CA2506082A1 - Novel medicaments for the treatment of chronic obstructive pulmonary disease - Google Patents

Novel medicaments for the treatment of chronic obstructive pulmonary disease Download PDF

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Publication number
CA2506082A1
CA2506082A1 CA002506082A CA2506082A CA2506082A1 CA 2506082 A1 CA2506082 A1 CA 2506082A1 CA 002506082 A CA002506082 A CA 002506082A CA 2506082 A CA2506082 A CA 2506082A CA 2506082 A1 CA2506082 A1 CA 2506082A1
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denotes
alkyl
compounds
methyl
general formula
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CA002506082A
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French (fr)
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CA2506082C (en
Inventor
Thierry Bouyssou
Frank Buettner
Ingo Konetzki
Sabine Pestel
Andreas Schnapp
Hermann Schollenberger
Kurt Schromm
Claudia Heine
Klaus Rudolf
Philipp Lustenberger
Christoph Hoenke
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Boehringer Ingelheim Pharma GmbH and Co KG
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Publication of CA2506082A1 publication Critical patent/CA2506082A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/5381,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/341,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/361,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to the use of compounds of general formula (1):

(see formula I) including those wherein n denotes 1;

R1 denotes hydrogen, halogen, C1-C4-alkyl or -O-C1-C4-alkyl;

R2 denotes hydrogen, halogen, C1-C4-alkyl or -O-C1-C4-alkyl; and R3 denotes hydrogen, halogen, C1-C4-alkyl, -O-C1-C4-alkyl, -O-CH2-COOH, -O-CH2-COOmethyl or -O-CH2-COOethyl for the production of a medicament for the treatment of COPD (Chronic Obstructive Pulmonary Disease) and novel compounds of general formula (I) as such.

Claims (27)

