NO133892B - - Google Patents
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- Publication number
- NO133892B NO133892B NO2578/72A NO257872A NO133892B NO 133892 B NO133892 B NO 133892B NO 2578/72 A NO2578/72 A NO 2578/72A NO 257872 A NO257872 A NO 257872A NO 133892 B NO133892 B NO 133892B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- sulfamoyl
- furfuryl
- anthranilic acid
- melting point
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000243 solution Substances 0.000 description 23
- ARXFRBACTHTEIR-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(methoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOC)(=O)=O ARXFRBACTHTEIR-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- -1 propargyl - Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 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 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000008098 formaldehyde solution Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JBCBWDYSSJINSH-UHFFFAOYSA-N 5-(butoxymethylsulfamoyl)-4-chloro-2-(furan-2-ylmethylamino)benzoic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NCOCCCC)=CC(C(O)=O)=C1NCC1=CC=CO1 JBCBWDYSSJINSH-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002934 diuretic Substances 0.000 description 8
- 230000001882 diuretic effect Effects 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 229960003883 furosemide Drugs 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 230000000894 saliuretic effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- KYJJBIRFWWKUDB-UHFFFAOYSA-N 4-chloro-2-(cyclohexylamino)-5-(methoxymethylsulfamoyl)benzoic acid Chemical compound C1(CCCCC1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOC)(=O)=O KYJJBIRFWWKUDB-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- QQLJBZFXGDHSRU-UHFFFAOYSA-N 2-amino-4-chloro-5-sulfamoylbenzoic acid Chemical class NC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O QQLJBZFXGDHSRU-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- YQTFSCMJUQBPPY-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(phenylmethoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCC1=CC=CC=C1)(=O)=O YQTFSCMJUQBPPY-UHFFFAOYSA-N 0.000 description 2
- QJWXANVPYJXQJI-UHFFFAOYSA-N 4-chloro-5-(ethoxymethylsulfamoyl)-2-(furan-2-ylmethylamino)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCC)(=O)=O QJWXANVPYJXQJI-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PBFKVYVGYHNCGT-UHFFFAOYSA-N 1-sulfanylpropane-1,2,3-triol Chemical compound OCC(O)C(O)S PBFKVYVGYHNCGT-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
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZREBDJHRDGKLKD-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(heptoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCCCCCCC)(=O)=O ZREBDJHRDGKLKD-UHFFFAOYSA-N 0.000 description 1
- FMUNLWXBVNIMFF-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(hexoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCCCCCC)(=O)=O FMUNLWXBVNIMFF-UHFFFAOYSA-N 0.000 description 1
- CZLHCCNZLJNEAB-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(pentoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCCCCC)(=O)=O CZLHCCNZLJNEAB-UHFFFAOYSA-N 0.000 description 1
- RIKUCWGPRSFGQD-UHFFFAOYSA-N 4-chloro-5-(ethylsulfanylmethylsulfamoyl)-2-(furan-2-ylmethylamino)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCSCC)(=O)=O RIKUCWGPRSFGQD-UHFFFAOYSA-N 0.000 description 1
- OQQUANZQPRLBMY-UHFFFAOYSA-N 4-chloro-5-(furan-2-ylmethoxymethylsulfamoyl)-2-(furan-2-ylmethylamino)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCC1=CC=CO1)(=O)=O OQQUANZQPRLBMY-UHFFFAOYSA-N 0.000 description 1
- LBKINWGISPHNQB-UHFFFAOYSA-N 5-(butoxymethylsulfamoyl)-4-chloro-2-(cyclohexylamino)benzoic acid Chemical compound C1(CCCCC1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCCCC)(=O)=O LBKINWGISPHNQB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000001632 acidimetric titration Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- FRGKKTITADJNOE-UHFFFAOYSA-N sulfanyloxyethane Chemical compound CCOS FRGKKTITADJNOE-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000721 toxic potential Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL37345A IL37345A (en) | 1971-07-20 | 1971-07-20 | Derivatives of 4-chloro-5-sulfamoyl-anthranilic acid,their preparation and pharmaceutical compositions comprising them |
