RS20050669A - Novel process for the preparation of roflumilast - Google Patents

Novel process for the preparation of roflumilast

Info

Publication number
RS20050669A
RS20050669A YUP-2005/0669A YUP20050669A RS20050669A RS 20050669 A RS20050669 A RS 20050669A YU P20050669 A YUP20050669 A YU P20050669A RS 20050669 A RS20050669 A RS 20050669A
Authority
RS
Serbia
Prior art keywords
preparation
roflumilast
novel process
dichloropyridine
cyclopropylmethoxy
Prior art date
Application number
YUP-2005/0669A
Other languages
English (en)
Inventor
Bernhard Kohl
Bernd Mueller
Walter Palosch
Original Assignee
Altana Pharma Ag.,
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32981730&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RS20050669(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Altana Pharma Ag., filed Critical Altana Pharma Ag.,
Publication of RS20050669A publication Critical patent/RS20050669A/sr

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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pronalazak se donosi na nove postupke za dobijanje roflumilasta sa visokom čistoćom. Postupak obuhvata reakciju 4-amino-3,5-dihloropiridin anjona (1) sa aktivnim derivatom 3-ciklopropilmetoksi-4-difluorometiksibenzojeve kiseline (2), naznačen time, što je molarni odnos upotrebljenog 4-amino-3,5-dihloropiridin anjona na aktivni derivat 3-ciklopropilmetoksi-4-difluorometoksibenzojeve kiseline najmanje 1.5, a najviše 3, poželjno najmanje 1.8, a najviše 2.7, posebno poželjno najmanje 2, a najviše 2.5 i naročito poželjno 2.2.
YUP-2005/0669A 2003-03-10 2004-03-08 Novel process for the preparation of roflumilast RS20050669A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03005245 2003-03-10
PCT/EP2004/050272 WO2004080967A1 (en) 2003-03-10 2004-03-08 Novel process for the preparation of roflumilast

Publications (1)

Publication Number Publication Date
RS20050669A true RS20050669A (en) 2008-04-04

Family

ID=32981730

Family Applications (2)

Application Number Title Priority Date Filing Date
YUP-2005/0669A RS20050669A (en) 2003-03-10 2004-03-08 Novel process for the preparation of roflumilast
RS20050669A RS52908B (sr) 2003-03-10 2004-03-08 Novi postupak za dobijanje roflumilasta

Family Applications After (1)

Application Number Title Priority Date Filing Date
RS20050669A RS52908B (sr) 2003-03-10 2004-03-08 Novi postupak za dobijanje roflumilasta

Country Status (30)

Country Link
US (5) US7470791B2 (sr)
EP (1) EP1606261B1 (sr)
JP (1) JP4742026B2 (sr)
KR (1) KR101179012B1 (sr)
CN (1) CN100471840C (sr)
AR (1) AR043531A1 (sr)
AT (1) ATE447555T1 (sr)
AU (1) AU2004220357B2 (sr)
BR (1) BRPI0406427B8 (sr)
CA (1) CA2503290C (sr)
CY (1) CY1109580T1 (sr)
DE (1) DE602004023921D1 (sr)
DK (1) DK1606261T3 (sr)
EA (1) EA009985B1 (sr)
ES (1) ES2335498T3 (sr)
HK (1) HK1085480A1 (sr)
HR (1) HRP20050399B1 (sr)
IL (1) IL168170A (sr)
IS (1) IS2723B (sr)
ME (1) ME00524B (sr)
MX (1) MXPA04008070A (sr)
NO (1) NO329301B1 (sr)
NZ (1) NZ539542A (sr)
PL (1) PL1606261T3 (sr)
PT (1) PT1606261E (sr)
RS (2) RS20050669A (sr)
SI (1) SI1606261T1 (sr)
TW (1) TWI340741B (sr)
WO (1) WO2004080967A1 (sr)
ZA (1) ZA200503191B (sr)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
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
ES2335498T3 (es) 2003-03-10 2010-03-29 Nycomed Gmbh Nuevo proceso para la preparacion de reflumilast.
JP2007536350A (ja) * 2004-05-10 2007-12-13 ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング 肺気腫の予防又は治療のためのロフルミラストの使用
CA2601250C (en) 2005-03-16 2014-10-28 Nycomed Gmbh Taste masked dosage form containing roflumilast
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
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
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
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
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
WO2014012954A1 (en) 2012-07-18 2014-01-23 Takeda Gmbh Treatment of partly controlled or uncontrolled severe asthma
US9321726B2 (en) 2012-10-17 2016-04-26 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
DK3033082T3 (da) 2013-08-16 2021-09-20 Univ Maastricht Behandling af kognitiv svækkelse med pde4-hæmmer
EP3033077A1 (en) * 2013-08-16 2016-06-22 Universiteit Maastricht Treatment of cognitive impairment with combination therapy
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
US20210161870A1 (en) 2017-06-07 2021-06-03 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
US9895359B1 (en) 2017-06-07 2018-02-20 Arcutis, Inc. Inhibition of crystal growth of roflumilast
US12011437B1 (en) 2017-06-07 2024-06-18 Arcutis Biotherapeutics, Inc. Roflumilast formulations with an improved pharmacokinetic profile
US11129818B2 (en) 2017-06-07 2021-09-28 Arcutis Biotherapeutics, Inc. Topical roflumilast formulation having improved delivery and plasma half life
US11534493B2 (en) 2017-09-22 2022-12-27 Arcutis Biotherapeutics, Inc. Pharmaceutical compositions of roflumilast in aqueous blends of water-miscible, pharmaceutically acceptable solvents
CA3226153A1 (en) 2021-07-09 2023-01-12 Astrazeneca Pharmaceuticals Lp Compositions, methods and systems for aerosol drug delivery
WO2023119093A1 (en) 2021-12-20 2023-06-29 Astrazeneca Ab Compositions, methods and systems for aerosol drug delivery

