NO159444B - Analogifremgangsmaate ved fremstilling av terapeutisk aktive fenetylamin-derivater. - Google Patents
Analogifremgangsmaate ved fremstilling av terapeutisk aktive fenetylamin-derivater. Download PDFInfo
- Publication number
- NO159444B NO159444B NO843675A NO843675A NO159444B NO 159444 B NO159444 B NO 159444B NO 843675 A NO843675 A NO 843675A NO 843675 A NO843675 A NO 843675A NO 159444 B NO159444 B NO 159444B
- Authority
- NO
- Norway
- Prior art keywords
- dimethylamino
- methyl
- starting materials
- cyclohexanol
- cis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical class CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 title 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 9
- 239000007858 starting material Substances 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003198 secondary alcohol group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (10)
1. Analogifremgangsmåte ved fremstilling av -terapeutisk aktive forbindelser med den generelle formel: 1 2
hvor R og R betyr hydrogen, halogen, trifluormetyl, laverealkoksy, laverealkyl, hydroksy eller 1 2 nitro, hvorunder minst en av R og R er forskjel
lig fra hydrogen, R 3 og R 4 betyr laverealkyl, n tallet 1, 2, 3 eller 4 og B gruppen -CO- eller -CHOH-, og farmasøytisk fordragelige syreaddisjonssalter derav, karakterisert ved at man a) i en forbindelse med den generelle formel
hvori R 1 , R 2 og n har ovennevnte betydninger, og
R betyr hydrogen eller laverealkyl, di- henh. mono-alkylerer den primære eller sekundære amino-gruppe, eller b) i en forbindelse med den generelle formel hvori R"'", R^, R"^, R4 og n har de forannevnte betydninger ,
oksyderer den sekundære alkoholgruppe, eller c) fra en forbindelse med den generelle formel
hvori R"^, R<4>, n og B har forannevnte betydninger, og en av restene R^ og R^ betyr en beskyttet hydroksylgruppe og den andre hydrogen, halogen, trifluormetyl, laverealkoksy, laverealkyl, nitro eller en beskyttet hydroksylgruppe,
avspalter beskyttelsesgruppen(e), eller d) nitrerer en forbindelse med den generelle formel
hvori R 3 , R 4 og n har forannevnte betydninger, i fenylrihgens p-stilling, og hvis ønsket
oppspalter en erholdt blanding av forskjellige racemater i racematene,
spalter et erholdt racemat i de optiske antipoder, og/eller
overfører en erholdt forbindelse med formel I i et farmasøytisk akseptabelt syreaddisjonssalt.
2o Fremgangsmåte ifølge krav 1 ved fremstilling av rac-(1S<+>)-cis-2-[(R<+>)-4-klor-a-[(dimetylamino)metyl)ben-zyl ]cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
3^ Fremgangsmåte ifølge krav 1 ved fremstilling av rac-(1S<+>)-cis-2-[(R<+>)-a-[(dimetylamino)metyl]-4-hydrok-sybenzyl]cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
4. Fremgangsmåte ifølge krav 1 ved fremstilling av (IS)-cis-2-[(R)-4-klor-a-[(dimetylamino)metyl]benzyl]-cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
5. Fremgangsmåte ifølge krav 1 ved fremstilling av (IR)-cis-2-t(S)-4-klor-a-[(dimetylamino)metyl]benzyl] - cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
6. Fremgangsmåte ifølge krav 1 ved fremstilling av rac-(1S<+>)-cis-2-[(R<+>)-3,4-diklor-a-[(dimetylamino)metyl]-benzyl]cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
7. Fremgangsmåte ifølge krav 1 ved fremstilling av rac-(1S<+>)-cis-2- [(R+)-4-metoksy-a-[ (dimetylamino) metyl] - benzyl]cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
8. Fremgangsmåte ifølge krav 1 ved fremstilling av rac- (1S + )-cis-2-[ (P+)_a-[ (dimetylamino) metyl ]-3 , 4-dimet-oksybenzyl]cykloheksanol, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
9. Fremgangsmåte ifølge krav 1 ved fremstilling av rac-(2S + )-2- [(R+)-4-klor-a-[(dimetylamino)metyl]benzyl ] cykloheksanon, karakterisert ved at man anvender tilsvarende substituerte utgangsmaterialer.
