CH550148A - Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques. - Google Patents
Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques.Info
- Publication number
- CH550148A CH550148A CH732672A CH732672A CH550148A CH 550148 A CH550148 A CH 550148A CH 732672 A CH732672 A CH 732672A CH 732672 A CH732672 A CH 732672A CH 550148 A CH550148 A CH 550148A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- salt
- base
- solution
- bis
- Prior art date
Links
- CJAZCKUGLFWINJ-UHFFFAOYSA-N 3,4-dihydroxybenzene-1,2-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1O CJAZCKUGLFWINJ-UHFFFAOYSA-N 0.000 title 2
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- NDGUAAJHDUBETK-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C=C1 NDGUAAJHDUBETK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- -1 cyclic amine Chemical class 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 150000001768 cations Chemical class 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 229940030225 antihemorrhagics Drugs 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000025 haemostatic effect Effects 0.000 abstract 1
- 210000003780 hair follicle Anatomy 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HDTBZPJATJFDOG-UHFFFAOYSA-N [NH4+].[NH4+].OC1=CC(S([O-])(=O)=O)C(O)(S([O-])(=O)=O)C=C1 Chemical compound [NH4+].[NH4+].OC1=CC(S([O-])(=O)=O)C(O)(S([O-])(=O)=O)C=C1 HDTBZPJATJFDOG-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CTLTUPWEUCZSIP-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical class OC1=CCC(O)(S(O)(=O)=O)C=C1 CTLTUPWEUCZSIP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- KKWDPSOYNDAZDR-UHFFFAOYSA-N N1CCNCC1.OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O Chemical compound N1CCNCC1.OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O KKWDPSOYNDAZDR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003956 methylamines Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- SNKQZROJNVIEFC-UHFFFAOYSA-N perchloric acid;piperazine Chemical compound OCl(=O)(=O)=O.C1CNCCN1 SNKQZROJNVIEFC-UHFFFAOYSA-N 0.000 description 2
- 229960003506 piperazine hexahydrate Drugs 0.000 description 2
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 2
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DPPPIVFSKJLJDJ-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonic acid;piperazine Chemical compound C1CNCCN1.C1CNCCN1.OC1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C=C1 DPPPIVFSKJLJDJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- 206010007191 Capillary fragility Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RQBFDSXRLNYOFZ-UHFFFAOYSA-L dipotassium 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonate Chemical compound [K+].OC1(C(C=C(C=C1)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[K+] RQBFDSXRLNYOFZ-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229940081543 potassium bitartrate Drugs 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH732672A CH550148A (fr) | 1972-05-17 | 1972-05-17 | Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques. |
| AR247787A AR204506A1 (es) | 1972-05-17 | 1973-01-01 | Procedimiento de preparacion de sales de acidos p-dihidroxibencenodisulfonicos |
| ES414365A ES414365A1 (es) | 1972-05-17 | 1973-04-07 | Procedimiento para la preparacion de nuevos derivados del acido p-dihidroxibencenodisulfonico. |
| GB2114173A GB1419995A (en) | 1972-05-17 | 1973-05-03 | Process for preparing p-dihydroxy benzene disulphonic acid derivatives |
| AU55467/73A AU481129B2 (en) | 1972-05-17 | 1973-05-09 | Process for preparing novel p-dihydroxy benzene disulfonic acid derivatives |