Family Cites Families (154)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3065142A (en) 1958-07-30 1962-11-20 Armour Pharma Gastric resistant medicinal preparation
US4006227A (en) 1973-11-15 1977-02-01 Gallegos Alfred J Compositions and methods for fertility control
US4024240A (en) 1975-07-18 1977-05-17 Eli Lilly And Company Antibiotic A-32390 compositions
US4343804A (en) 1979-03-26 1982-08-10 A. H. Robins Company, Inc. 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds
NZ196700A (en) 1980-04-18 1983-04-12 Smith & Nephew Ass Anti-inflammatory compositions containing 5-benzoyl-1-methylpyrrole-2-acetic acid derivatives
EP0068378B1 (en) 1981-06-26 1986-03-05 Schering Corporation Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them
US4464372A (en) 1982-08-16 1984-08-07 Schering Corporation Imidazo[1,2-b]pyridazines
GB8305245D0 (en) 1983-02-25 1983-03-30 Fujisawa Pharmaceutical Co Imidazo-heterocyclic compounds
GB8307865D0 (en) 1983-03-22 1983-04-27 Fujisawa Pharmaceutical Co Benzimidazole derivatives
GB8415540D0 (en) 1984-06-18 1984-07-25 Fujisawa Pharmaceutical Co Imidazoisoquinoline compounds
US4725601A (en) 1985-06-04 1988-02-16 Fujisawa Pharmaceutical Co., Ltd. Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers
JPS625966A (ja) 1985-07-03 1987-01-12 Nippon Shinyaku Co Ltd ベンズイミダゾ−ル誘導体
EP0228006A1 (en) 1985-12-16 1987-07-08 Fujisawa Pharmaceutical Co., Ltd. Imidazopyridine compounds and processes for preparation thereof
US4753945A (en) 1986-02-19 1988-06-28 Eye Research Institute Of Retina Foundation Stimulation of tear secretion with phosphodiesterase inhibitors
US5286494A (en) 1986-07-02 1994-02-15 Schering Aktiengesellschaft Medicinal agents with sustained action
GB8621425D0 (en) 1986-09-05 1986-10-15 Smith Kline French Lab Compounds
US4833149A (en) 1986-09-22 1989-05-23 Ortho Pharmaceutical Corporation 2- or 3-aryl substituted imidazo[1,2-a]pyridines
US4791117A (en) 1986-09-22 1988-12-13 Ortho Pharmaceutical Corporation 2- or 3-aryl substituted imidazo[1,2-a]pyridines and their use as calcium channel blockers
EP0264883A3 (en) 1986-10-21 1990-04-04 Banyu Pharmaceutical Co., Ltd. Substituted pyridine derivatives
US4831041A (en) 1986-11-26 1989-05-16 Fujisawa Pharmaceutical Co., Ltd. Imidazopyridine compounds and processes for preparation thereof
WO1989000570A1 (en) 1987-07-16 1989-01-26 Byk Gulden Lomberg Chemische Fabrik Gmbh New diazols
GB8717644D0 (en) 1987-07-24 1987-09-03 Smithkline Beckman Intercredit Compounds
GB8722488D0 (en) 1987-09-24 1987-10-28 Fujisawa Pharmaceutical Co Imidazopyridine compound
GB8804444D0 (en) 1988-02-25 1988-03-23 Smithkline Beckman Intercredit Compounds
US4900775A (en) 1988-02-29 1990-02-13 Gaf Chemicals Corporation Solubilization of complexes of water-insoluble organic compounds by aqueous solutions of polyvinylpyrrolidone
US5011843A (en) 1988-05-31 1991-04-30 Iolab Corporation Treatment of glaucoma using phosphodiesterase inhibitors
