JP2019518781A - 合成方法 - Google Patents
合成方法 Download PDFInfo
- Publication number
- JP2019518781A JP2019518781A JP2018567649A JP2018567649A JP2019518781A JP 2019518781 A JP2019518781 A JP 2019518781A JP 2018567649 A JP2018567649 A JP 2018567649A JP 2018567649 A JP2018567649 A JP 2018567649A JP 2019518781 A JP2019518781 A JP 2019518781A
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- gsk2330672
- compound
- ethyloxirane
- reaction
- 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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- 0 CCCCC(CC)(C1)N[C@](c2ccccc2)c2cc(*C)c(CNC(CC)CI)cc2S1(=O)=O Chemical compound CCCCC(CC)(C1)N[C@](c2ccccc2)c2cc(*C)c(CNC(CC)CI)cc2S1(=O)=O 0.000 description 2
- GWSUPIWDJZYLAP-AJTFRIOCSA-N CCCC[C@](CC)(C1)N=C(c2ccccc2)c(cc(c(O)c2)OC)c2[S@@+]1[O-] Chemical compound CCCC[C@](CC)(C1)N=C(c2ccccc2)c(cc(c(O)c2)OC)c2[S@@+]1[O-] GWSUPIWDJZYLAP-AJTFRIOCSA-N 0.000 description 1
- WGAOPGXUNXERAO-VHFRWLAGSA-N CCCC[C@](CC)(C1)N[C@H](c2ccccc2)c(cc(c(O)c2)OC)c2[S@@+]1[O-] Chemical compound CCCC[C@](CC)(C1)N[C@H](c2ccccc2)c(cc(c(O)c2)OC)c2[S@@+]1[O-] WGAOPGXUNXERAO-VHFRWLAGSA-N 0.000 description 1
- CWJGZTBAAWBKJL-OAHLLOKOSA-N CCCC[C@](CC)(CSc(cc1)cc(O)c1OC)N Chemical compound CCCC[C@](CC)(CSc(cc1)cc(O)c1OC)N CWJGZTBAAWBKJL-OAHLLOKOSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/001—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by metabolizing one of the enantiomers
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y303/00—Hydrolases acting on ether bonds (3.3)
- C12Y303/02—Ether hydrolases (3.3.2)
- C12Y303/02009—Microsomal epoxide hydrolase (3.3.2.9), i.e. styreneepoxide hydrolase
Abstract
Description
Bz ベンゾイル
TfOH トリフルオロメタンスルホン酸
BzCl 塩化ベンゾイル
S-BINOL (S)-(−)-1,1′-ビ(2-ナフトール)
Ti(OiPr)4 チタンイソプロポキシド
t-BuOOH tert-ブチルヒドロペルオキシド
DCM ジクロロメタン
NaBH4 水素化ホウ素ナトリウム
MeOH メタノール
mCPBA メタクロロ過安息香酸
TFA トリフルオロ酢酸
MTBE メチルt-ブチルエーテル
1H NMR (400 MHz, CDCl3) δ 2.61 (d, J = 4.9 Hz, 1H), 2.59 (d, J = 4.9 Hz, 1H), 1.72-1.46 (m, 4H), 1.42-1.26 (m, 4H), 0.99-0.87 (m, 6H). 13C NMR (125 MHz, CDCl3) δ 60.2, 52.2, 33.7, 27.0, 26.9, 22.9, 14.0, 8.9.
1H NMR (400 MHz, CDCl3) δ 6.94 (d, J = 2.2 Hz, 1H), 6.85 (dd, J = 8.4, 2.2 Hz, 1H), 6.67 (d, J = 8.4 Hz, 1H), 5.23 (s, 1H), 3.78 (s, 3H), 2.87 (s, 2H), 1.46-1.28 (m, 4H), 1.25-1.05 (m, 4H), 0.81 (t, J = 6.9 Hz, 3H), 0.76 (t, J = 7.45 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 146.0, 129.1, 122.9, 117.7, 111.2, 56.0, 54.8, 47.5, 38.6, 31.8, 25.8, 23.3, 14.1, 8.0.
1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.60-7.54 (m, 2H), 7.46-7.40 (m, 1H), 7.39-7.33 (m, 2H), 6.67 (s, 1H), 3.81 (d, J = 12.4 Hz, 1H), 3.79 (s, 3H), 3.30 (d, J = 12.4 Hz, 1H), 2.07-1.84 (m, 2H), 1.24-0.94 (m, 9H), 0.74 (t, J = 6.6 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 163.4, 149.0, 148.9, 140.5, 135.7, 130.4, 129.1, 128.2, 123.2, 112.3, 109.1, 70.6, 60.7, 56.5, 38.2, 37.2, 25.4, 22.9, 13.9, 8.6.
