DK2516394T3 - Fremgangsmåde til fremstillingen af et farmaceutisk aktivt middel - Google Patents
Fremgangsmåde til fremstillingen af et farmaceutisk aktivt middel Download PDFInfo
- Publication number
- DK2516394T3 DK2516394T3 DK10803222.8T DK10803222T DK2516394T3 DK 2516394 T3 DK2516394 T3 DK 2516394T3 DK 10803222 T DK10803222 T DK 10803222T DK 2516394 T3 DK2516394 T3 DK 2516394T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- compound
- reactor
- rani
- alcoholic solvent
- Prior art date
Links
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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- 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
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Claims (14)
1. Fremgangsmåde til fremstillingen af forbindelsen med formel IV,
formel IV omfattende trinnene at: (a) blande (6-fluor-lH-indol-3-yl)acetonitril, NH3 i vand og en overgangsmetal-katalysator i et alkoholisk opløsningsmiddel; og (b) hydrogenere blandingen med H2.
2. Fremgangsmåden ifølge krav 1, hvor overgangsmetal-katalysatoren er RaNi.
3. Fremgangsmåden ifølge krav 1, hvor det alkoholiske opløsningsmiddel er methanol.
4. Fremgangsmåden ifølge et hvilket som helst af kravene 1-3, hvor hydrogeneringen gennemføres ved et tryk på 250000 pascal (2,5 bar) i 16 timer.
5. Fremgangsmåden ifølge et hvilket som helst af kravene 1-4, hydrogeneringen gennemføres ved en temperatur fra 55 til 65°C.
6. Fremgangsmåden ifølge krav 2, hvor den anvendte RaNi er en svampe-metal katalysator ("sponge metal catalyst").
7. Fremgangsmåden ifølge krav 2 eller 6, hvor den nominelle sammensætning af aluminium i RaNi er 5% og median partikelstørrelsen af RaNi er 33 mikrometer.
8. Fremgangsmåden ifølge et hvilket som helst af kravene 1-7, hvor NH3 er til stede i vandopløsning i en koncentration på 25%.
9. Fremgangsmåden ifølge et hvilket som helst af de foregående krav, yderligere omfattende oprensning af forbindelsen med formel IV, oprensningen omfattende: (a) at opløse forbindelsen med formel IV i et alkoholisk opløsningsmiddel; (b) at tilsætte en opløsning af L(+)-vinsyre; og (c) at indfange vinsyresaltet som et bundfald.
10. Fremgangsmåden ifølge krav 9, hvor det alkoholiske opløsningsmiddel er methanol.
11. Fremgangsmåden ifølge krav 9 eller 10, hvor ethylacetat anvendes med det alkoholiske opløsningsmiddel.
12. Fremgangsmåden ifølge et hvilket som helst af de foregående krav, yderligere omfattende omsætning af forbindelsen med formel IV for at danne en forbindelse med formel I, ved kobling af aminen med 3-(2,2,3,3-tetrafluorpropoxy)-benzaldehyd i tilstedeværelsen af et opløsningsmiddel, efterfulgt af reduktion af iminbindingen med et reduktionsmiddel
formel I.
13. Fremgangsmåden ifølge krav 12, hvor reduktionsmidlet er natriumborhydrid.
14. Fremgangsmåden ifølge krav 12 eller 13, yderligere omfattende omdannelse af forbindelsen med formel I til HCI-saltet deraf ved tilsætning af HCI, eventuelt efterfulgt af oprensning af det resulterende salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28953009P | 2009-12-23 | 2009-12-23 | |
| PCT/DK2010/050348 WO2011076212A2 (en) | 2009-12-23 | 2010-12-20 | Processes for the manufacture of a pharmaceutically active agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2516394T3 true DK2516394T3 (da) | 2016-06-13 |
Family
ID=43567689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10803222.8T DK2516394T3 (da) | 2009-12-23 | 2010-12-20 | Fremgangsmåde til fremstillingen af et farmaceutisk aktivt middel |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US8461353B2 (da) |
| EP (1) | EP2516394B1 (da) |
| JP (2) | JP5864435B2 (da) |
| KR (2) | KR101873182B1 (da) |
| CN (2) | CN102656146B (da) |
| AR (1) | AR079580A1 (da) |
| AU (1) | AU2010335659B2 (da) |
| BR (1) | BR112012015749A2 (da) |
| CA (1) | CA2785440C (da) |
| CL (1) | CL2012001725A1 (da) |
| CR (1) | CR20120316A (da) |
| CY (1) | CY1118032T1 (da) |