1. Use of compounds of general formula 1 wherein n denotes 1 or 2, R1 denotes hydrogen, C1-C4-alkyl, halogen, OH or -O-C1-C4-alkyl;
R2 denotes hydrogen, C1-C4-alkyl, halogen, OH or -O-C1-C4-alkyl;
R3 denotes hydrogen, C1-C4-alkyl, OH, halogen, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, for preparing a pharmaceutical composition for the treatment of COPD.
2) Use of compounds of general formula 1 according to claim 1, wherein n denotes 1 or 2, R1 denotes hydrogen, halogen or C1-C4-alkyl;
R2 denotes hydrogen, halogen or C1-C4-alkyl;
R3 denotes hydrogen, C1-C4-alkyl, OH, halogen, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH or -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, for preparing a pharmaceutical composition for the treatment of COPD.
3) Use of compounds of general formula 1 according to claim 1 or 2, wherein n denotes 1 or 2;
R1 denotes hydrogen, fluorine, chlorine or methyl;
R2 denotes hydrogen, fluorine, chlorine or methyl;
R3 denotes hydrogen, C1-C4-alkyl, OH, fluorine, chlorine, bromine, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH, -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, for preparing a pharmaceutical composition for the treatment of COPD.
4) ~Use of compounds of general formula 1 according to claim 1 or 2, wherein n ~denotes 1 or 2, R' ~denotes hydrogen, methyl or ethyl;
R2 ~denotes hydrogen, methyl or ethyl;
R3 ~denotes hydrogen, methyl, ethyl, OH, methoxy, ethoxy, -O-CH2-COOH, -O-CH2-CO-O-methyl or -O-CH2-COOethyl;
for preparing a pharmaceutical composition for the treatment of COPD.
5) ~Use of compounds of general formula 1, according to one of claims 1 to 4, wherein n ~denotes 1 or 2, R1 ~denotes hydrogen or methyl;
R2 ~denotes hydrogen or methyl;
R3 ~denotes hydrogen, methyl, OH, methoxy, -O-CH2-COOH or -O-CH2-COOethyl;
for preparing a pharmaceutical composition for the treatment of COPD.
6) ~Use of compounds of general formula 1 according to one of claims 1 to 5, wherein the compounds of formula 1 are present in the form of the individual optical isomers, mixtures of the individual enantiomers or racemates, preferably in the form of the enantiomerically pure compounds.
7) ~Use of compounds of general formula 1 according to one of claims 1 to 6, wherein the compounds of formula 1 are present in the form of the acid addition salts with pharmacologically acceptable acids as well as optionally in the form of the solvates and/or hydrates.
8) ~Compounds of general formula 1 wherein n ~denotes 1;
R1 ~denotes hydrogen, halogen, C1-C4-alkyl or -O-C1-C4-alkyl;
R2 ~denotes hydrogen, halogen, C1-C4-alkyl or -O-C1-Ca-alkyl;
R3 ~denotes C1-C4-alkyl, OH, halogen, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH, -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, with the proviso that if R1 and R2 each represent ortho-methyl, R3 cannot simultaneously be OH.
9) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;
R1 ~denotes hydrogen, fluorine, chlorine, methyl or methoxy;
R2 ~denotes hydrogen, fluorine, chlorine, methyl or methoxy;
R3 ~denotes C1-C4-alkyl, OH, fluorine, chlorine, bromine, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH, -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, with the proviso that if R1 and R2 each represent ortho-methyl, R3 cannot simultaneously be OH.
10) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;
R1 ~denotes hydrogen or C1-C4-alkyl;
R2 ~denotes hydrogen or C1-C4-alkyl;
R3 ~denotes C1-C4-alkyl, OH, -O-C1-C4-alkyl, -O-C1-C4-alkylene-COOH
or -O-C1-C4-alkylene-CO-O-C1-C4-alkyl, with the proviso that if R1 and R2 each represent ortho-methyl, R3 cannot simultaneously be OH.
11) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;
R1 ~denotes hydrogen, methyl or ethyl;
R2 ~denotes hydrogen, methyl or ethyl;
R3 ~denotes methyl, ethyl, OH, methoxy, ethoxy, -O-CH2-COOH, -O-CH2-COOmethyl or -O-CH2-COOethyl, with the proviso that if R1 and R2 each represent ortho-methyl, R3 cannot simultaneously be OH.
12) ~Compounds of general formula 1 according to one of claims 8 to 11, wherein R3 ~denotes methoxy, ethoxy, -O-CH2-COOH, -O-CH2-COOmethyl or -O-CH2-COOethyl, and R1, R2 and n may have the meanings given in claims 8 to 11.
13) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;
R1 ~denotes halogen, C1-C4-alkyl or -O-C1-C4-alkyl;
R2 ~denotes halogen, C1-C4-alkyl or -O-C1-C4-alkyl;
R3 ~denotes halogen, C1-C4-alkyl or -O-C1-C4-alkyl.
14) ~Compounds of general formula 1 according to claim 13, wherein n ~denotes 1;
R1 ~denotes fluorine, chlorine, methyl or methoxy;
R2 ~denotes fluorine, chlorine, methyl or methoxy;
R3 ~denotes fluorine, chlorine, methyl or methoxy.
15) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;
R1 ~denotes hydrogen;
R2 ~denotes hydrogen, fluorine, chlorine or methyl;
R3 ~denotes methyl, ethyl, iso-propyl, tert.-butyl, OH, fluorine, chlorine, bromine, methoxy, ethoxy, -O-CH2-COOH, -O-CH2-CH2-COOH, -O-CH2-CH2-CH2-COOH, -O-CH2-COOmethyl, -O-CH2-COOethyl, -O-CH2-CH2-COOmethyl, -O-CH2-CH2-COOethyl, -O-CH2-CH2-CH2-COOmethyl, -O-CH2-CH2-CH2-COOethyl.
16) ~Compounds of general formula 1 according to claim 15, wherein n ~denotes 1;
R1 ~denotes hydrogen;
R2 ~denotes hydrogen, fluorine, chlorine or methyl;
R3 ~denotes OH, fluorine, chlorine, methyl, methoxy, ethoxy or -O-CH2-COOH.
17) ~Compounds of general formula 1 according to claim 8, wherein n ~denotes 1;

