DK142579B - Fremgangsmåde til fremstilling af 4-substituerede 5-sulfamoyl-N-furfuryl-antranilsyrer. - Google Patents
Fremgangsmåde til fremstilling af 4-substituerede 5-sulfamoyl-N-furfuryl-antranilsyrer. Download PDFInfo
- Publication number
- DK142579B DK142579B DK64872A DK64872A DK142579B DK 142579 B DK142579 B DK 142579B DK 64872 A DK64872 A DK 64872A DK 64872 A DK64872 A DK 64872A DK 142579 B DK142579 B DK 142579B
- Authority
- DK
- Denmark
- Prior art keywords
- furfuryl
- substituted
- preparation
- sulfamoyl
- anthranilic acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- -1 4-substituted 5-sulfamoyl-N-furfuryl-anthranilic acids Chemical class 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 5
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000008707 rearrangement Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 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 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical class NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OLYMKHFFLBFZGU-UHFFFAOYSA-N 1,2-dimethoxyethane;1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOC.COCCOCCOC OLYMKHFFLBFZGU-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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- FQDAYGLXJHLEOA-UHFFFAOYSA-N methyl 2-amino-4-chloro-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1N FQDAYGLXJHLEOA-UHFFFAOYSA-N 0.000 description 1
- XYTYMWLXTKOCNZ-UHFFFAOYSA-N methyl 2-amino-4-phenoxy-5-sulfamoylbenzoate Chemical compound COC(C1=C(C=C(C(=C1)S(N)(=O)=O)OC1=CC=CC=C1)N)=O XYTYMWLXTKOCNZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002211 ultraviolet spectrum 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB467271 | 1971-02-15 | ||
| GB467271 | 1971-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142579B true DK142579B (da) | 1980-11-24 |
| DK142579C DK142579C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-07-27 |
Family
ID=9781607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK64872A DK142579B (da) | 1971-02-15 | 1972-02-14 | Fremgangsmåde til fremstilling af 4-substituerede 5-sulfamoyl-N-furfuryl-antranilsyrer. |
Country Status (6)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ548830A (en) | 2004-02-20 | 2010-03-26 | Aventis Pharma Inc | Furosemide derivatives as modulators of HM74 and their use for the treatment of inflammation |
-
1972
- 1972-02-11 AT AT110372A patent/AT324318B/de not_active IP Right Cessation
- 1972-02-11 DE DE19722206424 patent/DE2206424A1/de active Pending
- 1972-02-14 NL NL7201885A patent/NL7201885A/xx unknown
- 1972-02-14 CH CH204672A patent/CH564548A5/xx not_active IP Right Cessation
- 1972-02-14 DK DK64872A patent/DK142579B/da unknown
- 1972-02-14 SE SE174972A patent/SE373580B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2206424A1 (de) | 1972-08-24 |
| NL7201885A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-17 |
| CH564548A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-31 |
| AT324318B (de) | 1975-08-25 |
| DK142579C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-07-27 |
| SE373580B (sv) | 1975-02-10 |
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