GB909688A - 5-substituted-2,4-disulfamyl (halo) acylanilides - Google Patents
5-substituted-2,4-disulfamyl (halo) acylanilidesInfo
- Publication number
- GB909688A GB909688A GB3672360A GB3672360A GB909688A GB 909688 A GB909688 A GB 909688A GB 3672360 A GB3672360 A GB 3672360A GB 3672360 A GB3672360 A GB 3672360A GB 909688 A GB909688 A GB 909688A
- Authority
- GB
- United Kingdom
- Prior art keywords
- disulphamoyl
- aniline
- bromo
- fluoro
- chloro
- 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
- 125000001475 halogen functional group Chemical group 0.000 title 1
- -1 chloro- Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000001882 diuretic effect Effects 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- RMWRDSUVZPSOGU-UHFFFAOYSA-N 2-bromo-N-(5-bromo-2,4-disulfamoylphenyl)acetamide Chemical compound BrC=1C(=CC(=C(NC(CBr)=O)C1)S(N)(=O)=O)S(N)(=O)=O RMWRDSUVZPSOGU-UHFFFAOYSA-N 0.000 abstract 1
- OCVVWACYFQOSAC-UHFFFAOYSA-N 2-chloro-N-(2,4-disulfamoylphenyl)acetamide Chemical compound S(N)(=O)(=O)C1=C(NC(CCl)=O)C=CC(=C1)S(N)(=O)=O OCVVWACYFQOSAC-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- 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
- 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 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical class CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 229940050410 gluconate Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen 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 class [H]* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000008174 sterile solution Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/30—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with hydrocarbon radicals, substituted by hetero atoms, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises 2,4-disulphamoyl acylanilides of the formula <FORM:0909688/IV (b)/1> wherein A is hydrogen, Cl, F, Br, NO2, CF3 or C1-3 alkyl or alkoxy, B is a halogen atom and Z is an alkylene chain of 1 to 3 carbon atoms and their preparation by reacting the corresponding 5-substituted-2:4-disulphamoyl aniline with an acylating agent such as a haloalkanoyl halide or a halo-alkanoic anhydride e.g. chloro-, bromo-, fluoro- and iodo-acetic, propionic and butyric anhydrides. The compounds have diuretic activity, specified products being 5-methyl-, -chloro-, -trifluoromethyl- and -fluoro-, 2,4-disulphamoyl-chloroacetyl-aniline and 5-bromo-2,4-disulphamoyl-bromoacetyl-aniline. Pharmaceutical preparations, having diuretic activity comprise the above compounds or acid addition or base salts thereof, particularly salts containing pharmacologically acceptable anions or cations such as iodide, chloride, bromide, sulphate, methylsulphate, acetate, propionate, tartrate, citrate and gluconate, sodium, potassium, calcium and magnesium. The preparations suitably take the form of tablets, capsules, troches, lozenges or solutions for oral administration or sterile solutions for parenteral administration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US715482A US3110716A (en) | 1958-02-17 | 1958-02-17 | Derivatives of 3, 6-disubstituted-7-sulfamylbenzothiadiazine dioxides |
| US78067558A | 1958-12-16 | 1958-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB909688A true GB909688A (en) | 1962-10-31 |
Family
ID=27109350
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3672460A Expired GB909689A (en) | 1958-02-17 | 1959-02-17 | 3,6-disubstituted-7-sulfamyl-2,4-benzothiadiazine-1,1-dioxides |
| GB545059A Expired GB909687A (en) | 1958-02-17 | 1959-02-17 | Benzothiadiazine derivatives |
| GB3672360A Expired GB909688A (en) | 1958-02-17 | 1959-02-17 | 5-substituted-2,4-disulfamyl (halo) acylanilides |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3672460A Expired GB909689A (en) | 1958-02-17 | 1959-02-17 | 3,6-disubstituted-7-sulfamyl-2,4-benzothiadiazine-1,1-dioxides |
| GB545059A Expired GB909687A (en) | 1958-02-17 | 1959-02-17 | Benzothiadiazine derivatives |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE575758A (en) |
| CH (2) | CH427745A (en) |
| DK (1) | DK117072B (en) |
| GB (3) | GB909689A (en) |
| SE (1) | SE308527B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653181A1 (en) * | 1975-11-24 | 1977-06-02 | Merck & Co Inc | SUBSTITUTED BENZOLE DISULPHONAMIDES AND METHOD FOR PREPARING THEREOF |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3325485A (en) * | 1960-11-25 | 1967-06-13 | Merck & Co Inc | 3-(halophenyl-oxoaliphatic)benzo-thiadiazine-1, 1-dioxides |
| CN107721949A (en) * | 2017-08-16 | 2018-02-23 | 广东艾时代生物科技有限责任公司 | A kind of compound and its pharmaceutical composition for being used to treat demyelinating disease |
-
1959
- 1959-02-16 BE BE575758A patent/BE575758A/en unknown
- 1959-02-17 GB GB3672460A patent/GB909689A/en not_active Expired
- 1959-02-17 CH CH6964959A patent/CH427745A/en unknown
- 1959-02-17 GB GB545059A patent/GB909687A/en not_active Expired
- 1959-02-17 CH CH1591064A patent/CH440301A/en unknown
- 1959-02-17 GB GB3672360A patent/GB909688A/en not_active Expired
-
1961
- 1961-08-07 DK DK320861A patent/DK117072B/en unknown
-
1964
- 1964-09-25 SE SE1152564A patent/SE308527B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653181A1 (en) * | 1975-11-24 | 1977-06-02 | Merck & Co Inc | SUBSTITUTED BENZOLE DISULPHONAMIDES AND METHOD FOR PREPARING THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| GB909687A (en) | 1962-10-31 |
| CH427745A (en) | 1967-01-15 |
| GB909689A (en) | 1962-10-31 |
| BE575758A (en) | 1959-08-17 |
| DK117072B (en) | 1970-03-16 |
| CH440301A (en) | 1967-07-31 |
| SE308527B (en) | 1969-02-17 |
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