GB1000528A - 18-o-acyl-17-hydroxy-yohimbane derivatives - Google Patents
18-o-acyl-17-hydroxy-yohimbane derivativesInfo
- Publication number
- GB1000528A GB1000528A GB1285564A GB1285564A GB1000528A GB 1000528 A GB1000528 A GB 1000528A GB 1285564 A GB1285564 A GB 1285564A GB 1285564 A GB1285564 A GB 1285564A GB 1000528 A GB1000528 A GB 1000528A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- formula
- hydroxy
- organic
- reaction
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000007529 inorganic bases Chemical class 0.000 abstract 3
- 150000007530 organic bases Chemical class 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- -1 C1-C3 alkyl radical Chemical group 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004036 acetal group Chemical group 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 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 abstract 1
- SZLZWPPUNLXJEA-UHFFFAOYSA-N 11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-UHFFFAOYSA-N 0.000 abstract 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- SZLZWPPUNLXJEA-FMCDHCOASA-N Rescinnamine Natural products O=C(O[C@H]1[C@@H](OC)[C@@H](C(=O)OC)[C@@H]2[C@H](C1)CN1[C@@H](c3[nH]c4c(c3CC1)ccc(OC)c4)C2)/C=C/c1cc(OC)c(OC)c(OC)c1 SZLZWPPUNLXJEA-FMCDHCOASA-N 0.000 abstract 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 150000003855 acyl compounds Chemical class 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229960001993 deserpidine Drugs 0.000 abstract 1
- 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 abstract 1
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000007928 imidazolide derivatives Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229960001965 rescinnamine Drugs 0.000 abstract 1
- SMSAPZICLFYVJS-QEGASFHISA-N rescinnamine 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)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 SMSAPZICLFYVJS-QEGASFHISA-N 0.000 abstract 1
- 229960003147 reserpine Drugs 0.000 abstract 1
- 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 abstract 1
- 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 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- JUPDIHMJFPDGMY-DEYYWGMASA-N yohimban Chemical class C1=CC=C2C(CCN3C[C@@H]4CCCC[C@H]4C[C@H]33)=C3NC2=C1 JUPDIHMJFPDGMY-DEYYWGMASA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D459/00—Heterocyclic compounds containing benz [g] indolo [2, 3-a] quinolizine ring systems, e.g. yohimbine; 16, 18-lactones thereof, e.g. reserpic acid lactone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB71326A DE1186072B (de) | 1963-03-28 | 1963-03-28 | Verfahren zur Herstellung von Rescidin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1000528A true GB1000528A (en) | 1965-08-04 |
Family
ID=6976987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1285564A Expired GB1000528A (en) | 1963-03-28 | 1964-03-26 | 18-o-acyl-17-hydroxy-yohimbane derivatives |
Country Status (7)
-
1963
- 1963-03-28 DE DEB71326A patent/DE1186072B/de active Pending
-
1964
- 1964-03-25 DK DK153064A patent/DK105035C/da active
- 1964-03-26 NL NL6403268A patent/NL6403268A/xx unknown
- 1964-03-26 LU LU45749D patent/LU45749A1/xx unknown
- 1964-03-26 GB GB1285564A patent/GB1000528A/en not_active Expired
- 1964-03-26 AT AT266764A patent/AT255663B/de active
- 1964-03-27 BE BE645871D patent/BE645871A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1186072B (de) | 1965-01-28 |
| DK105035C (da) | 1966-08-08 |
| AT255663B (de) | 1967-07-10 |
| NL6403268A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-09-29 |
| LU45749A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-05-26 |
| BE645871A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB922023A (en) | Mixed fatty acid esters of mono- and di-saccharides and their preparation | |
| GB1387447A (en) | Carboxylic acids and derivatives | |
| GB1457569A (en) | Method for the preparation of esters of polyalcohols | |
| KR840003614A (ko) | 항염 작용을 갖는 피롤아세트 아미드의 제조방법 | |
| GB799271A (en) | Production of intermediates for the synthesis of reserpine and allied compounds | |
| ES468895A1 (es) | Un procedimiento para la preparacion de antibioticos de ce- falosporina. | |
| GB966541A (en) | Preparation of esters of polyhydric alcohols | |
| NO144481B (no) | Utforming av et oensket bruddsted for en under innertrykk staaende beholder. | |
| GB1000528A (en) | 18-o-acyl-17-hydroxy-yohimbane derivatives | |
| GB802668A (en) | Caffeic esters of quinic acid and quinide | |
| GB1411858A (en) | Alkali metal salts of polyester carboxylic acids | |
| US2763645A (en) | Amino alcohol esters of etiocholene 17 alpha hydroxy 3 one 17 beta carboxylic acid | |
| GB724256A (en) | Improvements in the production of esters of pyridine carboxylic acids | |
| GB602974A (en) | Improvements in or relating to the production of aqueous solutions of polyvinyl acetate derivatives | |
| GB909263A (en) | 18-oxygenated steroids and process for their manufacture | |
| GB808279A (en) | Manufacture of hydrophenanthryl-carboxylic acids and functional derivatives thereof | |
| US2621181A (en) | Steroid adducts | |
| GB987576A (en) | Process for the manufacture of 16ª‡-alkyl-20:21-ketols of the pregnane series | |
| GB796311A (en) | Improvements in or relating to esters of spiramycins | |
| ES252227A1 (es) | Procedimiento para la obtenciën de compuestos parecidos a la reserpina, hasta ahora desconocidos | |
| GB976513A (en) | Alicyclic carboxylic acids and their salts and esters | |
| GB989476A (en) | Process for the preparation of cyclic carboxylic acids and their esters | |
| GB700186A (en) | Production of alpha-acetotetronic acids | |
| GB822723A (en) | New quaternary ammonium compounds related to reserpine and process for their manufacture | |
| GB1181000A (en) | Manufacture of Dicarboxylic Acid Esters of Polyvinyl Alcohols |