PE20061350A1 - DERIVATIVES OF 5H-BENZOCICLOHEPTENO, PROCEDURES FOR THEIR PREPARATION AND USE AS ANTI-INFLAMMATORY - Google Patents

DERIVATIVES OF 5H-BENZOCICLOHEPTENO, PROCEDURES FOR THEIR PREPARATION AND USE AS ANTI-INFLAMMATORY

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Publication number
PE20061350A1
PE20061350A1 PE2006000307A PE2006000307A PE20061350A1 PE 20061350 A1 PE20061350 A1 PE 20061350A1 PE 2006000307 A PE2006000307 A PE 2006000307A PE 2006000307 A PE2006000307 A PE 2006000307A PE 20061350 A1 PE20061350 A1 PE 20061350A1
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PE
Peru
Prior art keywords
alkyl
benzociclohepten
tetrahydro
hydroxy
dimethyl
Prior art date
Application number
PE2006000307A
Other languages
Spanish (es)
Inventor
Hartmut Rehwinkel
Duy Nguyen
Heike Schacke
Markus Berger
Original Assignee
Schering Ag
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Publication date
Application filed by Schering Ag filed Critical Schering Ag
Publication of PE20061350A1 publication Critical patent/PE20061350A1/en

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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86Oxygen atoms
    • C07D211/88Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • 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
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/04Antipruritics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
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    • A61P27/16Otologicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P35/00Antineoplastic agents
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
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    • A61P37/08Antiallergic agents
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/14Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A61P5/16Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06Antianaemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
    • C07D215/20Oxygen atoms
    • C07D215/22Oxygen atoms attached in position 2 or 4
    • C07D215/227Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56Benzopyrazoles; Hydrogenated benzopyrazoles
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Reproductive Health (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Cardiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Urology & Nephrology (AREA)
  • Neurosurgery (AREA)
  • Pregnancy & Childbirth (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

SE REFIERE A COMPUESTOS DE 5H-BENZOCICLOHEPTENOS DE FORMULA (I) DONDE R1 Y R2 SON INDEPENDIENTEMENTE H, HIDROXI, HALOGENO, ALQUILO(C1-C10), CIANO, -CF3, ENTRE OTROS; R11Y R12 SON H; R3 ES ALQUILO(C1-C10), FENILO OPCIONALMENTE SUSTITUIDOS, HETEROARILO MONO- O BICICLICO QUE CONTIENE DE 1 A 3 ATOMOS DE N, Y/O O U S, OPCIONALMENTE SUSTITUIDOS CON CETO, ALQUILO(C1-C5), ENTRE OTROS , TAL COMO FTALIDILO, ISOINDOLILO, DIHIDROISOINDOLILO, ENTRE OTROS; A ES -CR6R7-CH2- O -CH2-CR6R7- DONDE R6 Y R7 SON H, METILO, ETILO O JUNTO CON EL CARBONO DE 5H-BENZOCICLOHEPTENO SON UN ANILLO CICLOALQUILO(C3-C6); D ES -CR4R5-CH2- O -CH2-CR4R5- DONDE R4 ES HIDROXI, ENTRE OTROS Y R5 ES ALQUILO(C1-C5) OPCIONALMENTE FLUORADO, CICLOALQUILO(C3-C7), ENTRE OTROS. SON COMPUESTOS PREFERIDOS: 1-BROMO-6,7,8,9-TETRAHIDRO-5-[(1H-INDAZOL-4-IL)AMINO]-8,8-DIMETIL-6-(TRIFLUOROMETIL)-5H-BENZOCICLOHEPTEN-6-OL, 4-{[1-BROMO-6,7,8,9-TETRAHIDRO-6-HIDROXI-8,8-DIMETIL-6-(TRIFLUOROMETIL)-5H-BENZOCICLOHEPTEN-5-IL]AMINO}-1,3-DIHIDRO-2H-INDOL-2-ONA, 2-CLORO-6,7,8,9-TETRAHIDRO-5-(1H-INDAZOL-4-ILAMINO)-8,8-DIMETIL-6-(TRIFLUOROMETIL)-5H-BENZOCICLOHEPTEN-6-OL, ENTRE OTROS. SE REFIERE TAMBIEN A UN PROCEDIMIENTO DE PREPARACION Y A UNA COMPOSICION FARMACEUTICA. DICHOS COMPUESTOS INHIBEN LA SECRECION DE LA CITOQUINA IL-8 PROVOCADA POR LIPOPOLISACARIDOS (LPS) SIENDO UTILES EN EL TRATAMIENTO DE ENFERMEDADES INFLAMATORIAS TALES COMO ASMA BRONQUIAL, ARTRITIS REUMATOIDEA, DERMATITIS ATOPICA, PSORIASISREFERS TO COMPOUNDS OF 5H-BENZOCYCLOHEPTENES OF FORMULA (I) WHERE R1 AND R2 ARE INDEPENDENTLY H, HYDROXY, HALOGEN, ALKYL (C1-C10), CYANE, -CF3, AMONG OTHERS; R11 AND R12 ARE H; R3 IS ALKYL (C1-C10), OPTIONALLY SUBSTITUTED PHENYL, MONO- OR BICYCLIC HETEROARYL, CONTAINING 1 TO 3 N ATOMS, AND / OOUS, OPTIONALLY SUBSTITUTED WITH CETUS, ALKYL (C1-C5), BETWEEN OTHERS , ISOINDOLYL, DIHYDROISOINDOLYL, AMONG OTHERS; A IS -CR6R7-CH2- OR -CH2-CR6R7- WHERE R6 AND R7 ARE H, METHYL, ETHYL OR TOGETHER WITH THE CARBON OF 5H-BENZOCICLOHEPTENO IS A CYCLOALKYL RING (C3-C6); D IS -CR4R5-CH2- OR -CH2-CR4R5- WHERE R4 IS HYDROXY, AMONG OTHERS AND R5 IS ALKYL (C1-C5) OPTIONALLY FLUORATED, CYCLOALKYL (C3-C7), AMONG OTHERS. THE PREFERRED COMPOUNDS ARE: 1-BROMO-6,7,8,9-TETRAHYDRO-5 - [(1H-INDAZOL-4-IL) AMINO] -8,8-DIMETHYL-6- (TRIFLUOROMETIL) -5H-BENZOCICLOHEPTEN-6 -OL, 4 - {[1-BROMO-6,7,8,9-TETRAHYDRO-6-HYDROXY-8,8-DIMETHYL-6- (TRIFLUORomethyl) -5H-BENZOCICLOHEPTEN-5-IL] AMINO} -1, 3-DIHYDRO-2H-INDOL-2-ONA, 2-CHLORO-6,7,8,9-TETRAHYDRO-5- (1H-INDAZOL-4-ILAMINO) -8,8-DIMETHYL-6- (TRIFLUOROMETHYL) - 5H-BENZOCICLOHEPTEN-6-OL, AMONG OTHERS. IT ALSO REFERS TO A PREPARATION PROCEDURE AND A PHARMACEUTICAL COMPOSITION. SUCH COMPOUNDS INHIBIT THE SECRETION OF CYTOKINE IL-8 CAUSED BY LIPOPOLYSACCHARIDES (LPS), BEING USEFUL IN THE TREATMENT OF INFLAMMATORY DISEASES SUCH AS BRONCHIAL ASTHMA, RHEUMATOID ARTHRITIS, ATOPIC DERMATITIS, PSORIASIS

