JP4851937B2 - β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 - Google Patents
β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 Download PDFInfo
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- JP4851937B2 JP4851937B2 JP2006541552A JP2006541552A JP4851937B2 JP 4851937 B2 JP4851937 B2 JP 4851937B2 JP 2006541552 A JP2006541552 A JP 2006541552A JP 2006541552 A JP2006541552 A JP 2006541552A JP 4851937 B2 JP4851937 B2 JP 4851937B2
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- YUSMZDVTEOAHDL-NTMALXAHSA-N tert-butyl (3z)-3-(dimethylaminomethylidene)-4-oxopiperidine-1-carboxylate Chemical compound CN(C)\C=C1\CN(C(=O)OC(C)(C)C)CCC1=O YUSMZDVTEOAHDL-NTMALXAHSA-N 0.000 description 1
- VTIGGLBAGFVFQI-UHFFFAOYSA-N tert-butyl 2-[3-(hydroxymethyl)phenyl]acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=CC(CO)=C1 VTIGGLBAGFVFQI-UHFFFAOYSA-N 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- FMTUFNCQKOLKON-UHFFFAOYSA-N tert-butyl n-[(4-amino-3-chlorophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(N)C(Cl)=C1 FMTUFNCQKOLKON-UHFFFAOYSA-N 0.000 description 1
- HFYJFKDJYCFNIC-UHFFFAOYSA-N tert-butyl n-[[3-chloro-4-(prop-2-enoylamino)phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(NC(=O)C=C)C(Cl)=C1 HFYJFKDJYCFNIC-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229940110309 tiotropium Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
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- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- 229960004479 trihexyphenidyl hydrochloride Drugs 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
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- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Document Processing Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52423403P | 2003-11-21 | 2003-11-21 | |
| US60/524,234 | 2003-11-21 | ||
| PCT/US2004/038975 WO2005051946A2 (en) | 2003-11-21 | 2004-11-19 | Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011121065A Division JP2011190271A (ja) | 2003-11-21 | 2011-05-30 | β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 |
Publications (3)
| Publication Number | Publication Date |
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| JP2007514662A JP2007514662A (ja) | 2007-06-07 |
| JP2007514662A5 JP2007514662A5 (https=) | 2007-12-06 |
| JP4851937B2 true JP4851937B2 (ja) | 2012-01-11 |
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| JP2006541552A Expired - Fee Related JP4851937B2 (ja) | 2003-11-21 | 2004-11-19 | β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 |
| JP2011121065A Withdrawn JP2011190271A (ja) | 2003-11-21 | 2011-05-30 | β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2011121065A Withdrawn JP2011190271A (ja) | 2003-11-21 | 2011-05-30 | β２アドレナリン作動性受容体作動薬活性およびムスカリン受容体拮抗薬活性を有する化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US7345060B2 (https=) |
| EP (1) | EP1685118B1 (https=) |
| JP (2) | JP4851937B2 (https=) |
| CN (1) | CN100569760C (https=) |
| AT (1) | ATE435855T1 (https=) |
| CA (1) | CA2543858C (https=) |
| DE (1) | DE602004021959D1 (https=) |
| ES (1) | ES2329586T3 (https=) |
| WO (1) | WO2005051946A2 (https=) |
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| US6693202B1 (en) * | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| PE20040950A1 (es) * | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| PE20050711A1 (es) * | 2003-07-17 | 2005-09-10 | Glaxo Group Ltd | Compuestos 8-azoniabiciclo[3.2.1] octanos como antagonistas de los receptores muscarinicos de la acetilcolina |
| TW200523261A (en) * | 2003-07-17 | 2005-07-16 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| PE20050250A1 (es) * | 2003-07-17 | 2005-04-08 | Glaxo Group Ltd | Antagonistas de los receptores muscarinicos de la acetilcolina |
