JP4376065B2 - 2−アミノインダン誘導体の製造方法 - Google Patents
2−アミノインダン誘導体の製造方法 Download PDFInfo
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- JP4376065B2 JP4376065B2 JP2003574609A JP2003574609A JP4376065B2 JP 4376065 B2 JP4376065 B2 JP 4376065B2 JP 2003574609 A JP2003574609 A JP 2003574609A JP 2003574609 A JP2003574609 A JP 2003574609A JP 4376065 B2 JP4376065 B2 JP 4376065B2
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- Japan
- Prior art keywords
- compound
- formula
- dihydro
- acetyl
- inden
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- 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.)
- Expired - Lifetime
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- 0 CCc1ccc(CC(C2)NC(*)=O)c2c1 Chemical compound CCc1ccc(CC(C2)NC(*)=O)c2c1 0.000 description 1
- JUKKOFDOKRVDKM-UHFFFAOYSA-N CCc1ccc(CC(C2)NC(C(F)(F)F)=O)c2c1 Chemical compound CCc1ccc(CC(C2)NC(C(F)(F)F)=O)c2c1 JUKKOFDOKRVDKM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/06—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
- C07C233/32—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 ring other than a six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Description
(i)2−アミノインダンのアミノ基を、有機溶媒の存在下にてアシル基で保護し、式(I)
(ii)式(I)の化合物を、ルイス酸の存在下でアセチルハライドと反応させ、式(II)
(iii)式(II)の化合物を、触媒および有機溶媒の存在下にて還元剤で処理し、式(III)
(iv)式(III)の化合物を、ルイス酸の存在下でアセチルハライドと反応させ、式(IV)
(v)式(IV)の化合物を、触媒および有機溶媒の存在下にて還元剤で処理し、式(V)
(vi)式(V)の化合物を、塩基の存在下で加水分解し、式(VI)
で示される5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−アミンを形成させること、
からなる方法を提供する。
を有する酸付加塩を形成させる。アニオンは、工程(vii)において使用された酸に対応する。好適なアニオンはCl−である。
で示される化合物を提供する。
(i')2−アミノインダンを、酢酸のエステル中でエチル トリフルオロ酢酸塩と反応させて、N−(2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを形成させること;
(ii')N−(2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを、ルイス酸の存在下でアセチルハライドと反応させて、N−(5−アセチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを形成させること;
(iii')N−(5−アセチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドのアセチル基を、酢酸のエステル中で触媒の存在下にて水素ガスで還元して、N−(5−エチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを形成させること;
(iv')N−(5−エチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを、ルイス酸の存在下でアセチルハライドと反応させて、N−(5−アセチル−6−エチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを形成させること;
(v')N−(5−アセチル−6−エチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドのアセチル基を、酢酸のエステル中で触媒の存在下にて水素ガスで還元して、N−(5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを形成させること;および
(vi')塩基の存在下でN−(5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドを加水分解して、5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−アミンを形成させることを含む。
あるいは、ヘプタンの代わりのトルエン中で結晶化が行われる。
あるいは、実施例4の反応溶媒は、酢酸エチルの代わりにエタノールであり、そして結晶化のためにヘプタンのために水が使用される。
本発明の方法の工程(iv)にしたがって、ハロゲン化溶媒、ジクロロメタンを用いるN−(5−アセチル−6−エチル−2,3−ジヒドロ−1H−インデン−2−イル)−2,2,2−トリフルオロアセトアミドの製造
あるいは、実施例6における結晶化は、ヘプタンの代わりに1:1のエタノール/水混合液で行われる。
あるいは、実施例7の反応溶媒は酢酸エチルの代わりにエタノールであり、そして結晶化のためにヘプタンの代わりに水が使用される。
Claims (4)
- 5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−アミンの製造方法であって、
(i)2−アミノインダンのアミノ基をアシル化し、式(I)
の化合物を形成させること、
(ii)式(I)の化合物を、BF3、AlCl3、TiCl4、SnCl4、BCl3、(C2H5)2AlClおよびC2H5AlCl2から選択されるルイス酸の存在下でアセチルハライドと反応させ、式(II)
の化合物を形成させること、
(iii)式(II)の化合物を、還元剤として水素ガス、そして触媒として炭素担持パラジウムを用いて還元し、式(III)
の化合物を形成させること、
(iv)式(III)の化合物を、BF3、AlCl3、TiCl4、SnCl4、BCl3、(C2H5)2AlClおよびC2H5AlCl2から選択されるルイス酸の存在下でアセチルハライドと反応させ、式(IV)
の化合物を形成させること、
(v)式(IV)の化合物を、還元剤として水素ガス、そして触媒として炭素担持パラジウムを用いて還元し、式(V)
の化合物を形成させること、
(vi)式(V)の化合物を、塩基の存在下で加水分解し、5,6−ジエチル−2,3−ジヒドロ−1H−インデン−2−アミンを形成させること、
を含んでなる方法。 - Rがトリフルオロメチルである、請求項1に記載の方法。
- 工程(ii)または工程(iv)で用いるルイス酸がAlCl3である、請求項1または2に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36273502P | 2002-03-08 | 2002-03-08 | |
PCT/EP2003/002366 WO2003076387A2 (en) | 2002-03-08 | 2003-03-07 | Process for preparing 2-aminoindan derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005519133A JP2005519133A (ja) | 2005-06-30 |
JP2005519133A5 JP2005519133A5 (ja) | 2006-04-20 |
JP4376065B2 true JP4376065B2 (ja) | 2009-12-02 |
Family
ID=27805221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003574609A Expired - Lifetime JP4376065B2 (ja) | 2002-03-08 | 2003-03-07 | 2−アミノインダン誘導体の製造方法 |