54~

R1 and R2 ~denote hydrogen;
R3 ~~denotes methyl, ethyl, iso-propyl, tert.-butyl, OH, fluorine, chlorine, bromine, methoxy, ethoxy, -O-CH2-COOH, -O-CH2-CH2-COOH, -O-CH2-CH2-CH2-COOH, -O-CH2-COOmethyl, -O-CH2-COOethyl, -O-CH2-CH2-COOmethyl, -O-CH2-CH2-COOethyl, -O-CH2-CH2-CH2-COOmethyl, -O-CH2-CH2-CH2-COOethyl.
18) ~~Compounds of general formula 1 according to claim 17, wherein n ~~denotes 1;
R' and R2 ~denote hydrogen;
R3 ~~denotes OH, fluorine, chlorine, methoxy, ethoxy,-O-CH2-COOH, preferably OH, fluorine, chlorine, ethoxy or methoxy.
19) ~~Compounds of general formula 1 according to claim 8, wherein n ~~denotes 1;
R1 ~~denotes hydrogen, halogen, C1-C4-alkyl or-O-C1-C4-alkyl;
R2 ~~denotes hydrogen, halogen, C1-C4-alkyl or -O-C1-C4-alkyl;
R3 ~~denotes hydrogen.
20) ~~Compounds of general formula 1 according to claim 19, wherein n ~~denotes 1;
R1 ~~denotes hydrogen, fluorine, chlorine, methyl or methoxy;
R2 ~~denotes hydrogen, fluorine, chlorine, methyl or methoxy;
R3 ~~denotes hydrogen.
21) ~~Compounds of general formula 1 according to one of claims 8 to 20, wherein the compounds of formula 1 are present in the form of the individual optical isomers, mixtures of the individual enantiomers or racemates, preferably in the form of the enantiomerically pure compounds.
22) ~~Compounds of general formula 1 according to one of claims 8 to 21, wherein the compounds of formula 1 are present in the form of the acid addition salts thereof with pharmacologically acceptable acids as well as optionally in the form of the solvates and/or hydrates.
23) ~~Use of the compounds of general formula 1 according to one of claims 8 to 22 as pharmaceutical compositions.
24) ~Use of the compounds of general formula 1 according to one of claims 8 to 22, for preparing a pharmaceutical composition for the treatment of COPD.
25) ~Pharmaceutical formulation, characterised in that it contains a compound of formula 1 according to one of claims 8 to 22.
26) ~Pharmaceutical formulation for administration by inhalation, characterised in that it contains a compound of formula 1 according to one of claims 8 to 22.
27) ~Pharmaceutical formulation for administration by inhalation according to claim 26, characterised in that it is selected from among the inhalable powders, propellant-containing metered-dose aerosols and propellant-free inhalable solutions.
CA2506082A 2002-11-15 2003-11-11 Novel medicaments for the treatment of chronic obstructive pulmonary disease Expired - Lifetime CA2506082C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10253282.6 2002-11-15
DE10253282A DE10253282A1 (en) 2002-11-15 2002-11-15 Treatment of chronic obstructive pulmonary disease, using new or known N-substituted 2-amino-1-(benz-(1,4)-oxazin-3-on-8-yl)-ethanol derivative beta-mimetic agents, suitable for once-daily administration
PCT/EP2003/012565 WO2004045618A2 (en) 2002-11-15 2003-11-11 Novel medicaments for the treatment of chronic obstructive pulmonary diseases

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CA2506082A1 true CA2506082A1 (en) 2004-06-03
CA2506082C CA2506082C (en) 2011-06-21

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EP (2) EP2025338A1 (en)
JP (1) JP4317138B2 (en)
KR (1) KR101092247B1 (en)
CN (3) CN1713914A (en)
AR (2) AR041969A1 (en)
AT (1) ATE430569T1 (en)
AU (1) AU2003285326B2 (en)
BE (1) BE2014C016I2 (en)
BR (1) BRPI0316264B8 (en)
CA (1) CA2506082C (en)
CO (1) CO5570670A2 (en)
CY (2) CY1110500T1 (en)
DE (2) DE10253282A1 (en)
DK (1) DK1562603T3 (en)
EA (1) EA008665B1 (en)
EC (1) ECSP055774A (en)
ES (1) ES2326878T7 (en)
FR (1) FR14C0049I2 (en)
HR (1) HRP20050432B1 (en)
HU (1) HUS1400011I1 (en)
IL (1) IL167900A (en)
LT (1) LTC1562603I2 (en)
LU (1) LU92433I2 (en)
ME (1) ME00354B (en)
MX (1) MXPA05005081A (en)
MY (1) MY136034A (en)
NL (1) NL300650I2 (en)
NO (2) NO334314B1 (en)
NZ (1) NZ540661A (en)
PE (1) PE20040694A1 (en)
PL (1) PL212238B1 (en)
PT (1) PT1562603E (en)
RS (1) RS51607B (en)
SI (1) SI1562603T1 (en)
TW (1) TWI343812B (en)
UA (1) UA81276C2 (en)
WO (1) WO2004045618A2 (en)
ZA (1) ZA200502246B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7423036B2 (en) 2005-02-19 2008-09-09 Boehringer Ingelheim International Gmbh Long-acting betamimetics for the treatment of respiratory complaints
US7491719B2 (en) 2004-05-14 2009-02-17 Boehringer Ingelheim International Gmbh Enantiomerically pure beta agonists, process for the manufacture thereof, and use thereof as medicaments
US7534789B2 (en) 2006-03-15 2009-05-19 Boehringer Ingelheim International Gmbh Enantiomeric pure β agonists, manufacturing and use as a medicament thereof
US7727984B2 (en) 2002-11-15 2010-06-01 Boehringer Ingelheim Pharma Gmbh & Co., Kg Medicaments for the treatment of chronic obstructive pulmonary disease
US20120035169A1 (en) * 2004-05-14 2012-02-09 Boehringer Ingelheim International Gmbh Aerosol formulation for the inhalation of beta-agonists
US8420809B2 (en) 2005-08-15 2013-04-16 Boehringer Ingelheim International Gmbh Process for the manufacturing of betamimetics
EP1940349B1 (en) 2005-10-10 2018-02-14 Boehringer Ingelheim International GmbH Aerosol formulation for the inhalation of beta agonists

