JP2011530566A - 4−オキソ−オクタヒドロ−インドール−1−カルボサイリックアシッドメチルエステルとその誘導体の調製方法 - Google Patents
4−オキソ−オクタヒドロ−インドール−1−カルボサイリックアシッドメチルエステルとその誘導体の調製方法 Download PDFInfo
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- JP2011530566A JP2011530566A JP2011522496A JP2011522496A JP2011530566A JP 2011530566 A JP2011530566 A JP 2011530566A JP 2011522496 A JP2011522496 A JP 2011522496A JP 2011522496 A JP2011522496 A JP 2011522496A JP 2011530566 A JP2011530566 A JP 2011530566A
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- QUXHUSWHPDPBAI-UHFFFAOYSA-N O=C(CCC1)CC1N1CC1 Chemical compound O=C(CCC1)CC1N1CC1 QUXHUSWHPDPBAI-UHFFFAOYSA-N 0.000 description 3
- 0 *N(CC1)[C@@](CCC2)[C@]1C2=O Chemical compound *N(CC1)[C@@](CCC2)[C@]1C2=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
Description
21.6mmolの3−(1−アジリジニル)シクロヘキサノンを15mlのトルエンに溶解し、0℃へ冷却する。得られた透明な溶液へ21.6mmolのアルキルクロロホルメートを20分以内で添加する(発熱反応)。温度を0〜10℃に維持する。得られたやや黄色〜褐色の溶液を室温まで温め、さらに1時間撹拌する。溶剤および過剰の試薬を真空下で除去(60℃/20mbar)し、残存する油分を5mlのトルエンで3回処理し、未反応のアルキルクロロホルメートを真空下で除去すると、以下の化合物が得られる。
4.95gのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−メチルエステル(実施例1)
5.22gのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−エチルエステル(実施例2)
5.53gのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−プロピルエステル(実施例3)
5.92gのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−ブチルエステル(実施例4)
6.27gのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−ネオペンチルエステル(実施例5)
5gのラセミカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−アルキルエステルを50mlのヘプタン/2−プロパノール=1/1(V/V)に溶解し、分取用Chiralpak−ADカラム(粒子径:20μm、カラム寸法:長さ30cm×内径10cm)へ注入する。ヘプタン/2−プロパノール/メタノール=90/7.5/2.5(V/V/V)を移動相として室温かつ400ml/分の流速で用い、R−エナンチオマーを常にS−エナンチオマーよりも先に溶出させながらベースラインの分離を60分以内に達成する。同一の条件下で2回目のクロマトグラフィーを行い、相当する画分同士を合わせる。溶剤を真空下で除去すると、以下の化合物が得られる:
4.6gの(R)−カルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−メチルエステル(実施例6)
15mmolのカルバミン酸(2−クロロエチル)(3−オキソシクロヘキシル)−アルキルエステルを15mlの塩化メチレンに溶解する。得られた橙色の溶液へ、1.07gのピロリジンおよび1.52gのトリエチルアミンを添加する。反応混合物を16時間室温で撹拌し、最後に45mlのイソプロピルアセテートと30mlの水で希釈する。撹拌下、エマルションのpHをpH=2へ調整し、撹拌をさらに30分間続ける。相分離させた後、水相を20mlのイソプロピルアセテートで2回抽出し、合わせた有機相を20mlずつの水で3回洗浄する。溶剤を真空下で除去(50℃/20mbar)すると、以下の化合物が得られる:
2.55gの1−カルボメトキシ(carbmethoxy)−4−ケトパーヒドロインドール(実施例16)
2.70gの1−カルボエトキシ(carbethoxy)−4−ケトパーヒドロインドール(実施例17)
2.98gの1−カルボプロポキシ(carbpropoxy)−4−ケトパーヒドロインドール(実施例18)
3.15gの1−カルボブトキシ(carbbutoxy)−4−ケトパーヒドロインドール(実施例19)
3.34gの1−カルボネオペントキシ(carbneopentoxy)−4−ケトパーヒドロインドール(実施例20)
5gのラセミ1−カルボアルコキシ−4−ケトパーヒドロインドールを50mlのヘプタン/2−プロパノール=1/1(V/V)に溶解し、分取用Chiralpak−ADカラム(粒子径:20□m、カラム寸法:長さ30cm×内径10cm)へ注入する。ヘプタン/2−プロパノール/メタノール=90/7.5/2.5(V/V/V)を移動相として室温かつ400ml/分の流速で用い、S,S−エナンチオマーを常にR,R−エナンチオマーよりも先に溶出させながらベースラインの分離を60分間以内に達成する。溶剤を真空下で除去すると、以下の化合物が得られる:
Claims (14)
- 上記式(IV)の化合物が、シクロヘキセン−2−オンとアジリジンまたはその塩とを反応させることにより得られるものである、請求項3に記載の方法。
- 上記式(I)の化合物を医薬組成物へ製剤化する工程をさらに含む、請求項1〜4のいずれか一項に記載の方法。
- 上記式(III)の化合物が、請求項3または4に従って得られるものである、請求項6に記載の方法。
- 上記式(IV)の化合物が、請求項4に従って得られるものである、請求項8に記載の方法。
- 請求項1に記載の式(I)の化合物またはその医薬的に許容可能な塩を製造するための、請求項10または11に記載の化合物の使用。
- 請求項1に記載の式(I)の化合物またはその医薬的に許容可能な塩を製造するための、シクロヘキセン−2−オン、アジリジンまたはその塩の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8815608P | 2008-08-12 | 2008-08-12 | |
