GB815203A - Substituted-4-metathiazanones - Google Patents
Substituted-4-metathiazanonesInfo
- Publication number
- GB815203A GB815203A GB2099357A GB2099357A GB815203A GB 815203 A GB815203 A GB 815203A GB 2099357 A GB2099357 A GB 2099357A GB 2099357 A GB2099357 A GB 2099357A GB 815203 A GB815203 A GB 815203A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenyl
- dichlorophenyl
- phenyl
- methyl
- metathiazanones
- 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 biphenylyl Chemical group 0.000 abstract 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000012286 potassium permanganate Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- 239000003826 tablet Substances 0.000 abstract 2
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 241000220479 Acacia Species 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 abstract 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 abstract 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 229960001948 caffeine Drugs 0.000 abstract 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940117975 chromium trioxide Drugs 0.000 abstract 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229960000482 pethidine Drugs 0.000 abstract 1
- 229960003893 phenacetin Drugs 0.000 abstract 1
- 229960000581 salicylamide Drugs 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0815203/IV (b)/1> wherein Z is S or SO2; Ar is an aromatic radical, including substituted or unsubstituted phenyl, naphthyl, biphenylyl, furyl, pyridyl and thienyl radicals; R is H or a lower hydrocarbyl radical having an aliphatic carbon atom linked to the ring-nitrogen atom (containing 1-8 carbon atoms); R1, R2 and R3 are each H or a lower alkyl radical (containing 1-3 carbon atoms) and the manufacture thereof by heating an aldehyde of the formula Ar-CAO, a betamercapto propionic acid of the general formula HS.CH(R1)C(R2)(R3)COOH and an aminating agent, i.e. a compound having a high ammonia partial pressure which usually loses ammonia on standing and which readily decomposes when heated to lose ammonia, or a hydrocarbylamine of the general formula R-NH2 and, if desired, oxidizing (for example, by potassium permanganate, hydrogen peroxide or chromium trioxide) the resulting compound where Z is S to the analogue where Z is SO2. Examples are given of the preparation of 2-(3,4-dichlorophenyl) - 3 - methyl - 4 - metathiazanone by reacting 3,4-dichlorobenzaldehyde, beta-mercaptopropionic acid and methylamine; of 2-(2,4-dichlorophenyl) -, 2 - (4 - isopropylphenyl) -, 2-(4 - chlorophenyl) -, 2 - (4 - methoxyphenyl)-, 2 - phenyl -, 2 - (2 - chlorophenyl) -, 2 - (3-chlorophenyl) -, 2 - (2 - thienyl) -, and 2 - (3-pyridyl) - 3 - methyl - 4 - metathiazanones, 4-(4 - chloro phenyl) - 3 - ethyl -, 2 - (4 - chlorophenyl) - 3 - n - propyl and 2 - phenyl - 3-benzyl - 4 - metathiazanones by a similar method using the appropriately substituted benzaldehyde and amine; of 2-phenyl-, 2-(4-methoxyphenyl) -, 2 - (4 - bromophenyl) -, 2-(3,4 - dichlorophenyl) -, 2 - (2,4 - dichlorophenyl)-, and 2-(4-chlorophenyl)-4-metathiazanones by reacting the corresponding aldehyde with ammonium carbonate, or carbamate, and betamercaptopropionic acid or its ammonium salt alone, whilst similarly may be prepared 2 - (3 - chlorophenyl) - 5 - methyl -, 2-(3,4 - dibromophenyl) - 6 - methyl -, 2 - (3,4 - dichlorophenyl) - 5 - ethyl - 6 - n - propyl -, 2 - (4-iodophenyl) -, 2 - (4 - fluorophenyl) -, 2 - (2,4,6-trichlorophenyl) - 5,6 - dimethyl -, 2 - (4 - isobutoxyphenyl) - 5,5,6 - trimethyl -, 2 - (3,4,5-trimethylphenyl) - 5,5,6 - trimethyl -, 2 - (4-ethylphenyl) - 5,5 - diethyl -, 2 - (3 - ethyl - 4-isopropoxyphenyl) - 5 - isopropoxy -, 2 - (3-ethoxy - 4 - chlorophenyl) -, 2 - (3 - n - hexylphenyl) - 5 - methyl - 2 - (1 - naphthyl) -, and 2 - (2 - biphenylyl) - 4 - metathiazanones. Further examples are also given of the preparation of 2 - (4 - chlorophenyl) - and 2 - (3,4 - dichlorophenyl) - 3 - methyl - 4 - metathiazanone-1-dioxides by oxidizing the corresponding 4-metathiazanones with potassium permanganate in aqueous acetic acid and, using a similar process and the corresponding 4 - metathiazanones, of 2-(2,4-dichlorophenyl)-, 2-phenyl-, 2 - (4 - methoxyphenyl) -, 2 - (4 - isopropylphenyl) -, 2 - (2 - chlorophenyl) -, 2 - (3 - chlorophenyl) -, 2 - (2 - thienyl) -, and 2 - (3 - pyridyl)-3 - methyl - 4 - metathiazanone - 1 - dioxides, 2-(4 - chlorophenyl) - 3 - n - propyl -, 2 - (4 - chlorophenyl) - 3 - ethyl -, 2 - phenyl - 3 - benzyl -, 2-(3,4 - dichlorophenyl) -, 2 - (4 - chlorophenyl)-, 2 - (4 - bromophenyl) -, and 2 - phenyl - 4-metathiazanone-1-dioxides.ALSO:Tablets, capsules, solutions and suspensions for oral or injectable administration may contain <FORM:0815203/VI/1> wherein Z is S or SO2; Ar is an aromatic radical, including substituted or unsubstituted phenyl, naphthyl, biphenylyl, furyl, pyridyl, and thienyl radicals; R is H, or a lower hydrocarbyl radical having an aliphatic carbon atom linked to a ring-nitrogen atom and containing 1-8 carbon atoms; R1-3 are each H, or a lower alkyl radical containing 1-3 carbon atoms, either alone or in combination with one or other medicinals such as asprin, phenacetin, salicylamide, para-acetylaminophenol, caffeine, and meperidine. Tablets may contain as adjuvants, calcium carbonate, starch, gelatin talc, magnesium stearate or acacia, and solutions and suspension may be made in water, alcohol/water oil or oil/water emulsions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59901156A | 1956-07-20 | 1956-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815203A true GB815203A (en) | 1959-06-17 |
Family
ID=24397835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2099357A Expired GB815203A (en) | 1956-07-20 | 1957-07-03 | Substituted-4-metathiazanones |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH367826A (en) |
| DE (1) | DE1111192B (en) |
| GB (1) | GB815203A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093639A (en) * | 1961-07-27 | 1963-06-11 | Sterling Drug Inc | 2, 3-disubstituted-4-metathiazanones, -1-oxides and -1, 1-dioxides |
| US3155655A (en) * | 1964-11-03 | Dh chj | ||
| US3244703A (en) * | 1961-10-19 | 1966-04-05 | Shell Oil Co | Thiazine, thiazoline, and thiazolinone compounds |
| CN104817518A (en) * | 2014-09-23 | 2015-08-05 | 河南九势制药股份有限公司 | Optimized chlormezanone synthesis method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2585064A (en) * | 1952-02-12 | Meta-thiazines |
-
1957
- 1957-07-03 GB GB2099357A patent/GB815203A/en not_active Expired
- 1957-07-16 CH CH4843857A patent/CH367826A/en unknown
- 1957-07-16 DE DEST12771A patent/DE1111192B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155655A (en) * | 1964-11-03 | Dh chj | ||
| US3093639A (en) * | 1961-07-27 | 1963-06-11 | Sterling Drug Inc | 2, 3-disubstituted-4-metathiazanones, -1-oxides and -1, 1-dioxides |
| US3244703A (en) * | 1961-10-19 | 1966-04-05 | Shell Oil Co | Thiazine, thiazoline, and thiazolinone compounds |
| CN104817518A (en) * | 2014-09-23 | 2015-08-05 | 河南九势制药股份有限公司 | Optimized chlormezanone synthesis method |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1111192B (en) | 1961-07-20 |
| CH367826A (en) | 1963-03-15 |
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