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
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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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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 (enExample) |
| EP (3) | EP4406950A3 (enExample) |
| JP (3) | JP6607780B2 (enExample) |
| KR (2) | KR102157608B1 (enExample) |
| CN (2) | CN104797574B (enExample) |
| AU (5) | AU2013295706A1 (enExample) |
| BR (1) | BR112015001608B1 (enExample) |
| CA (1) | CA2879982C (enExample) |
| HK (1) | HK1210782A1 (enExample) |
| IN (1) | IN2015DN00847A (enExample) |
| MX (2) | MX2015001098A (enExample) |
| RU (1) | RU2658015C2 (enExample) |
| SI (1) | SI3715345T1 (enExample) |
| WO (1) | WO2014018748A1 (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006125119A1 (en) * | 2005-05-17 | 2006-11-23 | Sarcode Corporation | Compositions and methods for treatment of eye disorders |
| EP3632444A3 (en) * | 2008-04-15 | 2020-08-26 | SARcode Bioscience Inc. | Topical lfa-1 antagonists for use in localized treatment of immune related disorders |
| EP4406950A3 (en) * | 2012-07-25 | 2025-04-23 | Bausch + Lomb Ireland Limited | Lfa-1 inhibitor and polymorph thereof |
| CA2960392A1 (en) | 2014-09-25 | 2016-03-31 | Sarcode Bioscience Inc. | Process to prepare 5,7-dichloro-3,4-dihydro-1h-isoquinolin-6-carboxylic acid using a continuous flow carboxylation reaction |
| WO2016115050A1 (en) | 2015-01-12 | 2016-07-21 | Lagunita Llc | Micro-droplet delivery device and methods |
| JP2019507193A (ja) | 2016-03-04 | 2019-03-14 | ジェームズ・エム・ライナーソン | 細菌のバイオフィルム形成を阻止又は妨害することによって眼障害を治療する方法 |
| 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 |
| KR102275012B1 (ko) | 2016-08-12 | 2021-07-07 | 실크 테크놀로지스 리미티드 | 염증 치료용 실크 유래 단백질 |
| 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 |
| KR102866401B1 (ko) | 2017-01-20 | 2025-10-01 | 보슈 롬 아일랜드 리미티드 | 압전 유체 분배기 |
| 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 |
| ES2971845T3 (es) | 2017-06-30 | 2024-06-10 | Scinopharm Taiwan Ltd | Procedimiento de preparación de lifitegrast y los productos intermedios del mismo |
| ES2876292T3 (es) | 2017-07-24 | 2021-11-12 | Interquim Sa | Procedimiento de preparación y purificación del antagonista de LFA-1 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 |
| US11246862B2 (en) | 2017-10-10 | 2022-02-15 | Mankind Pharma Ltd. | Process for the preparation of 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 |
| CA3083219A1 (en) | 2017-12-08 | 2019-06-13 | Reynaldo Quintana | Fluid delivery alignment system |
| CN111601685B (zh) | 2018-01-15 | 2021-08-06 | 康格尼博提克斯股份公司 | 工业机器人手臂 |
| US10435395B1 (en) | 2018-03-30 | 2019-10-08 | Scinopharm Taiwan, Ltd. | Crystal forms of lifitegrast |
| US11345683B2 (en) * | 2018-03-31 | 2022-05-31 | Aurobindo Pharma Ltd | Process for the preparation of lifitegrast |
| US20190314196A1 (en) | 2018-04-12 | 2019-10-17 | Kedalion Therapeutics, Inc. | Topical Ocular Delivery Methods and Devices for Use in the Same |
| US12350194B1 (en) | 2018-04-12 | 2025-07-08 | Bausch + Lomb Ireland Limited | Topical ocular delivery of fluids with controlled mass dosing and wireless communication |
| IT201800006337A1 (it) | 2018-06-14 | 2019-12-14 | Procedimento per la preparazione di lifitegrast | |