CA2011086A1 (en) 1989-03-17 1990-09-17 Karl-Heinz Geiss 2-alkyl-4-arylmethylaminoquinolines, the use thereof and drugs prepared therefrom
GB8908229D0 (en) 1989-04-12 1989-05-24 Smithkline Beckman Intercredit Compounds
DE3917233A1 (de) 1989-05-26 1990-11-29 Basf Ag 8-substituierte 4-(heterocyclylmethylamino)-chinoline, ihre verwendung und daraus hergestellte arzneimittel
DE3917232A1 (de) 1989-05-26 1990-11-29 Basf Ag 4-arylmethamino-2,3-dialkyl-chinoline, ihre verwendung und daraus hergestellte arzneimittel
DE3943385A1 (de) 1989-12-27 1991-07-04 Schering Ag Mittel zur transdermalen applikation enthaltend rolipram
FR2657257B1 (fr) 1990-01-19 1994-09-02 Rhone Poulenc Sante Procede de preparation de medicaments sous forme de perles.
DE69128682T2 (de) 1990-03-28 1998-06-04 Otsuka Pharma Co Ltd Chinolinderivat, antiulcus-mittel das dieses derivat enthält und darstellung dieses derivates
US5041442A (en) 1990-07-31 1991-08-20 Syntex (U.S.A.) Inc. Pyrrolo(1,2-a)pyrazines as inhibitors of gastric acid secretion
US5698711A (en) * 1991-01-28 1997-12-16 Rhone-Poulenc Rorer Limited Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group
SE9100920D0 (sv) 1991-03-27 1991-03-27 Astra Ab New active compounds
JP2948317B2 (ja) 1991-05-28 1999-09-13 マクニール―ピーピーシー・インコーポレーテツド 噛める薬物投与用組成物
JP3108483B2 (ja) 1991-09-30 2000-11-13 日清製粉株式会社 インドール誘導体およびこれを有効成分とする抗潰瘍薬
JP3038064B2 (ja) 1991-10-07 2000-05-08 日清製粉株式会社 インドール誘導体およびこれを有効成分とする抗潰瘍薬
WO1993008190A1 (de) 1991-10-25 1993-04-29 Byk Gulden Lomberg Chemische Fabrik Gmbh Pyrrolo-pyridazine mit magen- und darmschutzwirkungen
US5262171A (en) 1991-11-25 1993-11-16 Isp Investments Inc. Pharmaceutical tablet with PVP having enhanced drug dissolution rate
SG43179A1 (en) 1991-12-18 1997-10-17 Warner Lambert Co A process for the prepatation of a solid dispersion
GB9201693D0 (en) 1992-01-27 1992-03-11 Smithkline Beecham Intercredit Compounds
GB9212693D0 (en) * 1992-06-15 1992-07-29 Celltech Ltd Chemical compounds
DE69309030T2 (de) 1992-06-15 1997-09-25 Celltech Therapeutics Ltd Trisubstituierte phenylderivate als selektive phosphodiesterase iv inhibitoren
NZ254881A (en) 1992-07-28 1996-09-25 Rhone Poulenc Rorer Ltd Diether, dithioether or diether thioether derivatives of 1,2-dihydroxybenzenes substituted in position-4 by an (hetero)aryl-containing group;
US5891904A (en) 1992-09-14 1999-04-06 Wolf-Georg Forssmann Use of inhibitors of phosphodiesterase IV
JP3284622B2 (ja) 1992-10-23 2002-05-20 ソニー株式会社 ディスク装置
US5429824A (en) 1992-12-15 1995-07-04 Eastman Kodak Company Use of tyloxapole as a nanoparticle stabilizer and dispersant
KR0144833B1 (ko) 1992-12-28 1998-07-15 김태훈 신규의 퀴나졸린 유도체 및 그의 제조방법
IL108520A (en) 1993-02-15 1997-09-30 Byk Gulden Lomberg Chem Fab 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
AU6646094A (en) 1993-04-22 1994-11-08 Byk Gulden New pyridinium salts and their use for controlling helicobacter bacteria
DE122010000043I1 (de) * 1993-07-02 2011-01-27 Nycomed Gmbh Fluoralkoxy substituierte benzamide und ihre verwendung als zyklisch-nukleotid phosphodiesterase-inhibitoren