10. Fremgangsmåte ifølge krav 1 ved fremstilling av (IS)-cis-2-[(R)-a-[(dimetylamino)metyl]-4-hydroksyben-zyl]cykloheksanol, karakterisert ved at man fremstiller tilsvarende substituerte utgangsmaterialer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH503283 | 1983-09-15 | ||
| CH323184 | 1984-07-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO843675L NO843675L (no) | 1985-03-18 |
| NO159444B true NO159444B (no) | 1988-09-19 |
| NO159444C NO159444C (no) | 1988-12-28 |
Family
ID=25692520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO843675A NO159444C (no) | 1983-09-15 | 1984-09-14 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive fenetylamin-derivater. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4820734A (no) |
| EP (1) | EP0138030B1 (no) |
| KR (1) | KR850002454A (no) |
| AR (1) | AR240670A1 (no) |
| AT (1) | ATE30015T1 (no) |
| AU (1) | AU566673B2 (no) |
| BR (1) | BR8404617A (no) |
| CS (1) | CS249145B2 (no) |
| DE (1) | DE3466531D1 (no) |
| DK (1) | DK407584A (no) |
| DO (1) | DOP1984004262A (no) |
| ES (2) | ES535913A0 (no) |
| FI (1) | FI82926C (no) |
| GR (1) | GR80351B (no) |
| HU (1) | HU201903B (no) |
| IE (1) | IE57907B1 (no) |
| IL (1) | IL72891A (no) |
| MC (1) | MC1624A1 (no) |
| NO (1) | NO159444C (no) |
| NZ (1) | NZ209479A (no) |
| PH (1) | PH20361A (no) |
| PT (1) | PT79215B (no) |
| ZW (1) | ZW13184A1 (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT639374E (pt) * | 1993-06-28 | 2002-07-31 | American Home Prod | Novos tratamentos utilizado derivados fenetilo |
| DE19915601A1 (de) * | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-3-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
| US20020022662A1 (en) * | 1999-06-15 | 2002-02-21 | American Home Products Corporation | Enantiomers of O-desmethyl venlafaxine |
| JP2006514021A (ja) * | 2002-12-09 | 2006-04-27 | ザ・ボード・オブ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・テキサス・システム | Ｊａｎｕｓチロシンキナーゼ３（Ｊａｋ３）を選択的に阻害するための方法 |
| US20080081067A1 (en) * | 2006-10-03 | 2008-04-03 | Gupta Manishkumar | Sustained release pharmaceutical compositions of venlafaxine and process for preparation thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1098835A (en) * | 1965-07-13 | 1968-01-10 | Jacques Logeais Sa Lab | Spiro-oxazolidinones, spiro-oxazines, their process of preparation and therapeutic compositions containing said derivatives |
| US4017637A (en) * | 1973-03-26 | 1977-04-12 | American Home Products Corporation | Benzylamine analgesics |
| IL49034A (en) * | 1975-03-20 | 1980-02-29 | Hoechst Ag | 5-aryl-2-azabicycloalkanes their preparation their intermediates and pharmaceutical compositions comprising them |
| IE56324B1 (en) * | 1982-12-13 | 1991-06-19 | American Home Prod | Phenethylamine derivatives and intermediates therefor |
| US4535189A (en) * | 1984-03-21 | 1985-08-13 | Texaco Inc. | Polyol purification process |
-
1984
- 1984-08-08 AU AU31846/84A patent/AU566673B2/en not_active Ceased
- 1984-08-15 ZW ZW131/84A patent/ZW13184A1/xx unknown
- 1984-08-24 DK DK407584A patent/DK407584A/da not_active Application Discontinuation
- 1984-09-05 EP EP84110558A patent/EP0138030B1/de not_active Expired
- 1984-09-05 DE DE8484110558T patent/DE3466531D1/de not_active Expired
- 1984-09-05 AT AT84110558T patent/ATE30015T1/de not_active IP Right Cessation
- 1984-09-07 FI FI843523A patent/FI82926C/fi not_active IP Right Cessation
- 1984-09-07 NZ NZ209479A patent/NZ209479A/en unknown
- 1984-09-07 IL IL72891A patent/IL72891A/xx unknown
- 1984-09-11 CS CS846835A patent/CS249145B2/cs unknown
- 1984-09-12 HU HU843442A patent/HU201903B/hu not_active IP Right Cessation
- 1984-09-13 GR GR80351A patent/GR80351B/el unknown
- 1984-09-13 MC MC841725A patent/MC1624A1/fr unknown
- 1984-09-13 AR AR29793784A patent/AR240670A1/es active
- 1984-09-13 DO DO1984004262A patent/DOP1984004262A/es unknown
- 1984-09-14 IE IE2354/84A patent/IE57907B1/en not_active IP Right Cessation
- 1984-09-14 NO NO843675A patent/NO159444C/no unknown
- 1984-09-14 ES ES535913A patent/ES535913A0/es active Granted
- 1984-09-14 BR BR8404617A patent/BR8404617A/pt unknown
- 1984-09-14 KR KR1019840005594A patent/KR850002454A/ko not_active Ceased
- 1984-09-14 PH PH31211A patent/PH20361A/en unknown
- 1984-09-14 PT PT79215A patent/PT79215B/pt not_active IP Right Cessation
-
1985
- 1985-05-22 ES ES543366A patent/ES8609207A1/es not_active Expired
-
1987
- 1987-11-04 US US07/117,190 patent/US4820734A/en not_active Expired - Fee Related
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