GB873777A - 5-hydroxy-ª--alkyltryptophans - Google Patents
5-hydroxy-ª--alkyltryptophansInfo
- Publication number
- GB873777A GB873777A GB1843/60A GB184360A GB873777A GB 873777 A GB873777 A GB 873777A GB 1843/60 A GB1843/60 A GB 1843/60A GB 184360 A GB184360 A GB 184360A GB 873777 A GB873777 A GB 873777A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- benzyloxy
- methyl
- general formula
- 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.)
- Expired
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JMFZKYABNMMQHH-UHFFFAOYSA-N 1-methyl-5-phenylmethoxyindole Chemical compound C=1C=C2N(C)C=CC2=CC=1OCC1=CC=CC=C1 JMFZKYABNMMQHH-UHFFFAOYSA-N 0.000 abstract 1
- ZNULQHFXMKIBMJ-UHFFFAOYSA-N 1-methyl-5-phenylmethoxyindole-3-carboxylic acid Chemical compound CN1C=C(C2=CC(=CC=C12)OCC1=CC=CC=C1)C(=O)O ZNULQHFXMKIBMJ-UHFFFAOYSA-N 0.000 abstract 1
- VMPPPYLQGQTGBO-UHFFFAOYSA-N 2-methyl-5-phenylmethoxy-1h-indole Chemical compound C=1C=C2NC(C)=CC2=CC=1OCC1=CC=CC=C1 VMPPPYLQGQTGBO-UHFFFAOYSA-N 0.000 abstract 1
- JCQLPDZCNSVBMS-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1OCC1=CC=CC=C1 JCQLPDZCNSVBMS-UHFFFAOYSA-N 0.000 abstract 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 239000006035 Tryptophane Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 230000020335 dealkylation Effects 0.000 abstract 1
- 238000006900 dealkylation reaction Methods 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229960004799 tryptophan Drugs 0.000 abstract 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0873777/IV (b)/1> wherein R1 and R2 are hydrogen atoms or a C1-C6 alkyl group and R3 represents a C1-C6 alkyl group, and the preparation thereof by heating a compound of the general formula: <FORM:0873777/IV (b)/2> wherein R is an alkyl or aralkyl group with an alkyl a -nitroalkanoate in the presence of an inert solvent to obtain the correspondingly substituted alkyl a -alkyl-a -nitro-3-indolepropionate, reducing the latter compound, after N-alkylation if desired in the case where R1 is hydrogen, to yield the corresponding alkyl ester of 5-substituted hydroxy-a -alkyl-tryptophane, hydrolysing the latter compound, and subjecting to hydrogenolysis where R is aralkyl or to dealkylation where R is alkyl. The compounds of the invention form salts with acids and bases both inorganic and organic. 5-Benzyloxy-1-methylgramine is prepared by reacting 5-benzyloxyindole with dimethylformamide and phosphorus oxychloride to form 5 - benzyloxy - 3 - indolecarboxyaldehyde methylating this to form 1-methyl-5-benzyloxy-3-indolecarboxyaldehyde, oxidising the aldehyde to 1 - methyl - 5 - benzyloxy-3-indolecarboxylic acid, decarboxylating the acid to 1-methyl-5-benzyloxyindole and reacting the indole with formaldehyde and dimethylamine. 5-Benzyloxy-2-methylgramine is prepared from 5-benzyloxy-2-methylindole, formaldehyde and dimethylene. Specification 744,774 and U.S.A. Specifications 1,915,334, 2,075,359, 2,425,320, 2,557,041, 2,606,155, and 2,616,896 are referred to.ALSO:Pharmaceutical compositions comprise a compound of the general formula <FORM:0873777/VI/1> wherein R1 and R2 are hydrogen or C1-6 alkyl groups and R3 is a C1-6 alkyl group or a salt thereof with an organic or inorganic acid or base, together with a solid or liquid diluent. The compositions may include tablets, capsules, powder packets, or suspensions or solutions in suitable solvents for oral or parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US873777XA | 1959-01-26 | 1959-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB873777A true GB873777A (en) | 1961-07-26 |
Family
ID=22204826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1843/60A Expired GB873777A (en) | 1959-01-26 | 1960-01-19 | 5-hydroxy-ª--alkyltryptophans |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB873777A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299838A (en) * | 1974-12-23 | 1981-11-10 | La Cooperation Pharmaceutique Francaise | Tryptophan derivatives having an increased effect on the central nervous system |
| US4456611A (en) * | 1981-02-02 | 1984-06-26 | Laboratoires Panmedica | Derivatives of 2-[3-(3-indoly)2-amino propionyloxy] acetic acid, and seritoning increasing use thereof |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
-
1960
- 1960-01-19 GB GB1843/60A patent/GB873777A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299838A (en) * | 1974-12-23 | 1981-11-10 | La Cooperation Pharmaceutique Francaise | Tryptophan derivatives having an increased effect on the central nervous system |
| US4456611A (en) * | 1981-02-02 | 1984-06-26 | Laboratoires Panmedica | Derivatives of 2-[3-(3-indoly)2-amino propionyloxy] acetic acid, and seritoning increasing use thereof |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
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