JP3284686B2 (ja) 1993-08-30 2002-05-20 株式会社明電舎 ブレーキダイナモメータシステムのブレーキトルク制御方式
UA48122C2 (uk) 1993-10-11 2002-08-15 Бік Гульден Ломберг Хеміше Фабрік Гмбх АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ
HU220874B1 (en) 1994-07-28 2002-06-29 Byk Gulden Lomberg Chem Fab Imidazopyridine-azolidinones, process for producing them, the use thereof and pharmaceutical compositions containing them
JP3031280B2 (ja) 1994-08-19 2000-04-10 東陶機器株式会社 便器洗浄装置
GB9514473D0 (en) 1995-07-14 1995-09-13 Glaxo Lab Sa Chemical compounds
SE512835C2 (sv) 1996-01-08 2000-05-22 Astrazeneca Ab Doseringsform innehållande en mångfald enheter alla inneslutande syralabil H+K+ATPas-hämmare
US6114537A (en) 1996-02-26 2000-09-05 Apotex Inc. Process for scavenging thiols
US5677302A (en) 1996-02-26 1997-10-14 Apotex Inc. Thiadiazole compounds useful as proton pump inhibitors
FR2746800B1 (fr) 1996-03-29 1998-06-05 Jouveinal Inst Rech Diazepino-indoles inhibiteurs de phosphodiesterases 4
US5972381A (en) 1996-06-28 1999-10-26 Schering Corporation Solid solution of an antifungal agent with enhanced bioavailability
US5762953A (en) 1996-08-22 1998-06-09 Theratech, Inc. Transdermal propentofylline compositions for the treatment of Alzheimers disease
IL130658A (en) 1997-02-17 2004-07-25 Altana Pharma Ag Preparations for the treatment of ARDS or IRDS containing 3 - (cyclopropylmethoxy) - N - (3, 5 - dichloro - 4 - pyridinyl) - 4 - (difluoromethoxy) benzamide and solvent for the lungs
SE9700661D0 (sv) 1997-02-25 1997-02-25 Astra Ab New compounds
US6624181B1 (en) 1997-02-28 2003-09-23 Altana Pharma Ag Synergistic combination
CN1257505A (zh) 1997-05-28 2000-06-21 比克·古尔顿·劳姆贝尔格化学公司 稠合的二氢吡喃类化合物
IT1294748B1 (it) 1997-09-17 1999-04-12 Permatec Tech Ag Formulazione per un dispositivo transdermico
ATE303809T1 (de) 1997-12-08 2005-09-15 Altana Pharma Ag Orale verabreichungsform enthaltend einen protonenpumpeninhbitor (z.b. pantoprazole)
SE9801526D0 (sv) 1998-04-29 1998-04-29 Astra Ab New compounds
ES2296390T3 (es) 1998-05-07 2008-04-16 Corixa Corporation Composicion coadyuvante y procedimiento para su uso.
EP1085846A2 (en) 1998-06-08 2001-03-28 Advanced Medicine, Inc. Multibinding inhibitors of microsomal triglyceride transferase protein
SE9802794D0 (sv) 1998-08-21 1998-08-21 Astra Ab New compounds
SE9802793D0 (sv) 1998-08-21 1998-08-21 Astra Ab New compounds
DZ2876A1 (fr) 1998-08-26 2003-12-15 Smithkline Beecham Corp Composition comprenant un inhibiteur de pde4 et unbroncho-dilatateur beta-andrenergique, et procédé pour leur préparation.
EE04677B1 (et) 1998-09-23 2006-08-15 Byk Gulden Lomberg Chemische Fabrik Gmbh Tetrahdropridoeetrid, nende kasutamine ja ravim
BR9914399A (pt) 1998-09-29 2002-01-22 Fujisawa Pharmaceutical Co Composto de piridopirazina, processo para sua produção e seu uso
CA2346350C (en) 1998-10-05 2008-01-08 Eisai Co., Ltd. Intraoral quickly disintegrating tablets
US20020006418A1 (en) 1998-10-13 2002-01-17 John Kung Composition to enhance permeation of topical skin agents
