NO123928B - - Google Patents
Download PDFInfo
- Publication number
- NO123928B NO123928B NO4985/69A NO498569A NO123928B NO 123928 B NO123928 B NO 123928B NO 4985/69 A NO4985/69 A NO 4985/69A NO 498569 A NO498569 A NO 498569A NO 123928 B NO123928 B NO 123928B
- Authority
- NO
- Norway
- Prior art keywords
- reserpine
- parts
- volume
- rauwolfia
- rhodanide
- Prior art date
Links
- 229960003147 reserpine Drugs 0.000 claims description 61
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 claims description 59
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 claims description 59
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 claims description 59
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- CVBMAZKKCSYWQR-BPJCFPRXSA-N Deserpidine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cccc3 CVBMAZKKCSYWQR-BPJCFPRXSA-N 0.000 claims description 17
- 229960001993 deserpidine Drugs 0.000 claims description 17
- ISMCNVNDWFIXLM-WCGOZPBSSA-N deserpidine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ISMCNVNDWFIXLM-WCGOZPBSSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 241000208332 Rauvolfia Species 0.000 claims description 14
- 239000000284 extract Substances 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 14
- 229930013930 alkaloid Natural products 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 hydrogen salt Chemical class 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 244000061121 Rauvolfia serpentina Species 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000512005 Alstonia Species 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 claims 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 20
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 19
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 150000003797 alkaloid derivatives Chemical class 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012485 toluene extract Substances 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B23/00—Arrangements specially adapted for the production of shaped articles with elements wholly or partly embedded in the moulding material; Production of reinforced objects
- B28B23/02—Arrangements specially adapted for the production of shaped articles with elements wholly or partly embedded in the moulding material; Production of reinforced objects wherein the elements are reinforcing members
- B28B23/18—Arrangements specially adapted for the production of shaped articles with elements wholly or partly embedded in the moulding material; Production of reinforced objects wherein the elements are reinforcing members for the production of elongated articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B1/00—Producing shaped prefabricated articles from the material
- B28B1/08—Producing shaped prefabricated articles from the material by vibrating or jolting
- B28B1/084—Producing shaped prefabricated articles from the material by vibrating or jolting the vibrating moulds or cores being moved horizontally for making strands of moulded articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B11/00—Apparatus or processes for treating or working the shaped or preshaped articles
- B28B11/12—Apparatus or processes for treating or working the shaped or preshaped articles for removing parts of the articles by cutting
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B28—WORKING CEMENT, CLAY, OR STONE
- B28B—SHAPING CLAY OR OTHER CERAMIC COMPOSITIONS; SHAPING SLAG; SHAPING MIXTURES CONTAINING CEMENTITIOUS MATERIAL, e.g. PLASTER
- B28B7/00—Moulds; Cores; Mandrels
- B28B7/16—Moulds for making shaped articles with cavities or holes open to the surface, e.g. with blind holes
- B28B7/168—Moulds for making shaped articles with cavities or holes open to the surface, e.g. with blind holes for holders or similar hollow articles, e.g. vaults, sewer pits
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Mechanical Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Structural Engineering (AREA)
- Processing Of Stones Or Stones Resemblance Materials (AREA)
- On-Site Construction Work That Accompanies The Preparation And Application Of Concrete (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Manufacturing Of Tubular Articles Or Embedded Moulded Articles (AREA)