| AU2019297326B2 (en) | 2018-07-03 | 2025-01-09 | Bausch + Lomb Ireland Limited | Topical ocular delivery devices and methods for using the same |
| 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 |
| 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 |
| 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 |
| JP7700045B2 (ja) | 2019-04-18 | 2025-06-30 | アズーラ オフサルミックス エルティーディー． | 眼障害を処置するための化合物および方法 |
| 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 |
| 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 |
| IL297215A (en) | 2020-04-17 | 2022-12-01 | Kedallon Therapeutics Inc | A hydrodynamically activated preservative free distribution system |
| US12290472B2 (en) | 2020-04-17 | 2025-05-06 | Bausch + Lomb Ireland Limited | Hydrodynamically actuated preservative free dispensing system |
| US11938057B2 (en) | 2020-04-17 | 2024-03-26 | Bausch + Lomb Ireland Limited | Hydrodynamically actuated preservative free dispensing system |
| 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 |
| CN113880819B (zh) * | 2021-09-18 | 2024-09-20 | 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 |
| 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 |
| WO2025186765A1 (en) * | 2024-03-08 | 2025-09-12 | Olon S.P.A. | Process for preparing lifitegrast |
| WO2025186758A1 (en) * | 2024-03-08 | 2025-09-12 | Olon S.P.A. | Process for preparing lifitegrast |
Family Cites Families (113)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| JPS5759843A (en) * | 1980-09-30 | 1982-04-10 | Neos Co Ltd | Perfluoroalkyl ether amide derivative and its preparation |
| IE52535B1 (en) | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| US4931279A (en) | 1985-08-16 | 1990-06-05 | Bausch & Lomb Incorporated | Sustained release formulation containing an ion-exchange resin |
| US4713244A (en) | 1985-08-16 | 1987-12-15 | Bausch & Lomb Incorporated | Sustained-release formulation containing an amino acid polymer with a lower alkyl (C1 -C4) polar solvent |
| US4668506A (en) | 1985-08-16 | 1987-05-26 | Bausch & Lomb Incorporated | Sustained-release formulation containing and amino acid polymer |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5001139A (en) | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| US4992445A (en) | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| GB2209937B (en) | 1987-09-21 | 1991-07-03 | Depiopharm S A | Water insoluble polypeptides |
| ATE114972T1 (de) | 1987-11-02 | 1994-12-15 | Baylor College Medicine | Verwendung von icam-1 oder ihre funktionelle derivate zur behandlung unspezifischer entzündungen. |
| DE68907066T2 (de) | 1988-01-29 | 1993-12-16 | Koken Kk | Verbesserte Formulierungen mit kontrollierter Abgabe. |
| DE3802996A1 (de) | 1988-02-02 | 1989-08-10 | Cassella Ag | Verwendung von 2-oxo-pyrrolidin-1-acetamid zur bestimmung der glomerulaeren filtrationsrate beim menschen |
| US5424399A (en) | 1988-06-28 | 1995-06-13 | The Children's Medical Center Corporation | Human CR3α/β heterodimers |
| DE68923048T2 (de) | 1988-08-23 | 1995-11-16 | Dana Farber Cancer Inst Inc | Alpha-Subeinheit des LFA-1-Leukocyt-Adhäsions-Rezeptors. |
| DE68929096T2 (de) | 1988-09-01 | 2000-05-11 | Bayer Corp., Pittsburgh | Menschliches Rhinovirusrezeptorprotein, das die Virusinfektionsanfälligkeit hemmt |
