HUP0400517A2 - Eljárás cabergolin előállítására - Google Patents
Eljárás cabergolin előállításáraInfo
- Publication number
- HUP0400517A2 HUP0400517A2 HU0400517A HUP0400517A HUP0400517A2 HU P0400517 A2 HUP0400517 A2 HU P0400517A2 HU 0400517 A HU0400517 A HU 0400517A HU P0400517 A HUP0400517 A HU P0400517A HU P0400517 A2 HUP0400517 A2 HU P0400517A2
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- reacted
- xiv
- derivative
- compound
- Prior art date
Links
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 title abstract 3
- 229960004596 cabergoline Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000004808 allyl alcohols Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229910052801 chlorine Chemical group 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
- C07D457/06—Lysergic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Eljárás az (I) képletű cabergolin előállítására a (XIII) képletűergolin-8b-karbonsav észterből kiindulva úgy, hogy a XVI, XVII, XVIIIés XIX képletű intermedierek újak, (a) a (XIII) képletű vegyületet -ahol a képletben R1 jelentése C1-4 alkilcsoport-katalizátorjelenlétében (i) a (XIV) képletű vegyülettel reagáltatják, X-COOR2(XIV) ahol R2 jelentése kívánt esetben szubsztituált, egyenes vagyelágazó láncú C1-6 alkilcsoport, X jelentése bróm vagy klór, (ii) vagya (XV) képletű vegyülettel reagáltatják, O(COOR2)2 (XV) ahol R2jelentése mint (XIV) esetén, (b) a kapott (XVI) képletűkarbamátszármazékot - ahol R1 és R2 jelentése mint a korábbandefiniált - katalizátor jelenlétében 3-(dimetilamino)-propilaminnal(DMAPA) reagáltatják, (c) a kapott (XVII) képletű ergolin-8b-karboxamid származékot - ahol R2 jelentése mint (XIV) esetén - Ib ésIIb fémcsoport sói, mint katalizátor és ligandum(ok) jelenlétébenetilizocianáttal (EtNCO) reagáltatják, (d) a kapott (XVIII) képletűvédett N-acilkarbamid-származékot - ahol R2 jelentése mint (XIV)esetén - erős vizes szervetlen savval reagáltatják, (e) a kapott (XIX)képletű szekunder amint valamely elektrofil allil-alkohol-származékkalreagáltatják Pd vagy Ni tartalmú katalizátor és kívánt esetbenligandum(ok) jelenlétében, amikor az (I) képletű cabergolinhoz jutnak.Továbbá az amorf módosulat és annak előállítási eljárása.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0400517A HUP0400517A3 (en) | 2004-03-04 | 2004-03-04 | Process for producing cabergoline |
EA200601628A EA010689B1 (ru) | 2004-03-04 | 2005-03-02 | Новый способ получения каберголина |
DE602005021461T DE602005021461D1 (de) | 2004-03-04 | 2005-03-02 | Verfahren zur herstellung von cabergolin |
AT05718154T ATE469149T1 (de) | 2004-03-04 | 2005-03-02 | Verfahren zur herstellung von cabergolin |
PCT/HU2005/000022 WO2005085243A2 (en) | 2004-03-04 | 2005-03-02 | Process for the preparation of cabergoline |
US10/591,202 US7858791B2 (en) | 2004-03-04 | 2005-03-02 | Process for the preparation of cabergoline |
EP05718154A EP1720869B1 (en) | 2004-03-04 | 2005-03-02 | Process for the preparation of cabergoline |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0400517A HUP0400517A3 (en) | 2004-03-04 | 2004-03-04 | Process for producing cabergoline |
Publications (3)
Publication Number | Publication Date |
---|---|
HU0400517D0 HU0400517D0 (en) | 2004-05-28 |
HUP0400517A2 true HUP0400517A2 (hu) | 2005-11-28 |
HUP0400517A3 HUP0400517A3 (en) | 2006-05-29 |
Family
ID=89982034
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0400517A HUP0400517A3 (en) | 2004-03-04 | 2004-03-04 | Process for producing cabergoline |
Country Status (7)
Country | Link |
---|---|
US (1) | US7858791B2 (hu) |
EP (1) | EP1720869B1 (hu) |
AT (1) | ATE469149T1 (hu) |
DE (1) | DE602005021461D1 (hu) |
EA (1) | EA010689B1 (hu) |
HU (1) | HUP0400517A3 (hu) |
WO (1) | WO2005085243A2 (hu) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004101510A2 (en) * | 2003-05-08 | 2004-11-25 | Ivax Corporation | Polymorphs of cabergoline |
EP1925616A1 (en) * | 2006-10-26 | 2008-05-28 | LEK Pharmaceuticals D.D. | Process for the preparation of crystal forms of cabergoline via stable solvates of cabergoline |
WO2008104956A2 (en) * | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Process for the preparation of amorphous cabergoline |
EP2083008A1 (en) * | 2007-12-07 | 2009-07-29 | Axxonis Pharma AG | Ergoline derivatives as selective radical scavengers for neurons |
WO2011154827A2 (en) * | 2010-06-11 | 2011-12-15 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
CA2876321A1 (en) * | 2012-06-22 | 2013-12-27 | Map Pharmaceuticals, Inc. | Novel cabergoline derivatives |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9205439D0 (en) * | 1992-03-12 | 1992-04-22 | Erba Carlo Spa | Process for the synthesis of ergoline derivatives |
WO2002085902A1 (en) * | 2001-04-16 | 2002-10-31 | Finetech Laboratories Ltd. | Process and intermediates for production of cabergoline and related compounds |
US6696568B2 (en) * | 2001-04-16 | 2004-02-24 | Finetech Ltd. | Process and intermediates for production of cabergoline and related compounds |
-
2004
- 2004-03-04 HU HU0400517A patent/HUP0400517A3/hu unknown
-
2005
- 2005-03-02 EA EA200601628A patent/EA010689B1/ru not_active IP Right Cessation
- 2005-03-02 WO PCT/HU2005/000022 patent/WO2005085243A2/en active Application Filing
- 2005-03-02 US US10/591,202 patent/US7858791B2/en not_active Expired - Fee Related
- 2005-03-02 EP EP05718154A patent/EP1720869B1/en active Active
- 2005-03-02 DE DE602005021461T patent/DE602005021461D1/de active Active
- 2005-03-02 AT AT05718154T patent/ATE469149T1/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP1720869A2 (en) | 2006-11-15 |
ATE469149T1 (de) | 2010-06-15 |
WO2005085243A3 (en) | 2006-04-06 |
HUP0400517A3 (en) | 2006-05-29 |
US7858791B2 (en) | 2010-12-28 |
DE602005021461D1 (de) | 2010-07-08 |
EA010689B1 (ru) | 2008-10-30 |
US20070293677A1 (en) | 2007-12-20 |
HU0400517D0 (en) | 2004-05-28 |
EA200601628A1 (ru) | 2007-02-27 |
WO2005085243A2 (en) | 2005-09-15 |
EP1720869B1 (en) | 2010-05-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
HC9A | Change of name, address |
Owner name: RICHTER GEDEON NYRT., HU Free format text: FORMER OWNER(S): RICHTER GEDEON VEGYESZETI GYAR RT., HU |
|
FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |