Patent US4721149A successfully refreshed from Google Patents.
US4155874A
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Phenothiazinyl sulfides
Assignee: West Agro Chemical Inc
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Filing: 1977-07-28
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Granted: 1979-05-22
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Expires: 1997-07-28
Abstract
Abstract A new group of compounds, generically classed as phenothiazinyl sulfides, are described having the formula: ##STR1## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 may be H, alkyl, aryl, alkaryl, acyl, haloacyl and biologically activating aminoalkyl groups known in the medicinal arts, such as --(CH 2 ) 3 --N(CH 3 ) 2 , ##STR2## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio, and -S-phenothiazinyl substitutents; and as charge-transfer complexes of iodine therewith in which the number of moles of iodine associated with the molecule equals 1.5 (range 0.75 to 3.0) times the number of phenothiazinyl groups in the molecule. Methods for the preparation of the compounds are described. The phenothiazinyl sulfides appear to be active in the same industrial and biological applications as phenothiazine and its corresponding derivatives, and show distinctive activity in various uses and as charge-transfer complexes of novel electrochemical properties as illustrated, in-vitro, in combination with iodine as a cathode material.
Inventors
- 👤 Edward A. Nodiff
- 👤 Abraham Cantor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:16
CPC Classifications
C; C07; C07D; C07D279/00; C07D279/10; C07D279/14; C07D279/18; C09; C09K; C09K15/00; C09K15/04; C09K15/30
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
121 words
An essentially pure poly-phenothiazinyl sulfide of the formula: ##STR5## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acyl, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(C 2 ) 3 --N(CH 3 ) 2 , ##STR6## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and S-phenothiazinyl substituents; and wherein the terms ayryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents.
Claim 2
Dependent Claim
121 words
An essentially pure poly-phenothiazinyl sulfide of the formula: ##STR5## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acyl, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(C 2 ) 3 --N(CH 3 ) 2 , ##STR6## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and S-phenothiazinyl substituents; and wherein the terms ayryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents.
Claim 3
Dependent Claim
25 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 1, wherein phenothiazine moieties are joined by --S-- bridges, and the phenothiazine moieties are otherwise unsubstituted.
Claim 4
Dependent Claim
16 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 2, in the form of 3,3'-phenothiazinyl monosulfide.
Claim 5
Dependent Claim
26 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 1, wherein phenothiazine moieties are joined by an --S--S-- bridge, and the phenothiazine moieties are otherwise unsubstituted.
Claim 6
Dependent Claim
16 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 4, in the form of 3,3'-phenothiazinyl disulfide.
Claim 7
Dependent Claim
21 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 1, wherein each phenothiazine moiety contains at least one ring and/or N-substituent.
Claim 8
Dependent Claim
21 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein said substituents are selected as providing an electron donating effect.
Claim 9
Dependent Claim
21 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein said substituents are selected as providing an electron withdrawal effect.
Claim 10
Dependent Claim
21 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein said substituents are selected as providing a solubility modifying effect.
Claim 11
Dependent Claim
18 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein the phenothiazinyl moieties contain only ring substituents.
Claim 12
Dependent Claim
15 words
An essentially pure poly-phenothiazinyl sulfide according to claim 10 in the form of the 2,2'-dichloro-7,7'-monosulfide.
Claim 13
Dependent Claim
15 words
An essentially pure poly-phenothiazinyl sulfide according to claim 10 in the form of the 2,2'-dichloro-7,7'-disulfide.
Claim 14
Dependent Claim
17 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein the phenothiazine moieties contain only N-substituents.
Claim 15
Dependent Claim
16 words
An essentially pure poly-phenothiazinyl sulfide according to claim 13 in the form of the 10,10'-dimethyl monosulfide.
Claim 16
Dependent Claim
15 words
An essentially pure poly-phenothiazinyl sulfide according to claim 13 in the form of promazine 3,3'-monosulfide.
Claim 17
Dependent Claim
16 words
An essentially pure poly-phenothiazinyl sulfide according to claim 13 in the form of the 10,10'-diacetyl monosulfide.
Claim 18
Dependent Claim
19 words
An essentially pure poly-phenothiazinyl sulfide as defined in claim 6, wherein the phenothiazinyl moieties contain both ring and N-substituents.
Claim 19
Dependent Claim
15 words
An essentially pure poly-phenothiazinyl sulfide according to claim 17 in the form of chlorpromazine 7,7'-monosulfide.
Claim 20
Dependent Claim
14 words
An essentially pure oxide derivative of a poly-phenothiazinyl sulfide as defined in claim 1.
Claim 21
Dependent Claim
20 words
An oxide essentially pure oxide derivative according to claim 19 in the form of an oxide derivative of 3,3'-phenothiazinyl monosulfide.
Claim 22
Dependent Claim
19 words
An essentially pure oxide derivative according to claim 19 in the form of the trisulfone derivative of 3,3'-phenothiazinyl monosulfide.