1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.46-7.35 (m, 4H), 7.35-7.28 (m, 1H), 6.15 (s, 1H), 6.02 (s, 1H), 3.58 (s, 3H), 3.41 (d, J = 14.9 Hz, 1H), 3.05 (d, J = 14.9 Hz, 1H), 2.22-2.09 (m, 1H), 1.89-1.77 (m, 1H), 1.57-1.39 (m, 2H), 1.35-1.06 (m, 4H), 0.88 (t, J = 7.4 Hz, 3H), 0.83 (t, J = 6.9 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 149.6, 143.9, 142.3, 138.5, 132.5, 128.5, 127.8, 127.3, 114.5, 110.8, 63.9, 57.4, 55.8, 55.2, 34.1, 31.2, 25.3, 22.9, 14.1, 7.6.
原発性胆汁性胆管炎(PBC)及びそう痒症の徴候を有する患者における安全性、忍容性及びGSK672投与の反復投薬の効果を調査するために臨床試験を行った。この研究の結果を、要約し、clintrials.govで公開した。
要約すると、2週間の経口の毎日2回のGSK2330672は、十分に忍容され、そう痒症を有するPBC患者の高い比率でそう痒強度を減じた。血清中の総及び接合した原発性胆汁酸及びFGF19レベルでの実質的な減少、及び血清中C4レベルでの増加は、IBAT阻害の作用の機構と一致する。これらの結果は、胆汁うっ滞性そう痒症のための将来性のある治療としてのGSK2330672のさらなる調査を支持する。
Claims (14)
- 前記化合物Aが、エポキシド加水分解酵素を用いたラセミ体2-ブチル-2-エチルオキシランの速度論的分割により作製される、請求項1に記載の方法。
- 前記エポキシド加水分解酵素が、アグロマイセス・メジオラヌスZJB1202030ID: JX467176から得られる、請求項8に記載の方法。
- 前記エポキシド加水分解酵素が、アグロマイセス・メジオラヌスZJB1202030ID: JX467176から得られる、エポキシド加水分解酵素の突然変異株N240Dである、請求項9に記載の方法。
- 前記ラセミ体2-ブチル-2-エチルオキシランの濃度が、200〜330g/Lである、請求項8に記載の方法。
- 20〜200mgの間の前記化合物、微結晶性セルロース及びステアリン酸マグネシウムを含む、請求項12に記載の錠剤。
- 請求項12に記載の錠剤の投与を含む、胆汁うっ滞性肝疾患及び/又は関連したそう痒症を治療する方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022077311A JP2022116004A (ja) | 2016-06-27 | 2022-05-10 | 合成方法 |
Applications Claiming Priority (5)
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US201662355016P | 2016-06-27 | 2016-06-27 | |
US62/355,016 | 2016-06-27 | ||
US201662411776P | 2016-10-24 | 2016-10-24 | |
US62/411,776 | 2016-10-24 | ||
PCT/IB2017/053839 WO2018002827A1 (en) | 2016-06-27 | 2017-06-27 | Synthetic methods |
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JP2022077311A Division JP2022116004A (ja) | 2016-06-27 | 2022-05-10 | 合成方法 |
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JP2019518781A true JP2019518781A (ja) | 2019-07-04 |
JP7094899B2 JP7094899B2 (ja) | 2022-07-04 |
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JP2018567649A Active JP7094899B2 (ja) | 2016-06-27 | 2017-06-27 | 合成方法 |
JP2022077311A Pending JP2022116004A (ja) | 2016-06-27 | 2022-05-10 | 合成方法 |
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Country Status (11)
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US (2) | US11186558B2 (ja) |
EP (1) | EP3475266B1 (ja) |
JP (2) | JP7094899B2 (ja) |
KR (1) | KR20190020132A (ja) |
CN (2) | CN109415329B (ja) |
AU (1) | AU2017286943B2 (ja) |
BR (1) | BR112018076197A2 (ja) |
CA (1) | CA3027725A1 (ja) |
ES (1) | ES2965277T3 (ja) |
RU (1) | RU2019100575A (ja) |
WO (1) | WO2018002827A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA3129735A1 (en) * | 2019-02-12 | 2020-08-20 | Mirum Pharmaceuticals, Inc. | Methods for increasing growth in pediatric subjects having cholestatic liver disease |
WO2022084212A1 (en) | 2020-10-20 | 2022-04-28 | Glaxosmithkline Intellectual Property (No.2) Limited | Methods for treating cholestatic pruritus |
CN116490191A (zh) * | 2020-10-20 | 2023-07-25 | 葛兰素史克知识产权第二有限公司 | 治疗胆汁淤积性瘙痒的方法 |
CN116964041A (zh) | 2020-12-23 | 2023-10-27 | 葛兰素史克知识产权第二有限公司 | Linerixibat的形式 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011137135A1 (en) * | 2010-04-27 | 2011-11-03 | Glaxosmithkline Llc | Chemical compounds |
WO2016020785A1 (en) * | 2014-08-05 | 2016-02-11 | Glaxosmithkline Intellectual Property (No. 2) Limited | Synthesis of benzothiazepines |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9203347D0 (en) * | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