| WO2005037280A1 (en) * | 2003-10-14 | 2005-04-28 | Glaxo Group Limited | Muscarinic acetycholine receptor antagonists |
| AU2004281167A1 (en) * | 2003-10-17 | 2005-04-28 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists field of the invention |
| PE20050489A1 (es) * | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| ES2329586T3 (es) * | 2003-11-21 | 2009-11-27 | Theravance, Inc. | Compuestos que tienen actividad agonista del receptor beta2 adrenergico y antagonista del receptor muscarino. |
| WO2005087236A1 (en) * | 2004-03-11 | 2005-09-22 | Glaxo Group Limited | Novel m3 muscarinic acetylcholine receptor antagonists |
| TW200538095A (en) * | 2004-03-11 | 2005-12-01 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2007528413A (ja) * | 2004-03-11 | 2007-10-11 | セラヴァンス， インコーポレーテッド | ムスカリンレセプターアンタゴニストとしての有用なビフェニル化合物 |
| WO2005087737A1 (en) * | 2004-03-11 | 2005-09-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| EP1723112A1 (en) * | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| US7265133B2 (en) * | 2004-03-11 | 2007-09-04 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| EP1723110A1 (en) | 2004-03-11 | 2006-11-22 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TWI341836B (en) * | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| UY28871A1 (es) | 2004-04-27 | 2005-11-30 | Glaxo Group Ltd | Antagonistas del receptor de acetilcolina muscarinico |
| EP1747219A4 (en) * | 2004-05-13 | 2010-05-26 | Glaxo Group Ltd | Antagonists of muscarinic acetylcholine receptor |
| WO2006023457A1 (en) * | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| WO2006023460A2 (en) * | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| JP2008537931A (ja) * | 2005-03-10 | 2008-10-02 | セラヴァンス， インコーポレーテッド | ムスカリン性レセプターアンタゴニストとして有用なビフェニル化合物 |
| US7659403B2 (en) * | 2005-03-10 | 2010-02-09 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| TW200714587A (en) * | 2005-03-10 | 2007-04-16 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2008538104A (ja) * | 2005-03-10 | 2008-10-09 | セラヴァンス， インコーポレーテッド | ムスカリン受容体アンタゴニストとして有用なビフェニル化合物 |
| WO2006099032A1 (en) * | 2005-03-10 | 2006-09-21 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2008546695A (ja) * | 2005-06-13 | 2008-12-25 | セラヴァンス， インコーポレーテッド | ムスカリン受容体アンタゴニストとして有用なビフェニル化合物 |
| US8429052B2 (en) * | 2005-07-19 | 2013-04-23 | Lincoln National Life Insurance Company | Method and system for providing employer-sponsored retirement plan |
| EP1937267A4 (en) * | 2005-08-02 | 2009-08-26 | Glaxo Group Ltd | M3-MUSCARIN ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| US20080234315A1 (en) * | 2005-08-02 | 2008-09-25 | Jakob Busch-Petersen | M3 Muscarinic Acetylcholine Receptor Antagonists |
| WO2007022351A2 (en) * | 2005-08-18 | 2007-02-22 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
| GB0602778D0 (en) * | 2006-02-10 | 2006-03-22 | Glaxo Group Ltd | Novel compound |
| TW200811104A (en) * | 2006-04-25 | 2008-03-01 | Theravance Inc | Crystalline forms of a dimethylphenyl compound |
| TW200811105A (en) | 2006-04-25 | 2008-03-01 | Theravance Inc | Dialkylphenyl compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| TW201036957A (en) | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| JP5540075B2 (ja) * | 2009-04-14 | 2014-07-02 | グラクソ グループ リミテッド | ビフェニル−２−イルカルバミン酸エステルの調製方法 |
| PL3111927T3 (pl) | 2009-05-29 | 2020-06-29 | Pearl Therapeutics, Inc. | Kompozycje do wziewnego podawania środków aktywnych oraz związane z nimi sposoby i systemy |
| GB0913342D0 (en) * | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | Compounds - 801 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011081937A1 (en) | 2009-12-15 | 2011-07-07 | Gilead Sciences, Inc. | Corticosteroid-beta-agonist-muscarinic antagonist compounds for use in therapy |