| DK (1) | DK2516394T3 (da) |
| DO (1) | DOP2012000170A (da) |
| EA (1) | EA021440B1 (da) |
| ES (1) | ES2575666T3 (da) |
| GE (1) | GEP20146078B (da) |
| HK (2) | HK1174921A1 (da) |
| HR (1) | HRP20160518T1 (da) |
| HU (1) | HUE028806T2 (da) |
| IL (2) | IL220329A (da) |
| MA (1) | MA33945B1 (da) |
| ME (1) | ME02401B (da) |
| MX (1) | MX2012007078A (da) |
| MY (1) | MY159251A (da) |
| NZ (2) | NZ600639A (da) |
| PL (1) | PL2516394T3 (da) |
| PT (1) | PT2516394E (da) |
| RS (1) | RS54820B1 (da) |
| SG (1) | SG181910A1 (da) |
| SI (1) | SI2516394T1 (da) |
| SM (1) | SMT201600166B (da) |
| TN (1) | TN2012000279A1 (da) |
| TW (1) | TW201139370A (da) |
| UA (1) | UA111584C2 (da) |
| WO (1) | WO2011076212A2 (da) |
| ZA (1) | ZA201305936B (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201139370A (en) | 2009-12-23 | 2011-11-16 | Lundbeck & Co As H | Processes for the manufacture of a pharmaceutically active agent |
| JO3459B1 (ar) | 2012-09-09 | 2020-07-05 | H Lundbeck As | تركيبات صيدلانية لعلاج مرض الزهايمر |
| JO3639B1 (ar) * | 2014-07-04 | 2020-08-27 | H Lundbeck As | صورة متعددة الشكل جديدة لـ n-[2-(6-فلورو-1h-إندول-3-يل)إيثيل]-3-(2،2،3،3-تترا فلورو بروبوكسي)بنزيل أمين هيدروكلوريد |
| CN104130174A (zh) * | 2014-07-30 | 2014-11-05 | 天津市斯芬克司药物研发有限公司 | 一种吲唑衍生物及其制备方法 |
| CN105175307A (zh) * | 2014-11-18 | 2015-12-23 | 苏州晶云药物科技有限公司 | Lu AE58054的盐酸盐晶型A及其制备方法和用途 |
| TW201630881A (zh) | 2014-12-12 | 2016-09-01 | Ｈ 朗德貝克公司 | 用於生產艾達魯吡啶之方法 |
| CN104529865B (zh) * | 2014-12-12 | 2017-02-01 | 广东东阳光药业有限公司 | 苄胺类衍生物及其在药物上的应用 |
| MA41148A (fr) * | 2014-12-12 | 2017-10-17 | H Lundbeck As | Procédé de fabrication d'idalopirdine |
| CN108271369A (zh) * | 2015-10-23 | 2018-07-10 | 法尔玛赞公司 | 用于制备色胺及其衍生物的新工艺 |
| JP2019513742A (ja) | 2016-04-08 | 2019-05-30 | ハー・ルンドベック・アクチエゼルスカベット | イミンの水素化によるイダロピルジンの製造方法 |
| EP3333154A1 (en) * | 2016-12-07 | 2018-06-13 | Sandoz Ag | Crystalline form of a selective 5-ht6 receptor antagonist |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042685A (en) | 1962-07-03 | Process of making g-fluoro tryptamine | ||
| GB846675A (en) | 1958-04-18 | 1960-08-31 | Lab Francais Chimiotherapie | Process for the production of a tryptamine derivative |
| US4803218A (en) * | 1982-09-29 | 1989-02-07 | Mcneilab, Inc. | 3-aminoalkyl-1H-indole-5-urea and amide derivatives |
| DE69416697T2 (de) | 1993-12-28 | 1999-09-09 | Rhone Poulenc Fibres | Verfahren zur katalytischer hydrogenierung von nitrilen zu aminen in anwesenheit eines dosierten raney nickel katalysators |
| EP0737101B1 (fr) | 1993-12-28 | 1998-09-23 | RHODIA FIBER & RESIN INTERMEDIATES | Procede de preparation d'un catalyseur d'hydrogenation de nitriles en amines et application de ce catalyseur en hydrogenation |
| US5869653A (en) | 1997-10-30 | 1999-02-09 | Air Products And Chemicals, Inc. | Hydrogenation of nitriles to produce amines |
| KR20000069831A (ko) | 1997-10-31 | 2000-11-25 | 요트.게.아. 롤페즈 | 구성 신호에 대한 잡음 추가를 통한 엘피씨 원칙에 따라 인코딩된 음성의 오디오 표현을 위한 방법 및 장치 |
| US6156694A (en) | 1998-11-05 | 2000-12-05 | E. I. Dupont De Nemours & Company | Raney cobalt catalyst and a process for hydrogenating organic compounds using said catalyst |
| AU2002303094B2 (en) | 2001-03-29 | 2006-11-23 | Eli Lilly And Company | N-(2-arylethyl)benzylamines as antagonists of the 5-HT6 receptor |
| US7084154B2 (en) * | 2003-02-11 | 2006-08-01 | Pharmacopeia Drug Disclovery, Inc. | 2-(aminomethyl) arylamide analgesics |
| FR2866335B1 (fr) | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| JP2006169113A (ja) * | 2004-12-10 | 2006-06-29 | Dainippon Sumitomo Pharma Co Ltd | インドール類の合成方法および合成中間体 |
| WO2007070796A1 (en) * | 2005-12-15 | 2007-06-21 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| JO2704B1 (en) * | 2007-09-21 | 2013-03-03 | جانسين فارماسوتيكا ان في | Interference inhibition factors between MD2 and B53 |
| EP2219646A4 (en) | 2007-12-21 | 2010-12-22 | Univ Rochester | METHOD FOR MODIFYING THE LIFETIME OF EUKARYOTIC ORGANISMS |
