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DK164280C - 1h-imidazooe4,5-caaquinolin eller derivat deraf og farmaceutisk praeparat indeholdende en saadan forbindelse - Google Patents

1h-imidazooe4,5-caaquinolin eller derivat deraf og farmaceutisk praeparat indeholdende en saadan forbindelse

Info

Publication number
DK164280C
DK164280C DK542684A DK542684A DK164280C DK 164280 C DK164280 C DK 164280C DK 542684 A DK542684 A DK 542684A DK 542684 A DK542684 A DK 542684A DK 164280 C DK164280 C DK 164280C
Authority
DK
Denmark
Prior art keywords
carbon atoms
imidazooe4
caaquinoline
derivative
connection
Prior art date
Application number
DK542684A
Other languages
Danish (da)
English (en)
Other versions
DK164280B (da
DK542684A (da
DK542684D0 (da
Inventor
John F Gerster
Original Assignee
Riker Laboratories Inc
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
Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc
Publication of DK542684D0 publication Critical patent/DK542684D0/da
Publication of DK542684A publication Critical patent/DK542684A/da
Publication of DK164280B publication Critical patent/DK164280B/da
Application granted granted Critical
Publication of DK164280C publication Critical patent/DK164280C/da

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/08Bronchodilators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38Nitrogen atoms
    • C07D215/42Nitrogen atoms attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Physical Water Treatments (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Alarm Systems (AREA)
  • Quinoline Compounds (AREA)
  • Lubricants (AREA)
  • Luminescent Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
DK542684A 1983-11-18 1984-11-15 1h-imidazooe4,5-caaquinolin eller derivat deraf og farmaceutisk praeparat indeholdende en saadan forbindelse DK164280C (da)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US55315783A 1983-11-18 1983-11-18
US55315883A 1983-11-18 1983-11-18
US55315883 1983-11-18
US55315783 1983-11-18

Publications (4)

Publication Number Publication Date
DK542684D0 DK542684D0 (da) 1984-11-15
DK542684A DK542684A (da) 1985-05-19
DK164280B DK164280B (da) 1992-06-01
DK164280C true DK164280C (da) 1992-11-30

Family

ID=27070262

Family Applications (6)

Application Number Title Priority Date Filing Date
DK542684A DK164280C (da) 1983-11-18 1984-11-15 1h-imidazooe4,5-caaquinolin eller derivat deraf og farmaceutisk praeparat indeholdende en saadan forbindelse
DK135791A DK169179B1 (da) 1983-11-18 1991-07-16 1H-imidazo[4,5-c]quinolin-4-amin, farmaceutisk præparat indeholdende en sådan forbindelse og fremga ngsmåde til fremstilling af en sådan forbindelse
DK136091A DK164451C (da) 1983-11-18 1991-07-16 3-aminoquinolinderivat
DK136191A DK164452C (da) 1983-11-18 1991-07-16 3-nitroquinolinderivat
DK135991A DK165921C (da) 1983-11-18 1991-07-16 1h-imidazooe4,5-caaquinolin-5-oxyforbindelser
DK135891A DK164455C (da) 1983-11-18 1991-07-16 1h-imidazooe4,5-caaquinolin-4-chlorforbindelser

Family Applications After (5)

Application Number Title Priority Date Filing Date
DK135791A DK169179B1 (da) 1983-11-18 1991-07-16 1H-imidazo[4,5-c]quinolin-4-amin, farmaceutisk præparat indeholdende en sådan forbindelse og fremga ngsmåde til fremstilling af en sådan forbindelse
DK136091A DK164451C (da) 1983-11-18 1991-07-16 3-aminoquinolinderivat
DK136191A DK164452C (da) 1983-11-18 1991-07-16 3-nitroquinolinderivat
DK135991A DK165921C (da) 1983-11-18 1991-07-16 1h-imidazooe4,5-caaquinolin-5-oxyforbindelser
DK135891A DK164455C (da) 1983-11-18 1991-07-16 1h-imidazooe4,5-caaquinolin-4-chlorforbindelser

