JP2009526018A5 - - Google Patents
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- JP2009526018A5 JP2009526018A5 JP2008553758A JP2008553758A JP2009526018A5 JP 2009526018 A5 JP2009526018 A5 JP 2009526018A5 JP 2008553758 A JP2008553758 A JP 2008553758A JP 2008553758 A JP2008553758 A JP 2008553758A JP 2009526018 A5 JP2009526018 A5 JP 2009526018A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- steroidal anti
- inflammatory agent
- pharmaceutical composition
- solvate
- 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.)
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- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims 9
- -1 1,2-dihydroquinolin-5-yl Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229940086735 succinate Drugs 0.000 claims 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 4
- WMWTYOKRWGGJOA-CENSZEJFSA-N Fluticasone propionate Chemical group 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)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims 3
- 238000000862 absorption spectrum Methods 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- 229960000289 fluticasone propionate Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
- 208000009856 Lung Disease Diseases 0.000 claims 2
- QMOVGVNKXUTCQU-UHFFFAOYSA-M N-(2-phenylphenyl)carbamate Chemical compound [O-]C(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-M 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 208000006673 Asthma Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000008121 dextrose Substances 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000010419 fine particle Substances 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 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 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 229920000747 poly(lactic acid) polymer Polymers 0.000 claims 1
- 239000004626 polylactic acid Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000009331 sowing Methods 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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
Claims (22)
- 多形体１の結晶質固体である、ビフェニル-2-イルカルバミン酸1-[2-(2-クロロ-4-{[(R)-2-ヒドロキシ-2-(8-ヒドロキシ-2-オキソ-1,2-ジヒドロキノリン-5-イル)エチルアミノ]メチル}-5-メトキシフェニルカルバモイル)エチル]ピペリジン-4-イルエステルのコハク酸塩またはその溶媒和物。
- (a)約170℃〜約180℃の範囲の融点を示す示差走査熱量測定トレース；
(b)5.0±0.3および10.0±0.3の２θ値に回折ピークを有する粉末Ｘ線回折パターン；
(c)約3265、2832、1735、1718、1679、1669、1591、1540、1518、1493、1439、1405、1339、1302、1283、1239、1202、1163、1144、1107、1095、1039、1009、973、921、885、868、838、773、751、および707 cm -1 に顕著な吸収バンドのある赤外吸収スペクトル
を特徴とする、請求項１に記載の塩。 - ピーク位置が図４に示すパターンのピーク位置と実質的に一致する粉末Ｘ線回折パターンを特徴とする、請求項１に記載の塩。
- 図７に示す赤外吸収スペクトルと実質的に一致する赤外吸収スペクトルを特徴とする、請求項１に記載の塩。
- 微粒子化された形態である、請求項１〜４のいずれか１項に記載の塩。
- 製薬上許容される担体および請求項１〜４のいずれか１項に記載の塩を含む、医薬組成物。
- さらにステロイド系抗炎症剤を含む、請求項６に記載の医薬組成物。
- ステロイド系抗炎症剤が6α,9α-ジフルオロ-17α-[(2-フラニルカルボニル)オキシ]-11β-ヒドロキシ-16α-メチル-3-オキソアンドロスタ-1,4-ジエン-17β-カルボチオ酸S-フルオロメチルエステルまたはその溶媒和物である、請求項７に記載の医薬組成物。
- ステロイド系抗炎症剤がプロピオン酸フルチカゾンである、請求項７に記載の医薬組成物。
- 吸入投与用に製剤化されている、請求項６に記載の医薬組成物。
- 微粒子化された形態である、請求項６に記載の医薬組成物。
- 担体が乳糖、デンプン、マンニトール、デキストロース、ポリ乳酸、ポリラクチド-コ-グリコリド、またはこれらの組合せである、請求項１０に記載の医薬組成物。
- (a) 請求項１〜４のいずれか１項に記載の塩、および
(b) ステロイド系抗炎症剤