| KR900701846A (ko) | 1988-09-28 | 1990-12-04 | 원본미기재 | 세포간 점착분자 및 이의 결합 리간드 |
| US5149780A (en) | 1988-10-03 | 1992-09-22 | The Scripps Research Institute | Peptides and antibodies that inhibit integrin-ligand binding |
| WO1990010652A1 (en) | 1989-03-09 | 1990-09-20 | Dana Farber Cancer Institute | Method of treating viral infections using lfa-1 |
| AU5553290A (en) | 1989-04-28 | 1990-11-29 | Baylor College Of Medicine | Dissemination of hiv-1 infected cells |
| CH679207A5 (enExample) | 1989-07-28 | 1992-01-15 | Debiopharm Sa | |
| WO1991019511A1 (en) | 1990-06-18 | 1991-12-26 | The General Hospital Corporation | CONTROLLING CELLULAR IMMUNE/INFLAMMATORY RESPONSES WITH β2 INTEGRINS |
| CA2046830C (en) | 1990-07-19 | 1999-12-14 | Patrick P. Deluca | Drug delivery system involving inter-action between protein or polypeptide and hydrophobic biodegradable polymer |
| US5318965A (en) | 1990-08-24 | 1994-06-07 | Abbott Laboratories | Quinobenzoxazine, antineoplastic agents |
| CA2090427A1 (en) | 1990-08-27 | 1992-02-28 | Cetus Oncology Corporation | Cd18 peptide medicaments for the treatment of disease |
| JP2995860B2 (ja) | 1990-11-27 | 1999-12-27 | 味の素株式会社 | 新規ペプチド |
| US5288854A (en) | 1990-11-28 | 1994-02-22 | Center For Blood Research, Inc. | Functional derivatives of ICAM-1 which are substantially capable of binding to LFA-1 but are substantially incapable of binding to MAC-1 |
| CH683149A5 (fr) | 1991-07-22 | 1994-01-31 | Debio Rech Pharma Sa | Procédé pour la préparation de microsphères en matériau polymère biodégradable. |
| CA2120506C (en) | 1991-10-04 | 2000-12-12 | Scott M. Whitcup | Treatment of ocular inflammation by blockage of cell adhesion molecules |
| GB9211268D0 (en) | 1992-05-28 | 1992-07-15 | Ici Plc | Salts of basic peptides with carboxyterminated polyesters |
| US5298492A (en) | 1992-08-04 | 1994-03-29 | Schering Corporation | Diamino acid derivatives as antihypertensives |
| CA2140933A1 (en) | 1992-08-21 | 1994-02-22 | Paula M. Jardieu | Method for treating an lfa-1 mediated disorder |
| AU5466794A (en) | 1992-11-18 | 1994-06-08 | Helsinki University Licensing Ltd Oy | Peptides from human icam-2 and from human icam-1 and their analogs for use in therapy and diagnosis |
| US5672659A (en) | 1993-01-06 | 1997-09-30 | Kinerton Limited | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
| RU2185393C2 (ru) | 1993-01-06 | 2002-07-20 | Кинертон Лимитед | Сложный полиэфир и конъюгат на его основе |
| US5424289A (en) | 1993-07-30 | 1995-06-13 | Alza Corporation | Solid formulations of therapeutic proteins for gastrointestinal delivery |
| US5397791A (en) | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| ES2147210T3 (es) | 1993-12-03 | 2000-09-01 | Hoffmann La Roche | Derivados de acido acetico como medicamentos. |
| US5470953A (en) | 1993-12-23 | 1995-11-28 | Icos Corporation | Human β2 integrin α subunit |
| CA2188287A1 (en) | 1994-04-19 | 1995-10-26 | Stephen Benedict | Icam-1/lfa-1 short-chain peptides and method of using same |
| US5849327A (en) | 1994-07-29 | 1998-12-15 | Advanced Polymer Systems, Inc. | Delivery of drugs to the lower gastrointestinal tract |
| US5510495A (en) * | 1994-09-19 | 1996-04-23 | The Du Pont Merck Pharmaceutical Company | Process for the isolation and purification of ester functionalized imidazole intermediates by selective hydrolysis |
