DE2126465A1 - Neue pentacyclische Verbindung und Verfahren zu ihrer Herstellung - Google Patents
Neue pentacyclische Verbindung und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2126465A1 DE2126465A1 DE19712126465 DE2126465A DE2126465A1 DE 2126465 A1 DE2126465 A1 DE 2126465A1 DE 19712126465 DE19712126465 DE 19712126465 DE 2126465 A DE2126465 A DE 2126465A DE 2126465 A1 DE2126465 A1 DE 2126465A1
- Authority
- DE
- Germany
- Prior art keywords
- ajmalicin
- methoxy
- making
- compound
- pentacyclic compound
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 7
- FVMMOSQBOWPRQW-UHFFFAOYSA-N heterophylline Natural products CC(=O)OC1C2(C)C(OC(=O)C=3C=CC=CC=3)CC(C(O3)(C)C)C(OC(=O)C=4C=NC=CC=4)C32C(C)CC1OC(=O)C1=CC=CN=C1 FVMMOSQBOWPRQW-UHFFFAOYSA-N 0.000 claims description 15
- YWULOMNQOWMRFL-UHFFFAOYSA-N O-demethyl-cabucine Natural products C1=C(O)C=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 YWULOMNQOWMRFL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 3
- PEYPCTZOXFDFFW-UHFFFAOYSA-N 3-Iso-19-epi-ajnalicin Natural products C1=CC=C2C3CCN4CC5C(C)OC=C(C(=O)OC)C5CC4C3NC2=C1 PEYPCTZOXFDFFW-UHFFFAOYSA-N 0.000 description 2
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- DTDADHMBRZKXSC-GKASHWOUSA-N Aricine Chemical compound C1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DTDADHMBRZKXSC-GKASHWOUSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UHDJCSZGZJGMDR-UHFFFAOYSA-N aricine Natural products COC(=O)C1=COC(C)C2(C)CN3CCc4c([nH]c5ccc(OC)cc45)C3(C)CC12C UHDJCSZGZJGMDR-UHFFFAOYSA-N 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- -1 chairamine Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D491/22—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 four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR707019975A FR2092608B1 (enrdf_load_stackoverflow) | 1970-06-01 | 1970-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2126465A1 true DE2126465A1 (de) | 1971-12-30 |
Family
ID=9056473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126465 Pending DE2126465A1 (de) | 1970-06-01 | 1971-05-27 | Neue pentacyclische Verbindung und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT306257B (enrdf_load_stackoverflow) |
| BE (1) | BE767773A (enrdf_load_stackoverflow) |
| CH (1) | CH538505A (enrdf_load_stackoverflow) |
| DE (1) | DE2126465A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2092608B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1304633A (enrdf_load_stackoverflow) |
| NL (1) | NL7107300A (enrdf_load_stackoverflow) |
| ZA (1) | ZA713411B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1115417A (en) * | 1967-02-10 | 1968-05-29 | Boehringer & Soehne Gmbh | Compositions containing raubasine and a new method of using raubasine |
-
1970
- 1970-06-01 FR FR707019975A patent/FR2092608B1/fr not_active Expired
-
1971
- 1971-05-26 ZA ZA713411A patent/ZA713411B/xx unknown
- 1971-05-27 DE DE19712126465 patent/DE2126465A1/de active Pending
- 1971-05-27 NL NL7107300A patent/NL7107300A/xx unknown
- 1971-05-27 BE BE767773A patent/BE767773A/xx unknown
- 1971-05-28 CH CH787471A patent/CH538505A/fr not_active IP Right Cessation
- 1971-05-28 AT AT466671A patent/AT306257B/de not_active IP Right Cessation
- 1971-05-28 GB GB1794471A patent/GB1304633A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE767773A (enrdf_load_stackoverflow) | 1971-11-29 |
| FR2092608A1 (enrdf_load_stackoverflow) | 1972-01-28 |
| SU441708A3 (ru) | 1974-08-30 |
| NL7107300A (enrdf_load_stackoverflow) | 1971-12-03 |
| FR2092608B1 (enrdf_load_stackoverflow) | 1973-08-10 |
| AT306257B (de) | 1973-04-10 |
| ZA713411B (en) | 1972-01-26 |
| CH538505A (fr) | 1973-06-30 |
| GB1304633A (enrdf_load_stackoverflow) | 1973-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |