JP2008513358A5 - - Google Patents
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- Publication number
- JP2008513358A5 JP2008513358A5 JP2007527919A JP2007527919A JP2008513358A5 JP 2008513358 A5 JP2008513358 A5 JP 2008513358A5 JP 2007527919 A JP2007527919 A JP 2007527919A JP 2007527919 A JP2007527919 A JP 2007527919A JP 2008513358 A5 JP2008513358 A5 JP 2008513358A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- methyl
- ester
- compound
- methoxyphenylcarbamoyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
- QMOVGVNKXUTCQU-UHFFFAOYSA-N (2-phenylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-N 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- -1 2-furanylcarbonyl Chemical group 0.000 claims 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 230000003637 steroidlike Effects 0.000 claims 6
- 239000013078 crystal Substances 0.000 claims 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 208000019693 Lung disease Diseases 0.000 claims 4
- 238000002844 melting Methods 0.000 claims 4
- 230000008018 melting Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 238000000862 absorption spectrum Methods 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 239000003701 inert diluent Substances 0.000 claims 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 230000007883 bronchodilation Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 235000001727 glucose Nutrition 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 229920000747 poly(lactic acid) Polymers 0.000 claims 1
- 239000004626 polylactic acid Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60180504P | 2004-08-16 | 2004-08-16 | |
| US60/601,805 | 2004-08-16 | ||
| PCT/US2005/029013 WO2006023454A1 (en) | 2004-08-16 | 2005-08-15 | Crystalline form of a biphenyl compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012065767A Division JP2012121929A (ja) | 2004-08-16 | 2012-03-22 | 結晶性形態のビフェニル化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008513358A JP2008513358A (ja) | 2008-05-01 |
| JP2008513358A5 true JP2008513358A5 (enExample) | 2008-09-18 |
| JP5032990B2 JP5032990B2 (ja) | 2012-09-26 |
Family
ID=35687428
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007527919A Expired - Fee Related JP5032990B2 (ja) | 2004-08-16 | 2005-08-15 | 結晶性形態のビフェニル化合物 |
| JP2012065767A Withdrawn JP2012121929A (ja) | 2004-08-16 | 2012-03-22 | 結晶性形態のビフェニル化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012065767A Withdrawn JP2012121929A (ja) | 2004-08-16 | 2012-03-22 | 結晶性形態のビフェニル化合物 |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US7521558B2 (enExample) |
| EP (1) | EP1778672B1 (enExample) |
| JP (2) | JP5032990B2 (enExample) |
| KR (1) | KR101363352B1 (enExample) |
| CN (1) | CN101006077B (enExample) |
| AR (1) | AR051003A1 (enExample) |
| AU (1) | AU2005277601B2 (enExample) |
| BR (1) | BRPI0514413C1 (enExample) |
| CA (1) | CA2575874C (enExample) |
| DK (1) | DK1778672T3 (enExample) |
| ES (1) | ES2400958T3 (enExample) |
| HR (1) | HRP20130192T1 (enExample) |
| IL (1) | IL180853A (enExample) |
| MA (1) | MA28825B1 (enExample) |
| MX (1) | MX2007001688A (enExample) |
| MY (1) | MY141224A (enExample) |
| NO (1) | NO338770B1 (enExample) |
| NZ (1) | NZ552796A (enExample) |
| PL (1) | PL1778672T3 (enExample) |
| PT (1) | PT1778672E (enExample) |
| RU (1) | RU2381223C2 (enExample) |
| SI (1) | SI1778672T1 (enExample) |
| TW (1) | TWI374883B (enExample) |
| WO (1) | WO2006023454A1 (enExample) |
| ZA (1) | ZA200701057B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| TWI374883B (en) * | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| US8429052B2 (en) * | 2005-07-19 | 2013-04-23 | Lincoln National Life Insurance Company | Method and system for providing employer-sponsored retirement plan |
| 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 |
| AU2007303909A1 (en) * | 2006-10-04 | 2008-04-10 | Pfizer Limited | Sulfonamide derivatives as adrenergic agonists and muscarinic antagonists |
| ES2302447B1 (es) * | 2006-10-20 | 2009-06-12 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| ES2306595B1 (es) | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| ES2320961B1 (es) * | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| EP2096105A1 (en) * | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| US8519138B2 (en) * | 2009-04-14 | 2013-08-27 | Glaxo Group Limited | Process for the preparation of a biphenyl-2-yl carbamic acid ester |
| CN102405218B (zh) | 2009-04-23 | 2014-06-04 | 施万制药 | 具蕈毒碱受体拮抗剂和β2 肾上腺素受体激动剂活性的二酰胺化合物 |
| AU2015234331B2 (en) * | 2009-04-23 | 2017-08-03 | Theravance Biopharma R&D Ip, Llc | Diamide compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity |
| WO2011081937A1 (en) | 2009-12-15 | 2011-07-07 | Gilead Sciences, Inc. | Corticosteroid-beta-agonist-muscarinic antagonist compounds for use in therapy |