PE2006000307A 2005-03-22 2006-03-21 DERIVATIVES OF 5H-BENZOCICLOHEPTENO, PROCEDURES FOR THEIR PREPARATION AND USE AS ANTI-INFLAMMATORY PE20061350A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005014090A DE102005014090A1 (en) 2005-03-22 2005-03-22 5H-Benzocycloheptender derivatives, process for their preparation and their use as anti-inflammatory agents

Publications (1)

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PE20061350A1 true PE20061350A1 (en) 2006-12-20

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PE2006000307A PE20061350A1 (en) 2005-03-22 2006-03-21 DERIVATIVES OF 5H-BENZOCICLOHEPTENO, PROCEDURES FOR THEIR PREPARATION AND USE AS ANTI-INFLAMMATORY

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Country Link
EP (1) EP1863765A1 (en)
JP (1) JP2008534462A (en)
CN (1) CN101146773A (en)
AR (1) AR053189A1 (en)
CA (1) CA2598969A1 (en)
DE (1) DE102005014090A1 (en)
DO (1) DOP2006000065A (en)
GT (1) GT200600124A (en)
PA (1) PA8666801A1 (en)
PE (1) PE20061350A1 (en)
TW (1) TW200700389A (en)
UY (1) UY29435A1 (en)
WO (1) WO2006100099A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA038639B1 (en) * 2016-02-15 2021-09-28 Санофи 6,7-dihydro-5h-benzo[7]annulene derivatives as estrogen receptor modulators
CN107118173B (en) * 2017-07-12 2019-10-29 阿里生物新材料(常州)有限公司 A kind of cycloheptatriene and oxazine compound and preparation method thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU8402275A (en) * 1974-08-26 1977-02-17 Takeda Chemical Industries Ltd Benzocycloheptene derivatives
AU617672B2 (en) * 1987-05-15 1991-12-05 Schering Corporation Aryl substituted naphthalene, benzoxepine, benzazepine, benzocycloheptene derivatives
ATE145907T1 (en) * 1987-07-16 1996-12-15 Byk Gulden Lomberg Chem Fab IMIDAZO(1,2-A>PYRIDINE
CA2297910A1 (en) * 1997-07-25 1999-02-04 Smithkline Beecham Corporation Vitronectin receptor antagonist
MXPA05007937A (en) * 2003-02-07 2005-09-30 Warner Lambert Co Oxazolidinone derivatives n-substituted by a bicyclic ring, for use as antibacterial agents.

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EP1863765A1 (en) 2007-12-12
CN101146773A (en) 2008-03-19
DOP2006000065A (en) 2006-10-15
AR053189A1 (en) 2007-04-25
CA2598969A1 (en) 2006-09-28
UY29435A1 (en) 2006-10-02
JP2008534462A (en) 2008-08-28
DE102005014090A1 (en) 2006-09-28
TW200700389A (en) 2007-01-01
GT200600124A (en) 2007-01-03
PA8666801A1 (en) 2006-09-22
WO2006100099A1 (en) 2006-09-28

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