| KR101742253B1 (ko) | 2010-07-13 | 2017-05-31 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 비페닐-2-일카르밤산의 제조방법 |
| WO2012032546A2 (en) * | 2010-09-08 | 2012-03-15 | Cadila Healthcare Limited | Process for the preparation of salmeterol and its intermediates |
| GB201016912D0 (en) | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
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| ME02297B (me) | 2011-06-10 | 2016-02-20 | Chiesi Farm Spa | Jedinjenja koja imaju aktivnost antagonista muskarinskih receptora i agonist beta2 adrenergičnog receptora |
| BR112013030302B1 (pt) | 2011-06-10 | 2021-08-24 | Chiesi Farmaceutici S.P.A. | Composto, composição farmacêutica, uso de um composto, combinação de um composto e dispositivo |
| JO3192B1 (ar) | 2011-09-06 | 2018-03-08 | Novartis Ag | مركب بنزوثيازولون |
| AR093832A1 (es) | 2012-12-06 | 2015-06-24 | Chiesi Farm Spa | COMPUESTOS CON ACTIVIDAD ANTAGONISTA DE LOS RECEPTORES MUSCARINICOS Y ACTIVIDAD AGONISTA DEL RECEPTOR b2 ADRENERGICO |
| BR112015012730B1 (pt) | 2012-12-06 | 2022-07-05 | Chiesi Farmaceutici S.P.A. | Composto, composição farmaceutica, dispositivo, uso de um composto e combinação |
| TWI703138B (zh) | 2015-02-12 | 2020-09-01 | 義大利商吉斯藥品公司 | 具有蕈毒鹼受體拮抗劑及β２腎上腺素受體促效劑活性之化合物 |
| CN107074816B (zh) * | 2015-03-27 | 2020-07-17 | 四川海思科制药有限公司 | 一种杂环衍生物及其制备方法和在医药上的用途 |
| AR104828A1 (es) | 2015-06-01 | 2017-08-16 | Chiesi Farm Spa | COMPUESTOS CON ACTIVIDAD ANTAGONISTA DE LOS RECEPTORES MUSCARÍNICOS Y ACTIVIDAD AGONISTA DEL RECEPTOR b2 ADRENÉRGICO |
| WO2017093208A1 (en) | 2015-12-03 | 2017-06-08 | Chiesi Farmaceutici S.P.A. | Compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity |
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| BR112018015018A2 (pt) * | 2016-01-22 | 2018-12-18 | Sichuan Haisco Pharmaceutical Co Ltd | derivado de amido azaciclo, método de preparação deste, e aplicação farmacêutica |
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| RU2722720C1 (ru) | 2016-12-14 | 2020-06-03 | Бейджинг Шоубай Фармасьютикэл Ко., Лтд. | Класс бифункциональных соединений со структурой соли четвертичного аммония |
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| CN111423434A (zh) * | 2019-01-09 | 2020-07-17 | 四川海思科制药有限公司 | 一种碳酰胺衍生物及其制备方法 |
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- 2004-11-19 ES ES04811663T patent/ES2329586T3/es not_active Expired - Lifetime
- 2004-11-19 DE DE602004021959T patent/DE602004021959D1/de not_active Expired - Lifetime
- 2004-11-19 AT AT04811663T patent/ATE435855T1/de not_active IP Right Cessation
- 2004-11-19 CA CA2543858A patent/CA2543858C/en not_active Expired - Fee Related
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- 2004-11-19 JP JP2006541552A patent/JP4851937B2/ja not_active Expired - Fee Related
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2007
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2010
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Also Published As
| Publication number | Publication date |
|---|---|
| US8247564B2 (en) | 2012-08-21 |
| CA2543858C (en) | 2014-04-15 |
| EP1685118A2 (en) | 2006-08-02 |
| WO2005051946A2 (en) | 2005-06-09 |
| CN100569760C (zh) | 2009-12-16 |
| US7838535B2 (en) | 2010-11-23 |
| CN1882556A (zh) | 2006-12-20 |
| US7345060B2 (en) | 2008-03-18 |
| JP2011190271A (ja) | 2011-09-29 |
| JP2007514662A (ja) | 2007-06-07 |
| WO2005051946A3 (en) | 2005-07-14 |
| ATE435855T1 (de) | 2009-07-15 |
| DE602004021959D1 (de) | 2009-08-20 |
| EP1685118B1 (en) | 2009-07-08 |
| US7842704B2 (en) | 2010-11-30 |
| US20080097105A1 (en) | 2008-04-24 |
| CA2543858A1 (en) | 2005-06-09 |
| ES2329586T3 (es) | 2009-11-27 |
| US20050113417A1 (en) | 2005-05-26 |
| US20080096911A1 (en) | 2008-04-24 |
| US20110034694A1 (en) | 2011-02-10 |
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