Families Citing this family (85)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0401334D0 (en) 2004-01-21 2004-02-25 Novartis Ag Organic compounds
ES2380370T3 (en) * 2004-04-22 2012-05-11 Boehringer Ingelheim International Gmbh Pharmacological combinations containing benzoxazine for the treatment of respiratory diseases
DE102004019539A1 (en) * 2004-04-22 2005-11-10 Boehringer Ingelheim Pharma Gmbh & Co. Kg New drugs for the treatment of respiratory diseases
JP2007537187A (en) * 2004-05-13 2007-12-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Hydroxy-substituted benzofused heterocyclic compounds for use as beta agonists in the treatment of respiratory diseases
DE102004024453A1 (en) * 2004-05-14 2006-01-05 Boehringer Ingelheim Pharma Gmbh & Co. Kg New long-acting bronchodilators for the treatment of respiratory diseases
DE102004024452A1 (en) * 2004-05-14 2005-12-08 Boehringer Ingelheim Pharma Gmbh & Co. Kg Aerosol formulation for the inhalation of beta agonists
DE102004024454A1 (en) * 2004-05-14 2005-12-08 Boehringer Ingelheim Pharma Gmbh & Co. Kg Novel enantiomerically pure beta agonists, process for their preparation and their use as pharmaceuticals
DE102004024451A1 (en) * 2004-05-14 2005-12-22 Boehringer Ingelheim Pharma Gmbh & Co. Kg Powder formulations for inhalation containing enantiomerically pure beta agonists
US7745621B2 (en) 2004-05-14 2010-06-29 Boehringer Ingelheim International Gmbh Long acting bronchodilators for the treatment of respiratory diseases
GB0411056D0 (en) 2004-05-18 2004-06-23 Novartis Ag Organic compounds
DE102004045648A1 (en) * 2004-09-21 2006-03-23 Boehringer Ingelheim Pharma Gmbh & Co. Kg New betamimetics for the treatment of respiratory diseases
GT200500281A (en) 2004-10-22 2006-04-24 Novartis Ag ORGANIC COMPOUNDS.
GB0424284D0 (en) 2004-11-02 2004-12-01 Novartis Ag Organic compounds
GB0426164D0 (en) 2004-11-29 2004-12-29 Novartis Ag Organic compounds
GB0507577D0 (en) 2005-04-14 2005-05-18 Novartis Ag Organic compounds
GB0510390D0 (en) 2005-05-20 2005-06-29 Novartis Ag Organic compounds
DE102005030733A1 (en) * 2005-07-01 2007-01-04 Boehringer Ingelheim Pharma Gmbh & Co. Kg New drug combinations for the treatment of respiratory diseases containing long-acting beta-2 agonists and at least one other active ingredient
GB0516313D0 (en) 2005-08-08 2005-09-14 Argenta Discovery Ltd Azole derivatives and their uses
KR20080036632A (en) 2005-08-08 2008-04-28 아젠터 디스커버리 리미티드 Bicyclo[2.2.1]hept-7-ylamine derivatives and their uses
US20070086957A1 (en) * 2005-10-10 2007-04-19 Thierry Bouyssou Combination of medicaments for the treatment of respiratory diseases
CA2625664C (en) 2005-10-21 2016-01-05 Novartis Ag Human antibodies against il13 and therapeutic uses
AU2006311060A1 (en) * 2005-11-09 2007-05-18 Boehringer Ingelheim International Gmbh Aerosolformulation for inhalation
GB0601951D0 (en) 2006-01-31 2006-03-15 Novartis Ag Organic compounds
JP2009526817A (en) * 2006-02-16 2009-07-23 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Pharmaceutical composition for the treatment of respiratory diseases
PT2322525E (en) 2006-04-21 2013-12-26 Novartis Ag Purine derivatives for use as adenosin a2a receptor agonists
EP2057152A1 (en) * 2006-08-07 2009-05-13 Boehringer Ingelheim International GmbH Single enantiomer beta-agonists, methods for the production thereof and the use thereof as medication
UY30542A1 (en) * 2006-08-18 2008-03-31 Boehringer Ingelheim Int AEROSOL FORMULATION FOR INHALATION OF BETA AGONISTS
UY30543A1 (en) * 2006-08-18 2008-03-31 Boehringer Ingelheim Int AEROSOL FORMULATION FOR INHALATION OF BETA- AGONISTS
CA2664378A1 (en) 2006-09-29 2008-04-03 Novartis Ag Pyrazolopyrimidines as pi3k lipid kinase inhibitors
CA2667962A1 (en) 2006-10-30 2008-05-08 Novartis Ag Heterocyclic compounds as antiinflammatory agents
AU2007342223B2 (en) 2007-01-10 2011-02-24 Irm Llc Compounds and compositions as channel activating protease inhibitors