WO2000026217A1 (en) 1998-11-03 2000-05-11 Byk Gulden Lomberg Chemische Fabrik Gmbh Imidazonaphthyridines
US6417190B1 (en) 1998-12-17 2002-07-09 Boehringer Ingelheim Pharma Kg Tricyclic nitrogen heterocycles as PDE IV inhibitors
DZ3019A1 (fr) 1999-03-01 2005-05-20 Smithkline Beecham Corp Utilisation d'un inhibiteur de pde4 dans la préparation d'un médicament contre la copd.
US6270807B1 (en) 1999-03-02 2001-08-07 L. Perrigo Company Taste-masked pharmaceutical composition
AU3284000A (en) 1999-03-10 2000-09-28 Byk Gulden Lomberg Chemische Fabrik Gmbh 3-cyclopropylmethoxy-4-difluoromethoxy-n-(3,5-dichloropyrid- 4-yl)benzamide in the treatment of multiple sclerosis
CN1126468C (zh) 1999-04-08 2003-11-05 王力田 一种黑玉米秸秆饮料及其制备方法
ES2199810T3 (es) 1999-04-17 2004-03-01 Altana Pharma Ag Haloalcoxi-imidazonaftiridinas.
KR100328972B1 (ko) 1999-04-23 2002-03-20 서경배 피부 유용 활성성분을 함유한 화장료 또는 피부도포용 의약품 조성물의 제조방법 및 이러한 방법에 의해 제조된 화장료 또는 피부도포용 의약품 조성물
SI1176960T1 (en) 1999-05-04 2005-04-30 Altana Pharma Ag Synergistic combination comprising roflumilast and a pde-3 inhibitor
DE19925710C2 (de) 1999-06-07 2002-10-10 Byk Gulden Lomberg Chem Fab Neue Zubereitung und Darreichungsform enthaltend einen säurelabilen Protonenpumpenhemmer
UA74339C2 (uk) 1999-06-07 2005-12-15 Алтана Фарма Аг Форма для введення, що включає інгібітор протонної помпи у вигляді окремих одиниць, та спосіб їх одержання
AU776722B2 (en) 1999-08-03 2004-09-16 Icos Corporation Beta-carboline pharmaceutical compositions
SI1212089T1 (sl) 1999-08-21 2006-08-31 Altana Pharma Ag Sinergisticna kombinacija roflumilasta in salmeterola
US6174878B1 (en) 1999-08-31 2001-01-16 Alcon Laboratories, Inc. Topical use of kappa opioid agonists to treat otic pain
US6375968B1 (en) 1999-10-22 2002-04-23 3M Innovative Properties Company Encapsulated active material immobilized in hydrogel microbeads
KR100729836B1 (ko) 1999-10-25 2007-06-18 소니 가부시끼 가이샤 콘텐츠 데이터 관리방법
EP1225884A4 (en) 1999-10-29 2005-06-15 Smithkline Beecham Corp METHOD FOR THE ADMINISTRATION OF A PHOSPHODIESTERASE-4 HEMMER
US6258833B1 (en) 1999-12-23 2001-07-10 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
US6348602B1 (en) 1999-12-23 2002-02-19 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
US6379682B1 (en) 2000-02-07 2002-04-30 Color Access, Inc. Clear water-in-oil emulsions
US20030207845A1 (en) 2001-02-08 2003-11-06 Keating Elizabeth T. Method and compositions for treating an inflammatory disease
JP2004500404A (ja) 2000-03-27 2004-01-08 カール　−　ツァイス　−　シュティフツング 生物活性ガラスを含む新規化粧品、ボディケア、洗浄剤および栄養サプリメント組成物および製造方法およびその使用
CA2407780A1 (en) * 2000-05-25 2001-11-29 Merck Frosst Canada & Co./Merck Frosst Canada & Cie Fluoroalkoxy-substituted benzamide dichloropyridinyl n-oxide pde4 inhibitor
EP1161950A1 (en) 2000-06-09 2001-12-12 Warner-Lambert Company Use of diazepinoindoles for the treatment of chronic obstructive pulmonary disease
US20040005995A1 (en) 2001-07-26 2004-01-08 Edelson Jeffrey D Method for reducing exacerbations associated with copd
