GB811959A - New phenthiazine derivatives and their preparation - Google Patents
New phenthiazine derivatives and their preparationInfo
- Publication number
- GB811959A GB811959A GB9885/57A GB988557A GB811959A GB 811959 A GB811959 A GB 811959A GB 9885/57 A GB9885/57 A GB 9885/57A GB 988557 A GB988557 A GB 988557A GB 811959 A GB811959 A GB 811959A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenothiazine
- methanesulphonyl
- methanesulphonylphenothiazine
- dimethylamino
- 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title abstract 2
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 abstract 9
- ACNKYFFUJOOQMW-UHFFFAOYSA-N 3-methylsulfonyl-10h-phenothiazine Chemical compound C1=CC=C2SC3=CC(S(=O)(=O)C)=CC=C3NC2=C1 ACNKYFFUJOOQMW-UHFFFAOYSA-N 0.000 abstract 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 229950000688 phenothiazine Drugs 0.000 abstract 3
- QQZAFHQMZSOMCS-UHFFFAOYSA-N 3-(3-methylsulfonylphenothiazin-10-yl)propyl 4-methylbenzenesulfonate Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCOS(=O)(=O)C1=CC=C(C=C1)C QQZAFHQMZSOMCS-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- DADMTKUSXOAQIX-UHFFFAOYSA-N N,N-dimethyl-3-(3-methylsulfonylphenothiazin-10-yl)propan-1-amine Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN(C)C DADMTKUSXOAQIX-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- IQAAHISUUUULCX-UHFFFAOYSA-N 1-(3-pyrrolidin-1-ylpropyl)-10H-phenothiazine Chemical compound N1(CCCC1)CCCC1=CC=CC=2SC3=CC=CC=C3NC12 IQAAHISUUUULCX-UHFFFAOYSA-N 0.000 abstract 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 abstract 1
- NAOWHGVOJFUINK-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl 3-methylsulfonylphenothiazine-10-carboxylate Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)C(=O)OC(C)CN(C)C NAOWHGVOJFUINK-UHFFFAOYSA-N 0.000 abstract 1
- QFXXARKSLAKVRL-UHFFFAOYSA-N 2-(3-chloropropoxy)oxane Chemical compound ClCCCOC1CCCCO1 QFXXARKSLAKVRL-UHFFFAOYSA-N 0.000 abstract 1
- DQAGUPYXACTVJF-UHFFFAOYSA-N 3-(3-methylsulfonylphenothiazin-10-yl)propan-1-amine Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN DQAGUPYXACTVJF-UHFFFAOYSA-N 0.000 abstract 1
- XRWBNPXDFIUYKD-UHFFFAOYSA-N 3-(3-methylsulfonylphenothiazin-10-yl)propan-1-ol Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCO XRWBNPXDFIUYKD-UHFFFAOYSA-N 0.000 abstract 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 abstract 1
- ZOCJCMGOBRHMJC-UHFFFAOYSA-N 3-methylsulfonyl-10-(oxan-3-yloxy)phenothiazine Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)OC1COCCC1 ZOCJCMGOBRHMJC-UHFFFAOYSA-N 0.000 abstract 1
- PBGKXZZTJUXDKA-UHFFFAOYSA-N 3-methylsulfonylphenothiazine-10-carbonyl chloride Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)C(=O)Cl PBGKXZZTJUXDKA-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- QIFBIRPRRKFRPA-UHFFFAOYSA-N CNCCCC1=CC=CC=2SC3=CC=CC=C3NC12 Chemical compound CNCCCC1=CC=CC=2SC3=CC=CC=C3NC12 QIFBIRPRRKFRPA-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 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
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000002990 phenothiazines Chemical class 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 238000006485 reductive methylation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR811959X | 1956-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811959A true GB811959A (en) | 1959-04-15 |
Family
ID=9263160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9885/57A Expired GB811959A (en) | 1956-04-07 | 1957-03-26 | New phenthiazine derivatives and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1094751B (enrdf_load_stackoverflow) |
| GB (1) | GB811959A (enrdf_load_stackoverflow) |
| NL (1) | NL97976C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837528A (zh) * | 2016-05-30 | 2016-08-10 | 大连理工大学 | 一种2-(甲基磺酰基)-10h-吩噻嗪的制备方法 |
| CN110615742A (zh) * | 2019-09-20 | 2019-12-27 | 广东省禾基生物科技有限公司 | 厚朴酚衍生物及其制备方法与应用 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL120362C (enrdf_load_stackoverflow) * | 1961-04-26 | |||
| NL278471A (enrdf_load_stackoverflow) * | 1961-05-15 | |||
| NL123137C (enrdf_load_stackoverflow) * | 1962-07-19 |
Family Cites Families (3)
| 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 |
| NL87657C (enrdf_load_stackoverflow) * | 1953-04-10 | |||
| DE939630C (de) * | 1953-10-25 | 1956-03-01 | Basf Ag | Verfahren zur Herstellung von heterocyclischen Verbindungen mit ringstaendiger Iminogruppe, die durch basische Gruppen substituiert ist |
-
0
- NL NL97976D patent/NL97976C/xx active
-
1957
- 1957-03-26 GB GB9885/57A patent/GB811959A/en not_active Expired
- 1957-04-03 DE DES52991A patent/DE1094751B/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837528A (zh) * | 2016-05-30 | 2016-08-10 | 大连理工大学 | 一种2-(甲基磺酰基)-10h-吩噻嗪的制备方法 |
| CN110615742A (zh) * | 2019-09-20 | 2019-12-27 | 广东省禾基生物科技有限公司 | 厚朴酚衍生物及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL97976C (enrdf_load_stackoverflow) | |
| DE1094751B (de) | 1960-12-15 |
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