GB990857A - 1,3-diazaphenothiazines - Google Patents
1,3-diazaphenothiazinesInfo
- Publication number
- GB990857A GB990857A GB2195160A GB2195160A GB990857A GB 990857 A GB990857 A GB 990857A GB 2195160 A GB2195160 A GB 2195160A GB 2195160 A GB2195160 A GB 2195160A GB 990857 A GB990857 A GB 990857A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- diazaphenthiazine
- amino
- compound
- prepared
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises 1,3-diazaphenthiazines of the formula <FORM:0990857/C2/1> (wherein R1 and R2 are hydrogen, halogen, alkyl or alkoxy; W is hydrogen, alkyl, amino or hydroxy; and X is hydrogen, halogen, amino, mono- or di-alkylamino, dialkylaminoalkylamino, pyrrolidino, piperidino, morpholino, 4-alkylpiperazino, hydrazino, hydroxy, alkoxy, alkoxyalkoxy, mercapto or alkylthio; the alkyl and alkoxy groups each containing at most 4 carbon atoms); and the preparation of these and other 1,3-diazaphenthiazines by treating with an acidic reagent a compound of the basic structure <FORM:0990857/C2/2> Suitable acidic reagents include phosphorus oxychloride (when it is preferable to acetylate before treatment with this) or, preferably, mineral acids used in aqueous, alcoholic or aqueous/alcoholic solution, desirably at a pH below 2. In Examples (1) and (2) 2-amino-5-bromo - 4 - hydroxypyrimidine and 2 - aminobenzenethiol give 2 - amino - 5 - (2 - aminophenylthio) - 4 - hydroxypyrimidine, this with acetic anhydride in pyridine gives the 2-acetamido compound, this on cyclization gives a product which is probably 2 - acetamido - 1,3-diazophenthiazine and this on boiling with alcoholic hydrochloric acid gives the 2-amino compound, also prepared in a phosphorylated form (probably 2-phosphoramido-1,3-diazaphenthiazine) by cyclization of the hydroxypyrimidine compound with phosphorus oxychloride, or as the hydrochloride of the free amino form by cyclization with ethanolic hydrochloric acid; (3) 5 - bromouracil and 2 - aminobenzenethiol give 5 - (2 - aminophenylthio) - 2,4 - dihydroxypyrimidine which on cyclization gives 2-hydroxy - 1,3 - diazaphenothiazine; (4), (5), (6), (8), (10), (12), (15), (18) and (19) similarly are prepared 5 - (2 - amino - 4 - chlorophenylthio)-2,4 - dihydroxypyrimidine and 8 - chloro - 2-hydroxy - 1,3 - diazaphenthiazine, 2 - mercapto-1,3 - diazaphenthiazine (also prepared from the 2 - chloro compound and thiourea), 5-(2 - aminophenylthio) - 2 - dimethylamino - 4-hydroxy - 6 - methyl - pyrimidine (by brominating 2 - dimethylamino - 4 - hydroxy - 6 - methyl-pyrimidine to give 5 - bromo - 2 - dimethylamino - 4 - hydroxy - 6 - methylpyrimidine and reacting this with 2-aminobenzenethiol) and 2-dimethylamino - 4 - methyl - 1,3 - diazaphenthiazine hydrochloride, 5 - (2 - amino - 4-chlorophenylthio) - 4 - hydroxy - 2 - (4 - methylpiperazino) - pyrimidine and the corresponding 6 - methyl compound and 8 - chloro - 2 - (4-methylpiperazino) - 1,3 - diazaphenthiazine and the corresponding 4-methyl compound respectively, and the corresponding 2-morpholino and 2 - piperidino compounds, 2 - amino - 5 - (2-aminophenylthio) - 4,6 - dihydroxypyrimidine and 2 - amino - 4 - hydroxy - 1,3 - diazaphenthiazine hydrochloride, and 2,4 - diamino - 5-(2 - aminophenylthio) - 6 - hydroxy - pyrimidine which on cyclization gives a mixture of hydroxy - and aminohydroxy - 1,3 - diazaphenthiazines; (7) 4 - hydroxy - 2 - methylthiopyrimidine and 4 - methylpiperazine give 4-hydroxy - 2 - (4 - methylpiperazino) - pyrimidine, this is brominated to give the 5-bromo hydrobromide and this with 2-aminobenzenethiol gives 2 - (4 - methylpiperazine) - 1,3 - diazaphenthiazine and, as a by-product, 2,21-diamino - diphenylsulphide; (9), (11), (13), (14), and (16) similarly are prepared the corresponding 6 - methyl - pyrimidines and 4-methyldiazaphenthiazines and the corresponding morpholino and piperidino compounds, as free bases or acid-addition salts; (17) 5-bromo-2 - (3 - dimethylaminopropylamino) - 4 - hydroxypyrimidine hydrobromide monohydrate is prepared by bromination and is treated with 2-aminobenzenethiol and the syrupy product cyclized to 2 - (3 - dimethylaminopropylamino)-1,3 - diazaphenthiazine; (20) 4 - amino - 5-bromo - 2 - dimethylamino - 6 - hydroxy - pyrimidine is prepared by bromination and reacted with 2 - aminobenzenethiol to give 4 - amino-5 - (2 - aminophenylthio) - 2 - dimethylamino - 6-hydroxypyrimidine, and this is cyclized to give a mixture of 4-amino-2-dimethylamino-1,3-diazaphenthiazine and the corresponding 4-hydroxy - compound, separated by recrystallization of their hydrochlorides; (21) and (23) to (29) 2-chloro-1,3-diazaphenthiazine is prepared from the 2-hydroxy-compound and phosphorus oxychloride, and is converted to the 2 - methoxy -, 2 - (2 - methoxyethoxy), - 2-hydrazino -, 2 - (3 - dimethylaminopropylamino) - and 2 - (2 - dimethylaminoethylamino)-compounds by reaction with, respectively, sodium