DE2315258A1 - Verfahren zur herstellung von phenothiazinylacetonitrilen - Google Patents
Verfahren zur herstellung von phenothiazinylacetonitrilenInfo
- Publication number
- DE2315258A1 DE2315258A1 DE2315258A DE2315258A DE2315258A1 DE 2315258 A1 DE2315258 A1 DE 2315258A1 DE 2315258 A DE2315258 A DE 2315258A DE 2315258 A DE2315258 A DE 2315258A DE 2315258 A1 DE2315258 A1 DE 2315258A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- methyl
- hydrogen atom
- radical
- phenothiazinyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- -1 alkylthio radical Chemical class 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000002990 phenothiazines Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- 229950000688 phenothiazine Drugs 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OVDUEDRSKNXRLW-UHFFFAOYSA-N 3-chloro-10-methylphenothiazine Chemical compound ClC1=CC=C2N(C)C3=CC=CC=C3SC2=C1 OVDUEDRSKNXRLW-UHFFFAOYSA-N 0.000 description 1
- DPUVPRWTWNQSOS-UHFFFAOYSA-N 3-chloro-10h-phenothiazine Chemical compound C1=CC=C2SC3=CC(Cl)=CC=C3NC2=C1 DPUVPRWTWNQSOS-UHFFFAOYSA-N 0.000 description 1
- MFTXIGCZNMOPDK-UHFFFAOYSA-N 7-methoxy-10-methylphenothiazin-3-amine Chemical compound C1=C(N)C=C2SC3=CC(OC)=CC=C3N(C)C2=C1 MFTXIGCZNMOPDK-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- WKHJZIRDAONVML-UHFFFAOYSA-N dichloromethane;tetrachloromethane Chemical compound ClCCl.ClC(Cl)(Cl)Cl WKHJZIRDAONVML-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7210653A FR2178304A5 (enrdf_load_stackoverflow) | 1972-03-27 | 1972-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2315258A1 true DE2315258A1 (de) | 1973-10-11 |
Family
ID=9095852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2315258A Pending DE2315258A1 (de) | 1972-03-27 | 1973-03-27 | Verfahren zur herstellung von phenothiazinylacetonitrilen |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2691459A1 (fr) * | 1992-05-25 | 1993-11-26 | Adir | Nouveaux dérivés de la phénothiazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7071211B2 (en) | 2002-09-27 | 2006-07-04 | Bausch & Lomb Inc. | Small organic molecules that increase the activity of gelatinase a in ocular cells |
-
1972
- 1972-03-27 FR FR7210653A patent/FR2178304A5/fr not_active Expired
-
1973
- 1973-03-19 NL NL7303834A patent/NL7303834A/xx unknown
- 1973-03-26 JP JP48033634A patent/JPS4992077A/ja active Pending
- 1973-03-26 AR AR247236A patent/AR193943A1/es active
- 1973-03-26 CH CH436673A patent/CH557836A/fr not_active IP Right Cessation
- 1973-03-26 BE BE129284A patent/BE797352A/xx unknown
- 1973-03-26 IL IL41884A patent/IL41884A0/xx unknown
- 1973-03-26 HU HURO715A patent/HU165603B/hu unknown
- 1973-03-26 GB GB1436073A patent/GB1365847A/en not_active Expired
- 1973-03-27 ES ES413044A patent/ES413044A1/es not_active Expired
- 1973-03-27 SU SU1895840A patent/SU457223A3/ru active
- 1973-03-27 DE DE2315258A patent/DE2315258A1/de active Pending
- 1973-03-27 AT AT267373A patent/AT322565B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2691459A1 (fr) * | 1992-05-25 | 1993-11-26 | Adir | Nouveaux dérivés de la phénothiazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
Also Published As
| Publication number | Publication date |
|---|---|
| HU165603B (enrdf_load_stackoverflow) | 1974-09-28 |
| IL41884A0 (en) | 1973-05-31 |
| JPS4992077A (enrdf_load_stackoverflow) | 1974-09-03 |
| BE797352A (fr) | 1973-09-26 |
| FR2178304A5 (enrdf_load_stackoverflow) | 1973-11-09 |
| CH557836A (fr) | 1975-01-15 |
| NL7303834A (enrdf_load_stackoverflow) | 1973-10-01 |
| ES413044A1 (es) | 1976-01-16 |
| SU457223A3 (ru) | 1975-01-15 |
| AR193943A1 (es) | 1973-05-31 |
| AT322565B (de) | 1975-05-26 |
| GB1365847A (en) | 1974-09-04 |
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