| ZA733134A ZA733134B (en) | 1972-05-17 | 1973-05-09 | Novel salts of p-dinydroxy benzene disulfonic acids |
| CA170,960A CA1024146A (en) | 1972-05-17 | 1973-05-10 | Process for preparing novel p-dihydroxy benzene disulfonic acid derivatives |
| DE2323723A DE2323723A1 (de) | 1972-05-17 | 1973-05-10 | Verfahren zur herstellung von neuen derivaten der p-dihydroxybenzoldisulfonsaeure |
| BE131068A BE799487A (fr) | 1972-05-17 | 1973-05-14 | Procede de preparation de nouveaux derives d'acide p-dihydroxybenzenedisulfonique |
| YU1264/73A YU41547B (en) | 1972-05-17 | 1973-05-14 | Process for obtaining new derivatives of p-dyhydroxibenzen-disuephonic acid |
| SE7306845A SE416729B (sv) | 1972-05-17 | 1973-05-15 | Forfarande for framstellning av salter av p-dihydroxibensendisulfonsyra |
| DD170840A DD107025A5 (ja) | 1972-05-17 | 1973-05-15 | |
| RO7383592A RO72544A (ro) | 1972-05-17 | 1973-05-15 | Procedeu de obtinere a unor derivati ai acidului p-dihidroxibenzendisulfonic |
| NLAANVRAGE7306734,A NL179186C (nl) | 1972-05-17 | 1973-05-15 | Werkwijze voor het bereiden en/of vervaardigen van een geneesmiddel met hemostatische en capillair beschermende werking op basis van een zout van een p-dihydroxybenzeensulfonzuur en werkwijze voor het bereiden van een verbinding, geschikt voor gebruik bij de bereiding van een dergelijk geneesmiddel. |
| RO7300074783A RO62887A (fr) | 1972-05-17 | 1973-05-15 | Procede pour obtenir des derives d'acide p-dihydroxybehzendisulfonique |
| PL1973162553A PL93785B1 (en) | 1972-05-17 | 1973-05-15 | Process for preparing p-dihydroxy benzene disulphonic acid derivatives[gb1419995a] |
| FR7317709A FR2201888B1 (ja) | 1972-05-17 | 1973-05-16 | |
| CS733534A CS194162B2 (en) | 1972-05-17 | 1973-05-17 | Process for preparing salts of p-dihydroxybenzendisulphonic acid |
| HUEE2140A HU169471B (ja) | 1972-05-17 | 1973-05-17 | |
| JP5419273A JPS5716982B2 (ja) | 1972-05-17 | 1973-05-17 | |
| US05/427,679 US3947448A (en) | 1972-05-17 | 1973-12-26 | Salts of novel p-dihydroxybenezene disulfonic acids |
| US05/601,834 US4038390A (en) | 1972-05-17 | 1975-08-04 | Salts of p-dihydroxybenzene disulfonic acids for combatting hemorrhages and fragility of the capillaries |
| JP56165550A JPS595579B2 (ja) | 1972-05-17 | 1981-10-16 | p−ジヒドロキシベンゼンジスルホン酸の塩の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH732672A CH550148A (fr) | 1972-05-17 | 1972-05-17 | Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH550148A true CH550148A (fr) | 1974-06-14 |
Family
ID=4323374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH732672A CH550148A (fr) | 1972-05-17 | 1972-05-17 | Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques. |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS595579B2 (ja) |
| BE (1) | BE799487A (ja) |
| CH (1) | CH550148A (ja) |
| ZA (1) | ZA733134B (ja) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204506A1 (es) * | 1972-05-17 | 1976-02-12 | Esteve Labor Dr | Procedimiento de preparacion de sales de acidos p-dihidroxibencenodisulfonicos |
-
1972
- 1972-05-17 CH CH732672A patent/CH550148A/fr not_active IP Right Cessation
-
1973
- 1973-05-09 ZA ZA733134A patent/ZA733134B/xx unknown
- 1973-05-14 BE BE131068A patent/BE799487A/xx not_active IP Right Cessation
-
1981
- 1981-10-16 JP JP56165550A patent/JPS595579B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU5546773A (en) | 1974-11-14 |
| JPS5798251A (en) | 1982-06-18 |
| ZA733134B (en) | 1974-04-24 |
| BE799487A (fr) | 1973-11-14 |
| JPS595579B2 (ja) | 1984-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: PROVESAN S.A. |
|
| PL | Patent ceased |