| ITRM20110083U1 (it) | 2010-05-13 | 2011-11-14 | De La Cruz Jose Antonio Freire | Piastra per la costruzione di carrelli per aeroplani |
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| GB201009801D0 (en) | 2010-06-11 | 2010-07-21 | Astrazeneca Ab | Compounds 950 |
| AR083115A1 (es) | 2010-09-30 | 2013-01-30 | Theravance Inc | Sales oxalato cristalinas de un compuesto diamida |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| IN2014CN02850A (enExample) * | 2011-10-31 | 2015-07-03 | Glaxosmithkline Intellectual Property Ltd | |
| EP2592077A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| JP6307091B2 (ja) | 2012-12-18 | 2018-04-04 | アルミラル・ソシエダッド・アノニマＡｌｍｉｒａｌｌ， Ｓ．Ａ． | β２アドレナリンアゴニスト活性およびＭ３ムスカリンアンタゴニスト活性を有する新規のシクロヘキシルおよびキヌクリジニルカルバメート誘導体 |
| TWI643853B (zh) | 2013-02-27 | 2018-12-11 | 阿爾米雷爾有限公司 | 同時具有β2腎上腺素受體促效劑和M3毒蕈鹼受體拮抗劑活性之2-氨基-1-羥乙基-8-羥基喹啉-2(1H)-酮衍生物之鹽類 |
| TWI641373B (zh) | 2013-07-25 | 2018-11-21 | 阿爾米雷爾有限公司 | 具有蕈毒鹼受體拮抗劑和β２腎上腺素受體促效劑二者之活性的２－胺基－１－羥乙基－８－羥基喹啉－２（１Ｈ）－酮衍生物之鹽 |
| TW201517906A (zh) | 2013-07-25 | 2015-05-16 | Almirall Sa | 含有ｍａｂａ化合物和皮質類固醇之組合 |
| TW201617343A (zh) | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物 |
| TW201835041A (zh) | 2017-02-17 | 2018-10-01 | 印度商托仁特生技有限公司 | 具β-腎上腺素促效劑及抗蕈毒活性化合物 |
| US11484531B2 (en) | 2018-08-30 | 2022-11-01 | Theravance Biopharma R&D Ip, Llc | Methods for treating chronic obstructive pulmonary disease |
| WO2022175982A1 (en) * | 2021-02-19 | 2022-08-25 | Gbr Laboratories Private Limited | A process for preparing batefenterol and intermediates thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS596860B2 (ja) * | 1975-05-19 | 1984-02-15 | オオツカセイヤク カブシキガイシヤ | ５−〔（２−アルキルアミノ−１−ヒドロキシ）アルキル〕カルボスチリル誘導体の製造法 |
| TW297025B (enExample) * | 1992-02-14 | 1997-02-01 | Squibb & Sons Inc | |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| AU783095B2 (en) | 1999-12-07 | 2005-09-22 | Theravance Biopharma R&D Ip, Llc | Carbamate derivatives having muscarinic receptor antagonist activity |
| UA73543C2 (uk) | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
| US20030018019A1 (en) * | 2001-06-23 | 2003-01-23 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics |
| US6653323B2 (en) * | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| 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 |
| JP2004356517A (ja) | 2003-05-30 | 2004-12-16 | Ebara Corp | 基板洗浄装置及び基板洗浄方法 |
| US20050025718A1 (en) * | 2003-07-31 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a betamimetic |
| US7320990B2 (en) * | 2004-02-13 | 2008-01-22 | Theravance, Inc. | Crystalline form of a biphenyl compound |
| TWI374883B (en) * | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
-
2005
- 2005-08-03 TW TW094126435A patent/TWI374883B/zh not_active IP Right Cessation
- 2005-08-08 AR ARP050103308A patent/AR051003A1/es active IP Right Grant
- 2005-08-15 WO PCT/US2005/029013 patent/WO2006023454A1/en not_active Ceased
- 2005-08-15 DK DK05803280.6T patent/DK1778672T3/da active
- 2005-08-15 MX MX2007001688A patent/MX2007001688A/es active IP Right Grant
- 2005-08-15 PL PL05803280T patent/PL1778672T3/pl unknown
- 2005-08-15 KR KR1020077005834A patent/KR101363352B1/ko not_active Expired - Fee Related
- 2005-08-15 CA CA2575874A patent/CA2575874C/en not_active Expired - Lifetime
- 2005-08-15 MY MYPI20053814A patent/MY141224A/en unknown
- 2005-08-15 SI SI200531675T patent/SI1778672T1/sl unknown
- 2005-08-15 NZ NZ552796A patent/NZ552796A/en not_active IP Right Cessation
- 2005-08-15 AU AU2005277601A patent/AU2005277601B2/en not_active Ceased
- 2005-08-15 CN CN2005800281254A patent/CN101006077B/zh not_active Expired - Fee Related
- 2005-08-15 ES ES05803280T patent/ES2400958T3/es not_active Expired - Lifetime
- 2005-08-15 JP JP2007527919A patent/JP5032990B2/ja not_active Expired - Fee Related
- 2005-08-15 BR BRPI0514413A patent/BRPI0514413C1/pt not_active IP Right Cessation
- 2005-08-15 US US11/204,065 patent/US7521558B2/en active Active
- 2005-08-15 EP EP05803280A patent/EP1778672B1/en not_active Expired - Lifetime
- 2005-08-15 RU RU2007109598/04A patent/RU2381223C2/ru active
- 2005-08-15 PT PT58032806T patent/PT1778672E/pt unknown
- 2005-08-15 HR HRP20130192TT patent/HRP20130192T1/hr unknown
-
2007
- 2007-01-22 IL IL180853A patent/IL180853A/en active IP Right Grant
- 2007-02-05 ZA ZA200701057A patent/ZA200701057B/xx unknown
- 2007-02-23 MA MA29717A patent/MA28825B1/fr unknown
- 2007-03-09 NO NO20071307A patent/NO338770B1/no unknown
-
2009
- 2009-02-11 US US12/369,605 patent/US8101766B2/en not_active Expired - Fee Related
-
2011
- 2011-12-16 US US13/328,386 patent/US8476299B2/en not_active Expired - Fee Related
-
2012
- 2012-03-22 JP JP2012065767A patent/JP2012121929A/ja not_active Withdrawn
-
2013
- 2013-06-05 US US13/910,708 patent/US8754223B2/en not_active Expired - Lifetime
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