IL44561A - Salts of 2,6-dioxocyclohexane thiocarboxylic acid 4'-halo-anilides and pharmaceutical compositions thereof - Google Patents
Salts of 2,6-dioxocyclohexane thiocarboxylic acid 4'-halo-anilides and pharmaceutical compositions thereofInfo
- Publication number
- IL44561A IL44561A IL44561A IL4456174A IL44561A IL 44561 A IL44561 A IL 44561A IL 44561 A IL44561 A IL 44561A IL 4456174 A IL4456174 A IL 4456174A IL 44561 A IL44561 A IL 44561A
- Authority
- IL
- Israel
- Prior art keywords
- dioxocyclohexane
- compound
- thiocarboxylic acid
- chloroanilide
- salt
- Prior art date
Links
- LSPXTOOYGWJBNU-UHFFFAOYSA-N cyclohexane-1,3-dione methanethioic S-acid Chemical class C(=S)O.O=C1CC(CCC1)=O LSPXTOOYGWJBNU-UHFFFAOYSA-N 0.000 title claims description 19
- 150000003839 salts Chemical class 0.000 title description 13
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 28
- KBMXZBWIWSRALH-UHFFFAOYSA-N n-(4-chlorophenyl)-2,6-dioxocyclohexane-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1NC(=S)C1C(=O)CCCC1=O KBMXZBWIWSRALH-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- -1 alkaline earth metal salt Chemical class 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000008139 complexing agent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 230000001857 anti-mycotic effect Effects 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 229910003002 lithium salt Inorganic materials 0.000 claims description 3
- 159000000002 lithium salts Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000002543 antimycotic Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 241001465754 Metazoa Species 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000011282 treatment Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000008399 tap water Substances 0.000 description 6
- 235000020679 tap water Nutrition 0.000 description 6
- 208000002474 Tinea Diseases 0.000 description 4
- 206010067409 Trichophytosis Diseases 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000223238 Trichophyton Species 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- LDUQUHXCYGDUFJ-UHFFFAOYSA-N 2,6-dioxocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1C(=O)CCCC1=O LDUQUHXCYGDUFJ-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TZZDOCMFMSDEKY-UHFFFAOYSA-N 2,3-dioxo-n-phenylcyclohexane-1-carboxamide Chemical class C1CCC(=O)C(=O)C1C(=O)NC1=CC=CC=C1 TZZDOCMFMSDEKY-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- LQFDPYJSONNAFO-UHFFFAOYSA-N cyclohexanecarbothioic s-acid Chemical compound SC(=O)C1CCCCC1 LQFDPYJSONNAFO-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732317579 DE2317579A1 (de) | 1973-04-07 | 1973-04-07 | Salze von 2,6-dioxocyclohexanthiocarbonsaeure-4'-halogenaniliden und deren pharmazeutische zubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44561A0 IL44561A0 (en) | 1974-06-30 |
| IL44561A true IL44561A (en) | 1977-01-31 |
Family
ID=5877353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44561A IL44561A (en) | 1973-04-07 | 1974-04-03 | Salts of 2,6-dioxocyclohexane thiocarboxylic acid 4'-halo-anilides and pharmaceutical compositions thereof |
Country Status (20)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS551724B2 (enrdf_load_stackoverflow) * | 1974-03-16 | 1980-01-16 |
-
1973
- 1973-04-07 DE DE19732317579 patent/DE2317579A1/de active Pending
-
1974
- 1974-03-28 CA CA196,562A patent/CA1019765A/en not_active Expired
- 1974-04-02 ES ES424848A patent/ES424848A1/es not_active Expired
- 1974-04-02 NL NL7404495A patent/NL7404495A/xx not_active Application Discontinuation
- 1974-04-03 CH CH463874A patent/CH599146A5/xx not_active IP Right Cessation
- 1974-04-03 IT IT4264174A patent/IT1043914B/it active
- 1974-04-03 IL IL44561A patent/IL44561A/en unknown
- 1974-04-04 DD DD17769774A patent/DD112994A5/xx unknown
- 1974-04-05 AT AT287774A patent/AT338231B/de not_active IP Right Cessation
- 1974-04-05 GB GB1524874A patent/GB1464878A/en not_active Expired
- 1974-04-05 ZA ZA00742190A patent/ZA742190B/xx unknown
- 1974-04-05 CS CS248474A patent/CS191911B2/cs unknown
- 1974-04-05 DK DK190174A patent/DK136154C/da active
- 1974-04-05 ZM ZM6274A patent/ZM6274A1/xx unknown
- 1974-04-05 IE IE73874A patent/IE39358B1/xx unknown
- 1974-04-06 HU HUHO001668 patent/HU168937B/hu unknown
- 1974-04-06 JP JP3849774A patent/JPS49126810A/ja active Pending
- 1974-04-08 BE BE142954A patent/BE813430A/xx unknown
- 1974-04-08 FR FR7412294A patent/FR2224161B1/fr not_active Expired
-
1977
- 1977-11-28 KE KE280277A patent/KE2802A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2317579A1 (de) | 1974-10-24 |
| FR2224161B1 (enrdf_load_stackoverflow) | 1977-11-04 |
| ZM6274A1 (en) | 1975-01-21 |
| KE2802A (en) | 1978-01-06 |
| BE813430A (fr) | 1974-10-08 |
| IE39358L (en) | 1974-10-07 |
| CH599146A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| IT1043914B (it) | 1980-02-29 |
| CS191911B2 (en) | 1979-07-31 |
| IE39358B1 (en) | 1978-09-27 |
| DK136154B (da) | 1977-08-22 |
| DK136154C (da) | 1978-01-23 |
| HU168937B (enrdf_load_stackoverflow) | 1976-08-28 |
| JPS49126810A (enrdf_load_stackoverflow) | 1974-12-04 |
| CA1019765A (en) | 1977-10-25 |
| AT338231B (de) | 1977-08-10 |
| AU6756774A (en) | 1975-10-09 |
| DD112994A5 (enrdf_load_stackoverflow) | 1975-05-12 |
| IL44561A0 (en) | 1974-06-30 |
| ES424848A1 (es) | 1976-11-16 |
| NL7404495A (enrdf_load_stackoverflow) | 1974-10-09 |
| ATA287774A (de) | 1976-12-15 |
| GB1464878A (en) | 1977-02-16 |
| FR2224161A1 (enrdf_load_stackoverflow) | 1974-10-31 |
| ZA742190B (en) | 1975-04-30 |
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