Country Status (15)

Country Link
EP (2) EP0310950B1 (no)
JP (1) JPS60123488A (no)
KR (1) KR900005657B1 (no)
AT (2) ATE84525T1 (no)
AU (2) AU581190B2 (no)
CA (1) CA1271477A (no)
DE (3) DE3481124D1 (no)
DK (6) DK164280C (no)
ES (1) ES537677A0 (no)
IE (1) IE57874B1 (no)
IL (2) IL84537A (no)
NL (2) NL980043I1 (no)
NO (7) NO163819C (no)
NZ (1) NZ210228A (no)
PH (1) PH22338A (no)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1306260C (en) * 1985-10-18 1992-08-11 Shionogi & Co., Ltd. Condensed imidazopyridine derivatives
US4942168A (en) * 1987-07-13 1990-07-17 Hoechst-Roussel Pharmaceuticals Inc. Hydroxyquinoline amines, and method of enhancing memory in mammals
CA1335996C (en) * 1988-02-16 1995-06-20 Susumu Takada 2-substituted carbonylimidazo¬4,5-c|quinolines
EP0361489A3 (en) * 1988-09-30 1991-06-12 Chugai Seiyaku Kabushiki Kaisha Novel 3,4-diaminoquinoline and pyridine compounds
EP0385630B1 (en) * 1989-02-27 1996-11-27 Riker Laboratories, Inc. 1H-imidazo(4,5-c)Quinolin-4-amines as antivirals
CA2011504C (en) * 1989-03-07 1998-06-02 Kenji Ohmori Imidazoquinolone derivatives
US4929624A (en) * 1989-03-23 1990-05-29 Minnesota Mining And Manufacturing Company Olefinic 1H-imidazo(4,5-c)quinolin-4-amines
JP2988692B2 (ja) * 1989-07-18 1999-12-13 協和醗酵工業株式会社 イミダゾキノロン誘導体
US4988815A (en) * 1989-10-26 1991-01-29 Riker Laboratories, Inc. 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines
FR2654021B1 (fr) * 1989-11-07 1992-02-28 Simond Jacques Procede de vitrification de cendres volantes et dispositif pour sa mise en óoeuvre.
GB8928281D0 (en) * 1989-12-14 1990-02-21 Smith Kline French Lab Compounds
JP3016905B2 (ja) * 1990-06-01 2000-03-06 協和醗酵工業株式会社 イミダゾナフチリジン誘導体
ES2131070T3 (es) * 1991-03-01 1999-07-16 Minnesota Mining & Mfg 1h-imidazo(4,5-c)quinolin-4-aminas sustituidas en posicion 1 y sustituidas en posicion 2.
US5266575A (en) * 1991-11-06 1993-11-30 Minnesota Mining And Manufacturing Company 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines
IL105325A (en) * 1992-04-16 1996-11-14 Minnesota Mining & Mfg Immunogen/vaccine adjuvant composition
US5395937A (en) * 1993-01-29 1995-03-07 Minnesota Mining And Manufacturing Company Process for preparing quinoline amines
US5693811A (en) * 1996-06-21 1997-12-02 Minnesota Mining And Manufacturing Company Process for preparing tetrahdroimidazoquinolinamines
EP0894797A4 (en) * 1997-01-09 2001-08-16 Terumo Corp NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS
JPH10298181A (ja) * 1997-04-25 1998-11-10 Sumitomo Pharmaceut Co Ltd タイプ2ヘルパーt細胞選択的免疫応答抑制剤
JP2000119271A (ja) 1998-08-12 2000-04-25 Hokuriku Seiyaku Co Ltd 1h―イミダゾピリジン誘導体
EP1438295B1 (en) * 2001-10-23 2012-08-15 Merck Serono SA Azole derivatives and pharmaceutical compositions containing them
GB0211649D0 (en) * 2002-05-21 2002-07-03 Novartis Ag Organic compounds
PT1543002E (pt) 2002-07-23 2006-11-30 Teva Gyogyszergyar Zartkoeruen Preparação de intermediários 1h-imidazo ( 4,5-c )quinolin-4-aminas via 1h- imidazo (4,5-c ) quinolina-4-ftalimida