Claim 23
Dependent Claim
157 words
An iodine complex of an essentially pure poly-phenothiazinyl sulfide of the formula: ##STR7## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acyl, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(CH 2 ) 3 --N(CH 3 ) 2 , ##STR8## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and --S-- phenothiazinyl substituents; wherein the terms aryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents; and wherein the number of moles of iodine associated with the molecule is about 1.5, and within the range of 0.75 to 3.0, times the number of phenothiazinyl groups in the molecule.
Claim 24
Dependent Claim
157 words
An iodine complex of an essentially pure poly-phenothiazinyl sulfide of the formula: ##STR7## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acyl, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(CH 2 ) 3 --N(CH 3 ) 2 , ##STR8## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and --S-- phenothiazinyl substituents; wherein the terms aryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents; and wherein the number of moles of iodine associated with the molecule is about 1.5, and within the range of 0.75 to 3.0, times the number of phenothiazinyl groups in the molecule.
Claim 25
Dependent Claim
22 words
An iodine complex according to claim 22 in the form of 3,3'-phenothiazinyl monosulfide complexed with iodine in the molar ratio of 1:3.
Claim 26
Dependent Claim
22 words
An iodine complex according to claim 22 in the form of 3,3'-phenothiazinyl disulfide complexed with iodine in the molar ratio of 1:3.
Claim 27
Dependent Claim
23 words
An iodine complex according to claim 22 in the form of 10,10'-dimethyl phenothiazinyl monosulfide complexed with iodine in the molar ratio of 1:3.
Claim 28
Dependent Claim
149 words
A composition comprising an organic medium subject to oxidative deterioration having uniformly blended therewith a stabilizing amount within the general range of 0.005 to 0.05% by weight of an essentially pure poly-phenothiazinyl sulfide of the formula: ##STR9## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acylo, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(CH 2 ) 3 --N(CH 3 ) 2 , ##STR10## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and --S-phenothiazinyl substituents; and wherein the terms aryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents.
Claim 29
Dependent Claim
149 words
A composition comprising an organic medium subject to oxidative deterioration having uniformly blended therewith a stabilizing amount within the general range of 0.005 to 0.05% by weight of an essentially pure poly-phenothiazinyl sulfide of the formula: ##STR9## wherein n is 1 or 2, x and/or y and/or z represent 0, 1 or 2; R 1 represents H, alkyl, aryl, alkaryl, acylo, haloacyl and the biologically activating aminoalkyl groups known in the medicinal arts, --(CH 2 ) 3 --N(CH 3 ) 2 , ##STR10## and -[2-(1-methyl-2-piperidyl)ethyl]; and R 2 and/or R 3 and/or R 4 and/or R 5 and/or R 6 and/or R 7 represent H, OH, Cl, Br, F, CF 3 , SH, NO 2 , CN, COOH, alkyl, alkoxy, sulfamoyl, dimethylsulfamoyl, dimethyl amino, aryl, alkaryl, acyl, aryloxy, methyl sulfonyl, methyl thio and --S-phenothiazinyl substituents; and wherein the terms aryl, alkaryl, aryloxy, acyl and haloacyl embrace typical phenothiazine substituents.
Claim 30
Dependent Claim
14 words
A composition according to claim 26, wherein the stabilizing agent is a poly-phenothiazinyl monosulfide.
Claim 31
Dependent Claim
31 words
A composition according to claim 27 wherein the organic medium is a polyoxyalkylene compound and the stabilizing agent is 3,3'-phenothiazinyl monosulfide in the amount of about 0.005 to 0.01% by weight.
Claim 32
Dependent Claim
14 words
A composition according to claim 26, wherein the stabilizing agent is a poly-phenothiazinyl disulfide.
Claim 33
Dependent Claim
31 words
A composition according to claim 29, wherein the organic medium is a polyoxyalkylene compound and the stabilizing agent is 3,3'-phenothiazinyl disulfide in the amount of about 0.01 to 0.05% by weight.
Claim 34
Dependent Claim
32 words
An essentially pure poly-phenothiazinyl sulfide according to claim 1, wherein the substituents aryl, alkaryl, aryloxy, acyl and haloacyl in said poly-phenothiazinyl sulfide, when present, are repectively phenyl, benzyl, phenoxy, acetyl and haloacetyl.
Claim 35
Dependent Claim
30 words
An iodine complex according to claim 22, wherein the substituents aryl, alkaryl, aryloxy, acyl and haloacyl in said poly-phenothiazinyl sulfide, when present, are respectively phenyl, benzyl, phenoxy, acetyl and haloacetyl.
Claim 36
Dependent Claim
28 words
A composition according to claim 26, wherein substituents aryl, alkaryl, aryloxy, acyl and haloacyl in said poly-phenothiazinyl sulfide, when present, are respectively phenyl, benzyl, phenoxy, acetyl and haloacetyl.
References Cited (Backward Citations)
US2659724A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-21 | 1982-11-20 | 1983-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-21 | 1986-11-20 | 1987-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-21 | 1990-11-20 | 1991-05-22 | $7700.00 | Window Closed / Lapsed |