JP2012533550A5 - - Google Patents
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- Publication number
- JP2012533550A5 JP2012533550A5 JP2012520734A JP2012520734A JP2012533550A5 JP 2012533550 A5 JP2012533550 A5 JP 2012533550A5 JP 2012520734 A JP2012520734 A JP 2012520734A JP 2012520734 A JP2012520734 A JP 2012520734A JP 2012533550 A5 JP2012533550 A5 JP 2012533550A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- crystalline
- compound
- free base
- further characterized
- 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 description 35
- 239000012458 free base Substances 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000001757 thermogravimetry curve Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- XTNXFLCCCBHRCK-UHFFFAOYSA-N [1-[2-[[2-[4-[(4-carbamoylpiperidin-1-yl)methyl]phenyl]-2-oxoethyl]amino]ethyl]piperidin-4-yl] n-(2-phenylphenyl)carbamate Chemical compound C1CC(C(=O)N)CCN1CC1=CC=C(C(=O)CNCCN2CCC(CC2)OC(=O)NC=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1 XTNXFLCCCBHRCK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000048 adrenergic agonist Substances 0.000 claims description 4
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000007883 bronchodilation Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- -1 4-carbamoylpiperidin-1-ylmethyl Chemical group 0.000 claims description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- LXZYLGUNAYNUGX-UHFFFAOYSA-N methyl n-(2-phenylphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC=C1C1=CC=CC=C1 LXZYLGUNAYNUGX-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- QMOVGVNKXUTCQU-UHFFFAOYSA-N (2-phenylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22580309P | 2009-07-15 | 2009-07-15 | |
| US61/225,803 | 2009-07-15 | ||
| PCT/US2010/041903 WO2011008809A1 (en) | 2009-07-15 | 2010-07-14 | Crystalline freebase forms of a biphenyl compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014206123A Division JP6338505B2 (ja) | 2009-07-15 | 2014-10-07 | ビフェニル化合物の結晶性遊離塩基形 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012533550A JP2012533550A (ja) | 2012-12-27 |
| JP2012533550A5 true JP2012533550A5 (https=) | 2013-06-20 |
| JP5651174B2 JP5651174B2 (ja) | 2015-01-07 |
Family
ID=42562758
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012520734A Active JP5651174B2 (ja) | 2009-07-15 | 2010-07-14 | ビフェニル化合物の結晶性遊離塩基形 |
| JP2014206123A Active JP6338505B2 (ja) | 2009-07-15 | 2014-10-07 | ビフェニル化合物の結晶性遊離塩基形 |
| JP2015216372A Pending JP2016026214A (ja) | 2009-07-15 | 2015-11-04 | ビフェニル化合物の結晶性遊離塩基形 |
| JP2017134632A Pending JP2017171692A (ja) | 2009-07-15 | 2017-07-10 | ビフェニル化合物の結晶性遊離塩基形 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014206123A Active JP6338505B2 (ja) | 2009-07-15 | 2014-10-07 | ビフェニル化合物の結晶性遊離塩基形 |
| JP2015216372A Pending JP2016026214A (ja) | 2009-07-15 | 2015-11-04 | ビフェニル化合物の結晶性遊離塩基形 |
| JP2017134632A Pending JP2017171692A (ja) | 2009-07-15 | 2017-07-10 | ビフェニル化合物の結晶性遊離塩基形 |
Country Status (20)
| Country | Link |
|---|---|
| US (12) | US8541451B2 (https=) |
| EP (2) | EP2453894B1 (https=) |
| JP (4) | JP5651174B2 (https=) |
| KR (1) | KR101742252B1 (https=) |
