CA2879982C - Lfa-1 inhibitor and polymorph thereof - Google Patents
Lfa-1 inhibitor and polymorph thereof Download PDFInfo
- Publication number
- CA2879982C CA2879982C CA2879982A CA2879982A CA2879982C CA 2879982 C CA2879982 C CA 2879982C CA 2879982 A CA2879982 A CA 2879982A CA 2879982 A CA2879982 A CA 2879982A CA 2879982 C CA2879982 C CA 2879982C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- polymorph
- various embodiments
- yield
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D405/10—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 aromatic rings
-
- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
- 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
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261675663P | 2012-07-25 | 2012-07-25 | |
| US61/675,663 | 2012-07-25 | ||
| US201261680099P | 2012-08-06 | 2012-08-06 | |
| US61/680,099 | 2012-08-06 | ||
| US201261729294P | 2012-11-21 | 2012-11-21 | |
| US61/729,294 | 2012-11-21 | ||
| PCT/US2013/052044 WO2014018748A1 (en) | 2012-07-25 | 2013-07-25 | Lfa-1 inhibitor and polymorph thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2879982A1 CA2879982A1 (en) | 2014-01-30 |
| CA2879982C true CA2879982C (en) | 2020-09-01 |
Family
ID=49995472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2879982A Active CA2879982C (en) | 2012-07-25 | 2013-07-25 | Lfa-1 inhibitor and polymorph thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US9085553B2 (OSRAM) |
| EP (3) | EP4406950A3 (OSRAM) |
| JP (3) | JP6607780B2 (OSRAM) |
| KR (2) | KR20200108932A (OSRAM) |
| CN (2) | CN110922393A (OSRAM) |
| AU (5) | AU2013295706A1 (OSRAM) |
| BR (1) | BR112015001608B1 (OSRAM) |
| CA (1) | CA2879982C (OSRAM) |
| HK (1) | HK1210782A1 (OSRAM) |
| IN (1) | IN2015DN00847A (OSRAM) |
| MX (2) | MX2015001098A (OSRAM) |
| RU (1) | RU2658015C2 (OSRAM) |
| SI (1) | SI3715345T1 (OSRAM) |
| WO (1) | WO2014018748A1 (OSRAM) |
Families Citing this family (54)
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|---|---|---|---|---|
| JP5794721B2 (ja) * | 2005-05-17 | 2015-10-14 | サーコード バイオサイエンス インコーポレイテッド | 眼障害の治療のための組成物および方法 |
| JP2011521896A (ja) * | 2008-04-15 | 2011-07-28 | サーコード コーポレイション | 免疫関連障害に対する局部治療に使用するための局所ｌｆａ−１アンタゴニスト |
| EP4406950A3 (en) | 2012-07-25 | 2025-04-23 | Bausch + Lomb Ireland Limited | Lfa-1 inhibitor and polymorph thereof |
| JP6754356B2 (ja) * | 2014-09-25 | 2020-09-09 | ノバルティス アーゲー | 連続流のカルボキシル化反応 |
| EP3244851B1 (en) | 2015-01-12 | 2024-10-16 | Bausch + Lomb Ireland Limited | Micro-droplet delivery device |
| CA3016546A1 (en) | 2016-03-04 | 2017-09-08 | James M. Rynerson | Method of treating an eye disorder by inhibiting or disrupting bacterial biofilm formation |
| CN107661302B (zh) * | 2016-07-29 | 2021-08-27 | 武汉朗来科技发展有限公司 | 一种口服固体制剂及其应用 |
| SG11201901137UA (en) | 2016-08-12 | 2019-03-28 | Silk Technologies Ltd | Silk-derived protein for treating inflammation |
| CN108084067B (zh) * | 2016-11-22 | 2019-08-30 | 重庆圣华曦药业股份有限公司 | 一种立他司特中间体的制备方法 |
| CA3039106A1 (en) | 2017-01-20 | 2018-07-26 | Kedalion Therapeutics, Inc. | Piezoelectric fluid dispenser |
| CN106947792A (zh) * | 2017-03-07 | 2017-07-14 | 上海倍殊生物科技有限公司 | 一种间甲砜基‑l‑苯丙氨酸的制备方法 |
| JP7232780B2 (ja) * | 2017-06-30 | 2023-03-03 | サイノファーム タイワン，リミティド | リフィテグラスト及びその中間体を調製するための方法 |
| US10723721B2 (en) * | 2017-07-24 | 2020-07-28 | Interquim, S.A. | Process for preparing and purifying the LFA-1 antagonist lifitegrast |
| WO2019026014A1 (en) * | 2017-08-03 | 2019-02-07 | Dr. Reddy's Laboratories Limited | METHODS FOR PREPARING LIFITEGRAST AND ITS INTERMEDIATES |
| WO2019053607A1 (en) * | 2017-09-18 | 2019-03-21 | Glenmark Pharmaceuticals Limited | PROCESS FOR PREPARING LIFITEGRAST |
| EP3694499A4 (en) * | 2017-10-10 | 2021-09-01 | Mankind Pharma Ltd. | NEW PROCESS FOR MANUFACTURING LIFITEGRAST |
