TWI649317B - 製備葡糖基神經醯胺合成酶抑制劑之方法 - Google Patents
製備葡糖基神經醯胺合成酶抑制劑之方法 Download PDFInfo
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- TWI649317B TWI649317B TW103108899A TW103108899A TWI649317B TW I649317 B TWI649317 B TW I649317B TW 103108899 A TW103108899 A TW 103108899A TW 103108899 A TW103108899 A TW 103108899A TW I649317 B TWI649317 B TW I649317B
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- 238000000034 method Methods 0.000 title claims abstract description 66
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 4
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- 229940125532 enzyme inhibitor Drugs 0.000 title 1
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 9
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- 238000006467 substitution reaction Methods 0.000 claims description 7
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- 229910005965 SO 2 Inorganic materials 0.000 claims description 4
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- 125000006824 (C1-C6) dialkyl amine group Chemical group 0.000 claims 2
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- 229960001512 miglustat Drugs 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000933 neural crest Anatomy 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 208000030761 polycystic kidney disease Diseases 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 108091006091 regulatory enzymes Proteins 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003410 sphingosines Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361791913P | 2013-03-15 | 2013-03-15 | |
| US61/791,913 | 2013-03-15 |
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| TW201524974A TW201524974A (zh) | 2015-07-01 |
| TWI649317B true TWI649317B (zh) | 2019-02-01 |
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| TW107132577A TW201900625A (zh) | 2013-03-15 | 2014-03-13 | 製備葡糖基神經醯胺合成酶抑制劑之方法 |
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| TW107132577A TW201900625A (zh) | 2013-03-15 | 2014-03-13 | 製備葡糖基神經醯胺合成酶抑制劑之方法 |
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| EP (2) | EP2970251B1 (https=) |
| JP (2) | JP6543242B2 (https=) |
| KR (1) | KR20150130386A (https=) |
| CN (2) | CN105189491B (https=) |
| AR (1) | AR095436A1 (https=) |
| AU (2) | AU2014235132B2 (https=) |
| BR (1) | BR112015020667A2 (https=) |
| CA (2) | CA2906581C (https=) |
| CY (1) | CY1121859T1 (https=) |
| DK (1) | DK3514157T3 (https=) |
| ES (2) | ES2968073T3 (https=) |
| HU (2) | HUE043394T2 (https=) |
| IL (2) | IL240617B (https=) |
| MX (2) | MX365464B (https=) |
| RU (1) | RU2015144035A (https=) |
| SG (2) | SG10201706575UA (https=) |
| TW (2) | TWI649317B (https=) |
| UY (1) | UY35438A (https=) |
| WO (1) | WO2014151291A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| TWI649317B (zh) | 2013-03-15 | 2019-02-01 | 健臻公司 | 製備葡糖基神經醯胺合成酶抑制劑之方法 |
| EP3583653B1 (de) * | 2017-02-17 | 2020-12-16 | Westfälische Wilhelms-Universität Münster | Elektrolyt-zusatz für lithium-ionen-batterien |
| JP2021506920A (ja) | 2017-12-21 | 2021-02-22 | リソソーマル・セラピューティクス・インコーポレイテッドＬｙｓｏｓｏｍａｌ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 結晶性の置換シクロヘキシルピラゾロ［１，５−ａ］ピリミジニルカルボキサミド化合物およびその治療的使用 |
| US10519157B2 (en) * | 2018-02-09 | 2019-12-31 | X-Cutag Therapeutics, Inc. | Deuterated compounds for treating Fabry, Gaucher, Parkinson's and related diseases and conditions, and compositions and methods thereof |
| CN114040762A (zh) | 2019-02-04 | 2022-02-11 | 建新公司 | 使用葡糖神经酰胺合酶(gcs)的抑制剂治疗纤毛疾病 |
| TW202142236A (zh) | 2020-02-03 | 2021-11-16 | 美商健臻公司 | 用於治療與溶體儲積症相關的神經症狀之方法 |
| JP7725076B2 (ja) | 2020-04-28 | 2025-08-19 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガン | グルコシルセラミド合成酵素のピリジン阻害剤及びそれらを使用する治療方法 |