| WO2010036362A1 (en) * | 2008-09-26 | 2010-04-01 | Wyeth | 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate nuclear receptor inhibitors |
| CN101531624A (zh) | 2009-04-08 | 2009-09-16 | 大连凯飞精细化工有限公司 | 6-氟吲哚-3-乙腈的合成方法 |
| TW201139370A (en) | 2009-12-23 | 2011-11-16 | Lundbeck & Co As H | Processes for the manufacture of a pharmaceutically active agent |
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2010
- 2010-12-16 TW TW099144129A patent/TW201139370A/zh unknown
- 2010-12-20 NZ NZ600639A patent/NZ600639A/en not_active IP Right Cessation
- 2010-12-20 EA EA201290552A patent/EA021440B1/ru not_active IP Right Cessation
- 2010-12-20 SG SG2012046793A patent/SG181910A1/en unknown
- 2010-12-20 CA CA2785440A patent/CA2785440C/en not_active Expired - Fee Related
- 2010-12-20 JP JP2012545093A patent/JP5864435B2/ja not_active Expired - Fee Related
- 2010-12-20 SI SI201031191A patent/SI2516394T1/sl unknown
- 2010-12-20 CN CN201080058864.9A patent/CN102656146B/zh not_active Expired - Fee Related
- 2010-12-20 ME MEP-2016-105A patent/ME02401B/me unknown
- 2010-12-20 NZ NZ625798A patent/NZ625798A/en not_active IP Right Cessation
- 2010-12-20 PT PT108032228T patent/PT2516394E/pt unknown
- 2010-12-20 GE GEAP201012807A patent/GEP20146078B/en unknown
- 2010-12-20 KR KR1020177031907A patent/KR101873182B1/ko active IP Right Grant
- 2010-12-20 BR BR112012015749A patent/BR112012015749A2/pt active Search and Examination
- 2010-12-20 EP EP10803222.8A patent/EP2516394B1/en active Active
- 2010-12-20 US US12/972,559 patent/US8461353B2/en not_active Expired - Fee Related
- 2010-12-20 MY MYPI2012002675A patent/MY159251A/en unknown
- 2010-12-20 RS RS20160382A patent/RS54820B1/sr unknown
- 2010-12-20 AU AU2010335659A patent/AU2010335659B2/en not_active Ceased
- 2010-12-20 HU HUE10803222A patent/HUE028806T2/en unknown
- 2010-12-20 MX MX2012007078A patent/MX2012007078A/es active IP Right Grant
- 2010-12-20 WO PCT/DK2010/050348 patent/WO2011076212A2/en active Application Filing
- 2010-12-20 MA MA35092A patent/MA33945B1/fr unknown
- 2010-12-20 ES ES10803222.8T patent/ES2575666T3/es active Active
- 2010-12-20 PL PL10803222.8T patent/PL2516394T3/pl unknown
- 2010-12-20 UA UAA201207977A patent/UA111584C2/uk unknown
- 2010-12-20 DK DK10803222.8T patent/DK2516394T3/da active
- 2010-12-20 KR KR1020127016217A patent/KR101796330B1/ko active IP Right Grant
- 2010-12-20 CN CN201410004542.6A patent/CN103694161B/zh not_active Expired - Fee Related
- 2010-12-21 AR ARP100104826A patent/AR079580A1/es active IP Right Grant
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2012
- 2012-05-31 TN TNP2012000279A patent/TN2012000279A1/en unknown
- 2012-06-12 IL IL220329A patent/IL220329A/en not_active IP Right Cessation
- 2012-06-12 CR CR20120316A patent/CR20120316A/es unknown
- 2012-06-18 DO DO2012000170A patent/DOP2012000170A/es unknown
- 2012-06-22 CL CL2012001725A patent/CL2012001725A1/es unknown
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2013
- 2013-02-25 HK HK13102334.6A patent/HK1174921A1/xx not_active IP Right Cessation
- 2013-05-02 US US13/875,623 patent/US8901318B2/en not_active Expired - Fee Related
- 2013-08-07 ZA ZA2013/05936A patent/ZA201305936B/en unknown
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2014
- 2014-02-25 IL IL231141A patent/IL231141A/en not_active IP Right Cessation
- 2014-09-26 HK HK14109681.9A patent/HK1196352A1/xx not_active IP Right Cessation
- 2014-11-25 US US14/553,029 patent/US9382205B2/en active Active
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2015
- 2015-12-24 JP JP2015251874A patent/JP6195605B2/ja not_active Expired - Fee Related
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2016
- 2016-05-16 HR HRP20160518TT patent/HRP20160518T1/hr unknown
- 2016-06-02 CY CY20161100488T patent/CY1118032T1/el unknown
- 2016-06-10 SM SM201600166T patent/SMT201600166B/it unknown
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