GB808239A - Improvements in or relating to phenthiazine derivatives and processes for their production - Google Patents
Improvements in or relating to phenthiazine derivatives and processes for their productionInfo
- Publication number
- GB808239A GB808239A GB104/57A GB10457A GB808239A GB 808239 A GB808239 A GB 808239A GB 104/57 A GB104/57 A GB 104/57A GB 10457 A GB10457 A GB 10457A GB 808239 A GB808239 A GB 808239A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenothiazine
- methoxycarbonyl
- dimethylaminopropyl
- methoxycarbonylphenothiazine
- hydrochloride
- 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 241000790917 Dioxys <bee> Species 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 229950000688 phenothiazine Drugs 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- ZDKGCAKRVSOXAU-UHFFFAOYSA-N 10-O-[1-(diethylamino)propan-2-yl] 3-O-methyl phenothiazine-3,10-dicarboxylate Chemical compound COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC=2C=1)C(=O)OC(C)CN(CC)CC ZDKGCAKRVSOXAU-UHFFFAOYSA-N 0.000 abstract 1
- WHCMAYHDCBTRGH-UHFFFAOYSA-N 10-O-[2-(diethylamino)ethyl] 3-O-methyl phenothiazine-3,10-dicarboxylate Chemical compound C(C)N(CCOC(=O)N1C2=CC=CC=C2SC=2C=C(C=CC1=2)C(=O)OC)CC WHCMAYHDCBTRGH-UHFFFAOYSA-N 0.000 abstract 1
- ZAZBAXPDYNCBBL-UHFFFAOYSA-N 10h-phenothiazine-3-carboxylic acid Chemical compound C1=CC=C2SC3=CC(C(=O)O)=CC=C3NC2=C1 ZAZBAXPDYNCBBL-UHFFFAOYSA-N 0.000 abstract 1
- DCKQEVRNJQFQRN-UHFFFAOYSA-N 3-O-methyl 10-O-[3-(4-methylpiperazin-1-yl)propyl] phenothiazine-3,10-dicarboxylate Chemical compound COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)C(=O)OCCCN1CCN(CC1)C DCKQEVRNJQFQRN-UHFFFAOYSA-N 0.000 abstract 1
- HXUVLIWHEKCWCK-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN(C)C Chemical compound C(C=C/C(=O)O)(=O)O.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN(C)C HXUVLIWHEKCWCK-UHFFFAOYSA-N 0.000 abstract 1
- IUQSZUFHIPBAQA-UHFFFAOYSA-N Cl.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CC(CN(C)C)C Chemical compound Cl.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CC(CN(C)C)C IUQSZUFHIPBAQA-UHFFFAOYSA-N 0.000 abstract 1
- QDSWUIKBJIIGIR-UHFFFAOYSA-N Cl.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCN(CC)CC Chemical compound Cl.COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCN(CC)CC QDSWUIKBJIIGIR-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- HZNXERFVAGTVSW-UHFFFAOYSA-N butyl 10-[3-(dimethylamino)propyl]phenothiazine-3-carboxylate Chemical compound C(CCC)OC(=O)C=1C=CC=2N(C3=CC=CC=C3SC=2C=1)CCCN(C)C HZNXERFVAGTVSW-UHFFFAOYSA-N 0.000 abstract 1
- SDDCUVXHUCLOCS-UHFFFAOYSA-N butyl 10H-phenothiazine-3-carboxylate Chemical compound C(CCC)OC(=O)C=1C=CC=2NC3=CC=CC=C3SC2C1 SDDCUVXHUCLOCS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- ZLYITGUERUQABZ-UHFFFAOYSA-N ethyl 10-[3-(dimethylamino)propyl]phenothiazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZLYITGUERUQABZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- IQUAOWNFQKOZOM-UHFFFAOYSA-N methyl 10-(2-methyl-3-pyrrolidin-1-ylpropyl)phenothiazine-3-carboxylate Chemical compound COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CC(CN1CCCC1)C IQUAOWNFQKOZOM-UHFFFAOYSA-N 0.000 abstract 1
- IUINEWURNYLXHR-UHFFFAOYSA-N methyl 10-(3-pyrrolidin-1-ylpropyl)phenothiazine-3-carboxylate Chemical compound COC(=O)C1=CC=C2N(CCCN3CCCC3)C3=CC=CC=C3SC2=C1 IUINEWURNYLXHR-UHFFFAOYSA-N 0.000 abstract 1
- RBANXTHPBZNSII-UHFFFAOYSA-N methyl 10-[2-(diethylamino)propyl]phenothiazine-3-carboxylate Chemical compound CCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC(=CC=C12)C(=O)OC RBANXTHPBZNSII-UHFFFAOYSA-N 0.000 abstract 1
- UBDJAJFQZDYRHD-UHFFFAOYSA-N methyl 10-[3-(dimethylamino)-2-methylpropyl]phenothiazine-3-carboxylate Chemical compound COC(=O)C1=CC=C2N(CC(C)CN(C)C)C3=CC=CC=C3SC2=C1 UBDJAJFQZDYRHD-UHFFFAOYSA-N 0.000 abstract 1
