DE10253282A1 - Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung - Google Patents
Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung Download PDFInfo
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- DE10253282A1 DE10253282A1 DE10253282A DE10253282A DE10253282A1 DE 10253282 A1 DE10253282 A1 DE 10253282A1 DE 10253282 A DE10253282 A DE 10253282A DE 10253282 A DE10253282 A DE 10253282A DE 10253282 A1 DE10253282 A1 DE 10253282A1
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- Prior art keywords
- hydrogen
- alkyl
- methyl
- compounds
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 title claims abstract description 26
- -1 N-substituted 2-amino-1-(benz-(1,4)-oxazin-3-on-8-yl)-ethanol Chemical class 0.000 title claims description 33
- 230000003454 betamimetic effect Effects 0.000 title description 7
- 239000003795 chemical substances by application Substances 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 230000003287 optical effect Effects 0.000 claims abstract description 27
- 239000003814 drug Substances 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 150000007513 acids Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 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 description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 11
- 239000003380 propellant Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000000443 aerosol Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- UBLDZULTXAPHDU-UHFFFAOYSA-N 4-(2-amino-1-hydroxyethyl)-4H-1,2-benzoxazin-3-one Chemical class O1NC(C(C2=C1C=CC=C2)C(O)CN)=O UBLDZULTXAPHDU-UHFFFAOYSA-N 0.000 abstract 2
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 abstract 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 22
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 239000000546 pharmaceutical excipient Substances 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
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- 229920002261 Corn starch Polymers 0.000 description 7
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
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- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 5
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- 238000004296 chiral HPLC Methods 0.000 description 5
- 239000003246 corticosteroid Substances 0.000 description 5
- 229960001334 corticosteroids Drugs 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 229940037001 sodium edetate Drugs 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
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- 239000000454 talc Substances 0.000 description 5
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- 229910052623 talc Inorganic materials 0.000 description 5
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 4
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- 125000001743 benzylic group Chemical group 0.000 description 4
- 229960004436 budesonide Drugs 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229940052760 dopamine agonists Drugs 0.000 description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 229960002714 fluticasone Drugs 0.000 description 4
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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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)
- 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)
Priority Applications (51)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10253282A DE10253282A1 (de) | 2002-11-15 | 2002-11-15 | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| US10/705,012 US7056916B2 (en) | 2002-11-15 | 2003-11-10 | Medicaments for the treatment of chronic obstructive pulmonary disease |
| DK03778312T DK1562603T3 (da) | 2002-11-15 | 2003-11-11 | Nye l gemidler til behandling af kronisk obstruktive lungesydomme |
| CNA2003801030945A CN1713914A (zh) | 2002-11-15 | 2003-11-11 | 用于治疗慢性阻塞性肺病的新药物 |
