GB847701A - Basic thio-ethers and their preparation - Google Patents
Basic thio-ethers and their preparationInfo
- Publication number
- GB847701A GB847701A GB738358A GB738358A GB847701A GB 847701 A GB847701 A GB 847701A GB 738358 A GB738358 A GB 738358A GB 738358 A GB738358 A GB 738358A GB 847701 A GB847701 A GB 847701A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- general formula
- oxide
- acid addition
- hydrogen atom
- 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
- 150000003568 thioethers Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical class C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000004264 Petrolatum Substances 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000783 alginic acid Chemical class 0.000 abstract 1
- 229920000615 alginic acid Chemical class 0.000 abstract 1
- 229960001126 alginic acid Drugs 0.000 abstract 1
- 235000010443 alginic acid Nutrition 0.000 abstract 1
- 150000004781 alginic acids Chemical class 0.000 abstract 1
- 229920003064 carboxyethyl cellulose Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940001468 citrate Drugs 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229940050410 gluconate Drugs 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- 239000008101 lactose Substances 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 229940066842 petrolatum Drugs 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000600 sorbitol Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0847701/IV(b)/1> and their acid addition salts (wherein R is an unsubstituted or substituted pyridine-N-oxide or quinoline-N-oxide group attached to the sulphur atom in the 2-position, wherein the substituents are halogen atoms, or alkyl or alkoxy groups containing no more than three carbon atoms and are attached to carbon atoms, R1 is a hydrogen atom or an alkyl group containing not more than twelve carbon atoms, each R2 is a hydrogen atom or an alkyl group containing not more than four carbon atoms and n is two or three), and the preparation thereof by reacting a compound of the general formula: RX or its acid addition salt (wherein X is a halogen atom in the 2-position) with a compound of the general formula: <FORM:0847701/IV(b)/2> Compounds of the general formula RX may be prepared by oxidising and halogenating the corresponding 2-amino compounds.ALSO:Therapeutic compositions comprise compounds of the general formula: <FORM:0847701/VI/1> and their acid addition salts (wherein R is an unsubstituted or-substituted pyridine-N-oxide or quinoline-N-oxide group attached to the sulphur atom in the 2-position, wherein the substituents are halogen atoms, or alkyl or alkoxy groups containing not more than three carbon atoms and are attached to carbon atoms, R1 is a hydrogen atom or an alkyl group containing not more than twelve carbon atoms, each R2 is a hydrogen atom or an alkyl group containing not more than four carbon atoms and n is two or three) in admixture with pharmaceutical carriers. Compositions containing at least 0,1-95,0% by weight of an above compound as the principal active ingredient are useful. They may be applied as ointments, powders, emulsions or suspensions. Suitable extending agents may be hydrophilic (e.g. condensation products of ethylene and propylene oxide with ethylene and propylene glycol), hydrophobic (e.g. petrolatum and other hydrocarbon greases), lactose or sorbitol, or carboxyethylcellulose and alginic acid derivatives. The compositions are useful in the treatment of superficial mycoses. Suitable acid addition salts are the bromide, chloride, iodide, sulphate, phosphate, citrate, gluconate and tartrate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64749757A | 1957-03-21 | 1957-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB847701A true GB847701A (en) | 1960-09-14 |
Family
ID=24597215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB738358A Expired GB847701A (en) | 1957-03-21 | 1958-03-07 | Basic thio-ethers and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE565868A (en) |
| DE (1) | DE1136708B (en) |
| GB (1) | GB847701A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| EP0196943A1 (en) * | 1985-03-04 | 1986-10-08 | Roussel-Uclaf | 8-Thiotetrahydroquinoleine derivatives and their salts |
| WO2020201096A1 (en) | 2019-03-29 | 2020-10-08 | Université de Paris | Imidazoline derivatives as cxcr4 modulators |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048488A (en) * | 1959-11-30 | 1962-08-07 | F & M Shaefer Brewing Company | Synthetic organic chemical preservative for beer |
-
0
- BE BE565868D patent/BE565868A/xx unknown
-
1958
- 1958-03-07 GB GB738358A patent/GB847701A/en not_active Expired
- 1958-03-21 DE DE1958P0020368 patent/DE1136708B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| EP0196943A1 (en) * | 1985-03-04 | 1986-10-08 | Roussel-Uclaf | 8-Thiotetrahydroquinoleine derivatives and their salts |
| WO2020201096A1 (en) | 2019-03-29 | 2020-10-08 | Université de Paris | Imidazoline derivatives as cxcr4 modulators |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1136708B (en) | 1962-09-20 |
| BE565868A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES483767A1 (en) | PROCEDURE FOR PRODUCING N-ARYLSULFONYL-L-ARGININAMIDES | |
| GB1087831A (en) | Benztriazines | |
| FI854445A0 (en) | KINOLONKARBOXYLSYRADERIVAT. | |
| GB1087243A (en) | Improvements in or relating to naphthalene derivatives and the manufacture thereof | |
| GB847701A (en) | Basic thio-ethers and their preparation | |
| GB1269619A (en) | Bistriazolyl-bisphenyl-methanes and their salts, process for their preparation, and their use as growth regulators | |
| GB1069797A (en) | ª-aminoketone derivatives | |
| DE2965701D1 (en) | 1-imidazol-2-ylidene-3-thienyl-urea derivatives, processes therefor, and pharmaceutical compositions | |
| GB1451477A (en) | Phenylamidinourea derivatives processes for their preparation and compositions incorporating them | |
| GB1008470A (en) | New cyanacetamide derivatives | |
| GB1096301A (en) | 1,4-benzodioxane derivatives | |
| US2561948A (en) | Aminoalkylated diamino diphenyl sulfones | |
| GB1353508A (en) | Aminoisoquinolines | |
| US3321481A (en) | Heterocyclic n-oxide-tri-phenylchlorotin salts | |
| GB1094982A (en) | 1,4-benzodioxanes | |
| GB1058258A (en) | Alkyl derivatives of imidazo[1,2-a]pyridines | |
| GB1019462A (en) | Improvements in or relating to novel 3-azabicyclo-[3.2.2]-nonane derivatives | |
| US2487707A (en) | Beta-(5.7-dichloroquinolyl-(8)-oxy)-ethyl]-dimethyl-dodecyl ammonium bromide | |
| GB976719A (en) | New derivatives of heparin and processes for their preparation | |
| GB1010231A (en) | Substituted 3-phenyl-5-imino-4,5 dihydro-1,2,4-oxadiazoles, process for their manufacture and therapeutic compositions containing same | |
| IL59358A (en) | Hydroxytetrahydro(phenoxymethyl)-imidazothiazole and thiazolopyrimidine derivatives,their preparation and pharmaceutical compositions containing them | |
| GB1017450A (en) | 2-amino-4-alkoxy-úË-triazines | |
| GB975924A (en) | N-heterocyclic 2,6-dialkylbenzoic acid esters | |
| GB947001A (en) | Substituted phenoxyalklylguanidines | |
| ES274740A1 (en) | Quaternary ammonium salts having anti-arrhythmic activity |