JP5540075B2 - ビフェニル−2−イルカルバミン酸エステルの調製方法 - Google Patents
ビフェニル−2−イルカルバミン酸エステルの調製方法 Download PDFInfo
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- JP5540075B2 JP5540075B2 JP2012505154A JP2012505154A JP5540075B2 JP 5540075 B2 JP5540075 B2 JP 5540075B2 JP 2012505154 A JP2012505154 A JP 2012505154A JP 2012505154 A JP2012505154 A JP 2012505154A JP 5540075 B2 JP5540075 B2 JP 5540075B2
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- 0 COc(cc1NC(CCN(CC2)CCC2OC(Nc2ccccc2-c2ccccc2)=*)=O)c(CNC[C@@](c(c(C=C2)c3NC2=O)ccc3O)O)cc1Cl Chemical compound COc(cc1NC(CCN(CC2)CCC2OC(Nc2ccccc2-c2ccccc2)=*)=O)c(CNC[C@@](c(c(C=C2)c3NC2=O)ccc3O)O)cc1Cl 0.000 description 1
- WFCNFBRLTWSHJI-UHFFFAOYSA-N COc(cc1NC(CCN(CCC2)CCC2OC(Nc2ccccc2-c2ccccc2)=O)=O)c(C=O)cc1Cl Chemical compound COc(cc1NC(CCN(CCC2)CCC2OC(Nc2ccccc2-c2ccccc2)=O)=O)c(C=O)cc1Cl WFCNFBRLTWSHJI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms 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
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
m/z(ES+)236(M+H)
工程B:4−アミノ−5−クロロ−2−メトキシベンズアルデヒドの調製
m/z(ES+)186(M+H)
工程C:N−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミドの調製
アクリル酸(例えば、Aldrichから市販されている)(46ml、0.67mol)を酢酸エチル(0.85L)中の4−アミノ−5−クロロ−2−メトキシベンズアルデヒド(工程B)(50.0g、0.27mol)およびトリエチルアミン(204g、2.02mol)の撹拌懸濁液に25℃でゆっくりと添加した。反応温度を30℃から40℃の範囲で維持してプロパンホスホン酸無水物(酢酸エチル中50%、429g、0.67mol)を30分かけて添加した。混合物を30℃から40℃の範囲でさらに1時間撹拌し、次に25℃まで冷却し、水(0.26L)で希釈し、32%塩酸(108g)でpH2〜3まで酸性化した。有機相を分離し、水(0.23L)と32%水酸化ナトリウム(14g)の混合液で洗浄した。水相は約pH7であった。有機相を水(0.23L)で洗浄し、次に減圧下(約300ミリバール)で濃縮して0.56kgの蒸留物を除去した。メチルシクロヘキサン(335g)を添加し、さらに286gの蒸留物を減圧下で除去した。メチルシクロヘキサン(111g)を添加し、さらに得られた懸濁液を20℃まで冷却し、濾過してメチルシクロヘキサンで洗浄した。濾過ケーキを減圧下において40℃で12時間乾燥し、N−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミド(46g、71%)を得た。
反応温度が20℃を超えないようにしながら、3−クロロプロピオニルクロリド(98.4ml、1.0mol)を30分かけて4−アミノ−5−クロロ−2−メトキシベンズアルデヒドの撹拌懸濁液に添加した。添加完了後、混合物を20℃でさらに2時間撹拌し、次に濾過した。濾液を減圧下で150mlまで濃縮し、次に酢酸エチル(100ml)と水(400ml)で希釈した。混合物を20℃で1時間撹拌し、次に濾過してオフホワイト色の固体として3−クロロ−N−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]プロピオンアミドを得、これを単離せずにテトラヒドロフラン(730ml)中に懸濁してジイソプロピルエチルアミン(154ml、0.88mol)で処理した。得られた混合物を45℃で46時間撹拌し、次に減圧下で濃縮し残渣を得、これを酢酸エチル(300ml)で希釈し、2M塩酸(4x100ml)で洗浄し、さらに減圧下で濃縮してN−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミド(37.8g、62%)を得た。
m/z(ES+)240(M+H)
工程D:ビフェニル−2−イルカルバミン酸1−[2−(2−クロロ−4−ホルミル−5−メトキシフェニル−カルバモイルエチル]ピペリジン−4−イルエステルの調製
ビフェニル−2−イルカルバミン酸ピペリジン−4−イルエステル(WO2004/074246Aの調製8に従い調製することができる)(1.03kg、3.48mol)を、2−メチルテトラヒドロフラン(8.1L)中のN−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミド(工程C(調製1)またはC(調製2)に従い調製することができる)(0.81kg、3.38mol)および酢酸(0.39L、6.62mol)の撹拌溶液に60℃で5分間かけて少しずつ加えた。得られた溶液を75℃に加熱し、2時間この温度を保持した。溶液を60℃まで冷却し、ビフェニル−2−イルカルバミン酸1−[2−(2−クロロ−4−ホルミル−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(4.0g)を種結晶として添加して、60℃で30分熟成させてから4時間かけて20℃まで冷却した。得られた懸濁液を真空下で濾過して濾過ケーキをIMS(3x1.6L)で洗浄した。固体を真空オーブン中で50℃で10時間乾燥させ白色の固体としてビフェニル−2−イルカルバミン酸1−[2−(2−クロロ−4−ホルミル−5−メトキシフェニル−カルバモイルエチル]ピペリジン−4−イルエステルを得た(1.50kg、82%th)。
