CA2506082A1 - Novel medicaments for the treatment of chronic obstructive pulmonary disease - Google Patents
Novel medicaments for the treatment of chronic obstructive pulmonary disease Download PDFInfo
- 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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- Prior art keywords
- denotes
- alkyl
- compounds
- methyl
- general formula
- Prior art date
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 title claims abstract 9
- 239000003814 drug Substances 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 38
- 239000001257 hydrogen Substances 0.000 claims abstract 38
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 150000002431 hydrogen Chemical class 0.000 claims abstract 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract 17
- 150000002367 halogens Chemical class 0.000 claims abstract 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 18
- 229910052801 chlorine Inorganic materials 0.000 claims 18
- 239000000460 chlorine Substances 0.000 claims 18
- 229910052731 fluorine Inorganic materials 0.000 claims 18
- 239000011737 fluorine Substances 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- -1 methoxy, ethoxy Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 239000000443 aerosol Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/14—Heterocyclic 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
-
- 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
- A61K31/535—Heterocyclic 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
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
-
- 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
- A61K31/535—Heterocyclic 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (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.
(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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| DE10253282.6 | 2002-11-15 | ||
| PCT/EP2003/012565 WO2004045618A2 (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2506082A1 true CA2506082A1 (en) | 2004-06-03 |
| CA2506082C CA2506082C (en) | 2011-06-21 |
Family
ID=32185709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2506082A Expired - Lifetime CA2506082C (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary disease |
Country Status (38)
| Country | Link |
|---|---|
| EP (2) | EP2025338A1 (en) |
| JP (1) | JP4317138B2 (en) |
| KR (1) | KR101092247B1 (en) |
| CN (3) | CN101817800A (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) |
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| 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 |
| EA200201056A1 (en) * | 2000-04-27 | 2003-04-24 | Бёрингер Ингельхайм Фарма Кг | NEW, OWNED BY THE LONG-TERM EFFECT OF BETAMIMETIC, THE METHOD OF THEIR PREPARATION AND THEIR APPLICATION AS A MEDICINE |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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