| AU2003285326A AU2003285326B2 (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases |
| BRPI0316264A BRPI0316264B8 (pt) | 2002-11-15 | 2003-11-11 | compostos, seu uso e formulação farmacêutica que os contém |
| UAA200505926A UA81276C2 (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases, pharmaceutical preparation |
| NZ540661A NZ540661A (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases |
| MEP-2008-536A ME00354B (me) | 2002-11-15 | 2003-11-11 | Novi lekovi za tretiranje hronićnog opstruktivnog oboljenja pluća |
| PCT/EP2003/012565 WO2004045618A2 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
| AT03778312T ATE430569T1 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
| DE50311502T DE50311502D1 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
| EA200500715A EA008665B1 (ru) | 2002-11-15 | 2003-11-11 | Лекарственные средства для лечения хронического обструктивного заболевания лёгких |
| EP08169872A EP2025338A1 (de) | 2002-11-15 | 2003-11-11 | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| SI200331634T SI1562603T1 (sl) | 2002-11-15 | 2003-11-11 | Nova zdravila za zdravljenje kroničnih obstrukcijskih pljučnih bolezni |
| KR1020057008679A KR101092247B1 (ko) | 2002-11-15 | 2003-11-11 | 만성 폐쇄 폐질환 치료용 신규 약제 |
| CN200910266327A CN101735166A (zh) | 2002-11-15 | 2003-11-11 | 用于治疗慢性阻塞性肺病的新药物 |
| CA2506082A CA2506082C (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary disease |
| JP2004552561A JP4317138B2 (ja) | 2002-11-15 | 2003-11-11 | 慢性閉塞性肺疾患を治療するための新規医薬 |
| PL375270A PL212238B1 (pl) | 2002-11-15 | 2003-11-11 | Nowe związki betamimetyczne, ich zastosowanie, oraz preparat farmaceutyczny zawierający związek |
| CN201010004697A CN101817800A (zh) | 2002-11-15 | 2003-11-11 | 用于治疗慢性阻塞性肺病的新药物 |
| YU20050361A RS51607B (sr) | 2002-11-15 | 2003-11-11 | Novi lekovi za tretiranje hroničnog opstruktivnog oboljenja pluća |
| HR20050432A HRP20050432B1 (en) | 2002-11-15 | 2003-11-11 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases |
| MXPA05005081A MXPA05005081A (es) | 2002-11-15 | 2003-11-11 | Nuevos medicamentos para tratamiento de enfermedades pulmonares obstructivas cronicas. |
| PT03778312T PT1562603E (pt) | 2002-11-15 | 2003-11-11 | Novos medicamentos para o tratamento de doenças pulmonares obstrutivas crónicas |
| EP03778312.3A EP1562603B3 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
| ES03778312.3T ES2326878T7 (es) | 2002-11-15 | 2003-11-11 | Nuevos medicamentos para el tratamiento de enfermedad pulmonar obstructiva crónica |
| MYPI20034360A MY136034A (en) | 2002-11-15 | 2003-11-13 | New medicaments for the treatment of chronic obstructive pulmonary disease |
| PE2003001147A PE20040694A1 (es) | 2002-11-15 | 2003-11-13 | Derivados de benzoxazolinonas |
| TW092132031A TWI343812B (en) | 2002-11-15 | 2003-11-14 | New medicaments for the treatment of chronic obstructive pulmonary disease |
| ARP030104201A AR041969A1 (es) | 2002-11-15 | 2003-11-14 | Medicamento para el tratamiento de la enfermedad pulmonar obstructiva cronica |
| ZA2005/02246A ZA200502246B (en) | 2002-11-15 | 2005-03-17 | Novel medicaments for the treatment of chronic obstructive pulmonary diseases |
| IL167900A IL167900A (en) | 2002-11-15 | 2005-04-07 | Use of betamimetics to prepare a medical preparation for the treatment of chronic obstructive pulmonary disease |
| EC2005005774A ECSP055774A (es) | 2002-11-15 | 2005-05-02 | Nuevo medicamento para el tratamiento de la enfermedad pulmonar obstructiva crónica |
| US11/132,075 US8044046B2 (en) | 2002-11-15 | 2005-05-18 | Medicaments for the treatment of chronic obstructive pulmonary disease |
| CO05057641A CO5570670A2 (es) | 2002-11-15 | 2005-06-14 | Pulmonar obstructiva cronica |
| NO20052883A NO334314B1 (no) | 2002-11-15 | 2005-06-14 | Forbindelser, farmasøytiske formuleringer inneholdende slike samt anvendelse av disse for fremstilling av medikamenter for behandling av kronisk obstruktiv lungesykdom |