DE19916108C1 (de) * | 1999-04-09 | 2001-01-11 | Aventis Pharma Gmbh | Mit Zuckerresten substituierte 1,4-Benzothiazepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und deren Verwendung |
DE102005033100B3 (de) * | 2005-07-15 | 2007-01-25 | Sanofi-Aventis Deutschland Gmbh | Neues 1,4-Benzothiazepin-1,1-Dioxidderivat mit verbesserten Eigenschaften, diese Verbindung enthaltene Arzneimittel und Verfahren zu deren Herstellung |
CN102978220B (zh) * | 2012-11-13 | 2015-03-04 | 浙江工业大学 | 环氧化物水解酶基因、编码酶、载体、工程菌及应用 |
RU2015139731A (ru) * | 2013-03-15 | 2017-04-20 | ЛУМЕНА ФАРМАСЬЮТИКАЛС ЭлЭлСи | Ингибиторы рециркуляции желчных кислот для лечения первичного склерозирующего холангита и воспалительного заболевания кишечника |
CA2956699C (en) * | 2014-07-30 | 2020-09-29 | Aetas Pharma Co., Ltd. | Optical isomer of 1,4-benzothiazepine-1-oxide derivative, and pharmaceutical composition prepared using same |
-
2017
- 2017-06-27 EP EP17742549.3A patent/EP3475266B1/en active Active
- 2017-06-27 BR BR112018076197A patent/BR112018076197A2/pt unknown
- 2017-06-27 CN CN201780039490.8A patent/CN109415329B/zh active Active
- 2017-06-27 KR KR1020197002396A patent/KR20190020132A/ko unknown
- 2017-06-27 CA CA3027725A patent/CA3027725A1/en active Pending
- 2017-06-27 WO PCT/IB2017/053839 patent/WO2018002827A1/en unknown
- 2017-06-27 ES ES17742549T patent/ES2965277T3/es active Active
- 2017-06-27 JP JP2018567649A patent/JP7094899B2/ja active Active
- 2017-06-27 US US16/305,439 patent/US11186558B2/en active Active
- 2017-06-27 AU AU2017286943A patent/AU2017286943B2/en not_active Ceased
- 2017-06-27 CN CN202310038025.XA patent/CN116042742A/zh active Pending
- 2017-06-27 RU RU2019100575A patent/RU2019100575A/ru not_active Application Discontinuation
-
2021
- 2021-11-02 US US17/516,957 patent/US20220055999A1/en not_active Abandoned
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2022
- 2022-05-10 JP JP2022077311A patent/JP2022116004A/ja active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011137135A1 (en) * | 2010-04-27 | 2011-11-03 | Glaxosmithkline Llc | Chemical compounds |
WO2016020785A1 (en) * | 2014-08-05 | 2016-02-11 | Glaxosmithkline Intellectual Property (No. 2) Limited | Synthesis of benzothiazepines |
Non-Patent Citations (2)
Title |
---|
HAGADE, VS ET AL.: "P1323: A STUDY TO EVALUATE THE SAFETY, TOLERABILITY, PHARMACOKINETICS AND PHARMACODYNAMICS OF REPEAT", JOURNAL OF HEPTALOGY, vol. 62, JPN6021017417, 2015, pages 851 - 852, ISSN: 0004503405 * |
KRENN, W ET AL.: "Bacterial epoxide hydrolases of opposite enantiopreference", BIOTECHNOLOGY LETTERS, vol. 21, JPN6021017416, 1999, pages 687 - 690, XP001056430, ISSN: 0004503404, DOI: 10.1023/A:1005565108510 * |
Also Published As
Publication number | Publication date |
---|---|
EP3475266B1 (en) | 2023-09-06 |
CN109415329B (zh) | 2023-05-12 |
AU2017286943A1 (en) | 2019-01-17 |
JP2022116004A (ja) | 2022-08-09 |
EP3475266A1 (en) | 2019-05-01 |
AU2017286943B2 (en) | 2019-05-09 |
RU2019100575A (ru) | 2020-07-28 |
CN116042742A (zh) | 2023-05-02 |
CN109415329A (zh) | 2019-03-01 |
JP7094899B2 (ja) | 2022-07-04 |
US20220055999A1 (en) | 2022-02-24 |
US11186558B2 (en) | 2021-11-30 |
BR112018076197A2 (pt) | 2019-03-26 |
KR20190020132A (ko) | 2019-02-27 |
CA3027725A1 (en) | 2018-01-04 |
ES2965277T3 (es) | 2024-04-11 |
WO2018002827A1 (en) | 2018-01-04 |
US20200325110A1 (en) | 2020-10-15 |
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