AU2004276354B2 - Resolution of a narwedine amide derivative - Google Patents
Resolution of a narwedine amide derivative Download PDFInfo
- Publication number
- AU2004276354B2 AU2004276354B2 AU2004276354A AU2004276354A AU2004276354B2 AU 2004276354 B2 AU2004276354 B2 AU 2004276354B2 AU 2004276354 A AU2004276354 A AU 2004276354A AU 2004276354 A AU2004276354 A AU 2004276354A AU 2004276354 B2 AU2004276354 B2 AU 2004276354B2
- Authority
- AU
- Australia
- Prior art keywords
- bromoamide
- mixed solution
- enantiomer
- producing
- galantamine
- Prior art date
- 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.)
- Ceased
Links
- -1 narwedine amide Chemical class 0.000 title claims description 8
- QENVUHCAYXAROT-UHFFFAOYSA-N Galanthaminon Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(=O)C=C2 QENVUHCAYXAROT-UHFFFAOYSA-N 0.000 title description 9
- WCRYNEMFWLZAAZ-WMLDXEAASA-N Narwedine Natural products COc1ccc2CCCC[C@@]34C=CC(=O)C[C@@H]3Oc1c24 WCRYNEMFWLZAAZ-WMLDXEAASA-N 0.000 title description 7
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 22
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 21
- 229960003980 galantamine Drugs 0.000 claims description 17
- 239000011259 mixed solution Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000011149 active material Substances 0.000 claims description 5
- 238000010899 nucleation Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims description 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QENVUHCAYXAROT-YOEHRIQHSA-N Narwedine Chemical class O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1CC(=O)C=C2 QENVUHCAYXAROT-YOEHRIQHSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229940086542 triethylamine Drugs 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ASUTZQLVASHGKV-SUYBPPKGSA-N ent-galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@@]23[C@H]1C[C@H](O)C=C2 ASUTZQLVASHGKV-SUYBPPKGSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- QENVUHCAYXAROT-RHSMWYFYSA-N (+)-narwedine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@@]23[C@H]1CC(=O)C=C2 QENVUHCAYXAROT-RHSMWYFYSA-N 0.000 description 1
- 229940124810 Alzheimer's drug Drugs 0.000 description 1
- 241000234270 Amaryllidaceae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000015256 Chionanthus virginicus Nutrition 0.000 description 1
- 241000234271 Galanthus Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50646903P | 2003-09-26 | 2003-09-26 | |
| US60/506,469 | 2003-09-26 | ||
| PCT/US2004/031936 WO2005030713A2 (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004276354A1 AU2004276354A1 (en) | 2005-04-07 |
| AU2004276354B2 true AU2004276354B2 (en) | 2009-07-09 |
Family
ID=34393160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004276354A Ceased AU2004276354B2 (en) | 2003-09-26 | 2004-09-27 | Resolution of a narwedine amide derivative |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7307162B2 (enExample) |
| EP (1) | EP1670767B2 (enExample) |
| JP (1) | JP5020633B2 (enExample) |
| CN (1) | CN1875004B (enExample) |
| AU (1) | AU2004276354B2 (enExample) |
| CA (1) | CA2540248C (enExample) |
| IL (1) | IL174551A0 (enExample) |
| NZ (1) | NZ546768A (enExample) |
| WO (1) | WO2005030713A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090253654A1 (en) | 2005-09-22 | 2009-10-08 | Galantos Pharma Gmbh | Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment |
| US7985879B2 (en) * | 2007-04-12 | 2011-07-26 | Scinopharm Taiwan Ltd. | Process for making galantamine |
| ES2463715T3 (es) | 2008-04-14 | 2014-05-29 | Neurodyn Life Sciences Inc. | Derivados de galantamina como profármacos para el tratamiento de enfermedades del cerebro humano |
| WO2011151359A1 (en) | 2010-06-02 | 2011-12-08 | Noscira, S.A. | Combined treatment with a cholinesterase inhibitor and a thiadiazolidinedione derivative |
| BG66818B1 (bg) | 2013-03-07 | 2019-01-31 | Berbee Beheer B. V. | Състав на екстракт от hippeastrum papilio за производство на лекарствени средства и хранителни добавки |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG28325A1 (en) * | 1978-11-21 | 1980-04-15 | Vlakhov | Method of obtaining of enons navedine type and their derivatives |
| US4290862A (en) * | 1979-11-14 | 1981-09-22 | Edinen Centar P Chimia | Method for the preparation of narwedine-type enones |
| US5428159A (en) | 1994-04-08 | 1995-06-27 | Ciba-Geigy Corporation | Method of manufacture of (-)-galanthamine in high yield and purity substantially free of epigalanthamine |
| US6407229B1 (en) * | 1994-10-21 | 2002-06-18 | Sanochemia Pharmazeutika Ag | Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2] benzazapine |
| GB9506843D0 (en) * | 1995-04-03 | 1995-05-24 | Chiroscience Ltd | Oxidative process and products thereof |
| US6018043A (en) * | 1995-04-06 | 2000-01-25 | Janssen Pharmaceutica, N.V. | Process for preparing galanthamine derivatives by asymmetric reduction |
| GB9707413D0 (en) * | 1997-04-11 | 1997-05-28 | Chiroscience Ltd | Process |
-
2004
- 2004-09-27 AU AU2004276354A patent/AU2004276354B2/en not_active Ceased
- 2004-09-27 JP JP2006528320A patent/JP5020633B2/ja not_active Expired - Fee Related
- 2004-09-27 CN CN2004800276266A patent/CN1875004B/zh not_active Expired - Fee Related
- 2004-09-27 WO PCT/US2004/031936 patent/WO2005030713A2/en not_active Ceased
- 2004-09-27 CA CA2540248A patent/CA2540248C/en not_active Expired - Fee Related
- 2004-09-27 US US10/951,748 patent/US7307162B2/en not_active Expired - Lifetime
- 2004-09-27 EP EP04789228.6A patent/EP1670767B2/en not_active Expired - Lifetime
- 2004-09-27 NZ NZ546768A patent/NZ546768A/en not_active IP Right Cessation
-
2006
- 2006-03-26 IL IL174551A patent/IL174551A0/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP1670767A4 (en) | 2007-08-29 |
| NZ546768A (en) | 2009-07-31 |
| CN1875004A (zh) | 2006-12-06 |
| WO2005030713A3 (en) | 2006-01-26 |
| WO2005030713A2 (en) | 2005-04-07 |
| US20050070522A1 (en) | 2005-03-31 |
| CA2540248A1 (en) | 2005-04-07 |
| EP1670767B2 (en) | 2014-10-29 |
| EP1670767A2 (en) | 2006-06-21 |
| JP5020633B2 (ja) | 2012-09-05 |
| AU2004276354A1 (en) | 2005-04-07 |
| CN1875004B (zh) | 2010-06-23 |
| US7307162B2 (en) | 2007-12-11 |
| EP1670767B1 (en) | 2011-08-24 |
| IL174551A0 (en) | 2006-08-20 |
| JP2007506794A (ja) | 2007-03-22 |
| CA2540248C (en) | 2010-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: SCINOPHARM TAIWAN, LTD. Free format text: FORMER APPLICANT(S): SCHLOEMER, GEORGE |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |