CA2861493C - Methods and compounds useful in the synthesis of orexin-2 receptor antagonists - Google Patents
Methods and compounds useful in the synthesis of orexin-2 receptor antagonists Download PDFInfo
- Publication number
- CA2861493C CA2861493C CA2861493A CA2861493A CA2861493C CA 2861493 C CA2861493 C CA 2861493C CA 2861493 A CA2861493 A CA 2861493A CA 2861493 A CA2861493 A CA 2861493A CA 2861493 C CA2861493 C CA 2861493C
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- Prior art keywords
- compound
- formula
- group
- 6alkyl
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/36—Polyhydroxylic alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261600109P | 2012-02-17 | 2012-02-17 | |
| US61/600,109 | 2012-02-17 | ||
| PCT/US2013/026204 WO2013123240A1 (en) | 2012-02-17 | 2013-02-14 | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2861493A1 CA2861493A1 (en) | 2013-08-22 |
| CA2861493C true CA2861493C (en) | 2019-09-24 |
Family
ID=47755050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2861493A Active CA2861493C (en) | 2012-02-17 | 2013-02-14 | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US9416109B2 (enExample) |
| EP (1) | EP2814798B1 (enExample) |
| JP (1) | JP6147279B2 (enExample) |
| CN (1) | CN104114524B (enExample) |
| BR (1) | BR112014019909B1 (enExample) |
| CA (1) | CA2861493C (enExample) |
| ES (1) | ES2733750T3 (enExample) |
| HU (1) | HUE043995T2 (enExample) |
| IL (1) | IL232949A (enExample) |
| MX (1) | MX352881B (enExample) |
| RU (1) | RU2617696C2 (enExample) |
| SG (1) | SG11201403216UA (enExample) |
| WO (1) | WO2013123240A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013119639A1 (en) | 2012-02-07 | 2013-08-15 | Eolas Therapeutics, Inc. | Substituted prolines / piperidines as orexin receptor antagonists |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| WO2013123240A1 (en) * | 2012-02-17 | 2013-08-22 | Eisai R&D Management Co., Ltd | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
| ES2731648T3 (es) | 2014-08-06 | 2019-11-18 | Eisai R&D Man Co Ltd | Método para producir un compuesto de pirimidina-1-ol y compuesto intermedio del mismo |
| TW201613902A (en) | 2014-08-13 | 2016-04-16 | Eolas Therapeutics Inc | Difluoropyrrolidines as orexin receptor modulators |
| LT3414241T (lt) | 2016-02-12 | 2022-08-25 | Astrazeneca Ab | Halogenu pakeisti piperidinai kaip oreksino receptoriaus moduliatoriai |
| CN115710250A (zh) | 2017-08-01 | 2023-02-24 | 博健制药有限责任公司 | 一种食欲素受体拮抗剂的晶型及其制备方法和用途 |
| GB201807898D0 (en) * | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
| WO2020050339A1 (ja) * | 2018-09-07 | 2020-03-12 | 住友化学株式会社 | シクロプロパン化合物の製造方法 |
| KR102930546B1 (ko) | 2019-05-15 | 2026-02-25 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 오렉신-2 수용체 길항제의 제조에 유용한 방법 및 화합물, 및 약간의 불순물을 갖는 렘보렉산트 |
| WO2020249690A1 (en) | 2019-06-12 | 2020-12-17 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| ES2963356T3 (es) * | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Método para aislar ácido carboxílico a partir de una corriente lateral acuosa |
| US12215074B2 (en) | 2019-06-12 | 2025-02-04 | Nouryon Chemicals International B.V. | Process for the production of peroxyesters |
| EP3983370B1 (en) | 2019-06-12 | 2023-08-02 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| JP7336541B2 (ja) | 2019-06-12 | 2023-08-31 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップ | 過酸化ジアシルを生成するためのプロセス |
| WO2020263253A1 (en) * | 2019-06-26 | 2020-12-30 | Moline Margaret | Lemborexant for treating sleep issues |
| EP4073058A1 (en) | 2019-12-11 | 2022-10-19 | Teva Czech Industries s.r.o. | Solid state form of lemborexant |
| KR20220119065A (ko) | 2019-12-20 | 2022-08-26 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 불면증 치료를 위한 렘보렉산트의 용도 |
| TW202140014A (zh) | 2020-01-16 | 2021-11-01 | 日商衛材R&D企管股份有限公司 | 萊博雷生的原料藥及含有其的醫藥組成物 |
| ES2933074B2 (es) | 2021-07-26 | 2023-09-29 | Moehs Iberica Sl | Procedimiento de sintesis de 2,4-dimetilpirimidin-5-ol, nuevos intermedios de dicho procedimiento y uso del producto en la sintesis de lemborexant |
| CN118871427A (zh) * | 2022-03-25 | 2024-10-29 | 浙江华海药业股份有限公司 | 一种莱博雷生及其中间体的制备方法 |