AR029984A1 (es) 2000-07-27 2003-07-23 Smithkline Beecham Corp Metodo para reducir las exacerbaciones asociadas copd ambito
EP1199074A1 (en) 2000-09-15 2002-04-24 Warner-Lambert Company Pharmaceutical composition for preventing or treating a disease associated with an excess of il-12 production
US20020193393A1 (en) 2001-03-07 2002-12-19 Michel Pairet Pharmaceutical compositions based on anticholinergics and PDE-IV inhibitors
US20100310477A1 (en) 2000-11-28 2010-12-09 Boehringer Ingelheim Pharma Gmbh & Co. Kg. Pharmaceutical compositions based on anticholingerics and additional active ingredients
CA2430816C (en) 2000-12-07 2012-05-15 Altana Pharma Ag Pharmaceutical preparation in the form of a paste comprising an acid-labile active ingredient
UA80393C2 (uk) 2000-12-07 2007-09-25 Алтана Фарма Аг Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці
KR20030072555A (ko) 2000-12-07 2003-09-15 알타나 파마 아게 산 불안정성 활성 성분을 포함하는 신속 붕해 정제
KR20030059318A (ko) 2000-12-07 2003-07-07 알타나 파마 아게 산 불안정성 활성 성분을 포함하는 현탁액 형태의 약학 제제
DE10061137B4 (de) 2000-12-07 2016-10-06 Takeda Gmbh Neue pharmazeutische Zubereitung
KR100750554B1 (ko) 2001-02-15 2007-08-20 다나베 세이야꾸 가부시키가이샤 구강 내 속붕괴성 정제
AU2002254036A1 (en) 2001-03-05 2002-09-19 Ortho-Mcneil Pharmaceutical, Inc. Taste masked pharmaceutical compositions
FR2821745B1 (fr) 2001-03-09 2004-07-02 Ethypharm Lab Prod Ethiques Granules et granules enrobes au gout masque
US6702796B2 (en) 2001-03-26 2004-03-09 The Procter & Gamble Company Absorbent interlabial device having an improved tab
UA77656C2 (en) 2001-04-07 2007-01-15 Glaxo Group Ltd S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent
US6872382B1 (en) 2001-05-21 2005-03-29 Alcon, Inc. Use of selective PDE IV inhibitors to treat dry eye disorders
US20030092706A1 (en) 2001-11-09 2003-05-15 Johannes Barsig Combination
US6723348B2 (en) 2001-11-16 2004-04-20 Ethypharm Orodispersible tablets containing fexofenadine
US6756392B2 (en) 2002-02-11 2004-06-29 Pfizer Inc Nicotinamide derivatives useful as PDE4 inhibitors
MY140561A (en) 2002-02-20 2009-12-31 Nycomed Gmbh Dosage form containing pde 4 inhibitor as active ingredient
DE60325354D1 (de) 2002-05-28 2009-01-29 Nycomed Gmbh Topisch anwendbare pharmazeutische zubereitung
US20040058950A1 (en) 2002-07-09 2004-03-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Pharmaceutical compositions based on anticholinergics and PDE-IV inhibitors
CN102755646A (zh) 2002-07-19 2012-10-31 艾博特生物技术有限公司 TNF α相关疾病的治疗
US20030018071A1 (en) 2002-08-09 2003-01-23 Rennard Stephen I. Method and compositions for treating fibrotic diseases
US7220746B2 (en) 2002-08-10 2007-05-22 Altana Pharma Ag Pyrrolidinedione substituted piperidine-phthalazones as PDE4 inhibitors
CA2495827C (en) 2002-08-29 2012-05-08 Altana Pharma Ag 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors
CA2497176A1 (en) 2002-09-04 2004-03-18 Ranbaxy Laboratories Limited Taste masked dosage forms and processes for their preparation