ES2370952T3 (en) * 2007-01-25 2011-12-26 Boehringer Ingelheim International Gmbh PROCEDURE FOR THE PREPARATION OF BETAMIMETICS.
ES2361595T3 (en) 2007-05-07 2011-06-20 Novartis Ag ORGANIC COMPOUNDS.
MX2010006421A (en) 2007-12-10 2010-06-25 Novartis Ag Organic compounds.
AU2009203693B2 (en) 2008-01-11 2012-06-07 Novartis Ag Pyrimidines as kinase inhibitors
EP2300010B1 (en) 2008-06-10 2015-03-04 Novartis AG Pyrazine derivatives as epithelial sodium channel blockers
US8236786B2 (en) 2008-08-07 2012-08-07 Pulmagen Therapeutics (Inflammation) Limited Respiratory disease treatment
EA019441B1 (en) 2008-12-30 2014-03-31 Палмаджен Терепьютикс (Инфлеммейшн) Лимитед Sulfonamide compounds for the treatment of respiratory disorders
TW201031406A (en) 2009-01-29 2010-09-01 Novartis Ag Substituted benzimidazoles for the treatment of astrocytomas
WO2010150014A1 (en) 2009-06-24 2010-12-29 Pulmagen Therapeutics (Inflammation) Limited 5r- 5 -deuterated glitazones for respiratory disease treatment
US8389526B2 (en) 2009-08-07 2013-03-05 Novartis Ag 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
CA2770873A1 (en) 2009-08-12 2011-02-17 Novartis Ag Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation
IN2012DN01961A (en) 2009-08-17 2015-08-21 Intellikine Llc
WO2011050325A1 (en) 2009-10-22 2011-04-28 Vertex Pharmaceuticals Incorporated Compositions for treatment of cystic fibrosis and other chronic diseases
GB0918923D0 (en) 2009-10-28 2009-12-16 Vantia Ltd Aminothiazole derivatives
GB0918922D0 (en) 2009-10-28 2009-12-16 Vantia Ltd Aminopyridine derivatives
GB0918924D0 (en) 2009-10-28 2009-12-16 Vantia Ltd Azaindole derivatives
WO2011098746A1 (en) 2010-02-09 2011-08-18 Pulmagen Therapeutics (Inflammation) Limited Crystalline acid addition salts of ( 5r) -enanti0mer of pioglitazone
GB201002224D0 (en) 2010-02-10 2010-03-31 Argenta Therapeutics Ltd Respiratory disease treatment
GB201002243D0 (en) 2010-02-10 2010-03-31 Argenta Therapeutics Ltd Respiratory disease treatment
US8247436B2 (en) 2010-03-19 2012-08-21 Novartis Ag Pyridine and pyrazine derivative for the treatment of CF
UY33597A (en) 2010-09-09 2012-04-30 Irm Llc COMPOUNDS AND COMPOSITIONS AS INHIBITORS OF THE TRK
WO2012034095A1 (en) 2010-09-09 2012-03-15 Irm Llc Compounds and compositions as trk inhibitors
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US8809340B2 (en) 2012-03-19 2014-08-19 Novartis Ag Crystalline form
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EP2906218B1 (en) 2012-10-09 2016-12-14 Boehringer Ingelheim International GmbH Beta-2-adrenoceptor agonist for the treatment of cough
US9073921B2 (en) 2013-03-01 2015-07-07 Novartis Ag Salt forms of bicyclic heterocyclic derivatives
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JP2019536812A (en) 2016-12-12 2019-12-19 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Nintedanib for use in methods of treating interstitial lung disease by co-administration with olodaterol
WO2018114887A1 (en) 2016-12-20 2018-06-28 Laboratorios Lesvi, S.L. Improved process for the manufacture of r-6-hydroxy-8-[1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylaminoethyl]-2h-1,4-benzoxazin-3(4h)-one hydrochloride
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CN109096218B (en) * 2018-08-06 2020-10-27 上海方予健康医药科技有限公司 Oxydterol hydrochloride crystal form A and preparation method thereof
CN113891744A (en) 2019-06-10 2022-01-04 诺华股份有限公司 Pyridine and pyrazine derivatives for the treatment of CF, COPD and bronchiectasis
KR20220052934A (en) 2019-08-28 2022-04-28 노파르티스 아게 Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of diseases
WO2021252577A1 (en) * 2020-06-09 2021-12-16 Anovent Pharmaceutical (U.S.), Llc Pharmaceutical formulation containing umeclidinium bromide and vilanterol trifenatate
US11331322B1 (en) 2021-09-15 2022-05-17 Santen Pharmaceutical Co., Ltd. Medicament for preventing and/or treating dry eye