| IL38812A IL38812A (en) | 1972-02-22 | 1972-02-22 | Derivatives of n-furfuryl-4-chloro-5-sulfamoylanthranilic acid,their preparation and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133892B true NO133892B (ja) | 1976-04-05 |
| NO133892C NO133892C (ja) | 1976-07-14 |
Family
ID=26320464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2578/72A NO133892C (ja) | 1971-07-20 | 1972-07-19 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3860582A (ja) |
| JP (1) | JPS516660B1 (ja) |
| AR (1) | AR212746A1 (ja) |
| AT (1) | AT315827B (ja) |
| AU (1) | AU446727B2 (ja) |
| BE (1) | BE786432A (ja) |
| CA (1) | CA1024988A (ja) |
| CH (1) | CH566972A5 (ja) |
| CS (1) | CS183664B2 (ja) |
| DD (1) | DD99572A1 (ja) |
| DK (1) | DK133503B (ja) |
| ES (1) | ES404965A1 (ja) |
| FR (1) | FR2146249B1 (ja) |
| GB (1) | GB1364366A (ja) |
| HU (1) | HU164158B (ja) |
| IE (1) | IE36684B1 (ja) |
| NL (1) | NL151705B (ja) |
| NO (1) | NO133892C (ja) |
| OA (1) | OA04139A (ja) |
| PH (1) | PH10267A (ja) |
| RO (1) | RO60274A (ja) |
| SE (1) | SE384675B (ja) |
| SU (1) | SU455533A3 (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2334973A1 (de) * | 1973-07-10 | 1975-01-23 | Boehringer Mannheim Gmbh | Neue biphenyl-derivate |
| FR2302101A1 (fr) * | 1975-02-27 | 1976-09-24 | Joullie International Sa | Nouveaux derives de l'acide chloro-4 |
| DE3006686A1 (de) * | 1980-02-22 | 1981-08-27 | Hoechst Ag, 6000 Frankfurt | 5-sulfamoyl-orthanilsaeuren, verfahren zu ihrer herstellung und ihre verwendung als heilmittel |
| US9422235B2 (en) * | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2908716A (en) * | 1957-04-08 | 1959-10-13 | Crown Zellerbach Corp | Preparing organic sulfides |
| US3567714A (en) * | 1965-09-03 | 1971-03-02 | Smith Kline French Lab | N - (oxa- or thiacycloalkyl)methyl-5-sulfamoylanthranilic acid derivatives |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| US3678039A (en) * | 1967-04-27 | 1972-07-18 | Lincoln Harvey Werner | 4-trifluoromethyl-anthranilic acids |
-
1972
- 1972-06-30 GB GB3071172A patent/GB1364366A/en not_active Expired
- 1972-07-04 IE IE941/72A patent/IE36684B1/xx unknown
- 1972-07-06 AU AU44308/72A patent/AU446727B2/en not_active Expired
- 1972-07-06 CA CA146,492A patent/CA1024988A/en not_active Expired
- 1972-07-07 SE SE7209055A patent/SE384675B/xx unknown
- 1972-07-11 FR FR7225075A patent/FR2146249B1/fr not_active Expired
- 1972-07-12 US US271314A patent/US3860582A/en not_active Expired - Lifetime
- 1972-07-17 ES ES404965A patent/ES404965A1/es not_active Expired
- 1972-07-18 DD DD164494A patent/DD99572A1/xx unknown
- 1972-07-18 CS CS7200005097A patent/CS183664B2/cs unknown
- 1972-07-19 AR AR243158A patent/AR212746A1/es active
- 1972-07-19 DK DK358472AA patent/DK133503B/da unknown
- 1972-07-19 SU SU1814329A patent/SU455533A3/ru active
- 1972-07-19 NO NO2578/72A patent/NO133892C/no unknown
- 1972-07-19 BE BE786432A patent/BE786432A/xx unknown
- 1972-07-19 HU HU72TE661A patent/HU164158B/hu unknown
- 1972-07-19 CH CH1078872A patent/CH566972A5/xx not_active IP Right Cessation
- 1972-07-19 AT AT623172A patent/AT315827B/de not_active IP Right Cessation
- 1972-07-20 NL NL727210054A patent/NL151705B/xx unknown
- 1972-07-20 OA OA54646A patent/OA04139A/xx unknown
- 1972-07-20 RO RO71689A patent/RO60274A/ro unknown
- 1972-07-20 JP JP47073330A patent/JPS516660B1/ja active Pending
- 1972-08-19 PH PH13727A patent/PH10267A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2146249A1 (ja) | 1973-03-02 |
| NL151705B (nl) | 1976-12-15 |
| GB1364366A (en) | 1974-08-21 |
| CA1024988A (en) | 1978-01-24 |
| US3860582A (en) | 1975-01-14 |
| ES404965A1 (es) | 1976-04-01 |
| DK133503C (ja) | 1976-10-18 |
| JPS516660B1 (ja) | 1976-03-01 |
| SE384675B (sv) | 1976-05-17 |
| HU164158B (ja) | 1973-12-28 |
| DE2235400B2 (de) | 1977-06-30 |
| AR212746A1 (es) | 1978-09-29 |
| DD99572A1 (ja) | 1973-08-20 |
| BE786432A (fr) | 1972-11-16 |
| CH566972A5 (ja) | 1975-09-30 |
| CS183664B2 (en) | 1978-07-31 |
| RO60274A (ja) | 1976-09-15 |
| PH10267A (en) | 1976-10-20 |
| AU446727B2 (en) | 1974-03-28 |
| NO133892C (ja) | 1976-07-14 |
| IE36684B1 (en) | 1977-02-02 |
| DE2235400A1 (de) | 1973-02-01 |
| NL7210054A (ja) | 1973-01-23 |
| AU4430872A (en) | 1974-02-21 |
| FR2146249B1 (ja) | 1975-10-17 |
| IE36684L (en) | 1973-01-20 |
| DK133503B (da) | 1976-05-31 |
| OA04139A (fr) | 1979-11-30 |
| SU455533A3 (ru) | 1974-12-30 |
| AT315827B (de) | 1974-06-10 |
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