DE1493500A1 - Verfahren zur Herstellung von substituierten Chlor-sulfamyl-antharanilsaeuren - Google Patents
Verfahren zur Herstellung von substituierten Chlor-sulfamyl-antharanilsaeurenInfo
- Publication number
- DE1493500A1 DE1493500A1 DE19651493500 DE1493500A DE1493500A1 DE 1493500 A1 DE1493500 A1 DE 1493500A1 DE 19651493500 DE19651493500 DE 19651493500 DE 1493500 A DE1493500 A DE 1493500A DE 1493500 A1 DE1493500 A1 DE 1493500A1
- Authority
- DE
- Germany
- Prior art keywords
- acids
- substituted
- chlorosulfamyl
- het
- general formula
- 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 8
- 239000002253 acid Substances 0.000 title description 7
- 150000007513 acids Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- -1 chlorosulfamyl-anthranic acids Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OCVILNKSPWSHDQ-UHFFFAOYSA-N ClN(C=1C(C(=O)O)=CC=CC=1)S(N)(=O)=O Chemical class ClN(C=1C(C(=O)O)=CC=CC=1)S(N)(=O)=O OCVILNKSPWSHDQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- ZSHHRBYVHTVRFK-UHFFFAOYSA-N 2,4-dichloro-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1Cl ZSHHRBYVHTVRFK-UHFFFAOYSA-N 0.000 description 1
- QQLNFWFHBAFHPR-UHFFFAOYSA-N 2-(benzylamino)-4-chloro-5-sulfamoylbenzoic acid Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CC=C1 QQLNFWFHBAFHPR-UHFFFAOYSA-N 0.000 description 1
- BMBNEIGPGNXTRH-UHFFFAOYSA-N 3-(furan-2-yl)propan-1-amine Chemical compound NCCCC1=CC=CO1 BMBNEIGPGNXTRH-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0084818 | 1965-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493500A1 true DE1493500A1 (de) | 1969-08-07 |
Family
ID=6982612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651493500 Pending DE1493500A1 (de) | 1965-12-03 | 1965-12-03 | Verfahren zur Herstellung von substituierten Chlor-sulfamyl-antharanilsaeuren |
Country Status (11)
-
1965
- 1965-12-03 DE DE19651493500 patent/DE1493500A1/de active Pending
-
1966
- 1966-11-19 OA OA52665A patent/OA02173A/xx unknown
- 1966-11-30 ES ES0333990A patent/ES333990A1/es not_active Expired
- 1966-12-01 CH CH1717466A patent/CH484090A/de not_active IP Right Cessation
- 1966-12-01 FI FI663187A patent/FI46378C/fi active
- 1966-12-02 BE BE690589D patent/BE690589A/xx unknown
- 1966-12-02 BR BR185060/66A patent/BR6685060D0/pt unknown
- 1966-12-02 FR FR85981A patent/FR1505670A/fr not_active Expired
- 1966-12-02 GB GB53975/66A patent/GB1100419A/en not_active Expired
- 1966-12-02 AT AT1117566A patent/AT261600B/de active
- 1966-12-02 NL NL6617045A patent/NL6617045A/xx unknown
-
1967
- 1967-03-01 FR FR96959A patent/FR6140M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI46378C (fi) | 1973-03-12 |
| CH484090A (de) | 1970-01-15 |
| FR1505670A (fr) | 1967-12-15 |
| AT261600B (de) | 1968-05-10 |
| BE690589A (enrdf_load_stackoverflow) | 1967-06-02 |
| BR6685060D0 (pt) | 1973-10-25 |
| GB1100419A (en) | 1968-01-24 |
| FI46378B (enrdf_load_stackoverflow) | 1972-11-30 |
| FR6140M (enrdf_load_stackoverflow) | 1968-06-24 |
| OA02173A (fr) | 1973-05-05 |
| ES333990A1 (es) | 1967-10-16 |
| NL6617045A (enrdf_load_stackoverflow) | 1967-06-05 |
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