methoxide/methanol, 2-methoxyethanol, hydrazine, 3-dimethylaminopropylamine and 2-dimethylamino-ethylamine, an additional product of the second named reaction being 1,3-diazaphenthiazine (also prepared by heating the 2-hydrazine-compound with dilute hydrochloric acid and copper sulphate); (22) 2,8 - dichloro - 1,3 - diazaphenthiazine is prepared by chlorination of the 2-hydroxy-8-chloro - compound; and (30) 2 - amino - 7,8-dimethyl - 1,3 - diazaphenthiazine hydrochloride, 2 - hydroxy - 7,8 - dimethyl - 1,3 - diazaphenthiazine hydrate and 2-chloro-7,8-dimethyl - 1,3 - diazaphenthiazine are prepared by the methods of (2), (3) and (4) and (21) and (22) respectively. The diazaphenthiazines of the invention are stated to possess anti-bacterial activity and to have a tranquillizing action, and may be made up into pharmaceutical compositions with suitable carriers. These may take the form of tablets, capsules, cachets, ampoules, suppositories, powders, granules, solutions, suspensions, emulsions or ointments, and may contain buffers, flavouring or dispersing agents, preservatives and antioxidants. Specification 951,431 is referred to.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US123342A US3248393A (en) | 1960-06-23 | 1961-06-05 | 1, 3-diazaphenothiazines and method |
ES0268439A ES268439A1 (en) | 1960-06-23 | 1961-06-21 | A method to produce organic compounds heterocyclic (Machine-translation by Google Translate, not legally binding) |
BE605296A BE605296A (en) | 1960-06-23 | 1961-06-22 | Heterocyclic organic chemical compounds and method. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3692361A GB1015784A (en) | 1961-10-13 | 1961-10-13 | 10 - substituted 1,3 - diazaphenothiazines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB990857A true GB990857A (en) | 1965-05-05 |
Family
ID=10392273
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2195160A Expired GB990857A (en) | 1960-06-23 | 1960-06-23 | 1,3-diazaphenothiazines |
GB3692261A Expired GB1014881A (en) | 1961-10-13 | 1961-10-13 | 1,3-diazaphenothiazines and method |
GB3692361A Expired GB1015784A (en) | 1960-06-23 | 1961-10-13 | 10 - substituted 1,3 - diazaphenothiazines |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3692261A Expired GB1014881A (en) | 1961-10-13 | 1961-10-13 | 1,3-diazaphenothiazines and method |
GB3692361A Expired GB1015784A (en) | 1960-06-23 | 1961-10-13 | 10 - substituted 1,3 - diazaphenothiazines |
Country Status (1)
Country | Link |
---|---|
GB (3) | GB990857A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0097297A1 (en) * | 1982-06-18 | 1984-01-04 | Beiersdorf Aktiengesellschaft | Substituted 5-phenylthio-6-amino-pyrimidinones, process for their preparation and their use, and preparations containing these compounds |
WO2000063182A2 (en) * | 1999-04-20 | 2000-10-26 | Bayer Aktiengesellschaft | 2,4-diamino-pyrimidine derivatives and their use as microbicides and herbicides |
US11512262B2 (en) | 2017-03-17 | 2022-11-29 | University Of Ottawa | Azaphenothiazines and azaphenoxazines as antioxidants |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101906146B1 (en) | 2009-08-17 | 2018-10-10 | 메모리얼 슬로안-케터링 캔서 센터 | Heat shock protein binding compounds, compositions, and methods for making and using same |
ES2774975T3 (en) | 2014-05-13 | 2020-07-23 | Memorial Sloan Kettering Cancer Center | Hsp70 modulators and methods of making and using it |
-
1960
- 1960-06-23 GB GB2195160A patent/GB990857A/en not_active Expired
-
1961
- 1961-10-13 GB GB3692261A patent/GB1014881A/en not_active Expired
- 1961-10-13 GB GB3692361A patent/GB1015784A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0097297A1 (en) * | 1982-06-18 | 1984-01-04 | Beiersdorf Aktiengesellschaft | Substituted 5-phenylthio-6-amino-pyrimidinones, process for their preparation and their use, and preparations containing these compounds |
US4594419A (en) * | 1982-06-18 | 1986-06-10 | Beiersdorf Aktiengesellschaft | Substituted 5-phenylthio-6-amino-pyrimidinones, a process for their preparation and their use, and formulations containing these compounds |
US4686223A (en) * | 1982-06-18 | 1987-08-11 | Beiersdorf Aktiengesellschaft | Substituted 5-phenylthio-6-amino-pyrimidinones, a process for their preparation and their use, and formulations containing these compounds |
WO2000063182A2 (en) * | 1999-04-20 | 2000-10-26 | Bayer Aktiengesellschaft | 2,4-diamino-pyrimidine derivatives and their use as microbicides and herbicides |
WO2000063182A3 (en) * | 1999-04-20 | 2001-10-11 | Bayer Ag | 2,4-diamino-pyrimidine derivatives and their use as microbicides and herbicides |
US11512262B2 (en) | 2017-03-17 | 2022-11-29 | University Of Ottawa | Azaphenothiazines and azaphenoxazines as antioxidants |
Also Published As
Publication number | Publication date |
---|---|
GB1014881A (en) | 1965-12-31 |
GB1015784A (en) | 1966-01-05 |
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