| CN (1) | CN102470130B (https=) |
| AU (1) | AU2010273514B2 (https=) |
| BR (1) | BR112012000890A2 (https=) |
| CA (2) | CA2765621C (https=) |
| DK (1) | DK2453894T3 (https=) |
| ES (2) | ES2557553T3 (https=) |
| HR (1) | HRP20151344T1 (https=) |
| HU (1) | HUE026414T2 (https=) |
| IL (1) | IL216995A (https=) |
| MX (1) | MX2012000682A (https=) |
| PL (2) | PL2987490T3 (https=) |
| PT (1) | PT2453894E (https=) |
| SG (2) | SG178036A1 (https=) |
| SI (1) | SI2453894T1 (https=) |
| SM (1) | SMT201600019B (https=) |
| WO (1) | WO2011008809A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI341836B (en) | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| DK2453894T3 (en) | 2009-07-15 | 2016-01-25 | Theravance Biopharma R&D Ip Llc | Crystalline free base of a biphenyl compound |
| SG186708A1 (en) * | 2010-07-13 | 2013-02-28 | Theravance Inc | Process for preparing a biphenyl-2-ylcarbamic acid |
| SI2958916T1 (sl) * | 2013-02-21 | 2018-11-30 | Pfizer Inc. | Trdne oblike selektivnih zaviralcev CDK4/6 |
| WO2015070366A1 (en) | 2013-11-12 | 2015-05-21 | Merck Sharp & Dohme Corp. | Aryl linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug |
| WO2020047225A1 (en) | 2018-08-30 | 2020-03-05 | Theravance Biopharma R&D Ip, Llc | Methods for treating chronic obstructive pulmonary disease |
| CN112694434B (zh) * | 2020-12-29 | 2023-06-16 | 浙江和泽医药科技股份有限公司 | 一种雷芬那辛新中间体及其活性亲电砌块和雷芬那辛的新制备方法 |
| CN118401497A (zh) | 2021-12-09 | 2024-07-26 | 医药化学公司 | 雷芬那辛的结晶型丙酮溶剂化物 |
| CN114276290B (zh) * | 2021-12-24 | 2024-05-28 | 浙江和泽医药科技股份有限公司 | 一种雷芬那辛无水晶型及其制备方法 |
| CN117180235A (zh) * | 2023-09-19 | 2023-12-08 | 山东京卫制药有限公司 | 一种无定型雷芬那辛吸入制剂 |
| CN117263849A (zh) * | 2023-09-19 | 2023-12-22 | 山东京卫制药有限公司 | 一种雷芬那辛三水合物晶型及其制备方法 |
| CN117263848A (zh) * | 2023-09-19 | 2023-12-22 | 山东京卫制药有限公司 | 一种雷芬那辛的吸入喷雾剂 |
| US20250136550A1 (en) | 2023-10-27 | 2025-05-01 | Theravance Biopharma R&D Ip, Llc | Processes for preparing revefenacin and compositions comprising the same |
| CN117700354A (zh) * | 2023-12-12 | 2024-03-15 | 江苏百奥信康医药科技有限公司 | 一种雷芬那辛的晶体形式及其制备方法 |
| CN119775192B (zh) * | 2024-12-31 | 2025-11-28 | 山东京卫制药有限公司 | 一种三苯乙酸雷芬那辛晶型及其制备方法 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2425983C3 (de) * | 1973-06-12 | 1978-09-14 | Toyama Chemical Co. Ltd., Tokio | Sulfonsäuresalze von Acylcholinen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzung |
| BR8007911A (pt) | 1979-12-06 | 1981-06-16 | Glaxo Group Ltd | Inalador aperfeicoado |
| DE3274065D1 (de) | 1981-07-08 | 1986-12-11 | Draco Ab | Powder inhalator |
| DE3682457D1 (de) | 1985-07-30 | 1991-12-19 | Glaxo Group Ltd | Geraet zur verabreichung von medikamenten an patienten. |
| US5225183A (en) | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| SK280968B6 (sk) | 1990-03-02 | 2000-10-09 | Glaxo Group Limited | Balenie medikamentu na použite v inhalačnom prístroji |
| US6006745A (en) | 1990-12-21 | 1999-12-28 | Minnesota Mining And Manufacturing Company | Device for delivering an aerosol |
| US5874063A (en) | 1991-04-11 | 1999-02-23 | Astra Aktiebolag | Pharmaceutical formulation |
| WO1992022286A1 (en) | 1991-06-12 | 1992-12-23 | Minnesota Mining And Manufacturing Company | Albuterol sulfate suspension aerosol formulations |
