CA2083597A1 - Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it - Google Patents
Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing itInfo
- Publication number
- CA2083597A1 CA2083597A1 CA002083597A CA2083597A CA2083597A1 CA 2083597 A1 CA2083597 A1 CA 2083597A1 CA 002083597 A CA002083597 A CA 002083597A CA 2083597 A CA2083597 A CA 2083597A CA 2083597 A1 CA2083597 A1 CA 2083597A1
- Authority
- CA
- Canada
- Prior art keywords
- antitussive
- preparation
- dibromo
- pharmaceutical compositions
- ambroxol
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 230000000954 anitussive effect Effects 0.000 title claims abstract description 9
- 229940124584 antitussives Drugs 0.000 title claims abstract description 9
- 210000003097 mucus Anatomy 0.000 title claims abstract description 6
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 5
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 12
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 claims 1
- MEYUFEONQBWJKB-UHFFFAOYSA-N n-[2,4-dibromo-6-[[(4-hydroxycyclohexyl)amino]methyl]phenyl]benzamide Chemical compound C1CC(O)CCC1NCC1=CC(Br)=CC(Br)=C1NC(=O)C1=CC=CC=C1 MEYUFEONQBWJKB-UHFFFAOYSA-N 0.000 abstract description 2
- 229960005174 ambroxol Drugs 0.000 description 15
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 206010011224 Cough Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003434 antitussive agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960004415 codeine phosphate Drugs 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 101100364844 Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440) salL gene Proteins 0.000 description 1
- 206010044314 Tracheobronchitis Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- KSNNEUZOAFRTDS-UHFFFAOYSA-N fominoben Chemical compound ClC=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1CN(C)CC(=O)N1CCOCC1 KSNNEUZOAFRTDS-UHFFFAOYSA-N 0.000 description 1
- 229960004594 fominoben Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- -1 vials or ampoules Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- 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
- A61P11/10—Expectorants
-
- 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
- A61P11/14—Antitussive agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20562A/90 | 1990-06-06 | ||
| IT02056290A IT1248702B (it) | 1990-06-06 | 1990-06-06 | Agente antitussivo e mucoregolatore,sua preparazione e composizioni farmaceutiche |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2083597A1 true CA2083597A1 (en) | 1991-12-07 |
Family
ID=11168835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002083597A Abandoned CA2083597A1 (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5352703A (OSRAM) |
| EP (1) | EP0532644B1 (OSRAM) |
| JP (1) | JPH05506450A (OSRAM) |
| AT (1) | ATE113029T1 (OSRAM) |
| CA (1) | CA2083597A1 (OSRAM) |
| DE (1) | DE69104723T2 (OSRAM) |
| ES (1) | ES2061252T3 (OSRAM) |
| IT (1) | IT1248702B (OSRAM) |
| WO (1) | WO1991018865A1 (OSRAM) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030166732A1 (en) * | 2002-02-27 | 2003-09-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ambroxol for the treatment of painful conditions in the mouth and pharyngeal cavity |
| WO2014037832A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment of epilepsy and neurological diseases |
| AU2013257742A1 (en) | 2012-05-07 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for treatment of neuromuscular disorders and neurodegenerative disorders |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| CN104350041A (zh) | 2012-05-07 | 2015-02-11 | 塞利克斯比奥私人有限公司 | 用于治疗神经系统疾病的组合物和方法 |
| WO2013167993A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological degenerative disorders |
| US9403826B2 (en) | 2012-05-08 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory disorders |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| WO2013168025A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of blood clotting disorders |
| WO2013168023A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of parkinson's disease |
| US9394288B2 (en) | 2012-05-10 | 2016-07-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of asthma and allergy |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| US9339484B2 (en) | 2012-05-10 | 2016-05-17 | Cellix Bio Private Limited | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| WO2013168016A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| US9499526B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| WO2013168004A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of fibromyalgia pain |