IL166307A0 (en) 2002-07-26 2006-01-15 Preparation of 1h-imidazoÄ4,5-cÜquinolin-4-amines via novel 1h-imidazoÄ4,5-cÜquinolin-4-cyano and 1h-imidazo Ä4,5-cÜquinolin-4-cyano and 1h-imidazoÄ4,5-cÜquinolin-4-carboxamide intermediates
AR045260A1 (es) 2003-08-12 2005-10-19 3M Innovative Properties Co Compuestos que contienen imidazo-oxima sustituidos
JP5128815B2 (ja) * 2003-08-27 2013-01-23 スリーエム イノベイティブ プロパティズ カンパニー アリールオキシ置換およびアリールアルキレンオキシ置換イミダゾキノリン
EP1660026A4 (en) 2003-09-05 2008-07-16 3M Innovative Properties Co TREATMENT FOR CD5 + B CELL LYMPHOMA
CA2536530A1 (en) 2003-10-01 2005-04-14 Taro Pharmaceuticals U.S.A., Inc. Method of preparing 4-amino-1h-imidazo(4,5-c)quinolines and acid addition salts thereof
EP1673087B1 (en) 2003-10-03 2015-05-13 3M Innovative Properties Company Alkoxy substituted imidazoquinolines
US7544697B2 (en) 2003-10-03 2009-06-09 Coley Pharmaceutical Group, Inc. Pyrazolopyridines and analogs thereof
ITMI20032121A1 (it) * 2003-11-04 2005-05-05 Dinamite Dipharma Spa In Forma Abbr Eviata Dipharm Procedimento per la preparazione di imiquimod e suoi intermedi
US8598192B2 (en) 2003-11-14 2013-12-03 3M Innovative Properties Company Hydroxylamine substituted imidazoquinolines
CA2545774A1 (en) 2003-11-14 2005-06-02 3M Innovative Properties Company Oxime substituted imidazo ring compounds
WO2005051317A2 (en) 2003-11-25 2005-06-09 3M Innovative Properties Company Substituted imidazo ring systems and methods
JP2007517035A (ja) 2003-12-29 2007-06-28 スリーエム イノベイティブ プロパティズ カンパニー アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン
WO2005066169A2 (en) 2003-12-30 2005-07-21 3M Innovative Properties Company Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides
AU2005228150A1 (en) 2004-03-24 2005-10-13 3M Innovative Properties Company Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
US8017779B2 (en) 2004-06-15 2011-09-13 3M Innovative Properties Company Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
US8026366B2 (en) 2004-06-18 2011-09-27 3M Innovative Properties Company Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
US7897609B2 (en) 2004-06-18 2011-03-01 3M Innovative Properties Company Aryl substituted imidazonaphthyridines
WO2006065280A2 (en) 2004-06-18 2006-06-22 3M Innovative Properties Company Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods
JP5543068B2 (ja) 2004-12-30 2014-07-09 スリーエム イノベイティブ プロパティズ カンパニー キラル縮合[1,2]イミダゾ[4,5−c]環状化合物
CA2594674C (en) 2004-12-30 2016-05-17 3M Innovative Properties Company Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
US9248127B2 (en) 2005-02-04 2016-02-02 3M Innovative Properties Company Aqueous gel formulations containing immune response modifiers
AU2006213746A1 (en) 2005-02-11 2006-08-17 Coley Pharmaceutical Group, Inc. Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods
US7943610B2 (en) 2005-04-01 2011-05-17 3M Innovative Properties Company Pyrazolopyridine-1,4-diamines and analogs thereof
WO2006107851A1 (en) 2005-04-01 2006-10-12 Coley Pharmaceutical Group, Inc. 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
EP1931352B1 (en) 2005-08-22 2016-04-13 The Regents of The University of California Tlr agonists