- VQFOIBGMQMSARX-UHFFFAOYSA-N methyl 10-[3-(dimethylamino)propyl]phenothiazine-3-carboxylate Chemical compound COC(=O)C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 VQFOIBGMQMSARX-UHFFFAOYSA-N 0.000 abstract 1
- SMBNVLIBBPJENX-UHFFFAOYSA-N methyl 10-carbonochloridoylphenothiazine-3-carboxylate Chemical compound COC(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)C(=O)Cl SMBNVLIBBPJENX-UHFFFAOYSA-N 0.000 abstract 1
- FVAPMHDGUQIJIQ-UHFFFAOYSA-N methyl 10H-phenothiazine-3-carboxylate Chemical compound COC(=O)C=1C=CC=2NC3=CC=CC=C3SC2C1 FVAPMHDGUQIJIQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- JIFBZEZAAPHGBB-UHFFFAOYSA-N phenothiazine-10-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C3=CC=CC=C3SC2=C1 JIFBZEZAAPHGBB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002990 phenothiazines Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR355147X | 1956-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808239A true GB808239A (en) | 1959-01-28 |
Family
ID=8893358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB104/57A Expired GB808239A (en) | 1956-01-10 | 1957-01-01 | Improvements in or relating to phenthiazine derivatives and processes for their production |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2941999A (enrdf_load_stackoverflow) |
| BE (1) | BE554020A (enrdf_load_stackoverflow) |
| CH (2) | CH355147A (enrdf_load_stackoverflow) |
| DE (1) | DE1059460B (enrdf_load_stackoverflow) |
| GB (1) | GB808239A (enrdf_load_stackoverflow) |
| NL (1) | NL96990C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0117302A3 (en) * | 1982-12-02 | 1984-10-17 | The Wellcome Foundation Limited | Phenothiazine derivatives |
| US4634699A (en) * | 1983-11-30 | 1987-01-06 | Burroughs Wellcome Co. | Branched chain phenothiazine |
| US4681878A (en) * | 1985-07-26 | 1987-07-21 | Burroughs Wellcome Co. | Fluoropheno-thiazine and pharmaceutical use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3435114A (en) * | 1965-11-08 | 1969-03-25 | Mead Johnson & Co | Topical antihistaminic compositions containing methdilazine sulfoxide |
| GB8413915D0 (en) * | 1984-05-31 | 1984-07-04 | Wellcome Found | Phenothiazine compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910301C (de) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Verfahren zur Herstellung von neuen Phenthiazinderivaten |
| CH298685A (fr) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Procédé de préparation d'un nouveau dérivé de la phénothiazine. |
| BE529656A (enrdf_load_stackoverflow) * | 1953-04-10 | |||
| US2789978A (en) * | 1954-07-15 | 1957-04-23 | Rath Stephen | Dimethylaminopropyl-dipyridothiazane |
-
0
- NL NL96990D patent/NL96990C/xx active
- BE BE554020D patent/BE554020A/xx unknown
-
1957
- 1957-01-01 GB GB104/57A patent/GB808239A/en not_active Expired
- 1957-01-05 DE DES51831A patent/DE1059460B/de active Pending
- 1957-01-09 CH CH355147D patent/CH355147A/fr unknown
- 1957-01-09 CH CH355148D patent/CH355148A/fr unknown
- 1957-01-10 US US633395A patent/US2941999A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0117302A3 (en) * | 1982-12-02 | 1984-10-17 | The Wellcome Foundation Limited | Phenothiazine derivatives |
| AU572105B2 (en) * | 1982-12-02 | 1988-05-05 | Wellcome Foundation Limited, The | N-substituted-phenothiazine derivatives |
| US4634699A (en) * | 1983-11-30 | 1987-01-06 | Burroughs Wellcome Co. | Branched chain phenothiazine |
| US4681878A (en) * | 1985-07-26 | 1987-07-21 | Burroughs Wellcome Co. | Fluoropheno-thiazine and pharmaceutical use |
Also Published As
| Publication number | Publication date |
|---|---|
| BE554020A (enrdf_load_stackoverflow) | |
| US2941999A (en) | 1960-06-21 |
| CH355148A (fr) | 1961-06-30 |
| DE1059460B (de) | 1959-06-18 |
| CH355147A (fr) | 1961-06-30 |
| NL96990C (enrdf_load_stackoverflow) |
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