からなる組合せ物。 - ステロイド系抗炎症剤が6α,9α-ジフルオロ-17α-[(2-フラニルカルボニル)オキシ]-11β-ヒドロキシ-16α-メチル-3-オキソアンドロスタ-1,4-ジエン-17β-カルボチオ酸S-フルオロメチルエステルまたはその溶媒和物である、請求項１３に記載の組合せ物。
- ステロイド系抗炎症剤がプロピオン酸フルチカゾンである、請求項１３に記載の組合せ物。
- 治療に使用するためのまたは医薬としての、請求項１に記載のビフェニル-2-イルカルバミン酸1-[2-(2-クロロ-4-{[(R)-2-ヒドロキシ-2-(8-ヒドロキシ-2-オキソ-1,2-ジヒドロキノリン-5-イル)エチルアミノ]メチル}-5-メトキシフェニルカルバモイル)エチル]ピペリジン-4-イルエステルのコハク酸塩またはその溶媒和物。
- 肺疾患の治療用の医薬の製造のための、請求項１に記載のビフェニル-2-イルカルバミン酸1-[2-(2-クロロ-4-{[(R)-2-ヒドロキシ-2-(8-ヒドロキシ-2-オキソ-1,2-ジヒドロキノリン-5-イル)エチルアミノ]メチル}-5-メトキシフェニルカルバモイル)エチル]ピペリジン-4-イルエステルのコハク酸塩またはその溶媒和物の使用。
- 肺疾患が慢性閉塞性肺疾患または喘息である、請求項１７に記載の使用。
- 医薬がステロイド系抗炎症剤をさらに含む、請求項１７または１８に記載の使用。
- ステロイド系抗炎症剤が6α,9α-ジフルオロ-17α-[(2-フラニルカルボニル)オキシ]-11β-ヒドロキシ-16α-メチル-3-オキソアンドロスタ-1,4-ジエン-17β-カルボチオ酸S-フルオロメチルエステルまたはその溶媒和物である、請求項１９に記載の使用。
- ステロイド系抗炎症剤がプロピオン酸フルチカゾンである、請求項１９に記載の使用。
- 請求項１に記載の多形体１のコハク酸塩の調製方法であって、以下の工程：
コハク酸塩を、18〜23℃の範囲の温度、例えば約20℃にて、THF水溶液(10〜18％、例えば10〜16％)中に溶解させること、
第１容量の低級アルコール、例えばエタノールまたはイソプロパノール、特にイソプロパノールを添加し、32〜40℃に加温すること、
場合により多形体１を播種すること、
第２容量の低級アルコールを、例えば数時間、好ましくは約12時間かけて、添加すること、
18〜23℃の範囲の温度、例えば約20℃へと冷却すること、ならびに
結晶質の生成物を回収すること、
を含む前記方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0602778.3A GB0602778D0 (en) | 2006-02-10 | 2006-02-10 | Novel compound |
| GB0602778.3 | 2006-02-10 | ||
| PCT/EP2007/051196 WO2007090859A1 (en) | 2006-02-10 | 2007-02-08 | Succinic acid salt of biphenyl-2-ylcarbamic acid 1-[2-(2-chloro-4-{ [ (r)-2-hydroxy-2- (8-hydroxy-2-oxo-1, 2-dihydroquinolin-5-yl) eth ylaminoimethyl] } -5-methoxyphenylcarbamoyl) ethyl] piperidin-4-yl ester and its use for the treatment of pulmonary disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009526018A JP2009526018A (ja) | 2009-07-16 |
| JP2009526018A5 true JP2009526018A5 (ja) | 2010-03-18 |
| JP5616021B2 JP5616021B2 (ja) | 2014-10-29 |
Family
ID=36119909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008553758A Active JP5616021B2 (ja) | 2006-02-10 | 2007-02-08 | ビフェニル−２−イルカルバミン酸１−［２−（２−クロロ−４−｛［（ｒ）−２−ヒドロキシ−２−（８−ヒドロキシ−２−オキソ−１，２−ジヒドロキノリン−５−イル）エチルアミノメチル］｝−５−メトキシフェニルカルバモイル）エチル］ピペリジン−４−イルエステルのコハク酸塩および肺疾患治療におけるその使用 |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7960551B2 (ja) |
| EP (1) | EP1981872B1 (ja) |
| JP (1) | JP5616021B2 (ja) |
| KR (1) | KR101488691B1 (ja) |
| CN (1) | CN101379057B (ja) |
| AR (2) | AR059409A1 (ja) |
| AU (1) | AU2007213767B2 (ja) |
| BR (1) | BRPI0707559B8 (ja) |
| CA (1) | CA2641769C (ja) |
| CR (1) | CR10227A (ja) |
| CY (1) | CY1119238T1 (ja) |
| DK (1) | DK1981872T3 (ja) |
| EA (1) | EA016580B1 (ja) |
| ES (1) | ES2640226T3 (ja) |
| GB (1) | GB0602778D0 (ja) |
| HR (1) | HRP20171304T1 (ja) |
| HU (1) | HUE034315T2 (ja) |
| IL (1) | IL193103A (ja) |
| JO (1) | JO3389B1 (ja) |
| LT (1) | LT1981872T (ja) |
| MA (1) | MA30273B1 (ja) |
| MY (1) | MY153656A (ja) |
| NO (1) | NO341343B1 (ja) |
| NZ (1) | NZ570242A (ja) |
| PE (2) | PE20110120A1 (ja) |
| PL (1) | PL1981872T3 (ja) |
| PT (1) | PT1981872T (ja) |
| SG (1) | SG169404A1 (ja) |
| SI (1) | SI1981872T1 (ja) |
| TW (1) | TWI401251B (ja) |
| UA (1) | UA100364C2 (ja) |
| WO (1) | WO2007090859A1 (ja) |
| ZA (1) | ZA200806782B (ja) |
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| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
