ES228143A1 - Improvements in or relating to the production of derivatives of phenothiazine - Google Patents
Improvements in or relating to the production of derivatives of phenothiazineInfo
- Publication number
- ES228143A1 ES228143A1 ES0228143A ES228143A ES228143A1 ES 228143 A1 ES228143 A1 ES 228143A1 ES 0228143 A ES0228143 A ES 0228143A ES 228143 A ES228143 A ES 228143A ES 228143 A1 ES228143 A1 ES 228143A1
- Authority
- ES
- Spain
- Prior art keywords
- phenothiazine
- dimethylaminopropyl
- acetyl
- carboxylic acid
- acid
- 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
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title 1
- 229950000688 phenothiazine Drugs 0.000 abstract 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000003891 oxalate salts Chemical class 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- JWGBOHJGWOPYCL-UHFFFAOYSA-N 1-(10H-phenothiazin-2-yl)ethanone Chemical compound C1=CC=C2NC3=CC(C(=O)C)=CC=C3SC2=C1 JWGBOHJGWOPYCL-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ILVINAZEYLXESX-UHFFFAOYSA-N 3-acetylphenothiazine-10-carboxylic acid Chemical compound C(C)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)C(=O)O ILVINAZEYLXESX-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- -1 aminoalkyl ester Chemical class 0.000 abstract 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 abstract 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 3-acyl-N-dialkylaminoalkyl-phenothiazines (Beilstein nomenclature), 3 - a - hydroxyethyl - N - g - dimethylaminopropyl-phenothiazine, their acid addition and quaternary salts, particularly the oxalates and maleates, and a process for the preparation of an N-aminoalkyl-phenothiazine by decarboxylating an aminoalkyl ester of a phenothiazine N-carboxylic acid, preferably by heating in a solvent, e.g. decahydronaphthalene, or distillation under vacuum. The intermediate ester is prepared by reacting an aminoalkanol with the appropriate phenothiazine N-carboxylic acid, or its acid chloride, prepared from the appropriate phenothiazine and phosgene. In examples: (1) to (3) 3-acetylphenothiazine in toluene containing phosgene is autoclaved, the resulting chloride of 3-acetylphenothiazine-N-carboxylic acid reacted with g -dimethylaminopropanol in acetone or benzene, the hydrochloride of the g -dimethylaminopropyl ester produced is then basified, refluxed in decahydronaphthalene, 1,3 - dimethoxybenzene, quinoline or collidine with the evolution of CO2, and the resulting 3-acetyl-N-g -dimethylaminopropyl-phenothiazine characterized as its acid oxalate, maleate, oxime, 2,4-dinitrophenylhydrazone and its hydrochloride, and the methiodide subsequent reduction of the base with lithium aluminium hydride gives 3-a -hydroxyethyl - N - g - dimethylaminopropyl - phenothiazine, characterized as its oxalate other examples describe the preparation of 3-methoxy - N - g - dimethylaminopropylphenothiazine, 3 - acetyl - N - b - dimethylaminoethylphenothiazine, 3 - acetyl - N - g - diethylaminopropylphenothiazine, 3 - propionyl - N - g - diethylaminopropylphenothiazine, 3 - propionyl - N - g - dimethylaminopropylphenothiazine and their oxalates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR694883 | 1955-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES228143A1 true ES228143A1 (en) | 1956-06-16 |
Family
ID=8701324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0228143A Expired ES228143A1 (en) | 1955-06-30 | 1956-04-25 | Improvements in or relating to the production of derivatives of phenothiazine |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE1420035B1 (en) |
| DK (1) | DK103299C (en) |
| ES (1) | ES228143A1 (en) |
| GB (1) | GB816582A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH298685A (en) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Process for the preparation of a novel derivative of phenothiazine. |
| DE939630C (en) * | 1953-10-25 | 1956-03-01 | Basf Ag | Process for the preparation of heterocyclic compounds with a ring-shaped imino group substituted by basic groups |
-
1956
- 1956-04-25 ES ES0228143A patent/ES228143A1/en not_active Expired
- 1956-05-04 DE DE19561420035 patent/DE1420035B1/en active Pending
- 1956-05-04 GB GB1386656A patent/GB816582A/en not_active Expired
- 1956-05-04 DE DEE17472A patent/DE1153020B/en active Pending
- 1956-06-29 DK DK232056A patent/DK103299C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE1153020B (en) | 1963-08-22 |
| DK103299C (en) | 1965-12-13 |
| GB816582A (en) | 1959-07-15 |
| DE1420035B1 (en) | 1970-01-29 |
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