GB934978A - Improvements in or relating to reserpine derivatives - Google Patents
Improvements in or relating to reserpine derivativesInfo
- Publication number
- GB934978A GB934978A GB3031559A GB3031559A GB934978A GB 934978 A GB934978 A GB 934978A GB 3031559 A GB3031559 A GB 3031559A GB 3031559 A GB3031559 A GB 3031559A GB 934978 A GB934978 A GB 934978A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- general formula
- compounds
- lactone
- radical
- 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
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical class 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 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- -1 C1-3 alkyl radical Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- 150000002596 lactones Chemical class 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 abstract 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 abstract 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 abstract 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- BQEXDUKMTVYBRK-UHFFFAOYSA-N 4-methyl-3-nitrophenol Chemical compound CC1=CC=C(O)C=C1[N+]([O-])=O BQEXDUKMTVYBRK-UHFFFAOYSA-N 0.000 abstract 1
- RPMWEGXHQSEPPH-UHFFFAOYSA-N 6-ethoxy-1h-indole Chemical compound CCOC1=CC=C2C=CNC2=C1 RPMWEGXHQSEPPH-UHFFFAOYSA-N 0.000 abstract 1
- RIDHVMSRVAXQTA-UHFFFAOYSA-N 6-ethoxy-1h-indole-2-carboxylic acid Chemical compound CCOC1=CC=C2C=C(C(O)=O)NC2=C1 RIDHVMSRVAXQTA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006407 Bischler-Napieralski reaction Methods 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 238000006683 Mannich reaction Methods 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract 1
- 238000006140 methanolysis reaction Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 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
-
- 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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6423058A CH372060A (de) | 1957-04-12 | 1958-09-23 | Verfahren zur Herstellung von bisher unbekannten reserpinähnlichen Verbindungen |
| CH6830159A CH383396A (de) | 1958-09-23 | 1959-01-14 | Verfahren zur Herstellung einer bisher unbekannten reserpinähnlichen Verbindung |
| CH664164A CH397709A (de) | 1958-09-23 | 1959-07-24 | Verfahren zur Herstellung von bisher unbekannten reserpinähnlichen Verbindungen |
| CH7616859A CH383397A (de) | 1958-09-23 | 1959-07-24 | Verfahren zur Herstellung einer bisher unbekannten reserpinähnlichen Verbindung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB934978A true GB934978A (en) | 1963-08-21 |
Family
ID=27429007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3031559A Expired GB934978A (en) | 1958-09-23 | 1959-09-04 | Improvements in or relating to reserpine derivatives |
Country Status (3)
| Country | Link |
|---|---|
| CH (3) | CH383396A (de) |
| DE (1) | DE1159955B (de) |
| GB (1) | GB934978A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459767A (en) * | 1965-08-10 | 1969-08-05 | Pfizer & Co C | Aminomethylindoles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE933628C (de) * | 1952-06-30 | 1955-09-29 | Hoffmann La Roche | Verfahren zur Herstellung von optisch aktiven 3-Oxy-N-methyl-morphinanen |
-
1958
- 1958-04-10 DE DE1958S0057777 patent/DE1159955B/de active Pending
-
1959
- 1959-01-14 CH CH6830159A patent/CH383396A/de unknown
- 1959-07-24 CH CH7616859A patent/CH383397A/de unknown
- 1959-07-24 CH CH664164A patent/CH397709A/de unknown
- 1959-09-04 GB GB3031559A patent/GB934978A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459767A (en) * | 1965-08-10 | 1969-08-05 | Pfizer & Co C | Aminomethylindoles |
Also Published As
| Publication number | Publication date |
|---|---|
| CH383397A (de) | 1964-10-31 |
| CH397709A (de) | 1965-08-31 |
| DE1159955B (de) | 1963-12-27 |
| CH383396A (de) | 1964-10-31 |
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