CA2653941C (en) 2006-05-31 2013-01-08 The Regents Of The University Of California Substituted amino purine derivatives and uses thereof
WO2008008432A2 (en) 2006-07-12 2008-01-17 Coley Pharmaceutical Group, Inc. Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods
EA019151B1 (ru) 2007-02-07 2014-01-30 Дзе Регентс Оф Дзе Юниверсити Оф Калифорния Конъюгаты синтетических агонистов tlr и их применение
EP2009002A1 (en) * 2007-06-21 2008-12-31 Institut National De La Sante Et De La Recherche Medicale (Inserm) New process for the manufacture of 1H-imidazo [4,5-c]-quinoline ring systems
WO2010088924A1 (en) 2009-02-06 2010-08-12 Telormedix Sa Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration
AU2010214112B2 (en) 2009-02-11 2015-04-09 The Regents Of The University Of California Toll-like receptor modulators and treatment of diseases
CN103097386A (zh) * 2010-08-17 2013-05-08 3M创新有限公司 脂质化免疫反应调节剂化合物的组合物、制剂及方法
US8728486B2 (en) 2011-05-18 2014-05-20 University Of Kansas Toll-like receptor-7 and -8 modulatory 1H imidazoquinoline derived compounds
US9873694B2 (en) 2011-10-04 2018-01-23 Janus Biotherapeutics, Inc. Imidazole quinoline-based immune system modulators
MX369611B (es) * 2013-02-01 2019-11-14 Wellstat Therapeutics Corp Compuestos de amina que tienen actividad anti-inflamatoria, antifungica, antiparasitaria y anticancer.
CA2902833A1 (en) * 2013-03-15 2014-09-18 Syngenta Participations Ag Microbicidally active imidazopyridine derivatives
ES2538880B1 (es) * 2013-12-24 2016-09-08 Laboratorios Viñas S.A. Un procedimiento para obtener 4-amino-1-isobutil-1H-imidazo[4,5-c]quinoleína
AU2015205753A1 (en) 2014-01-10 2016-07-21 Birdie Biopharmaceuticals Inc. Compounds and compositions for treating HER2 positive tumors
JP6760919B2 (ja) 2014-07-09 2020-09-23 バーディー バイオファーマシューティカルズ インコーポレイテッド 腫瘍を治療するための抗pd−l1組み合わせ
CN108137586B (zh) * 2015-09-14 2021-04-13 辉瑞大药厂 作为LRRK2抑制剂的新颖咪唑并[4,5-c]喹啉和咪唑并[4,5-c][1,5]萘啶衍生物
CN106943596A (zh) 2016-01-07 2017-07-14 博笛生物科技(北京)有限公司 用于治疗肿瘤的抗-cd20组合
CN115252792A (zh) 2016-01-07 2022-11-01 博笛生物科技有限公司 用于治疗肿瘤的抗-egfr组合
US10533007B2 (en) 2016-04-19 2020-01-14 Innate Tumor Immunity, Inc. NLRP3 modulators
JP7104633B6 (ja) 2016-04-19 2023-12-22 イネイト・テューマー・イミュニティ・インコーポレイテッド Nlrp3修飾因子
US11697851B2 (en) 2016-05-24 2023-07-11 The Regents Of The University Of California Early ovarian cancer detection diagnostic test based on mRNA isoforms
TWI674261B (zh) 2017-02-17 2019-10-11 美商英能腫瘤免疫股份有限公司 Nlrp3 調節劑
CN118515666A (zh) 2017-04-27 2024-08-20 博笛生物科技有限公司 2-氨基-喹啉衍生物
EP3641771A4 (en) 2017-06-23 2020-12-16 Birdie Biopharmaceuticals, Inc. PHARMACEUTICAL COMPOSITIONS
FR3113287B1 (fr) 2020-08-07 2023-06-23 Phv Pharma Procédé industriel de synthèse de l’imiquimod à partir de la quinolèine-2,4-diol applicable à son utilisation pharmaceutique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3700674A (en) * 1969-04-30 1972-10-24 American Cyanamid Co 4-alkylamino-3-nitroquinolines
IL68495A0 (en) * 1982-05-03 1983-07-31 Lilly Co Eli 2-phenylimidazo(4,5-c)pyridines