m/z(ES+)536(M+H)
調製2
ビフェニル−2−イルカルバミン酸ピペリジン−4−イルエステル(WO2004/074246Aの調製8に従い調製することができる)(63.0kg、212.57mol)を、2−メチルテトラヒドロフラン(430kg)中のN−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミド(工程C(調製1)またはC(調製2)に従い調製することができる)(50.0kg、208.62mol)および酢酸(12.6kg、209.83mol)の撹拌懸濁液に25℃で添加した。次に混合物を60分かけて50℃まで加熱し、この温度を2時間保持した。得られた懸濁液を90分かけて20℃まで冷却し、この温度で4時間保持した。懸濁液を真空下で濾過して濾過ケーキをIMS(3x78.9kg)で洗浄した。固体を真空オーブン中で50℃で10時間乾燥し、白色の固体としてビフェニル−2−イルカルバミン酸1−[2−(2−クロロ−4−ホルミル−5−メトキシフェニル−カルバモイルエチル]ピペリジン−4−イルエステルを得た(90.7kg、80.6%th)。
LC Rt=4.58分
装置
1H NMRスペクトルはCDCl3またはDMSO−d6のいずれかにおいて、Bruker DPX400、400MHz機器に記録した。
Claims (11)
- 前記方法が有機酸源の添加をさらに含む、請求項1に記載の方法。
- 前記有機酸源が有機カルボン酸である、請求項2に記載の方法。
- 前記有機カルボン酸が酢酸である、請求項3に記載の方法。
- 前記反応が、周囲温度と前記溶媒の還流温度の間の温度で実施される、請求項1〜4のいずれか1項に記載の方法。
- 反応後、前記反応混合物を60℃まで冷却し、ビフェニル−2−イルカルバミン酸1−[2−(2−クロロ−4−ホルミル−5−メトキシフェニル−カルバモイルエチル]ピペリジン−4−イルエステルを種結晶として添加し、60℃で30分熟成させ、次に4時間かけて20℃まで冷却する、請求項6に記載の方法。
- 反応後、前記反応混合物を90分かけて20℃まで冷却し、次に20℃で4時間維持する、請求項8に記載の方法。
- N−[2−クロロ−4−ホルミル−5−(メチルオキシ)フェニル]−2−プロペンアミド。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16904609P | 2009-04-14 | 2009-04-14 | |
US61/169,046 | 2009-04-14 | ||
PCT/EP2010/054893 WO2010119064A1 (en) | 2009-04-14 | 2010-04-14 | Process for the preparation of a biphenyl-2-ylcarbamic acid ester |
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JP2014094409A Division JP5714748B2 (ja) | 2009-04-14 | 2014-05-01 | ビフェニル−2−イルカルバミン酸エステルの調製方法 |
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JP2012523447A JP2012523447A (ja) | 2012-10-04 |
JP5540075B2 true JP5540075B2 (ja) | 2014-07-02 |
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JP2012505154A Active JP5540075B2 (ja) | 2009-04-14 | 2010-04-14 | ビフェニル−2−イルカルバミン酸エステルの調製方法 |
JP2014094409A Active JP5714748B2 (ja) | 2009-04-14 | 2014-05-01 | ビフェニル−2−イルカルバミン酸エステルの調製方法 |
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Country | Link |
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US (1) | US8519138B2 (ja) |
EP (1) | EP2419409B1 (ja) |
JP (2) | JP5540075B2 (ja) |
KR (1) | KR101720154B1 (ja) |
CN (1) | CN102395563B (ja) |
AU (1) | AU2010238504B2 (ja) |
BR (1) | BRPI1013562B1 (ja) |
CA (1) | CA2758353C (ja) |
EA (1) | EA022030B1 (ja) |
ES (1) | ES2535326T3 (ja) |
IL (1) | IL215550A (ja) |
MX (1) | MX2011010934A (ja) |
SG (1) | SG175023A1 (ja) |
WO (1) | WO2010119064A1 (ja) |
ZA (1) | ZA201107378B (ja) |
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PT107101A (pt) | 2013-08-02 | 2015-02-02 | Univ De Coimbra | Painéis flexíveis de aerogel hidrofóbico reforçado com feltro de fibras |
CN106632257B (zh) * | 2016-12-15 | 2019-02-12 | 上海市奉贤区中心医院 | Gsk961081及其中间体的合成方法 |
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AU506657B2 (en) * | 1975-12-10 | 1980-01-17 | Wellcome Foundation Limited, The | Isoquinoline derivatives |
ES2351392T3 (es) * | 2003-02-14 | 2011-02-03 | Theravance Inc | Derivados bifenilo que tienen actividad agonista de receptores beta2-adrenérgicos y actividad antagonista de receptores muscarínicos. |