| KR20230043024A (ko) | 2020-07-24 | 2023-03-30 | 젠자임 코포레이션 | 벤글루스타트를 포함하는 제약 조성물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB725228A (en) * | 1952-06-19 | 1955-03-02 | Roche Products Ltd | Substituted carbamic acid esters and process for the manufacture thereof |
| WO2012129084A2 (en) * | 2011-03-18 | 2012-09-27 | Genzyme Corporation | Glucosylceramide synthase inhibitors |
| WO2012175119A1 (en) * | 2011-06-22 | 2012-12-27 | Isochem | Process for the preparation of solifenacin and salts thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB725226A (en) * | 1952-06-03 | 1955-03-02 | Berger Brothers Co | Improvements in or relating to an inflatable surgical pad |
| NL130759C (https=) * | 1965-10-07 | |||
| DE4326510A1 (de) | 1993-08-06 | 1995-02-09 | Bayer Ag | Verfahren zur Herstellung von Cyclohexen-Derivaten |
| WO1995021820A1 (en) * | 1994-02-10 | 1995-08-17 | Yamanouchi Pharmaceutical Co., Ltd. | Novel carbamate derivative and medicinal composition containing the same |
| JPH08198751A (ja) * | 1995-01-19 | 1996-08-06 | Yamanouchi Pharmaceut Co Ltd | カルバメート誘導体 |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| GB0400812D0 (en) | 2004-01-14 | 2004-02-18 | Celltech R&D Ltd | Novel compounds |
| US8003617B2 (en) | 2004-11-10 | 2011-08-23 | Genzyme Corporation | Methods of treating diabetes mellitus |
| JP5285643B2 (ja) * | 2010-03-15 | 2013-09-11 | シャープ株式会社 | 半導体集積回路および電子情報機器 |
| RU2607084C2 (ru) | 2010-11-12 | 2017-01-10 | Сионоги Энд Ко., Лтд. | Кристаллы производных 6,7-ненасыщенного-7-карбамоилморфинана и способ их получения |
| JP2013053228A (ja) * | 2011-09-02 | 2013-03-21 | Asahi Kasei E-Materials Corp | エポキシ樹脂用硬化剤及びマイクロカプセル型エポキシ樹脂用硬化剤 |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| TWI649317B (zh) * | 2013-03-15 | 2019-02-01 | 健臻公司 | 製備葡糖基神經醯胺合成酶抑制劑之方法 |
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- 2014-03-13 DK DK19153389.2T patent/DK3514157T3/da active
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- 2014-03-13 RU RU2015144035A patent/RU2015144035A/ru not_active Application Discontinuation
- 2014-03-13 JP JP2016501840A patent/JP6543242B2/ja active Active
- 2014-03-13 EP EP14718835.3A patent/EP2970251B1/en active Active
- 2014-03-13 US US14/776,443 patent/US9682975B2/en active Active
- 2014-03-13 HU HUE14718835A patent/HUE043394T2/hu unknown
- 2014-03-13 KR KR1020157027836A patent/KR20150130386A/ko not_active Ceased
- 2014-03-13 TW TW107132577A patent/TW201900625A/zh unknown
- 2014-03-13 CA CA3092901A patent/CA3092901C/en active Active
- 2014-03-13 AU AU2014235132A patent/AU2014235132B2/en not_active Ceased
- 2014-03-13 MX MX2019000914A patent/MX389168B/es unknown
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- 2014-03-13 BR BR112015020667A patent/BR112015020667A2/pt not_active Application Discontinuation
- 2014-03-13 CN CN201810630738.4A patent/CN108658970A/zh active Pending
- 2014-03-13 SG SG11201506415XA patent/SG11201506415XA/en unknown
- 2014-03-13 AR ARP140100982A patent/AR095436A1/es unknown
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- 2018-08-01 US US16/051,892 patent/US10604518B2/en active Active
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- 2019-01-18 AU AU2019200350A patent/AU2019200350A1/en not_active Abandoned
- 2019-05-27 CY CY20191100562T patent/CY1121859T1/el unknown
- 2019-06-13 JP JP2019109986A patent/JP6813626B2/ja active Active
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2020
- 2020-02-14 US US16/791,854 patent/US10954230B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB725228A (en) * | 1952-06-19 | 1955-03-02 | Roche Products Ltd | Substituted carbamic acid esters and process for the manufacture thereof |
| WO2012129084A2 (en) * | 2011-03-18 | 2012-09-27 | Genzyme Corporation | Glucosylceramide synthase inhibitors |
| WO2012175119A1 (en) * | 2011-06-22 | 2012-12-27 | Isochem | Process for the preparation of solifenacin and salts thereof |
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