FR2466456A1 - Nouveaux derives sulfamides solubles - Google Patents
Nouveaux derives sulfamides solubles Download PDFInfo
- Publication number
- FR2466456A1 FR2466456A1 FR7924050A FR7924050A FR2466456A1 FR 2466456 A1 FR2466456 A1 FR 2466456A1 FR 7924050 A FR7924050 A FR 7924050A FR 7924050 A FR7924050 A FR 7924050A FR 2466456 A1 FR2466456 A1 FR 2466456A1
- Authority
- FR
- France
- Prior art keywords
- sep
- sulphonamide
- aldehyde
- derivatives
- new
- 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.)
- Granted
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 21
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 2
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 5
- 150000001408 amides Chemical class 0.000 title 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 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
- 230000001154 acute effect Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 235000011181 potassium carbonates Nutrition 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 235000011182 sodium carbonates Nutrition 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229960002135 sulfadimidine Drugs 0.000 description 4
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 241000191938 Micrococcus luteus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 2
- 229960004936 sulfamethoxypyridazine Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010016952 Food poisoning Diseases 0.000 description 1
- 208000019331 Foodborne disease Diseases 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
- 208000019693 Lung disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000607729 Salmonella enterica subsp. enterica serovar Abortus Species 0.000 description 1
- 241000607662 Salmonella enterica subsp. enterica serovar Abortusequi Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010633 broth Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- GTFMAONWNTUZEW-UHFFFAOYSA-N glutaramic acid Chemical compound NC(=O)CCCC(O)=O GTFMAONWNTUZEW-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924050A FR2466456A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux derives sulfamides solubles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924050A FR2466456A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux derives sulfamides solubles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2466456A1 true FR2466456A1 (fr) | 1981-04-10 |
| FR2466456B1 FR2466456B1 (OSRAM) | 1982-02-05 |
Family
ID=9230071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7924050A Granted FR2466456A1 (fr) | 1979-09-27 | 1979-09-27 | Nouveaux derives sulfamides solubles |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2466456A1 (OSRAM) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH239702A (de) * | 1943-08-20 | 1945-10-31 | Cilag Chemisches Ind Lab Ag | Verfahren zur Darstellung eines Sulfonamides. |
| DE921148C (de) * | 1952-09-04 | 1954-12-09 | Nordmark Werke Gmbh | Verfahren zur Herstellung eines Kondensationsproduktes aus einem p-Aminobenzolsulfonamidopyrimidin, Zimtaldehyd und Alkalibisulfit |
| FR1450539A (fr) * | 1965-05-14 | 1966-06-24 | Sobio Lab | Nouveaux dérivés substitués en n de la méthoxy-4-méthyl-2-sulfanilamido-6-pyrimidine |
| DE1931214A1 (de) * | 1969-06-20 | 1970-12-23 | Eckert Dr Theodor | Verfahren zur Erhoehung der Wasserloeslichkeit therapeutisch verwendbarer Arylamine |
-
1979
- 1979-09-27 FR FR7924050A patent/FR2466456A1/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH239702A (de) * | 1943-08-20 | 1945-10-31 | Cilag Chemisches Ind Lab Ag | Verfahren zur Darstellung eines Sulfonamides. |
| DE921148C (de) * | 1952-09-04 | 1954-12-09 | Nordmark Werke Gmbh | Verfahren zur Herstellung eines Kondensationsproduktes aus einem p-Aminobenzolsulfonamidopyrimidin, Zimtaldehyd und Alkalibisulfit |
| FR1450539A (fr) * | 1965-05-14 | 1966-06-24 | Sobio Lab | Nouveaux dérivés substitués en n de la méthoxy-4-méthyl-2-sulfanilamido-6-pyrimidine |
| DE1931214A1 (de) * | 1969-06-20 | 1970-12-23 | Eckert Dr Theodor | Verfahren zur Erhoehung der Wasserloeslichkeit therapeutisch verwendbarer Arylamine |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2466456B1 (OSRAM) | 1982-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0706512B1 (fr) | Derives d'acetamide et leur utilisation comme modificateurs du comportement de prise alimentaire | |
| CA2055859A1 (fr) | Derives d'oxazolopyridines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2558837A1 (fr) | Derives de l'acide methylenediphosphonique, procede d'obtention et medicaments antirhumatismaux les contenant | |
| FR2481118A1 (fr) | Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique | |
| EP0117771B1 (fr) | Imino-2 pyrrolidines, leur procédé de préparation et leurs applications en thérapeutique | |
| EP0173597B1 (fr) | Nouveaux éther-oxydes dérivés de cyclopropylphénols | |
| CH652387A5 (fr) | Derives d'acides phenyl aliphatique carboxyliques, leur preparation et les medicaments et compositions les renfermant. | |
| EP0063509A1 (fr) | Nouveaux dérivés de pipérazino-2 pyrimidine, procédés pour leur préparation, médicaments les contenant et leur utilisation comme intermédiaires pour la fabrication de médicaments | |
| EP0134179B1 (fr) | Nouveaux dérivés de l'acide 4-phényl 4-oxo-buten 2-oique, leur procédé de préparation, des médicaments et des compositions les renfermant | |
| CH655924A5 (fr) | Derives de l'acide 4-phenyl 4-oxo 2-butenoique, leurs sels, leur preparation, medicaments et compositions les renfermant. | |
| FR2466456A1 (fr) | Nouveaux derives sulfamides solubles | |
| FR2491761A1 (fr) | Derives de l'adenosine a activite anti-inflammatoire et analgesique et compositions therapeutiques qui les contiennent en tant que principe actif | |
| LU81554A1 (de) | Alkylthiophenoxyalkylamines | |
| EP0000452B1 (fr) | Dérivés d'oxadiazole-1,2,4, leur préparation et leur application en thérapeutique. | |
| FR2493702A1 (fr) | Compositions antivirales contenant des derives d'acide aminosulfonylhalogenobenzoique | |
| CA2727911C (fr) | Phenyl-alkyl-piperazines ayant une activite modulatrice du tnf | |
| CA2405076C (fr) | Molecules duales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques | |
| CH654289A5 (fr) | Medicaments constitues par certains derives de l'acide 4-phenyl 4-oxo 2-butenoique et compositions les renfermant. | |
| EP0196943A1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
| KR850000210B1 (ko) | 옥사졸린의 제조방법 | |
| EP0161143A1 (fr) | Nouvelles 1,2,4-thiadiazines et leurs sels, leur procédé et leurs intermédiaires de préparation, leur application à titre de médicaments et les compositions les renfermant | |
| CA1068270A (fr) | Diamino-2,4-bromo-5 chloro-6 pyrimidines utilisables comme medicaments et procede pour leur preparation | |
| MC1222A1 (fr) | Nouvelles 2,4-diamino-5-benzylpyrimidines,leur preparation et leur application en tant que medicaments | |
| EP0022022B1 (fr) | Nouveaux dérivés acylés de la taurine et leurs sels et procédé pour leur préparation | |
| CA1204770A (en) | Fluorinated diaminoalkene derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |