GB858140A - The preparation of new basic phenothiazine derivatives - Google Patents
The preparation of new basic phenothiazine derivativesInfo
- Publication number
- GB858140A GB858140A GB748158A GB748158A GB858140A GB 858140 A GB858140 A GB 858140A GB 748158 A GB748158 A GB 748158A GB 748158 A GB748158 A GB 748158A GB 858140 A GB858140 A GB 858140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- compound
- atom
- alkyl group
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000002926 oxygen Chemical group 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 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
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000007929 subcutaneous injection Substances 0.000 abstract 1
- 238000010254 subcutaneous injection Methods 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
-
- 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
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/08—Housing; Encapsulation
- H01G9/10—Sealing, e.g. of lead-in wires
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Power Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Microelectronics & Electronic Packaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0858140/IV(b)/1> and their acid addition salts (wherein R1 is a C2-3alkyl group ; R2 is a hydrogen atom or a C1-6 alkyl group ; and Y is the radical of a 5 or 6 membered heterocyclic, non-aromatic amine that may contain a second hetero atom in the form of an oxygen or an alkyl substituted nitrogen atom) ; and the preparation thereof by : (1) condensing a compound of the general formula : <FORM:0858140/IV(b)/2> with a compound of the general formula : <FORM:0858140/IV(b)/3> (wherein Hal is a bromine or chlorine atom); and (2) reacting a compound of the general formula: <FORM:0858140/IV(b)/4> with a compound of the general formula: <FORM:0858140/IV(b)/5> to get a compound of the general formula: <FORM:0858140/IV(b)/6> which is then decarboxylated by heating. 3 - Ethylmercepto - phenthiazine - 10 - carboxylic acid chloride is made from 3-ethylmercaptophenthiazine and phosgene.ALSO:Compounds of the general formula: <FORM:0858140/VI/1> and their acid addition salts (wherein R1 is a C2-3 alkyl group; R2 is a hydrogen atom or a C1-6 alkyl group; and Y is the radical of a 5 or 6 membered heterocyclic, non-aromatic amine that may contain a second hetero atom in the form of an oxygen atom or an alkyl substituted nitrogen atom) may be administered either orally in the form of pills or tablets, or parenterally, for example by sub-cutaneous injections. Specified salts are hydrochlorides, maleates, fumarates, tartrates and oxalates.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3228356A CH365379A (en) | 1956-04-18 | 1956-04-18 | Process for the preparation of new phenothiazines substituted in the 3-position by a monovalent sulfur function |
| CH4301757A CH364782A (en) | 1957-02-22 | 1957-02-22 | Process for the preparation of 3-sulfhydryl-10- (2 '- (N-methyl-piperidyl-2 ") - ethyl-1') - phenothiazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858140A true GB858140A (en) | 1961-01-04 |
Family
ID=25736343
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1105057A Expired GB863547A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazine |
| GB1738060A Expired GB863550A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazines |
| GB748158A Expired GB858140A (en) | 1956-04-18 | 1958-03-07 | The preparation of new basic phenothiazine derivatives |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1105057A Expired GB863547A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazine |
| GB1738060A Expired GB863550A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazines |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE556725A (en) |
| CH (2) | CH365379A (en) |
| CY (1) | CY275A (en) |
| DE (2) | DE1128856B (en) |
| FR (2) | FR1174268A (en) |
| GB (3) | GB863547A (en) |
| NL (3) | NL105267C (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL295220A (en) * | 1962-07-19 | |||
| CH457442A (en) * | 1965-01-12 | 1968-06-15 | Sandoz Ag | Process for the preparation of new phenothiazine derivatives |
| IT1237209B (en) * | 1989-12-21 | 1993-05-27 | Zambon Spa | PROCESS FOR DIRECT AND REGIO-SELECTIVE FUNCTIONALIZATION IN POSITION 2 OF PHENOTHIAZINE |
| EP1248777A2 (en) * | 2000-01-07 | 2002-10-16 | Warner-Lambert Company | Tricyclic compounds with antiviral activity |
| DE102010062810B4 (en) * | 2010-09-07 | 2014-03-13 | Immungenetics Ag | 2- (R2-thio) -10- [3- (4-R1-piperazin-1-yl) -propyl] -10H-phenothiazines for the treatment of neurodegenerative diseases selected from beta-amyloidopathies and alpha-synucleinopathies |
| WO2015135947A1 (en) * | 2014-03-10 | 2015-09-17 | Universite D'aix-Marseille | Piperazine phenothiazine derivatives for treating spasticity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910301C (en) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Process for the production of new phenthiazine derivatives |
| CH298685A (en) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Process for the preparation of a novel derivative of phenothiazine. |
| DE939630C (en) * | 1953-10-25 | 1956-03-01 | Basf Ag | Process for the preparation of heterocyclic compounds with a ring-shaped imino group substituted by basic groups |
| BE558008A (en) * | 1956-06-21 |
-
1956
- 1956-04-18 CH CH3228356A patent/CH365379A/en unknown
- 1956-04-19 CH CH360059D patent/CH360059A/en unknown
-
1957
- 1957-03-29 DE DE1957S0052942 patent/DE1128856B/en active Pending
- 1957-04-04 GB GB1105057A patent/GB863547A/en not_active Expired
- 1957-04-04 GB GB1738060A patent/GB863550A/en not_active Expired
- 1957-04-16 BE BE556725A patent/BE556725A/xx unknown
- 1957-04-17 NL NL216435A patent/NL105267C/xx active
- 1957-04-17 FR FR1174268D patent/FR1174268A/en not_active Expired
- 1957-04-17 NL NL216436A patent/NL105268C/xx active
-
1958
- 1958-03-06 BE BE565470A patent/BE565470A/xx unknown
- 1958-03-07 GB GB748158A patent/GB858140A/en not_active Expired
- 1958-03-07 NL NL225621A patent/NL108580C/xx active
- 1958-03-07 DE DE1958S0057244 patent/DE1090667B/en active Pending
- 1958-03-07 FR FR1203557D patent/FR1203557A/en not_active Expired
-
1964
- 1964-02-12 CY CY27564A patent/CY275A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE565470A (en) | 1958-09-06 |
| BE556725A (en) | 1957-10-16 |
| GB863547A (en) | 1961-03-22 |
| CY275A (en) | 1964-02-12 |
| DE1090667B (en) | 1960-10-13 |
| FR1203557A (en) | 1960-01-20 |
| GB863550A (en) | 1961-03-22 |
| NL105268C (en) | 1963-07-15 |
| CH360059A (en) | 1962-02-15 |
| NL108580C (en) | 1964-06-15 |
| CH365379A (en) | 1962-11-15 |
| NL105267C (en) | 1963-07-15 |
| FR1174268A (en) | 1959-03-09 |
| DE1128856B (en) | 1962-05-03 |
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