| WO2023178702A1 (zh) * | 2022-03-25 | 2023-09-28 | 浙江华海药业股份有限公司 | 莱博雷生及其中间体化合物的制备方法 |
| CN114778745B (zh) * | 2022-06-21 | 2022-09-16 | 南京威凯尔生物医药科技有限公司 | 一种高效液相色谱法检测仑布雷生中间体及其对映体杂质的方法 |
| CN121045084A (zh) * | 2024-06-01 | 2025-12-02 | 常州市第四制药厂有限公司 | 一种莱博雷生关键中间体及其合成方法 |
| CN119930526B (zh) * | 2025-04-07 | 2025-07-08 | 东北制药集团股份有限公司 | 一种莱博雷生中间体的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2302994A1 (fr) * | 1975-03-06 | 1976-10-01 | Fabre Sa Pierre | Procede de preparation d'acides aryl-1, hydroxy methyl-2 cyclopropanes carboxyliques et de leurs lactones utiles comme intermediaires de synthese dans l'industrie pharmaceutique |
| US5849954A (en) * | 1996-01-18 | 1998-12-15 | Research Corporation Technologies, Inc. | Method of peptide synthesis |
| AU2003285012A1 (en) | 2002-10-24 | 2004-05-13 | Sepracor, Inc. | Compositions comprising zopiclone derivatives and methods of making and using the same |
| US8138377B2 (en) * | 2006-11-07 | 2012-03-20 | Dov Pharmaceutical, Inc. | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| WO2008147518A1 (en) * | 2007-05-23 | 2008-12-04 | Merck & Co., Inc. | Pyridyl piperidine orexin receptor antagonists |
| US8030495B2 (en) | 2007-05-23 | 2011-10-04 | Coleman Paul J | Cyclopropyl pyrrolidine orexin receptor antagonists |
| EA201100368A1 (ru) | 2008-09-18 | 2011-12-30 | Пфайзер Лимитед | Амидные соединения, полезные в терапии |
| TW201031407A (en) | 2008-12-02 | 2010-09-01 | Glaxo Group Ltd | Novel compounds |
| FR2941454B1 (fr) * | 2009-01-29 | 2011-04-01 | Pf Medicament | Proced de synthese du (1s,2r)-milnacipran |
| US8101643B2 (en) | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| BRPI1013264A2 (pt) | 2009-03-09 | 2016-04-05 | Novozymes As | processo para reduzir o teor de glicosídeo esteroidal em uma composição, e, uso do processo |
| SI2626350T1 (sl) * | 2010-09-22 | 2015-09-30 | Eisai R&D Management Co., Ltd. | Spojina ciklopropana |
| WO2013123240A1 (en) * | 2012-02-17 | 2013-08-22 | Eisai R&D Management Co., Ltd | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
-
2013
- 2013-02-14 WO PCT/US2013/026204 patent/WO2013123240A1/en not_active Ceased
- 2013-02-14 RU RU2014137470A patent/RU2617696C2/ru active
- 2013-02-14 BR BR112014019909A patent/BR112014019909B1/pt active IP Right Grant
- 2013-02-14 EP EP13706874.8A patent/EP2814798B1/en active Active
- 2013-02-14 ES ES13706874T patent/ES2733750T3/es active Active
- 2013-02-14 HU HUE13706874A patent/HUE043995T2/hu unknown
- 2013-02-14 US US14/379,063 patent/US9416109B2/en active Active
- 2013-02-14 MX MX2014009917A patent/MX352881B/es active IP Right Grant
- 2013-02-14 CA CA2861493A patent/CA2861493C/en active Active
- 2013-02-14 CN CN201380009575.3A patent/CN104114524B/zh active Active
- 2013-02-14 JP JP2014557781A patent/JP6147279B2/ja active Active
- 2013-02-14 SG SG11201403216UA patent/SG11201403216UA/en unknown
-
2014
- 2014-06-02 IL IL232949A patent/IL232949A/en active IP Right Grant
-
2016
- 2016-05-19 US US15/158,687 patent/US9828336B2/en active Active
-
2017
- 2017-10-24 US US15/791,814 patent/US20180044285A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN104114524A (zh) | 2014-10-22 |
| EP2814798A1 (en) | 2014-12-24 |
| MX2014009917A (es) | 2014-11-13 |
| BR112014019909B1 (pt) | 2020-01-28 |
| EP2814798B1 (en) | 2019-04-03 |
| US20160318858A1 (en) | 2016-11-03 |
| JP6147279B2 (ja) | 2017-06-14 |
| US20150025237A1 (en) | 2015-01-22 |
| US20180044285A1 (en) | 2018-02-15 |
| US9828336B2 (en) | 2017-11-28 |
| SG11201403216UA (en) | 2014-12-30 |
| MX352881B (es) | 2017-12-13 |
| HUE043995T2 (hu) | 2019-09-30 |
| RU2617696C2 (ru) | 2017-04-26 |
| JP2015509939A (ja) | 2015-04-02 |
| RU2014137470A (ru) | 2016-04-10 |
| WO2013123240A1 (en) | 2013-08-22 |
| BR112014019909A2 (enExample) | 2017-06-20 |
| CA2861493A1 (en) | 2013-08-22 |
| IL232949A0 (en) | 2014-08-03 |
| CN104114524B (zh) | 2016-08-17 |
| BR112014019909A8 (pt) | 2017-07-11 |
| IL232949A (en) | 2016-08-31 |
| US9416109B2 (en) | 2016-08-16 |
| ES2733750T3 (es) | 2019-12-02 |
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