| US5337740A (en) | 1991-08-01 | 1994-08-16 | New England Pharmaceuticals, Inc. | Inhalation devices |
| EP0617610B1 (en) | 1991-12-18 | 1997-03-19 | Minnesota Mining And Manufacturing Company | Suspension aerosol formulations |
| US5239993A (en) | 1992-08-26 | 1993-08-31 | Glaxo Inc. | Dosage inhalator providing optimized compound inhalation trajectory |
| US5415162A (en) | 1994-01-18 | 1995-05-16 | Glaxo Inc. | Multi-dose dry powder inhalation device |
| WO1995021820A1 (en) | 1994-02-10 | 1995-08-17 | Yamanouchi Pharmaceutical Co., Ltd. | Novel carbamate derivative and medicinal composition containing the same |
| US5983956A (en) | 1994-10-03 | 1999-11-16 | Astra Aktiebolag | Formulation for inhalation |
| US5637820A (en) * | 1995-01-06 | 1997-06-10 | Wittman; Kenneth L. | Stringed instrument with on-board tuner |
| SE9501384D0 (sv) | 1995-04-13 | 1995-04-13 | Astra Ab | Process for the preparation of respirable particles |
| MX9707864A (es) | 1995-04-14 | 1997-11-29 | Glaxo Wellcome Inc | Inhalador de dosis medida por salmeterol. |
| US6040344A (en) | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| AU9281298A (en) | 1997-10-01 | 1999-04-23 | Kyowa Hakko Kogyo Co. Ltd. | Benzodioxole derivatives |
| JP2002506856A (ja) | 1998-03-14 | 2002-03-05 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | フタラジノンｐｄｅｉｉｉ／ｉｖ阻害剤 |
| ID27887A (id) | 1998-04-18 | 2001-05-03 | Glaxo Group Ltd | Formulasi aerosol farmasi |
| GB9808802D0 (en) | 1998-04-24 | 1998-06-24 | Glaxo Group Ltd | Pharmaceutical formulations |
| SE9804000D0 (sv) | 1998-11-23 | 1998-11-23 | Astra Ab | New composition of matter |
| US6693202B1 (en) * | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| PT1169019E (pt) | 1999-04-14 | 2003-07-31 | Glaxo Group Ltd | Formulacao farmaceutica em aerossol |
| UA73965C2 (en) | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| EP1366025B1 (en) | 2001-03-08 | 2007-06-27 | Glaxo Group Limited | Agonists of beta-adrenoreceptors |
| JP4143413B2 (ja) | 2001-03-22 | 2008-09-03 | グラクソ グループ リミテッド | β２−アドレナリン受容体アゴニストとしてのホルムアニリド誘導体 |
| US20030018019A1 (en) * | 2001-06-23 | 2003-01-23 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics |
| ES2438985T3 (es) | 2001-09-14 | 2014-01-21 | Glaxo Group Limited | Formulación de inhalación que comprende derivados de fenetanolamina para el tratamiento de enfermedades respiratorias |
| US6653323B2 (en) | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| PE20050973A1 (es) * | 2003-10-29 | 2005-11-19 | Theravance Inc | Sales de acido naftalen-1,5-disulfonico de un compuesto de 4-amino-1-(piridilmetil)piperidina como antagonistas de receptores muscarinicos |
| TWI341836B (en) | 2004-03-11 | 2011-05-11 | Theravance Inc | Biphenyl compounds useful as muscarinic receptor antagonists |
| TW200540154A (en) * | 2004-06-10 | 2005-12-16 | Theravance Inc | Crystalline form of a substituted pyrrolidine compound |
| US20060205949A1 (en) * | 2005-03-10 | 2006-09-14 | Theravance, Inc. | Crystalline forms of a biphenyl compound |
| TWI372749B (en) | 2005-03-10 | 2012-09-21 | Theravance Inc | Crystalline forms of a biphenyl compound |