Also Published As

Publication number Publication date
NO890823D0 (no) 1989-02-27
NO1999015I1 (no) 1999-07-08
ES8603477A1 (es) 1985-12-16
NO890823L (no) 1985-05-20
NO165146C (no) 1991-01-02
NO165147C (no) 1991-01-02
NO890825D0 (no) 1989-02-27
NO890825L (no) 1985-05-20
EP0145340A2 (en) 1985-06-19
EP0145340B1 (en) 1990-01-24
DK135791D0 (da) 1991-07-16
AU581190B2 (en) 1989-02-16
DK164280B (da) 1992-06-01
NO169437C (no) 1992-06-24
AU2991189A (en) 1989-06-15
KR850003890A (ko) 1985-06-29
DK136191A (da) 1991-07-16
NO890826L (no) 1985-05-20
NL980041I1 (nl) 1999-02-01
NO165145B (no) 1990-09-24
NO890824L (no) 1985-05-20
IE842952L (en) 1985-05-18
DK542684A (da) 1985-05-19
NO168705B (no) 1991-12-16
JPS60123488A (ja) 1985-07-02
AU611997B2 (en) 1991-06-27
NO890822L (no) 1985-05-20
ATE84525T1 (de) 1993-01-15
DK542684D0 (da) 1984-11-15
DK165921B (da) 1993-02-08
NO163819C (no) 1990-08-01
NL980043I1 (nl) 1999-02-01
DE3481124D1 (de) 1990-03-01
DK164455C (da) 1992-11-16
NO890826D0 (no) 1989-02-27
DE3486043T2 (de) 1993-06-03
CA1271477A (en) 1990-07-10
NO169437B (no) 1992-03-16
DK164451B (da) 1992-06-29
DK164451C (da) 1992-11-09
IL84537A (en) 1990-12-23
DK164455B (da) 1992-06-29
NO165146B (no) 1990-09-24
AU3540284A (en) 1985-05-23
DK135891A (da) 1991-07-16
ES537677A0 (es) 1985-12-16
DE19975027I2 (de) 2000-09-21
NO165145C (no) 1991-01-02
NO163819B (no) 1990-04-17
DK135991A (da) 1991-07-16
DK169179B1 (da) 1994-09-05
NL980041I2 (nl) 1999-07-01
DK164452B (da) 1992-06-29
DK135991D0 (da) 1991-07-16
NO890822D0 (no) 1989-02-27
DK135891D0 (da) 1991-07-16
EP0310950B1 (en) 1993-01-13
PH22338A (en) 1988-08-12
DK136191D0 (da) 1991-07-16
NO890824D0 (no) 1989-02-27
NO844565L (no) 1985-05-20
ATE49763T1 (de) 1990-02-15
EP0310950A1 (en) 1989-04-12
DK135791A (da) 1991-07-16
DE3486043D1 (de) 1993-02-25
DK136091A (da) 1991-07-16
DK165921C (da) 1993-06-28
KR900005657B1 (ko) 1990-08-03
IL84537A0 (en) 1988-04-29
JPH0586391B2 (no) 1993-12-10
NZ210228A (en) 1989-01-27
NO165147B (no) 1990-09-24
DK136091D0 (da) 1991-07-16
EP0145340A3 (en) 1986-06-11
IE57874B1 (en) 1993-05-05
DK164452C (da) 1992-11-09
NO168705C (no) 1992-03-25

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Publication Publication Date Title
DK164280C (da) 1h-imidazooe4,5-caaquinolin eller derivat deraf og farmaceutisk praeparat indeholdende en saadan forbindelse

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