GB977788A - Emetine derivatives and their preparation - Google Patents
Emetine derivatives and their preparationInfo
- Publication number
- GB977788A GB977788A GB2038760A GB2038760A GB977788A GB 977788 A GB977788 A GB 977788A GB 2038760 A GB2038760 A GB 2038760A GB 2038760 A GB2038760 A GB 2038760A GB 977788 A GB977788 A GB 977788A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reduction
- hydroxyalkyl
- alkyl
- emetine
- group
- 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
- AUVVAXYIELKVAI-CKBKHPSWSA-N emetine Chemical class N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC AUVVAXYIELKVAI-CKBKHPSWSA-N 0.000 title 1
- 238000000034 method Methods 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 229960002694 emetine Drugs 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- -1 bismuth halides Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052987 metal hydride Inorganic materials 0.000 abstract 2
- 150000004681 metal hydrides Chemical class 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052797 bismuth Inorganic materials 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000005188 oxoalkyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 0.000 abstract 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical class C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
- C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises N-substituted derivatives of 1-emetine having the general formula <FORM:0977788/C1/1> (wherein R represents an unsubstituted alkyl, hydroxyalkyl, or esterified hydroxyalkyl group, the N-alkyl portion of which contains 2 to 7 carbon atoms) their non-toxic acid addition salts, particularly the mono- and di-hydrochlorides, hydrobromides, hydroiodides, sulphates, nitrates, citrates and tartrates, also addition complexes with bismuth halides also processes for their preparation (a) by N-alkylating l-emetine to introduce an N-alkyl, N-hydroxyalkyl or N-(esterified hydroxyalkyl) group at the 21-position; (b) by reacting a compound of the general formula <FORM:0977788/C1/2> (wherein R11 is an alkyl or hydroxyalkyl group of from 1 to 7 carbon atoms) in one or more stages with reagents serving to reduce a ketonic carbonyl group to a methylene group. The principal methods for process (a) are (i) reaction of l-emetine with a functional derivative of an acid R1COOH (R1 is alkyl), and then reduction of the carbonyl group of the resulting amide, e.g. with complex metal hydrides; (ii) reaction of l-emetine with a vinyl ketone CH2:CHCOR11 (R11 being alkyl of from one to four atoms), followed by reduction of the carbonyl group in the resulting N-oxoalkyl compound, e.g. with hydrazine and alkali, or by conversion to the ethylene thioketal or benzylmercaptol derivative followed by reduction with a Raney metal, or, if a hydroxyalkyl compound is required by reduction of the carbonyl group with a complex metal hydride. The methods for process (b) involve direct reduction with hydrazine and alkali, or reduction of the thioketal derivative e.g. with a Raney metal. The compounds of second general formula above are themselves prepared by reduction of compounds of the formula <FORM:0977788/C1/3> R11 is alkyl, hydroxyalkyl or oxoalkyl with a metal/ammonia or metal/amine reducing system followed by isomerization of the 3b -acetyl compound obtained. Any methoxyl groups that are converted to hydroxyl during the processes are remethylated, e.g. using a phenyl trimethylammonium salt. The invention is illustrated by 11 detailed examples. Specifications 960,181 and 960,182 also are referred to.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2038760A GB977788A (en) | 1960-06-09 | 1960-06-09 | Emetine derivatives and their preparation |
| DK345262A DK107940C (en) | 1960-06-09 | 1961-06-01 | Process for the preparation of an emetine derivative or acid addition salts thereof. |
| CH661861A CH416637A (en) | 1960-06-09 | 1961-06-07 | Process for the preparation of derivatives of 1-emetine |
| BE604728A BE604728A (en) | 1960-06-09 | 1961-06-07 | New derivatives of emtine and their preparation. |
| BR12988261A BR6129882D0 (en) | 1960-06-09 | 1961-06-08 | PROCESS FOR PREPARATION OF L-EMETINE DERIVATIVES |
| SE606561A SE307357B (en) | 1960-06-09 | 1961-06-09 | |
| DE19611445058 DE1445058A1 (en) | 1960-06-09 | 1961-06-09 | Process for the preparation of N-substituted derivatives of 1-emitin |
| DE19611445833 DE1445833A1 (en) | 1960-06-09 | 1961-06-09 | Process for the preparation of N-substituted 1-emetine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2038760A GB977788A (en) | 1960-06-09 | 1960-06-09 | Emetine derivatives and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB977788A true GB977788A (en) | 1964-12-16 |
Family
ID=10145113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2038760A Expired GB977788A (en) | 1960-06-09 | 1960-06-09 | Emetine derivatives and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB977788A (en) |
-
1960
- 1960-06-09 GB GB2038760A patent/GB977788A/en not_active Expired
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