| US5585359A (en) | 1994-09-29 | 1996-12-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| DK0710657T3 (da) | 1994-11-02 | 1999-05-25 | Merck Patent Gmbh | Adhæsionsreceptor-antagonister |
| US5612052A (en) | 1995-04-13 | 1997-03-18 | Poly-Med, Inc. | Hydrogel-forming, self-solvating absorbable polyester copolymers, and methods for use thereof |
| US5747035A (en) | 1995-04-14 | 1998-05-05 | Genentech, Inc. | Polypeptides with increased half-life for use in treating disorders involving the LFA-1 receptor |
| US5877224A (en) | 1995-07-28 | 1999-03-02 | Rutgers, The State University Of New Jersey | Polymeric drug formulations |
| US5980945A (en) | 1996-01-16 | 1999-11-09 | Societe De Conseils De Recherches Et D'applications Scientifique S.A. | Sustained release drug formulations |
| US5840332A (en) | 1996-01-18 | 1998-11-24 | Perio Products Ltd. | Gastrointestinal drug delivery system |
| ES2234014T3 (es) | 1996-04-23 | 2005-06-16 | Ipsen Manufacturing Ireland Limited | Polimeros polilacticos acidos. |
| HRP970493A2 (en) | 1996-09-23 | 1998-08-31 | Wienman E. Phlips | Oral delayed immediate release medical formulation and method for preparing the same |
| CA2217134A1 (en) | 1996-10-09 | 1998-04-09 | Sumitomo Pharmaceuticals Co., Ltd. | Sustained release formulation |
| ES2270475T3 (es) | 1996-11-27 | 2007-04-01 | Bristol-Myers Squibb Pharma Company | Nuevos antagonistas de receptores de integrina. |
| US5968895A (en) | 1996-12-11 | 1999-10-19 | Praecis Pharmaceuticals, Inc. | Pharmaceutical formulations for sustained drug delivery |
| US5893985A (en) | 1997-03-14 | 1999-04-13 | The Lincoln Electric Company | Plasma arc torch |
| AR012443A1 (es) | 1997-04-16 | 2000-10-18 | Uriach & Cia Sa J | Nuevas carboxamidas como inhibidores de la agregacion plaquetaria, procedimiento para su preparacion, composiciones farmaceuticas que loscontienen y uso de los mismos en la manufactura de medicamentos |
| BR9909418A (pt) | 1998-03-27 | 2001-09-25 | Genentech Inc | Antagonistas para o tratamento de distúrbios mediados por receptor de aderência cd11/cd18 e método para tratar ou melhorar uma resposta ou distúrbio imunológico ou inflamatório em um mamìfero mediada através da famìlia cd11/cd18 em moléculas de aderência celular |
| US6331640B1 (en) | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| HK1043545A1 (zh) | 1998-11-27 | 2002-09-20 | 高田宽治 | 用於胃肠道药物传递的口服制剂 |
| IT1304152B1 (it) | 1998-12-10 | 2001-03-08 | Mediolanum Farmaceutici Srl | Composizioni comprendenti un peptide ed acido polilattico-glicolicoatte alla preparazione di impianti sottocutanei aventi un prolungato |
| US6670321B1 (en) | 1998-12-30 | 2003-12-30 | The Children's Medical Center Corporation | Prevention and treatment for retinal ischemia and edema |
| EP1140170B1 (en) | 1999-01-05 | 2006-06-21 | The Flinders University Of South Australia | Antibody fragments for the topical treatment of ocular diseases |
| WO2000044731A1 (en) | 1999-01-27 | 2000-08-03 | G.D. Searle & Co. | Novel hydroxyamidino carboxylate derivatives useful as nitric oxide synthase inhibitors |
| EP1028114A1 (en) | 1999-02-13 | 2000-08-16 | Aventis Pharma Deutschland GmbH | Novel guanidine derivatives as inhibitors of cell adhesion |
