GB808050A - Acyl phenothiazine-10-carboxylic acid esters - Google Patents
Acyl phenothiazine-10-carboxylic acid estersInfo
- Publication number
- GB808050A GB808050A GB1669058A GB1669058A GB808050A GB 808050 A GB808050 A GB 808050A GB 1669058 A GB1669058 A GB 1669058A GB 1669058 A GB1669058 A GB 1669058A GB 808050 A GB808050 A GB 808050A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- straight
- acyl
- carbon atoms
- alkyl
- 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
- -1 Acyl phenothiazine-10-carboxylic acid esters Chemical class 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005251 aryl acyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises acyl phenthiazine-10-carboxylic acid esters of the general formula <FORM:0808050/IV (b)/1> (where Ac is a straight or branched chain alkyl acyl radical containing 2-4 carbon atoms or an aryl acyl group, X and Y are hydrogen atoms, alkyl radicals containing up to eight carbon atoms, or halogen atoms, A is a straight or branched chain alkylene radical containing up to eight carbon atoms, R1 and R2 are alkyl groups or straight or branched alkylene chains which are either linked inter se or with a carbon atom of A to form a 5- or 6-membered nitrogen-containing ring, e.g. piperidine, pyrrolidine, morpholine and piperazine, which ring may further contain alkyl substituents), together with a process for their preparation by reacting the corresponding 10-unsubstituted phenthiazine with phosgene, preferably in an inert solvent, e.g. xylene, and reacting the resulting 10-carboxylic acid chloride with a basic alcohol HO.A.NR1R2, preferably in boiling benzene. In examples: (1) 3-acetylphenthiazine in boiling xylene is treated with phosgene, the solvent distilled off, benzene added and the mixture boiled with g -dimethylaminopropyl alcohol, giving the hydrochloride of g -dimethylaminopropyl - 3 - acetylphenthiazine-10-carboxylate; (2) as in (1) but using 3-propionylphenthiazine as starting material.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0018365 | 1955-09-07 | ||
| DEB0020224 | 1956-05-05 | ||
| DEB0020504 | 1956-06-12 | ||
| DEB0020503 | 1956-06-12 | ||
| GB1669056 | 1956-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808050A true GB808050A (en) | 1959-01-28 |
Family
ID=27511902
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2657256A Expired GB808049A (en) | 1955-09-07 | 1956-08-30 | Phenothiazine derivatives |
| GB1669058A Expired GB808050A (en) | 1955-09-07 | 1956-08-30 | Acyl phenothiazine-10-carboxylic acid esters |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2657256A Expired GB808049A (en) | 1955-09-07 | 1956-08-30 | Phenothiazine derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE550647A (en) |
| CH (1) | CH360060A (en) |
| DE (2) | DE1420041A1 (en) |
| DK (2) | DK111683B (en) |
| FR (1) | FR1223229A (en) |
| GB (2) | GB808049A (en) |
| NL (1) | NL108533C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070598A (en) * | 1962-12-25 | Method of preparing phenothiazine-io- |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3082208A (en) * | 1958-07-07 | 1963-03-19 | Sterling Drug Inc | 10-[(1-piperidyl)lower-alkyl]-loweralkanoylphenothiazines |
| DE1195756B (en) * | 1961-07-21 | 1965-07-01 | Novo Terapeutisk Labor As | Process for the preparation of aminoalkylated aromatic-heterocyclic secondary amines |
| DE1159954B (en) * | 1961-11-25 | 1963-12-27 | Boehringer & Soehne Gmbh | Process for the production of new 10- (alkoxypiperidinopropyl) -phenthiazines and their salts |
| EP2246349A1 (en) * | 2009-04-20 | 2010-11-03 | BKG Pharma ApS | Treatment of infectious diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587661A (en) * | 1952-03-04 | Chzchjcn | ||
| DE910301C (en) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Process for the production of new phenthiazine derivatives |
| DE922467C (en) * | 1951-11-25 | 1955-01-17 | Cassella Farbwerke Mainkur Ag | Process for the preparation of N-derivatives of phenothiazine |
-
0
- DE DENDAT1049865D patent/DE1049865B/en active Pending
- NL NL108533D patent/NL108533C/xx active
- BE BE550647D patent/BE550647A/xx unknown
-
1956
- 1956-05-05 DE DE19561420041 patent/DE1420041A1/en active Pending
- 1956-07-23 CH CH360060D patent/CH360060A/en unknown
- 1956-08-29 FR FR721125A patent/FR1223229A/en not_active Expired
- 1956-08-30 GB GB2657256A patent/GB808049A/en not_active Expired
- 1956-08-30 GB GB1669058A patent/GB808050A/en not_active Expired
-
1964
- 1964-12-07 DK DK599864A patent/DK111683B/en unknown
- 1964-12-07 DK DK599764A patent/DK111682B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070598A (en) * | 1962-12-25 | Method of preparing phenothiazine-io- |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1049865B (en) | 1959-02-03 |
| BE550647A (en) | |
| DK111683B (en) | 1968-09-30 |
| GB808049A (en) | 1959-01-28 |
| CH360060A (en) | 1962-02-15 |
| DE1420041A1 (en) | 1968-10-24 |
| NL108533C (en) | |
| DK111682B (en) | 1968-09-30 |
| FR1223229A (en) | 1960-06-15 |
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