| WO2019097547A1 (en) | 2017-11-15 | 2019-05-23 | Cipla Limited | An improved process for the preparation of lifitegrast or salts thereof |
| WO2019096996A1 (en) | 2017-11-17 | 2019-05-23 | Medichem, S.A. | A process to obtain a tetrahydroisoquinoline derivative |
| JP7436363B2 (ja) | 2017-12-08 | 2024-02-21 | ノバルティス アーゲー | 流体送達アライメントシステム |
| JP6914568B2 (ja) | 2018-01-15 | 2021-08-04 | コグニボティクス アクチエボラグＣｏｇｎｉｂｏｔｉｃｓ ＡＢ | 産業用ロボットアーム |
| US10435395B1 (en) | 2018-03-30 | 2019-10-08 | Scinopharm Taiwan, Ltd. | Crystal forms of lifitegrast |
| WO2019186520A1 (en) * | 2018-03-31 | 2019-10-03 | Aurobindo Pharma Limited | A process for the preparation of lifitegrast |
| US12350194B1 (en) | 2018-04-12 | 2025-07-08 | Bausch + Lomb Ireland Limited | Topical ocular delivery of fluids with controlled mass dosing and wireless communication |
| US20190314198A1 (en) | 2018-04-12 | 2019-10-17 | Kedalion Therapeutics, Inc. | Topical Ocular Delivery Methods and Devices for Use in the Same |
| IT201800006337A1 (it) | 2018-06-14 | 2019-12-14 | Procedimento per la preparazione di lifitegrast | |
| US12295881B2 (en) | 2018-07-03 | 2025-05-13 | Bausch + Lomb Ireland Limited | Topical ocular delivery devices and methods for using the same |
| CN111100118A (zh) * | 2018-10-29 | 2020-05-05 | 重庆圣华曦药业股份有限公司 | 一种立他司特杂质及其制备方法 |
| CN109384717A (zh) * | 2018-10-29 | 2019-02-26 | 广安凯特制药有限公司 | 5,7-二氯-1,2,3,4-四氢异喹啉-6-甲酸盐酸盐水合物及其制备方法和用途 |
| CN111285855A (zh) * | 2018-12-07 | 2020-06-16 | 苏州旺山旺水生物医药有限公司 | 一种制备化合物Lifitegrast的方法 |
| CN111471003B (zh) * | 2019-01-24 | 2022-09-23 | 上海皓元医药股份有限公司 | 一种立他司特中间体的制备方法 |
| US11679028B2 (en) | 2019-03-06 | 2023-06-20 | Novartis Ag | Multi-dose ocular fluid delivery system |
| US12097145B2 (en) | 2019-03-06 | 2024-09-24 | Bausch + Lomb Ireland Limited | Vented multi-dose ocular fluid delivery system |
| EP3955926A4 (en) * | 2019-04-18 | 2022-11-30 | Azura Ophthalmics Ltd. | Compounds and methods for the treatment of ocular disorders |
| CN110256343A (zh) * | 2019-05-28 | 2019-09-20 | 苏州芝宇生物科技有限公司 | 3,5-二氯-4-溴异喹啉衍生物及其制备方法和应用 |
| CN112409256B (zh) * | 2019-08-21 | 2024-04-02 | 山东福长药业有限公司 | 5,7-二氯四氢异喹啉缩醛胺类化合物、其制备方法与应用 |
| US12496218B1 (en) | 2019-11-12 | 2025-12-16 | Bausch + Lomb Ireland Limited | Fractionated topical ocular drug delivery methods and devices for use in the same |
| CN111057003A (zh) * | 2019-12-06 | 2020-04-24 | 广安凯特制药有限公司 | 一种立他司特中间体5,7-二氯-1,2,3,4-四氢异喹啉的合成方法 |
| US12090087B2 (en) | 2020-04-17 | 2024-09-17 | Bausch + Lomb Ireland Limited | Hydrodynamically actuated preservative free dispensing system having a collapsible liquid reservoir |
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| CN111205275A (zh) * | 2020-04-22 | 2020-05-29 | 南京佰麦生物技术有限公司 | 立他司特晶型及其制备方法 |
| CN112321506B (zh) * | 2020-11-26 | 2021-12-24 | 江西天戌药业有限公司 | 一种5,7-二氯-1,2,3,4-四氢异喹啉的制备方法 |
| CN112500343B (zh) * | 2020-12-26 | 2023-04-07 | 山东金城柯瑞化学有限公司 | 5,7-二氯-1,2,3,4-四氢异喹啉盐酸盐的合成方法 |
| CN112300139A (zh) * | 2020-12-29 | 2021-02-02 | 南京佰麦生物技术有限公司 | 立他司特水合物晶型及其制备方法 |
| US11459351B1 (en) | 2021-04-05 | 2022-10-04 | Azura Ophthalmics Ltd. | Compounds and methods for the treatment of ocular disorders |
| CN119060022A (zh) * | 2021-09-18 | 2024-12-03 | 浙江大学医学院附属第一医院 | 立他司特的制备方法及其中间体化合物 |
| CN116063286A (zh) * | 2021-10-29 | 2023-05-05 | 威智医药有限公司 | 一种立他司特及其中间体的制备方法 |
| CN114524767B (zh) * | 2022-03-11 | 2022-10-18 | 成都道合尔医药技术有限公司 | 立他司特中间体5,7-二氯-1,2,3,4-四氢异喹啉盐酸盐的合成方法 |
| CN115784950B (zh) * | 2022-12-08 | 2024-06-28 | 广东先强药业有限公司 | 一种立他司特中间体的制备方法 |
| CN116239532B (zh) * | 2022-12-19 | 2023-11-07 | 浙江博崤生物制药有限公司 | 一种二氯四氢异喹啉羧酸的中间体及其制备方法和应用 |
| CN116462644B (zh) * | 2023-05-06 | 2024-11-19 | 上海华默西医药科技有限公司 | 一种2-(呋喃-2-基亚甲基)-4-硝基丁酸酯化合物及其制备方法和应用 |
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