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3134590A1 (en) * 1981-09-01 1983-03-10 Boehringer Ingelheim KG, 6507 Ingelheim NEW BENZO HETEROCYCLES
US4460581A (en) 1982-10-12 1984-07-17 Boehringer Ingelheim Kg (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones
DE3743265A1 (en) * 1987-12-19 1989-06-29 Boehringer Ingelheim Kg NEW AMMONIUM COMPOUNDS, THEIR MANUFACTURE AND USE
HUP0300832A2 (en) * 2000-04-27 2003-08-28 Boehringer Ingelheim Pharma Gmbh & Co. Kg Novel, slow-acting betamimetics, a method for their production and their use as medicaments and pharmaceutical compositions containing them

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7727984B2 (en) 2002-11-15 2010-06-01 Boehringer Ingelheim Pharma Gmbh & Co., Kg Medicaments for the treatment of chronic obstructive pulmonary disease
US7786111B2 (en) 2002-11-15 2010-08-31 Boehringer Ingelheim Pharma Gmbh & Co. Kg Medicaments for the treatment of chronic obstructive pulmonary disease
US8044046B2 (en) 2002-11-15 2011-10-25 Boehringer Ingelheim Pharma Gmbh & Co Kg Medicaments for the treatment of chronic obstructive pulmonary disease
US7491719B2 (en) 2004-05-14 2009-02-17 Boehringer Ingelheim International Gmbh Enantiomerically pure beta agonists, process for the manufacture thereof, and use thereof as medicaments
US8034809B2 (en) 2004-05-14 2011-10-11 Boehringer Ingelheim International Gmbh Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments
US20120035169A1 (en) * 2004-05-14 2012-02-09 Boehringer Ingelheim International Gmbh Aerosol formulation for the inhalation of beta-agonists
US7423036B2 (en) 2005-02-19 2008-09-09 Boehringer Ingelheim International Gmbh Long-acting betamimetics for the treatment of respiratory complaints
US8420809B2 (en) 2005-08-15 2013-04-16 Boehringer Ingelheim International Gmbh Process for the manufacturing of betamimetics
EP1940349B1 (en) 2005-10-10 2018-02-14 Boehringer Ingelheim International GmbH Aerosol formulation for the inhalation of beta agonists
US7534789B2 (en) 2006-03-15 2009-05-19 Boehringer Ingelheim International Gmbh Enantiomeric pure β agonists, manufacturing and use as a medicament thereof
US7939658B2 (en) 2006-03-15 2011-05-10 Boehringer Ingelheim International Gmbh Enantiomeric pure beta agonists, manufacturing and use as a medicaments thereof

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