CN100471840C - 制备罗氟司特的方法 - Google Patents
制备罗氟司特的方法 Download PDFInfo
- Publication number
- CN100471840C CN100471840C CNB2004800012164A CN200480001216A CN100471840C CN 100471840 C CN100471840 C CN 100471840C CN B2004800012164 A CNB2004800012164 A CN B2004800012164A CN 200480001216 A CN200480001216 A CN 200480001216A CN 100471840 C CN100471840 C CN 100471840C
- Authority
- CN
- China
- Prior art keywords
- methoxy
- difluoro
- amino
- dichloropyridine
- benzoic acid
- 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.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03005245 | 2003-03-10 | ||
| EP03005245.0 | 2003-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1701062A CN1701062A (zh) | 2005-11-23 |
| CN100471840C true CN100471840C (zh) | 2009-03-25 |
Family
ID=32981730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004800012164A Expired - Lifetime CN100471840C (zh) | 2003-03-10 | 2004-03-08 | 制备罗氟司特的方法 |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US7470791B2 (enExample) |
| EP (1) | EP1606261B1 (enExample) |
| JP (1) | JP4742026B2 (enExample) |
| KR (1) | KR101179012B1 (enExample) |
| CN (1) | CN100471840C (enExample) |
| AR (1) | AR043531A1 (enExample) |
| AT (1) | ATE447555T1 (enExample) |
| AU (1) | AU2004220357B2 (enExample) |
| BR (1) | BRPI0406427B8 (enExample) |
| CA (1) | CA2503290C (enExample) |
| CY (1) | CY1109580T1 (enExample) |
| DE (1) | DE602004023921D1 (enExample) |
| DK (1) | DK1606261T3 (enExample) |
| EA (1) | EA009985B1 (enExample) |
| ES (1) | ES2335498T3 (enExample) |
| HR (1) | HRP20050399B1 (enExample) |
| IL (1) | IL168170A (enExample) |
| IS (1) | IS2723B (enExample) |
| ME (1) | ME00524B (enExample) |
| MX (1) | MXPA04008070A (enExample) |
| NO (1) | NO329301B1 (enExample) |
| NZ (1) | NZ539542A (enExample) |
| PL (1) | PL1606261T3 (enExample) |
| PT (1) | PT1606261E (enExample) |
| RS (2) | RS52908B (enExample) |
| SI (1) | SI1606261T1 (enExample) |
| TW (1) | TWI340741B (enExample) |
| WO (1) | WO2004080967A1 (enExample) |
| ZA (1) | ZA200503191B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617457A (zh) * | 2011-01-28 | 2012-08-01 | 天津药物研究院 | 一种制备罗氟司特的新方法 |
| CN103570610A (zh) * | 2012-07-18 | 2014-02-12 | 重庆华邦制药有限公司 | 一种罗氟司特微粒的制备方法 |
| CN104245672A (zh) * | 2012-03-07 | 2014-12-24 | 神隆医药(常熟)有限公司 | 制备罗氟司特的新方法 |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| MXPA04008070A (es) | 2003-03-10 | 2004-11-26 | Altana Pharma Ag | Novedoso proceso para la preparacion de roflumilasto. |
| EP1755595A1 (en) * | 2004-05-10 | 2007-02-28 | Altana Pharma AG | Use of roflumilast for the prophylaxis or treatment of emphysema |
| JP5383183B2 (ja) | 2005-03-16 | 2014-01-08 | タケダ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロフルミラストを含有する矯味された剤形 |
| CN102311382B (zh) * | 2010-06-29 | 2014-05-21 | 大道隆达(北京)医药科技发展有限公司 | 罗氟司特的晶态及其制备方法 |
| WO2012147098A2 (en) * | 2011-04-28 | 2012-11-01 | Glenmark Generics Limited | Novel process for the preparation of 3-(cyclopropylmethoxy)-n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy) benzamide |
| CN102775345A (zh) * | 2011-05-13 | 2012-11-14 | 上海特化医药科技有限公司 | 制备罗氟司特的方法及中间体 |
| CN102336703B (zh) * | 2011-07-20 | 2013-09-25 | 华润赛科药业有限责任公司 | 一种制备罗氟司特的方法 |
| CN102351787B (zh) * | 2011-08-18 | 2014-08-13 | 天津市汉康医药生物技术有限公司 | 高生物利用度的罗氟司特化合物 |
| CN103012255B (zh) * | 2011-09-21 | 2014-06-11 | 天津康鸿医药科技发展有限公司 | 罗氟司特晶型化合物、其制备方法、组合物及应用 |
| CN102336704B (zh) * | 2011-10-19 | 2013-04-17 | 丁克 | 一种制备罗氟司特的方法 |