Country Status (16)
Country | Link |
---|---|
US (1) | US6933410B2 (ja) |
EP (1) | EP1487781B8 (ja) |
JP (1) | JP4376065B2 (ja) |
KR (1) | KR100968650B1 (ja) |
CN (1) | CN1268605C (ja) |
AR (1) | AR038746A1 (ja) |
AT (1) | ATE402138T1 (ja) |
AU (1) | AU2003218704A1 (ja) |
DE (1) | DE60322356D1 (ja) |
EG (1) | EG23462A (ja) |
ES (1) | ES2311092T3 (ja) |
MY (1) | MY131849A (ja) |
PE (1) | PE20031054A1 (ja) |
PT (1) | PT1487781E (ja) |
TW (1) | TWI284528B (ja) |
WO (1) | WO2003076387A2 (ja) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
US20080027834A1 (en) * | 2006-07-31 | 2008-01-31 | Caterpillar Inc. | Systems and methods for inventory management |
CN103539677B (zh) * | 2012-07-16 | 2015-04-22 | 武汉万知生物医药有限公司 | 一种5,6-二乙基-2,3-二氢-1h-茚-2-胺盐酸盐的制备方法 |
CN103360264B (zh) * | 2013-07-18 | 2014-11-26 | 武汉恒和达生物医药有限公司 | 茚达特罗氨基片段5,6-二乙基-2,3-二氢-1h-茚-2-胺盐酸盐的合成方法 |
US11528924B2 (en) * | 2014-12-09 | 2022-12-20 | Clearmind Medicine, Inc. | Alcoholic beverage substitutes |
EP3705469A1 (en) | 2014-12-09 | 2020-09-09 | GOLAN, Ezekiel | Binge behavior regulators |
JP6637069B2 (ja) * | 2015-01-20 | 2020-01-29 | オロン ソシエタ ペル アチオニOlon Spa | インダンアミン誘導体の製法及び新規な合成中間体 |
ITUB20153978A1 (it) * | 2015-09-28 | 2017-03-28 | Laboratorio Chimico Int S P A | Procedimento per la preparazione di derivati di indanammina e di nuovi intermedi di sintesi. |
CN108752220A (zh) * | 2018-05-18 | 2018-11-06 | 成都伊诺达博医药科技有限公司 | 一种茚达特罗中间体的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3226947A1 (de) * | 1982-07-19 | 1984-01-19 | Henkel KGaA, 4000 Düsseldorf | Feuchtwischbezug fuer die fussbodenreinigung |
DE3623944A1 (de) | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
WO2000005234A1 (fr) | 1998-07-22 | 2000-02-03 | Suntory Limited | INHIBITEURS DE NF-λB CONTENANT DES DERIVES D'INDANE EN TANT QU'INGREDIENT ACTIF |
GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
-
2003
- 2003-02-14 US US10/367,402 patent/US6933410B2/en not_active Expired - Lifetime
- 2003-03-03 EG EG2003030216A patent/EG23462A/xx active
- 2003-03-06 PE PE2003000220A patent/PE20031054A1/es not_active Application Discontinuation
- 2003-03-06 TW TW092104808A patent/TWI284528B/zh not_active IP Right Cessation
- 2003-03-06 AR ARP030100758A patent/AR038746A1/es not_active Application Discontinuation
- 2003-03-07 AT AT03711939T patent/ATE402138T1/de active
- 2003-03-07 MY MYPI20030814A patent/MY131849A/en unknown
- 2003-03-07 EP EP03711939A patent/EP1487781B8/en not_active Expired - Lifetime
- 2003-03-07 PT PT03711939T patent/PT1487781E/pt unknown
- 2003-03-07 AU AU2003218704A patent/AU2003218704A1/en not_active Abandoned
- 2003-03-07 WO PCT/EP2003/002366 patent/WO2003076387A2/en active IP Right Grant
- 2003-03-07 CN CNB038055252A patent/CN1268605C/zh not_active Expired - Lifetime
- 2003-03-07 KR KR1020047013976A patent/KR100968650B1/ko active IP Right Grant
- 2003-03-07 ES ES03711939T patent/ES2311092T3/es not_active Expired - Lifetime
- 2003-03-07 JP JP2003574609A patent/JP4376065B2/ja not_active Expired - Lifetime
- 2003-03-07 DE DE60322356T patent/DE60322356D1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
MY131849A (en) | 2007-09-28 |
DE60322356D1 (de) | 2008-09-04 |
US6933410B2 (en) | 2005-08-23 |
TW200305393A (en) | 2003-11-01 |
CN1639111A (zh) | 2005-07-13 |
CN1268605C (zh) | 2006-08-09 |
AU2003218704A1 (en) | 2003-09-22 |
PE20031054A1 (es) | 2004-04-16 |
ATE402138T1 (de) | 2008-08-15 |
JP2005519133A (ja) | 2005-06-30 |
WO2003076387A2 (en) | 2003-09-18 |
ES2311092T3 (es) | 2009-02-01 |
TWI284528B (en) | 2007-08-01 |
US20030187301A1 (en) | 2003-10-02 |
KR100968650B1 (ko) | 2010-07-06 |
PT1487781E (pt) | 2008-10-30 |
EP1487781B1 (en) | 2008-07-23 |
AU2003218704A8 (en) | 2003-09-22 |
KR20040104490A (ko) | 2004-12-10 |
EP1487781B8 (en) | 2009-06-03 |
WO2003076387A3 (en) | 2004-03-25 |
EG23462A (en) | 2005-10-04 |
EP1487781A2 (en) | 2004-12-22 |
AR038746A1 (es) | 2005-01-26 |
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