- Devices For Post-Treatments, Processing, Supply, Discharge, And Other Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE543/69A SE318511B (en, 2012) | 1969-01-16 | 1969-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123928B true NO123928B (en, 2012) | 1972-02-07 |
Family
ID=20256730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4985/69A NO123928B (en, 2012) | 1969-01-16 | 1969-12-17 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3584354A (en, 2012) |
| JP (1) | JPS4915607B1 (en, 2012) |
| AT (1) | AT295379B (en, 2012) |
| CH (1) | CH497958A (en, 2012) |
| DK (1) | DK122586B (en, 2012) |
| FI (1) | FI43829B (en, 2012) |
| FR (1) | FR2028431A1 (en, 2012) |
| GB (1) | GB1258734A (en, 2012) |
| NL (1) | NL153796B (en, 2012) |
| NO (1) | NO123928B (en, 2012) |
| SE (1) | SE318511B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3941545A (en) * | 1974-01-21 | 1976-03-02 | Durastone Company | Means for curving side by side concrete curb sections |
| CN110948660A (zh) * | 2019-12-20 | 2020-04-03 | 江西佳鸿电瓷制造有限公司 | 一种瓷质绝缘子外形加工装置 |
| CN114407178B (zh) * | 2021-11-17 | 2024-03-01 | 贵州贵仁生态砂科技有限公司 | 蒸压加气混泥土切割余料自动回收装置 |
-
1969
- 1969-01-16 SE SE543/69A patent/SE318511B/xx unknown
- 1969-12-17 NO NO4985/69A patent/NO123928B/no unknown
- 1969-12-31 FI FI3800/69A patent/FI43829B/fi active
-
1970
- 1970-01-05 AT AT6270A patent/AT295379B/de not_active IP Right Cessation
- 1970-01-06 US US899A patent/US3584354A/en not_active Expired - Lifetime
- 1970-01-08 GB GB1258734D patent/GB1258734A/en not_active Expired
- 1970-01-09 FR FR7000827A patent/FR2028431A1/fr not_active Withdrawn
- 1970-01-09 DK DK9070AA patent/DK122586B/da unknown
- 1970-01-12 NL NL707000330A patent/NL153796B/xx unknown
- 1970-01-15 CH CH58270A patent/CH497958A/de not_active IP Right Cessation
- 1970-01-16 JP JP45003925A patent/JPS4915607B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH497958A (de) | 1970-10-31 |
| DK122586B (da) | 1972-03-20 |
| DE2000220A1 (de) | 1970-07-30 |
| US3584354A (en) | 1971-06-15 |
| JPS4915607B1 (en, 2012) | 1974-04-16 |
| SE318511B (en, 2012) | 1969-12-08 |
| DE2000220B2 (en, 2012) | 1975-07-24 |
| FR2028431A1 (en, 2012) | 1970-10-09 |
| FI43829B (en, 2012) | 1971-03-01 |
| NL7000330A (en, 2012) | 1970-07-20 |
| AT295379B (de) | 1971-12-27 |
| GB1258734A (en, 2012) | 1971-12-30 |
| NL153796B (nl) | 1977-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2813873A (en) | Derivatives of the ibogaine alkaloids | |
| SU508193A3 (ru) | Способ получени -(метоксиметил-фурилметил)-6,7-бензоморфанов или-морфинанов | |
| NO123928B (en, 2012) | ||
| RU2387656C2 (ru) | Способ получения гидробромида галантамина | |
| JPS6461482A (en) | Dehydrocamptothecin and production thereof | |
| EP0112629B1 (en) | Plant growth regulators | |
| US2350804A (en) | Derivatives of hesperidin and process for preparing the same | |
| Bottomley et al. | The chemistry of western Australian plants. IV. Duboisia hopwoodii | |
| NO311839B1 (no) | Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler | |
| US4162255A (en) | Process for extracting aristolochic acids | |
| Deulofeu et al. | Studies on argentine plants. VIII. The alkaloids of Erythrina crista galli. Chromatographic separation of erythratine and erysodine | |
| US2265217A (en) | D - lysergic acid - | |
| US2887489A (en) | Process and intermediate for | |
| US2866784A (en) | Process for obtaining voacanga alkaloids | |
| Govindachari et al. | Alkaloids of Mahonia nepalensis DC | |
| US3033877A (en) | Process of preparing same | |
| US3846434A (en) | Process for obtaining a germine adduct from germine values | |
| US2786844A (en) | Process of preparing reserpic acid esters | |
| US2086562A (en) | Method of sepaeating mixed ergot | |
| GB604563A (en) | Improvements in and relating to the purification of penicillin salts | |
| GB948769A (en) | New alkaloids of the funtumia species and processes for obtaining same | |
| US2938906A (en) | Certificate of correction | |
| Haworth et al. | CCCII.—The conversion of palmatine into its cryptopine analogue (cryptopalmatine) | |
| US3008954A (en) | Process for obtaining an koquinuclt | |
| Bergel et al. | 7. Aneurin. Part IX. A new synthesis of thiochrome. Note on the synthesis of aneurin |