US61/088,156 | 2008-08-12 | ||
PCT/EP2009/060351 WO2010018154A1 (en) | 2008-08-12 | 2009-08-10 | Processes for the preparation of 4-oxo-octahydro-indole-1-carbocylic acid methyl ester and derivatives thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011530566A true JP2011530566A (ja) | 2011-12-22 |
JP5468608B2 JP5468608B2 (ja) | 2014-04-09 |
Family
ID=41278189
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011522496A Active JP5468608B2 (ja) | 2008-08-12 | 2009-08-10 | 4−オキソ−オクタヒドロ−インドール−1−カルボサイリックアシッドメチルエステルとその誘導体の調製方法 |
Country Status (22)
Country | Link |
---|---|
US (1) | US8084487B2 (ja) |
EP (1) | EP2315748B1 (ja) |
JP (1) | JP5468608B2 (ja) |
KR (1) | KR101673634B1 (ja) |
CN (1) | CN102119151A (ja) |
AU (1) | AU2009281218B2 (ja) |
BR (1) | BRPI0917492A8 (ja) |
CA (1) | CA2732095C (ja) |
CL (1) | CL2011000296A1 (ja) |
CO (1) | CO6341608A2 (ja) |
EC (1) | ECSP11010883A (ja) |
ES (1) | ES2547269T3 (ja) |
HK (1) | HK1155733A1 (ja) |
IL (1) | IL210835A (ja) |
MA (1) | MA32618B1 (ja) |
MX (1) | MX2011001664A (ja) |
MY (1) | MY151183A (ja) |
NZ (1) | NZ590753A (ja) |
PE (1) | PE20110415A1 (ja) |
RU (1) | RU2513856C2 (ja) |
WO (1) | WO2010018154A1 (ja) |
ZA (1) | ZA201100558B (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2655326A1 (en) | 2010-12-20 | 2013-10-30 | Novartis AG | 4- (hetero) aryl - ethynyl - octahydro - indole - 1 - carboxylic acid esters |
US9067881B2 (en) | 2011-01-24 | 2015-06-30 | Novartis Ag | 4-tolyl-ethynyl-octahydro-indole-1-ester derivatives |
EP2650284A1 (en) | 2012-04-10 | 2013-10-16 | Merz Pharma GmbH & Co. KGaA | Heterocyclic derivatives as metabotropic glutamate receptor modulators |
WO2019025931A1 (en) | 2017-07-31 | 2019-02-07 | Novartis Ag | USE OF A MUSSEL FOR REDUCING THE USE OF COCAINE OR FOR PREVENTING A RECHUTE IN THE USE OF COCAINE |
JP2020529978A (ja) | 2017-07-31 | 2020-10-15 | ノバルティス アーゲー | アルコール使用の低減又はアルコール使用再燃の予防におけるマボグルラントの使用 |
CN113301894A (zh) * | 2019-01-29 | 2021-08-24 | 诺华股份有限公司 | mGluR5拮抗剂用于治疗阿片类物质镇痛耐受性的用途 |
AU2021307607A1 (en) | 2020-07-17 | 2022-11-17 | Novartis Ag | Mavoglurant, a mGluR5 antagonist, for use in the treatment in the reduction of opioid use |
AU2021397439A1 (en) | 2020-12-11 | 2023-07-06 | Novartis Ag | Use of mglur5 antagonists for treating amphetamine addiction |
IL303249A (en) | 2020-12-14 | 2023-07-01 | Novartis Ag | Use of MGLUR5 antagonists to treat gambling disorder |
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JP2005514381A (ja) * | 2001-12-04 | 2005-05-19 | ノバルティス アクチエンゲゼルシャフト | Mglur5アンタゴニスト活性を有するアセチレン誘導体 |
JP2009501171A (ja) * | 2005-07-12 | 2009-01-15 | ノバルティス アクチエンゲゼルシャフト | GI(とりわけGERD)におけるmGluR5(とりわけAFQ056)の使用 |
JP2010502664A (ja) * | 2006-09-11 | 2010-01-28 | ノバルティス アクチエンゲゼルシャフト | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
JP2011500529A (ja) * | 2007-10-12 | 2011-01-06 | ノバルティス アーゲー | パーキンソン病処置用代謝型グルタミン酸受容体モジュレーター |
JP2011526596A (ja) * | 2008-06-30 | 2011-10-13 | ノバルティス アーゲー | 組み合わせ製品 |
-
2009
- 2009-08-10 KR KR1020117005727A patent/KR101673634B1/ko active IP Right Grant
- 2009-08-10 MX MX2011001664A patent/MX2011001664A/es active IP Right Grant
