SK278715B6 - Spôsob prípravy (6r,7r,14s)-17-cyklopropylmetyl-7, - Google Patents
Spôsob prípravy (6r,7r,14s)-17-cyklopropylmetyl-7, Download PDFInfo
- Publication number
- SK278715B6 SK278715B6 SK387-94A SK38794A SK278715B6 SK 278715 B6 SK278715 B6 SK 278715B6 SK 38794 A SK38794 A SK 38794A SK 278715 B6 SK278715 B6 SK 278715B6
- Authority
- SK
- Slovakia
- Prior art keywords
- hydroxy
- trimethylpropyl
- formula
- dihydro
- methyl
- Prior art date
Links
- 229950006134 normorphine Drugs 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000004678 hydrides Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- -1 dictylene glycol Chemical compound 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 3
- 229960001736 buprenorphine Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ93587A CZ58793A3 (en) | 1993-04-05 | 1993-04-05 | Process for preparing (6r, 7r, 14s)-17-cyclopropylmethyl 7,8-dihydro-7-/(1s)-1-hydroxy-1,2,2-trimethylpropyl/ -6-0-methyl-6,14-ethano-17-normorphine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK38794A3 SK38794A3 (en) | 1995-02-08 |
| SK278715B6 true SK278715B6 (sk) | 1998-01-14 |
Family
ID=5461940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK387-94A SK278715B6 (sk) | 1993-04-05 | 1994-03-31 | Spôsob prípravy (6r,7r,14s)-17-cyklopropylmetyl-7, |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ58793A3 (cs) |
| SK (1) | SK278715B6 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9315514B2 (en) | 2012-08-27 | 2016-04-19 | Rhodes Technologies | 1,3-dioxanomorphides and 1,3-dioxanocodides |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ300995B6 (cs) * | 2005-12-20 | 2009-10-07 | Zentiva, A. S. | Zpusob výroby (2S,7´R)-2-[17´-(cyklopropylmethyl)-3´-hydroxy-4´,5´-epoxy-6´-methoxy-6´,14´-endoethanomorfinan-7´-yl]-3,3-dimethylbutan-2-olu |
| EP3023427A1 (en) | 2014-11-19 | 2016-05-25 | Siegfried AG | Improved method of manufacturing buprenorphine and analogues thereof from oripavine |
-
1993
- 1993-04-05 CZ CZ93587A patent/CZ58793A3/cs not_active IP Right Cessation
-
1994
- 1994-03-31 SK SK387-94A patent/SK278715B6/sk unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9315514B2 (en) | 2012-08-27 | 2016-04-19 | Rhodes Technologies | 1,3-dioxanomorphides and 1,3-dioxanocodides |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ279821B6 (cs) | 1995-07-12 |
| CZ58793A3 (en) | 1995-07-12 |
| SK38794A3 (en) | 1995-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2322486T5 (es) | Preparación de analgésicos opiáceos por alquilación reductiva | |
| JPS62242663A (ja) | １−デオキシノジリマイシンおよびそれのｎ−誘導体を製造する方法 | |
| US3703529A (en) | Nitrogen-containing tricyclic compounds | |
| HU213099B (en) | Process for producing 2,8-diazabicyclo[4.3.0]nonan | |
| AU2008338970B2 (en) | Sinomenine derivatives and processes for their synthesis | |
| Geen et al. | A versatile synthesis of fully aromatic benzo [c] phenanthridine alkaloids | |
| GB2175898A (en) | Morphinan derivatives | |
| Balalaie et al. | Novel one-pot synthesis of new derivatives of dihydropyrimidinones, unusual multisubstituted imidazoline-2-ones: X-ray crystallography structure | |
| SK278715B6 (sk) | Spôsob prípravy (6r,7r,14s)-17-cyklopropylmetyl-7, | |
| Mariano et al. | The chemistry of azocines. Intermediates for the synthesis of pyrrolizidines | |
| Kreutzberger | Condensations with 1, 2-Hydrazinedicarboxamidine. 2, 2'-Hydrazopyrimidines | |
| AU678587B2 (en) | Process for the preparation of 9-amino camptothecin | |
| US5508400A (en) | Preparation of cyclic urea compounds | |
| CA2726220C (en) | Processes and compounds for the preparation of normorphinans | |
| CN109053446A (zh) | 金属氢化物/钯化合物体系在缺电子烯化合物串联反应制备1,3-二羰基化合物中的应用 | |
| Liu et al. | A novel C–C radical–radical coupling reaction promoted by visible light: Facile synthesis of 6-substituted N-methyl 5, 6-dihydrobenzophenanthridine alkaloids | |
| HIGASHINO et al. | Triazolo [4, 5-d] pyrimidines. VIII. Aryl Migration of 7-Aroyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines to 7-Aryl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines | |
| Badger et al. | Porphyrins. IV. Further preliminary studies on the synthesis of porphyrin a | |
| Ozeryanskii et al. | peri-Naphthylenediamines. 31. Study of interconversions of 2, 3-dihydroperimidines and 1, 8-bis (dialkylamino) naphthalenes. Convenient synthesis of 1, 2, 2, 3-tetramethyl-2, 3-dihydroperimidine and a monoisopropyl analog of the “proton sponge” | |
| Orlek et al. | Diastereoselective routes to endo and exo ethyl 1-azabicyclo [2.2. 1] hept-3-YL carboxylates | |
| Kutney et al. | Total synthesis of indole and dihydroindole alkaloids. XVII. The total synthesis of catharine and vinamidine (catharinine) | |
| Konda et al. | Studies on the constituents of bocconia cordata. IV. Transformation of sanguinarine into bocconine | |
| US3221015A (en) | 3,8-diazabicyclo-[3,2,1]-octanes and process for preparing same | |
| CA1040628A (en) | 4-benzazonine derivatives and process for preparation thereof | |
| KR20190108383A (ko) | 옥사미드 및 수소화알루미늄리튬을 이용한 시클렌의 신규 합성법 |