| US9573927B2 (en) | 2012-05-10 | 2017-02-21 | Cellix Bio Private Limited | Compositions and methods for the treatment of severe pain |
| WO2013168014A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| US9315461B2 (en) | 2012-05-10 | 2016-04-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
| US9242939B2 (en) | 2012-05-10 | 2016-01-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| AU2013264896A1 (en) | 2012-05-23 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| WO2013175376A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of local pain |
| AU2013264894B2 (en) | 2012-05-23 | 2015-11-19 | Cellix Bio Private Limited | Compositions and methods for treatment of inflammatory bowel disease |
| WO2013175344A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| US9227974B2 (en) | 2012-05-23 | 2016-01-05 | Cellex Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| WO2013175377A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9187427B2 (en) | 2012-08-03 | 2015-11-17 | Cellix Bio Private Limited | N-substituted nicotinamide compounds and compositions for the treatment migraine and neurologic diseases |
| US9624168B2 (en) | 2012-09-06 | 2017-04-18 | Cellix Bio Private Limited | Compositions and methods for the treatment inflammation and lipid disorders |
| US9670153B2 (en) | 2012-09-08 | 2017-06-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammation and lipid disorders |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| WO2014195961A1 (en) | 2013-06-04 | 2014-12-11 | Mahesh Kandula | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| EP3240779B1 (en) | 2014-09-26 | 2020-10-28 | Cellixbio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| JP6698643B2 (ja) | 2014-09-29 | 2020-05-27 | セリックス バイオ プライヴェート リミテッドＣｅｌｌｉｘ Ｂｉｏ Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 多発性硬化症の治療のための組成物及び方法 |
| CA2965449C (en) | 2014-10-27 | 2020-11-10 | Cellix Bio Private Limited | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| CN107428697A (zh) | 2015-01-06 | 2017-12-01 | 塞尔利克斯生物私人有限公司 | 用于治疗炎症和疼痛的组合物和方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432904A (en) * | 1973-08-24 | 1976-04-22 | Uriach & Cia Sa J | N-2-n-cyclohexyl-n-methylaminomethyl-4,6-dibromo-phenyl-benzamides methods for their preparation and compositions containing them |
| FR2399276A1 (fr) * | 1977-08-03 | 1979-03-02 | Rhone Poulenc Ind | Procede de fabrication de billes d'alumine |
| EP0004026B1 (de) * | 1978-03-02 | 1982-05-05 | Ciba-Geigy Ag | Hydrolysestabile, ortho-alkylierte Phenylphosphonite und stabilisierte Massen |
| IT1094864B (it) * | 1978-05-29 | 1985-08-10 | Tosi Franco Ist | Derivati della bromexina e procedimento per la loro preparazione |
| DK110582A (da) * | 1981-03-19 | 1982-09-20 | Hokuriku Pharmaceutical | 2-benzoylamino-substituerede benzylaminderivater samt fremgangsmaade til fremstilling af samme |
| IT1213132B (it) * | 1984-02-02 | 1989-12-14 | Yason Srl | Agente antibroncopneumopatico. |
-
1990
- 1990-06-06 IT IT02056290A patent/IT1248702B/it active IP Right Grant
-
1991
- 1991-06-03 CA CA002083597A patent/CA2083597A1/en not_active Abandoned
- 1991-06-03 US US07/952,838 patent/US5352703A/en not_active Expired - Fee Related
- 1991-06-03 AT AT91911446T patent/ATE113029T1/de not_active IP Right Cessation
- 1991-06-03 JP JP91510028A patent/JPH05506450A/ja active Pending
- 1991-06-03 ES ES91911446T patent/ES2061252T3/es not_active Expired - Lifetime
- 1991-06-03 DE DE69104723T patent/DE69104723T2/de not_active Revoked
- 1991-06-03 WO PCT/EP1991/001023 patent/WO1991018865A1/en not_active Ceased
- 1991-06-03 EP EP91911446A patent/EP0532644B1/en not_active Revoked
Also Published As
| Publication number | Publication date |
|---|---|
| IT9020562A0 (OSRAM) | 1990-06-06 |
| ES2061252T3 (es) | 1994-12-01 |
| DE69104723D1 (de) | 1994-11-24 |
| JPH05506450A (ja) | 1993-09-22 |
| EP0532644B1 (en) | 1994-10-19 |
| ATE113029T1 (de) | 1994-11-15 |
| US5352703A (en) | 1994-10-04 |
| IT9020562A1 (it) | 1991-12-06 |
| EP0532644A1 (en) | 1993-03-24 |
| DE69104723T2 (de) | 1995-02-23 |
| WO1991018865A1 (en) | 1991-12-12 |
| IT1248702B (it) | 1995-01-26 |
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