーマシューティカル インダストリーズ リミティド | ガチフロキサシンの結晶形態および調製の方法 |
WO2007132482A2 (en) * | 2006-05-17 | 2007-11-22 | Manne Satyanarayana Reddy | Novel process for the preparation of pitavastatin and its pharmaceutically acceptable salts |
WO2008152086A2 (en) * | 2007-06-15 | 2008-12-18 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-(1h)-pyrazole derivatives as cannabinoid cb1 receptor modulators |
KR20100052230A (ko) * | 2008-11-10 | 2010-05-19 | 미래파인켐 주식회사 | 피타바스타틴 중간체의 제조방법 및 이를 이용한 피타바스타틴 헤미 칼슘염의 제조방법 |
Non-Patent Citations (1)
Title |
---|
JPN6014047536; 社団法人日本化学会: 化学便覧応用化学編第6版 , 20030130, 第178頁, 丸善株式会社 * |
Also Published As
Publication number | Publication date |
---|---|
KR100995882B1 (ko) | 2010-11-22 |
CN102971297A (zh) | 2013-03-13 |
WO2011155689A2 (ko) | 2011-12-15 |
CN102971297B (zh) | 2014-12-10 |
US20130072688A1 (en) | 2013-03-21 |
WO2011155689A3 (ko) | 2012-02-02 |
CN103833737A (zh) | 2014-06-04 |
JP5796836B2 (ja) | 2015-10-21 |
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