- 2009-08-10 MY MYPI20110380 patent/MY151183A/en unknown
- 2009-08-10 EP EP09781678.9A patent/EP2315748B1/en active Active
- 2009-08-10 US US13/058,608 patent/US8084487B2/en active Active
- 2009-08-10 JP JP2011522496A patent/JP5468608B2/ja active Active
- 2009-08-10 RU RU2011108663/04A patent/RU2513856C2/ru not_active IP Right Cessation
- 2009-08-10 CN CN2009801306666A patent/CN102119151A/zh active Pending
- 2009-08-10 BR BRPI0917492A patent/BRPI0917492A8/pt not_active IP Right Cessation
- 2009-08-10 NZ NZ590753A patent/NZ590753A/en not_active IP Right Cessation
- 2009-08-10 AU AU2009281218A patent/AU2009281218B2/en not_active Ceased
- 2009-08-10 CA CA2732095A patent/CA2732095C/en not_active Expired - Fee Related
- 2009-08-10 PE PE2011000147A patent/PE20110415A1/es not_active Application Discontinuation
- 2009-08-10 WO PCT/EP2009/060351 patent/WO2010018154A1/en active Application Filing
- 2009-08-10 ES ES09781678.9T patent/ES2547269T3/es active Active
-
2011
- 2011-01-21 ZA ZA2011/00558A patent/ZA201100558B/en unknown
- 2011-01-24 IL IL210835A patent/IL210835A/en not_active IP Right Cessation
- 2011-02-11 CL CL2011000296A patent/CL2011000296A1/es unknown
- 2011-03-07 MA MA33679A patent/MA32618B1/fr unknown
- 2011-03-11 EC EC2011010883A patent/ECSP11010883A/es unknown
- 2011-03-11 CO CO11030452A patent/CO6341608A2/es active IP Right Grant
- 2011-09-21 HK HK11109931.0A patent/HK1155733A1/xx not_active IP Right Cessation
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JP2005514381A (ja) * | 2001-12-04 | 2005-05-19 | ノバルティス アクチエンゲゼルシャフト | Mglur5アンタゴニスト活性を有するアセチレン誘導体 |
JP2009501171A (ja) * | 2005-07-12 | 2009-01-15 | ノバルティス アクチエンゲゼルシャフト | GI(とりわけGERD)におけるmGluR5(とりわけAFQ056)の使用 |
JP2010502664A (ja) * | 2006-09-11 | 2010-01-28 | ノバルティス アクチエンゲゼルシャフト | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
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JP2011526596A (ja) * | 2008-06-30 | 2011-10-13 | ノバルティス アーゲー | 組み合わせ製品 |
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Also Published As
Publication number | Publication date |
---|---|
AU2009281218B2 (en) | 2013-05-16 |
PE20110415A1 (es) | 2011-07-04 |
CL2011000296A1 (es) | 2011-11-04 |
KR101673634B1 (ko) | 2016-11-07 |
MX2011001664A (es) | 2011-03-25 |
HK1155733A1 (en) | 2012-05-25 |
CA2732095C (en) | 2017-04-25 |
RU2513856C2 (ru) | 2014-04-20 |
EP2315748A1 (en) | 2011-05-04 |
IL210835A0 (en) | 2011-04-28 |
MA32618B1 (fr) | 2011-09-01 |
US20110144352A1 (en) | 2011-06-16 |
MY151183A (en) | 2014-04-30 |
WO2010018154A1 (en) | 2010-02-18 |
AU2009281218A1 (en) | 2010-02-18 |
RU2011108663A (ru) | 2012-09-20 |
JP5468608B2 (ja) | 2014-04-09 |
US8084487B2 (en) | 2011-12-27 |
CA2732095A1 (en) | 2010-02-18 |
CN102119151A (zh) | 2011-07-06 |
CO6341608A2 (es) | 2011-11-21 |
EP2315748B1 (en) | 2015-06-24 |
NZ590753A (en) | 2012-06-29 |
ZA201100558B (en) | 2011-10-26 |
ES2547269T3 (es) | 2015-10-05 |
BRPI0917492A2 (pt) | 2015-08-04 |
ECSP11010883A (es) | 2011-04-29 |
IL210835A (en) | 2016-05-31 |
KR20110042222A (ko) | 2011-04-25 |
BRPI0917492A8 (pt) | 2016-07-05 |
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