| US11/275,730 US20060106213A1 (en) | 2002-11-15 | 2006-01-26 | New Medicaments for the Treatment of Chronic Obstructive Pulmonary Disease |
| US11/677,112 US7727984B2 (en) | 2002-11-15 | 2007-02-21 | Medicaments for the treatment of chronic obstructive pulmonary disease |
| US12/036,618 US20080167298A1 (en) | 2002-11-15 | 2008-02-25 | Medicaments for the treatment of chronic obstructive pulmonary disease |
| US12/258,830 US7786111B2 (en) | 2002-11-15 | 2008-10-27 | Medicaments for the treatment of chronic obstructive pulmonary disease |
| CY20091100826T CY1110500T1 (el) | 2002-11-15 | 2009-08-04 | Νεα φαρμακα για τη θεραπεια της χρονιας αποφρακτικης πνευμονοπαθειας |
| ARP120102613A AR087241A2 (es) | 2002-11-15 | 2012-07-19 | Derivados de 6-oh-4h-benzo[1,4]oxazin-3-ona para el tratamiento de la enfermedad pulmonar obstructiva cronica |
| BE2014C016C BE2014C016I2 (OSRAM) | 2002-11-15 | 2014-02-27 | |
| LTPA2014012C LTC1562603I2 (lt) | 2002-11-15 | 2014-03-06 | Nauji vaistai, skirti lėtinių obstrukcinių plaučių ligų gydymui |
| NL300650C NL300650I2 (nl) | 2002-11-15 | 2014-03-07 | Olodaterol, het R-enantiomeer daarvan, mengsels van isomeren daarvan, zuuradditiezouten met farmacologisch aanvaardbare zuren daarvan, evenals solvaten en/of hydraten daarvan, in het bijzonder Olodaterol en Olodaterolhydrochloride |
| HUS1400011C HUS1400011I1 (hu) | 2002-11-15 | 2014-03-07 | Új gyógyszer krónikus elzáródásos tüdõbetegség kezelésére |
| NO2014005C NO2014005I1 (no) | 2002-11-15 | 2014-03-10 | olodaterol, syreaddisjonssalter og farmakologisk akseptable syrer derav |
| LU92433C LU92433I2 (fr) | 2002-11-15 | 2014-04-22 | Olodatérol, ses isomères optiques individuels, mélanges d'énantiomères individuels ou de racémates, ses sels d'addition d'acide avec des acides pharmaceutiquement acceptables, ainsi que ses solvates et/ou ses hydrates, en particulier l'olodatérol et le chlorhydrate d'olodatérol |
| FR14C0049C FR14C0049I2 (fr) | 2002-11-15 | 2014-06-23 | Nouveaux medicaments destines au traitement de la bronchopneumopathie chronique obstructive |
| CY2014032C CY2014032I1 (el) | 2002-11-15 | 2014-08-13 | Νεα φαρμακα για τη θεραπεια της χρονιας αποφρακτικης πνευμονοπαθειας |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10253282A DE10253282A1 (de) | 2002-11-15 | 2002-11-15 | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10253282A1 true DE10253282A1 (de) | 2004-05-27 |
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| DE10253282A Withdrawn DE10253282A1 (de) | 2002-11-15 | 2002-11-15 | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| DE50311502T Expired - Lifetime DE50311502D1 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
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| DE50311502T Expired - Lifetime DE50311502D1 (de) | 2002-11-15 | 2003-11-11 | Neue arzneimittel zur behandlung von chronisch obstruktiver lungenerkrankung |
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| CN114341132A (zh) | 2019-08-28 | 2022-04-12 | 诺华股份有限公司 | 经取代的1,3-苯基杂芳基衍生物及其在治疗疾病中的用途 |
| CN115768404B (zh) * | 2020-06-09 | 2024-11-08 | 广州谷森制药有限公司 | 含乌美溴铵和三苯乙酸维兰特罗的药物制剂 |
| US11331322B1 (en) | 2021-09-15 | 2022-05-17 | Santen Pharmaceutical Co., Ltd. | Medicament for preventing and/or treating dry eye |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3134590A1 (de) * | 1981-09-01 | 1983-03-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue benzo-heterocyclen |
| US4460581A (en) * | 1982-10-12 | 1984-07-17 | Boehringer Ingelheim Kg | (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones |
| DE3743265A1 (de) * | 1987-12-19 | 1989-06-29 | Boehringer Ingelheim Kg | Neue ammoniumverbindungen, ihre herstellung und verwendung |
| PL362868A1 (en) * | 2000-04-27 | 2004-11-02 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Novel, slow-acting betamimetics, a method for their production and their use as medicaments |
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