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| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
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| 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 |
| 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 |
| 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 |
| 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 |
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| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| US20030018019A1 (en) * | 2001-06-23 | 2003-01-23 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics |
| WO2003042160A1 (en) * | 2001-11-13 | 2003-05-22 | Theravance, Inc. | Aryl aniline beta-2 adrenergic receptor agonists |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| CN1646527A (zh) | 2002-04-12 | 2005-07-27 | 贝林格尔英格海姆法玛两合公司 | 包含β模拟剂(BETAMIMETICS)及新颖抗胆碱酯酶的药物 |
| AU2003239880A1 (en) * | 2002-05-28 | 2003-12-12 | Theravance, Inc. | ALKOXY ARYL Beta2 ADRENERGIC RECEPTOR AGONISTS |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| PE20040892A1 (es) | 2002-08-06 | 2004-11-19 | Glaxo Group Ltd | Antagonistas del receptor muscarinico m3 de acetilcolina |
| 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 |
| EP1615881A2 (en) | 2003-04-01 | 2006-01-18 | Theravance, Inc. | Diarylmethyl and related compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| DE602004021921D1 (de) * | 2003-05-28 | 2009-08-20 | Theravance Inc | Azabicycloalkanverbindungen als muscarinrezeptor antagonisten |
| CA2543858C (en) * | 2003-11-21 | 2014-04-15 | Theravance, Inc. | Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| 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 |
| WO2006023457A1 (en) * | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| US7569586B2 (en) * | 2004-08-16 | 2009-08-04 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
-
2006
- 2006-02-10 GB GBGB0602778.3A patent/GB0602778D0/en not_active Ceased
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2007
- 2007-02-08 DK DK07704449.3T patent/DK1981872T3/en active
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- 2007-02-08 EP EP07704449.3A patent/EP1981872B1/en active Active
- 2007-02-08 ES ES07704449.3T patent/ES2640226T3/es active Active
- 2007-02-08 NZ NZ570242A patent/NZ570242A/en not_active IP Right Cessation
- 2007-02-08 AR ARP070100537A patent/AR059409A1/es not_active Application Discontinuation
- 2007-02-08 TW TW096104636A patent/TWI401251B/zh active
- 2007-02-08 US US11/672,536 patent/US7960551B2/en active Active
- 2007-02-08 JO JOP/2007/0037A patent/JO3389B1/ar active
- 2007-02-08 AU AU2007213767A patent/AU2007213767B2/en active Active
- 2007-02-08 CA CA2641769A patent/CA2641769C/en active Active
- 2007-02-08 BR BRPI0707559A patent/BRPI0707559B8/pt active IP Right Grant
- 2007-02-08 KR KR20087022160A patent/KR101488691B1/ko active IP Right Grant
- 2007-02-08 SG SG201100933-9A patent/SG169404A1/en unknown
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- 2007-02-08 CN CN2007800050282A patent/CN101379057B/zh active Active
- 2007-02-08 PL PL07704449T patent/PL1981872T3/pl unknown
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