| BR0009437A (pt) | 1999-03-31 | 2002-01-15 | Janssen Pharmaceutica Nv | Amido pré-gelatinizado em uma formulação de liberação controlada |
| AU1186401A (en) | 1999-06-23 | 2001-01-22 | Sedum Laboratories, Inc. | Ionically formulated biomolecule microcarriers |
| ES2209948T3 (es) | 1999-08-18 | 2004-07-01 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Formulacion de un peptico de liberacion sostenida. |
| ECSP003707A (es) | 1999-10-13 | 2002-05-23 | Novartis Ag | Diazepanes |
| US6294522B1 (en) | 1999-12-03 | 2001-09-25 | Cv Therapeutics, Inc. | N6 heterocyclic 8-modified adenosine derivatives |
| US6605597B1 (en) | 1999-12-03 | 2003-08-12 | Cv Therapeutics, Inc. | Partial or full A1agonists-N-6 heterocyclic 5′-thio substituted adenosine derivatives |
| ES2311483T3 (es) | 1999-12-14 | 2009-02-16 | Genentech, Inc. | Anatagonista del tnf-alfa y antagonista del lfa-1 para el tratamiento de la artritis reumatoide. |
| WO2001049249A2 (en) | 1999-12-31 | 2001-07-12 | Rutgers, The State University | Pharmaceutical formulation for regulating the timed release of biologically active compounds based on a polymer matrix |
| US7521061B2 (en) | 1999-12-31 | 2009-04-21 | Rutgers, The State University Of New Jersey | Pharmaceutical formulation for regulating the timed release of biologically active compounds based on a polymer matrix |
| WO2001049311A1 (en) | 1999-12-31 | 2001-07-12 | Rutgers, The State University | Pharmaceutical formulation composed of a polymer blend and an active compound for time-controlled release |
| US20030064105A1 (en) | 2000-08-25 | 2003-04-03 | Myung-Jin Kim | Lipophilic-coated microparticle containing a protein drug and formulation comprising same |
| US6515124B2 (en) | 2000-02-09 | 2003-02-04 | Hoffman-La Roche Inc. | Dehydroamino acids |
| EP1296943A1 (fr) | 2000-05-05 | 2003-04-02 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A. (S.C.R.A.S.) | Derives d'aminoacides et leur application a titre de medicaments |
| GB0011817D0 (en) | 2000-05-16 | 2000-07-05 | Pharmacia & Upjohn Spa | Antagonists of integrin receptors |
| CA2414461A1 (en) | 2000-06-29 | 2002-01-10 | Abbott Laboratories | Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents |
| JP2002030052A (ja) * | 2000-07-18 | 2002-01-29 | Tosoh Corp | ヒドロキシアミノカルボン酸、その用途、及びその製造法 |
| JPWO2002026686A1 (ja) * | 2000-09-27 | 2004-02-05 | 旭硝子株式会社 | アシルフルオリド類およびカルボン酸塩類の製造方法 |
| AR030817A1 (es) | 2000-10-02 | 2003-09-03 | Novartis Ag | Derivados de diazacicloalcanodiona |
| GB0025208D0 (en) | 2000-10-13 | 2000-11-29 | Euro Celtique Sa | Delayed release pharmaceutical formulations |
| US6653478B2 (en) | 2000-10-27 | 2003-11-25 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted benzimidazol-2-ones as vasopressin receptor antagonists and neuropeptide Y modulators |
| DE10055857A1 (de) | 2000-11-10 | 2002-08-22 | Creative Peptides Sweden Ab Dj | Neue pharmazeutische Depotformulierung |
| GB0028367D0 (en) | 2000-11-21 | 2001-01-03 | Celltech Chiroscience Ltd | Chemical compounds |
| CN1592746A (zh) | 2000-11-28 | 2005-03-09 | 杰南技术公司 | Lfa－1拮抗剂化合物 |
| WO2002050080A1 (en) | 2000-12-19 | 2002-06-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Small molecules useful in the treatment of inflammatory disease |
