DE2330508A1 - Neue n-substituierte 5-sulfamoylanthranilsaeurederivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel - Google Patents
Neue n-substituierte 5-sulfamoylanthranilsaeurederivate, verfahren zur herstellung derselben und diese enthaltende arzneimittelInfo
- Publication number
- DE2330508A1 DE2330508A1 DE19732330508 DE2330508A DE2330508A1 DE 2330508 A1 DE2330508 A1 DE 2330508A1 DE 19732330508 DE19732330508 DE 19732330508 DE 2330508 A DE2330508 A DE 2330508A DE 2330508 A1 DE2330508 A1 DE 2330508A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- acid
- formaldehyde
- new
- sulfamoylanthranilic
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title claims description 4
- 229940126601 medicinal product Drugs 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- -1 N-substituted 5- sulfamoylanthranilic acids Chemical class 0.000 claims description 13
- ALVGPPOPGPCDCG-UHFFFAOYSA-M potassium;formaldehyde;hydrogen sulfite Chemical class [K+].O=C.OS([O-])=O ALVGPPOPGPCDCG-UHFFFAOYSA-M 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
- 230000001882 diuretic effect Effects 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- OAZOBYBYAKXURF-UHFFFAOYSA-N 2-(sulfamoylamino)benzoic acid Chemical compound NS(=O)(=O)NC1=CC=CC=C1C(O)=O OAZOBYBYAKXURF-UHFFFAOYSA-N 0.000 claims description 4
- JRGAUAWPCLQHTF-UHFFFAOYSA-N 2-amino-5-sulfamoylbenzoic acid Chemical class NC1=CC=C(S(N)(=O)=O)C=C1C(O)=O JRGAUAWPCLQHTF-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 208000004880 Polyuria Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002934 diuretic Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 208000019025 Hypokalemia Diseases 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 208000024896 potassium deficiency disease Diseases 0.000 description 3
- 230000009291 secondary effect Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 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 2
- 206010030113 Oedema Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical class [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 description 1
- 206010050394 Hyperkaliuria Diseases 0.000 description 1
- UTKMGCOZWIOGCB-UHFFFAOYSA-N [K].C=O Chemical compound [K].C=O UTKMGCOZWIOGCB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000036230 kaliuresis Effects 0.000 description 1
- 230000002077 kaliuretic effect Effects 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7221737A FR2189024A1 (en) | 1972-06-16 | 1972-06-16 | 5-sulphamoyl-anthranilic acid derivs - useful as diuretics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2330508A1 true DE2330508A1 (de) | 1974-01-03 |
Family
ID=9100307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732330508 Pending DE2330508A1 (de) | 1972-06-16 | 1973-06-15 | Neue n-substituierte 5-sulfamoylanthranilsaeurederivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2330508A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2189024A1 (enrdf_load_stackoverflow) |
-
1972
- 1972-06-16 FR FR7221737A patent/FR2189024A1/fr active Granted
-
1973
- 1973-06-15 DE DE19732330508 patent/DE2330508A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2189024A1 (en) | 1974-01-25 |
| FR2189024B1 (enrdf_load_stackoverflow) | 1975-06-20 |
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