US6822114B1 (en) * 2002-10-08 2004-11-23 Albemarle Corporation Process for production of fluoroalkoxy-substituted benzamides and their intermediates
US20060142308A1 (en) 2002-11-27 2006-06-29 Atlanta Pharma Ag Synergistic combination comprising roflumilast and formoterol
DK1567140T3 (da) 2002-11-27 2008-11-03 Nycomed Gmbh Synergistisk kombination der omfatter roflumilast og (R,R)-formoterol
AU2003302881A1 (en) 2002-12-11 2004-06-30 Ranbaxy Laboratories Limited Coating composition for taste masking coating and methods for their application and use
AU2004208512B2 (en) 2003-01-30 2009-01-29 Ethypharm Taste-masking coated particles, process for the preparation thereof and orodispersible tablets containing said coated particles
ES2335498T3 (es) 2003-03-10 2010-03-29 Nycomed Gmbh Nuevo proceso para la preparacion de reflumilast.
WO2004084896A1 (en) 2003-03-28 2004-10-07 Altana Pharma Ag Synergistic combination comprising roflumilast and an anticholinergic agent selected from ipratropium, oxitropium and tiotropium salts for the treatment of respiratory diseases
JP2006528229A (ja) 2003-05-22 2006-12-14 アルタナ　ファルマ　アクチエンゲゼルシャフト Ｐｄｅ４阻害剤及びｐｄｅ５阻害剤を含有する組成物
US20050026883A1 (en) 2003-07-31 2005-02-03 Robinson Cynthia B. Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with a PDE-4 inhibitor for treatment of asthma or chronic obstructive pulmonary disease
EP1656117A1 (en) 2003-08-11 2006-05-17 Merck Frosst Canada Ltd. Flavored taste-masked pharmaceutical formulation made using a one-step coating process
BRPI0413881A (pt) 2003-08-28 2006-10-24 Sandoz Ag composição farmacêutica compreendendo anticonvulsivante com revestimento de mascaramento de gosto
EP1670742A1 (en) 2003-09-12 2006-06-21 Ranbaxy Laboratories Limited Process for the preparation of roflumilast
JP2007527409A (ja) 2003-10-09 2007-09-27 インバーセオン、インコーポレイテッド β−アドレナリンインバースアゴニストを用いて気道疾患を治療する方法
CA2542277A1 (en) 2003-10-21 2005-05-12 Pharmacia Corporation Method for the treatment or prevention of respiratory inflammation with a cyclooxygenase-2 inhibitor in combination with a phosphodiesterase 4 inhibitor and compositions therewith
JP2007536350A (ja) 2004-05-10 2007-12-13 ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング 肺気腫の予防又は治療のためのロフルミラストの使用
US20060035872A1 (en) 2004-08-12 2006-02-16 Marco Villa Process for the preparation of 3-oximino steroids
US20060105038A1 (en) 2004-11-12 2006-05-18 Eurand Pharmaceuticals Limited Taste-masked pharmaceutical compositions prepared by coacervation
WO2006094640A2 (en) 2005-03-04 2006-09-14 F.Hoffmann-La Roche Ag Roflumilast and integrin inhibitor combination and method of treatment
CA2601250C (en) 2005-03-16 2014-10-28 Nycomed Gmbh Taste masked dosage form containing roflumilast
MX2009000148A (es) 2006-07-07 2009-10-26 Kalypsys Inc Inhibidores heteroaril biciclicos de fosfodiesterasa 4.
USD580547S1 (en) 2007-07-31 2008-11-11 Nycomed Gmbh Tablet
JP2009167052A (ja) 2008-01-16 2009-07-30 Kyocera Corp 単結晶シリコン粒子の製造方法
JP5271070B2 (ja) 2008-12-24 2013-08-21 エスアイアイ・プリンテック株式会社 ヘッドチップ、液体噴射ヘッド及び液体噴射装置