| CA2435415A1 (en) | 2001-01-26 | 2002-08-01 | Debio Recherche Pharmaceutique S.A. | Microparticles of biodegradable polymer encapsulating a biologically active substance |
| ATE348829T1 (de) | 2001-02-06 | 2007-01-15 | Pfizer Prod Inc | Pharmazeutische zusammensetzungen zur behandlung von störungen des zns oder anderen erkrankungen |
| US20030044406A1 (en) | 2001-03-02 | 2003-03-06 | Christine Dingivan | Methods of preventing or treating inflammatory or autoimmune disorders by administering CD2 antagonists in combination with other prophylactic or therapeutic agents |
| WO2002074247A2 (en) | 2001-03-19 | 2002-09-26 | Praecis Pharmaceuticals Incorporated | Pharmaceutical formulations for sustained release |
| US6872382B1 (en) | 2001-05-21 | 2005-03-29 | Alcon, Inc. | Use of selective PDE IV inhibitors to treat dry eye disorders |
| MXPA03009660A (es) | 2001-06-06 | 2004-04-02 | Aventis Pharma Ltd | Tetrahidroisoquinolinas sustituidas para su uso en el tratamiento de enfermedades inflamatorias. |
| CA2471096A1 (en) | 2001-12-19 | 2003-07-03 | Alza Corporation | Formulation and dosage form for increasing oral bioavailability of hydrophilic macromolecules |
| ATE432689T1 (de) | 2002-03-04 | 2009-06-15 | Ipsen Pharma | Arzneimittelformulierungen mit verzögerter freisetzung mit einem trägerpeptid |
| JP2006502183A (ja) | 2002-09-20 | 2006-01-19 | アルコン，インコーポレイテッド | ドライアイ障害の処置のためのサイトカイン合成インヒビターの使用 |
| US7785578B2 (en) | 2002-10-11 | 2010-08-31 | Aciont, Inc. | Non-invasive ocular drug delivery |
| RU2005117343A (ru) * | 2002-12-20 | 2006-01-27 | Астразенека Аб (Se) | Новые производные пиперидина в качестве модуляторов хемокинового рецептора ccr5 |
| CN1832920A (zh) | 2003-08-08 | 2006-09-13 | 特兰斯泰克制药公司 | 芳基和杂芳基化合物,组合物及其使用方法 |
| WO2005014534A1 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| WO2005042710A1 (en) | 2003-10-28 | 2005-05-12 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Use of statin to kill ebv-transformed b cells |
| AU2004287875B2 (en) | 2003-11-05 | 2011-06-02 | Bausch + Lomb Ireland Limited | Modulators of cellular adhesion |
| GT200500139A (es) | 2004-06-08 | 2005-07-25 | Metodo para la preparacion de acidos hidroxamicos | |
| MX2007013469A (es) * | 2005-04-28 | 2008-01-22 | Wyeth Corp | Forma ii polimorfa de tanaproget. |
| WO2006125119A1 (en) | 2005-05-17 | 2006-11-23 | Sarcode Corporation | Compositions and methods for treatment of eye disorders |
| WO2007057919A2 (en) * | 2005-10-25 | 2007-05-24 | Alembic Limited | An improved process for preparation of (s)-n-(1-carboxy-2-methyl-prop-1-yl)-n-pentanoyl-n-[2'-(1h-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine |
| JP4193895B2 (ja) | 2006-10-12 | 2008-12-10 | 横河電機株式会社 | 欠陥検査装置 |
| CN101873797A (zh) | 2007-10-19 | 2010-10-27 | 萨可德公司 | 用于治疗糖尿病性视网膜病的组合物和方法 |
| CA2711043A1 (en) * | 2008-01-01 | 2009-07-09 | Cipla Limited | Method of synthesis of bosentan, its polymorphic forms and its salts |
| US8080562B2 (en) | 2008-04-15 | 2011-12-20 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
| WO2011050175A1 (en) | 2009-10-21 | 2011-04-28 | Sarcode Corporation | Crystalline pharmaceutical and methods of preparation and use thereof |
| EP4406950A3 (en) * | 2012-07-25 | 2025-04-23 | Bausch + Lomb Ireland Limited | Lfa-1 inhibitor and polymorph thereof |
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