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 |
WO2004089892A2 (en) * | 2003-04-01 | 2004-10-21 | Theravance, Inc. | Diarylmethyl and related compounds having beta2 andrenergic receptor agonist and muscarinic receptor antagonist activity |
CA2543858C (en) * | 2003-11-21 | 2014-04-15 | Theravance, Inc. | Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
TWI374883B (en) * | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
US7569586B2 (en) * | 2004-08-16 | 2009-08-04 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
WO2006138218A1 (en) * | 2005-06-13 | 2006-12-28 | Theravance, Inc. | Biphenyl compounds useful as muscarinic 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 |
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2010
- 2010-04-14 BR BRPI1013562-6A patent/BRPI1013562B1/pt active IP Right Grant
- 2010-04-14 AU AU2010238504A patent/AU2010238504B2/en active Active
- 2010-04-14 MX MX2011010934A patent/MX2011010934A/es active IP Right Grant
- 2010-04-14 ES ES10713940.4T patent/ES2535326T3/es active Active
- 2010-04-14 CN CN201080016905.8A patent/CN102395563B/zh active Active
- 2010-04-14 SG SG2011071719A patent/SG175023A1/en unknown
- 2010-04-14 WO PCT/EP2010/054893 patent/WO2010119064A1/en active Application Filing
- 2010-04-14 US US13/263,857 patent/US8519138B2/en active Active
- 2010-04-14 JP JP2012505154A patent/JP5540075B2/ja active Active
- 2010-04-14 KR KR1020117026946A patent/KR101720154B1/ko active IP Right Grant
- 2010-04-14 CA CA2758353A patent/CA2758353C/en active Active
- 2010-04-14 EA EA201190203A patent/EA022030B1/ru not_active IP Right Cessation
- 2010-04-14 EP EP10713940.4A patent/EP2419409B1/en active Active
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- 2011-10-05 IL IL215550A patent/IL215550A/en active IP Right Grant
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Also Published As
Publication number | Publication date |
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JP2012523447A (ja) | 2012-10-04 |
US20120046469A1 (en) | 2012-02-23 |
BRPI1013562B1 (pt) | 2021-08-03 |
EA022030B1 (ru) | 2015-10-30 |
MX2011010934A (es) | 2011-11-02 |
BRPI1013562A2 (pt) | 2020-08-18 |
JP2014193873A (ja) | 2014-10-09 |
KR20120006054A (ko) | 2012-01-17 |
AU2010238504B2 (en) | 2015-04-16 |
ZA201107378B (en) | 2013-03-27 |
CA2758353C (en) | 2017-06-06 |
CA2758353A1 (en) | 2010-10-21 |
WO2010119064A1 (en) | 2010-10-21 |
CN102395563A (zh) | 2012-03-28 |
CN102395563B (zh) | 2015-05-20 |
IL215550A0 (en) | 2011-12-29 |
US8519138B2 (en) | 2013-08-27 |
KR101720154B1 (ko) | 2017-03-27 |
JP5714748B2 (ja) | 2015-05-07 |
EP2419409B1 (en) | 2015-01-28 |
AU2010238504A1 (en) | 2011-11-03 |
ES2535326T3 (es) | 2015-05-08 |
SG175023A1 (en) | 2011-11-28 |
EA201190203A1 (ru) | 2012-05-30 |
IL215550A (en) | 2016-03-31 |
EP2419409A1 (en) | 2012-02-22 |
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