| CN102336705B (zh) * | 2011-10-28 | 2013-03-27 | 成都苑东药业有限公司 | 一种制备n-(3,5-二氯吡啶-4-基)-3-环丙基甲氧基-4-二氟甲氧基苯甲酰胺的方法 |
| CN102603623A (zh) * | 2011-12-26 | 2012-07-25 | 北京赛林泰医药技术有限公司 | 制备高纯度罗氟司特的方法 |
| CN102617340B (zh) * | 2012-03-05 | 2014-03-26 | 山西仟源制药股份有限公司 | 制备3-环丙基甲氧基-4-二氟甲氧基苯甲酸的方法 |
| WO2013131255A1 (en) * | 2012-03-07 | 2013-09-12 | Scinopharm (Changshu) Pharmaceutical, Ltd. | Preparation method of roflumilast |
| WO2014012954A1 (en) | 2012-07-18 | 2014-01-23 | Takeda Gmbh | Treatment of partly controlled or uncontrolled severe asthma |
| EP2909177B1 (en) | 2012-10-17 | 2017-03-29 | Interquim, S.A. | Process for preparing roflumilast |
| CN103319333B (zh) * | 2013-07-15 | 2014-12-10 | 天津南开允公医药科技有限公司 | 一种制备3-环丙基甲氧基-4-二氟甲氧基苯甲酰氯化合物的方法 |
| AU2014307802A1 (en) * | 2013-08-16 | 2016-03-10 | Universiteit Maastricht | Treatment of cognitive impairment with combination therapy |
| US10357486B2 (en) | 2013-08-16 | 2019-07-23 | Universiteit Maastricht | Treatment of cognitive impairment with PDE4 inhibitor |
| CN103536582A (zh) * | 2013-10-12 | 2014-01-29 | 云南龙海天然植物药业有限公司 | 罗氟司特干粉吸入剂 |
| CN104892500A (zh) * | 2015-05-18 | 2015-09-09 | 武汉利宝瑞医药科技有限公司 | 罗氟司特的合成工艺 |
| JP6727302B2 (ja) * | 2016-07-01 | 2020-07-22 | 久光製薬株式会社 | N−(3,5−ジクロロピリド−4−イル)−n−メチル−3−シクロプロピルメトキシ−4−ジフルオロメトキシベンズアミドの製造方法 |
| US12042487B2 (en) | 2018-11-16 | 2024-07-23 | Arcutis Biotherapeutics, Inc. | Method for reducing side effects from administration of phosphodiesterase-4 inhibitors |
| US9895359B1 (en) | 2017-06-07 | 2018-02-20 | Arcutis, Inc. | Inhibition of crystal growth of roflumilast |
| US11129818B2 (en) | 2017-06-07 | 2021-09-28 | Arcutis Biotherapeutics, Inc. | Topical roflumilast formulation having improved delivery and plasma half life |
| US20210161870A1 (en) | 2017-06-07 | 2021-06-03 | Arcutis Biotherapeutics, Inc. | Roflumilast formulations with an improved pharmacokinetic profile |
| US12011437B1 (en) | 2017-06-07 | 2024-06-18 | Arcutis Biotherapeutics, Inc. | Roflumilast formulations with an improved pharmacokinetic profile |
| US20200155524A1 (en) | 2018-11-16 | 2020-05-21 | Arcutis, Inc. | Method for reducing side effects from administration of phosphodiesterase-4 inhibitors |
| US11534493B2 (en) | 2017-09-22 | 2022-12-27 | Arcutis Biotherapeutics, Inc. | Pharmaceutical compositions of roflumilast in aqueous blends of water-miscible, pharmaceutically acceptable solvents |
| CA3102689C (en) | 2018-06-04 | 2023-08-29 | Arcutis, Inc. | Method and formulation for improving roflumilast skin penetration lag time |
| KR20230146513A (ko) | 2020-12-04 | 2023-10-19 | 아큐티스 바이오테라퓨틱스, 인크. | 항진균 특성을 갖는 국소 로플루밀라스트 제형 |
| SI4175619T1 (sl) | 2021-07-09 | 2024-08-30 | Astrazeneca Pharmaceuticals Lp | Sestavki, postopki in sistemi za aerosolno dostavo zdravila |
| US20250057764A1 (en) | 2021-12-20 | 2025-02-20 | Astrazeneca Ab | Compositions, methods and systems for aerosol drug delivery |
| IL313866A (en) | 2021-12-28 | 2024-08-01 | Arcutis Biotherapeutics Inc | Topical roflomilest spray foams |
| WO2024058848A1 (en) | 2022-09-15 | 2024-03-21 | Arcutis Biotherapeutics, Inc. | Pharmaceutical compositions of roflumilast and solvents capable of dissolving high amounts of the drug |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN104245672B (zh) * | 2012-03-07 | 2016-05-18 | 神隆医药(常熟)有限公司 | 制备罗氟司特的方法 |
| CN103570610A (zh) * | 2012-07-18 | 2014-02-12 | 重庆华邦制药有限公司 | 一种罗氟司特微粒的制备方法 |
| CN103570610B (zh) * | 2012-07-18 | 2017-08-11 | 重庆华邦制药有限公司 | 一种罗氟司特微粒的制备方法 |
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