| US7465870B1 (en) * | 2008-03-11 | 2008-12-16 | Homan Randy W | Illuminated heart-shaped guitar with strobe lights and a modified bridge |
| DK2453894T3 (en) * | 2009-07-15 | 2016-01-25 | Theravance Biopharma R&D Ip Llc | Crystalline free base of a biphenyl compound |
| SG186708A1 (en) | 2010-07-13 | 2013-02-28 | Theravance Inc | Process for preparing a biphenyl-2-ylcarbamic acid |
-
2010
- 2010-07-14 DK DK10732616.7T patent/DK2453894T3/en active
- 2010-07-14 AU AU2010273514A patent/AU2010273514B2/en active Active
- 2010-07-14 HR HRP20151344TT patent/HRP20151344T1/hr unknown
- 2010-07-14 CA CA2765621A patent/CA2765621C/en active Active
- 2010-07-14 CA CA2989129A patent/CA2989129C/en active Active
- 2010-07-14 EP EP10732616.7A patent/EP2453894B1/en active Active
- 2010-07-14 WO PCT/US2010/041903 patent/WO2011008809A1/en not_active Ceased
- 2010-07-14 HU HUE10732616A patent/HUE026414T2/hu unknown
- 2010-07-14 BR BR112012000890A patent/BR112012000890A2/pt not_active Application Discontinuation
- 2010-07-14 CN CN2010800304581A patent/CN102470130B/zh active Active
- 2010-07-14 ES ES10732616.7T patent/ES2557553T3/es active Active
- 2010-07-14 SG SG2012003067A patent/SG178036A1/en unknown
- 2010-07-14 PL PL15178848T patent/PL2987490T3/pl unknown
- 2010-07-14 SG SG10201407913UA patent/SG10201407913UA/en unknown
- 2010-07-14 KR KR1020127004005A patent/KR101742252B1/ko active Active
- 2010-07-14 US US12/835,964 patent/US8541451B2/en active Active
- 2010-07-14 EP EP15178848.6A patent/EP2987490B1/en active Active
- 2010-07-14 JP JP2012520734A patent/JP5651174B2/ja active Active
- 2010-07-14 PT PT107326167T patent/PT2453894E/pt unknown
- 2010-07-14 ES ES15178848.6T patent/ES2639642T3/es active Active
- 2010-07-14 SI SI201031095T patent/SI2453894T1/sl unknown
- 2010-07-14 MX MX2012000682A patent/MX2012000682A/es active IP Right Grant
- 2010-07-14 PL PL10732616T patent/PL2453894T3/pl unknown
-
2011
- 2011-12-15 IL IL216995A patent/IL216995A/en active IP Right Grant
-
2013
- 2013-08-22 US US13/973,174 patent/US8921396B2/en active Active
-
2014
- 2014-10-07 JP JP2014206123A patent/JP6338505B2/ja active Active
- 2014-11-19 US US14/547,455 patent/US9226896B2/en active Active
-
2015
- 2015-11-04 JP JP2015216372A patent/JP2016026214A/ja active Pending
- 2015-12-01 US US14/955,515 patent/US9415041B2/en active Active
-
2016
- 2016-01-20 SM SM201600019T patent/SMT201600019B/it unknown
- 2016-07-11 US US15/206,877 patent/US9765028B2/en active Active
-
2017
- 2017-07-10 JP JP2017134632A patent/JP2017171692A/ja active Pending
- 2017-08-15 US US15/677,264 patent/US10100013B2/en active Active
-
2018
- 2018-09-13 US US16/130,079 patent/US10550081B2/en active Active
-
2019
- 2019-12-16 US US16/715,225 patent/US11008289B2/en active Active
-
2021
- 2021-04-15 US US17/301,820 patent/US11691948B2/en active Active
-
2022
- 2022-06-15 US US17/841,567 patent/US11649209B2/en active Active
-
2023
- 2023-05-19 US US18/199,812 patent/US11858898B2/en active Active
-
2024
- 2024-07-02 US US18/762,102 patent/US20250179019A1/en active Pending
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