Also Published As

Publication number Publication date
KR101179012B1 (ko) 2012-09-03
KR20050106392A (ko) 2005-11-09
DK1606261T3 (da) 2010-01-18
BRPI0406427B8 (pt) 2021-05-25
NO20051957D0 (no) 2005-04-21
ES2335498T3 (es) 2010-03-29
RS52908B (sr) 2014-02-28
AU2004220357B2 (en) 2010-09-30
EA200501350A1 (ru) 2006-04-28
IL168170A (en) 2010-12-30
US20130231374A1 (en) 2013-09-05
US20060004061A1 (en) 2006-01-05
HRP20050399B1 (hr) 2013-09-30
US7470791B2 (en) 2008-12-30
NZ539542A (en) 2007-09-28
ME00524B (me) 2011-10-10
PL1606261T3 (pl) 2010-04-30
CA2503290A1 (en) 2004-09-23
AR043531A1 (es) 2005-08-03
CY1109580T1 (el) 2014-08-13
US8604064B2 (en) 2013-12-10
PT1606261E (pt) 2010-01-11
CN1701062A (zh) 2005-11-23
MXPA04008070A (es) 2004-11-26
ATE447555T1 (de) 2009-11-15
AU2004220357A1 (en) 2004-09-23
HRP20050399A2 (en) 2006-08-31
CN100471840C (zh) 2009-03-25
BRPI0406427A (pt) 2005-10-04
HK1085480A1 (en) 2006-08-25
SI1606261T1 (sl) 2010-03-31
US8618142B2 (en) 2013-12-31
ZA200503191B (en) 2006-02-22
TWI340741B (en) 2011-04-21
NO20051957L (no) 2005-10-06
TW200508201A (en) 2005-03-01
JP2006519818A (ja) 2006-08-31
JP4742026B2 (ja) 2011-08-10
BRPI0406427B1 (pt) 2019-05-14
DE602004023921D1 (de) 2009-12-17
US20120294942A1 (en) 2012-11-22
US20130224299A1 (en) 2013-08-29
IS7810A (is) 2005-04-19
US20090171096A1 (en) 2009-07-02
IS2723B (is) 2011-03-15
CA2503290C (en) 2012-12-04
EA009985B1 (ru) 2008-04-28
US8536206B2 (en) 2013-09-17
NO329301B1 (no) 2010-09-27
EP1606261A1 (en) 2005-12-21
EP1606261B1 (en) 2009-11-04
WO2004080967A1 (en) 2004-09-23

Similar Documents

Publication Publication Date Title
RS20050669A (en) Novel process for the preparation of roflumilast
MY142029A (en) Phenoxyacetic acid derivatives
YU31801A (sh) Amidi antranilne kiseline i njihova upotreba kao leka
MY132789A (en) Diarylcycloalkyl derivatives, process for their preparation and their use as pharmaceuticals
TW200510325A (en) 2-acylamino-4-phenylthiazole derivatives, preparation thereof and therapeutic application thereof
MXPA03009840A (es) Derivados de fenilurea sustituidos con carboxamida y metodo para la produccion de los mismos como farmacos.
MXPA02011458A (es) Derivados de acilfenilurea, metodos para su produccion y uso de los mismos como farmacos.
WO2002008194A8 (de) Acridin-derivate und deren verwendung als arzneimittel
HUP0201646A3 (en) Novel alpha-amino acid derivatives, process for producing them and pharmaceutical compositions containing them
MY133392A (en) Novel substituted pyrazole derivatives
TW200505837A (en) Novel compounds
YU7804A (sh) Stabilni polimorf flibanserina,postupak za njegovo dobijanje u industrijskim razmerama i njegova primena za pripremanje lekova
ZA200508862B (en) Process for the preparation of (4-hydroxy-6-oxo-tetrahydropyran-2-yl) acetonitrile and derivatives thereof
WO2002010152A3 (de) Neue indolderivate und deren verwendung als arzneimittel
AU2002336981A1 (en) Glycoconjugates of sialic acid derivates, methods for their production and use thereof
IL157046A0 (en) Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide
MXPA03002047A (es) Fenilciclohexanocarboxamidas substituidas y su uso.
WO2000073274A3 (de) Substituierte phenylcyclohexancarbonsäureamide und ihre verwendung als adenosinaufnahme-inhibitoren
AU5419699A (en) Methoximinophenylacetic acid amides
EE04632B1 (et) Meetod mittepaakuvast soolast pressitud produkti valmistamiseks, saadud produkt ja selle kasutamine
WO2003029221A8 (de) Tetrahydroisochinoline, ihre herstellung und verwendung als schmerzmittel
CA2534194A1 (en) Indoline-sulfanilic acid amides used as ppar delta modulators
AU2910800A (en) Novel substituted 3-phenoxy and 3-phenylalkyloxy-2-phenyl-propylamines
HK1071144A1 (en) Platinum complexes containing chemically modified bile acids, having antitumor activity
RS20060049A (en) Novel n-substituted indolyl-3-glycoxylic acid amides, use thereof as a medicament and method for the production thereof