DE2323723C2 - - Google Patents
Info
- Publication number
- DE2323723C2 DE2323723C2 DE2323723A DE2323723A DE2323723C2 DE 2323723 C2 DE2323723 C2 DE 2323723C2 DE 2323723 A DE2323723 A DE 2323723A DE 2323723 A DE2323723 A DE 2323723A DE 2323723 C2 DE2323723 C2 DE 2323723C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydroxybenzene
- acid
- salt
- solution
- disulfonic acid
- 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.)
- Expired
Links
- NDGUAAJHDUBETK-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonic acid Chemical class OC1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C=C1 NDGUAAJHDUBETK-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkaline earth metal cation Chemical class 0.000 claims description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- ICYPCIUPMUDVFU-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonic acid;n-ethylethanamine Chemical compound CCNCC.CCNCC.OC1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C=C1 ICYPCIUPMUDVFU-UHFFFAOYSA-N 0.000 description 4
- IYVFNTXFRYQLRP-VVSTWUKXSA-N 2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4h-chromen-4-one Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(OCCO)C=C3OC=2C=2C=C(OCCO)C(OCCO)=CC=2)=O)O1 IYVFNTXFRYQLRP-VVSTWUKXSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 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 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002439 hemostatic effect Effects 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000008728 vascular permeability Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000740 bleeding effect Effects 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
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001816 cooling Methods 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
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000002184 metal Substances 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
- 230000035699 permeability Effects 0.000 description 2
- 229960005141 piperazine Drugs 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
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- YXWWGQDGPFNTFR-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-3,5-diene-1,2-disulfonic acid;potassium Chemical compound [K].OC1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C=C1 YXWWGQDGPFNTFR-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- VSAZFRKEFQPOIS-UHFFFAOYSA-N 2,5-dihydroxybenzene-1,4-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=C(O)C=C1S(O)(=O)=O VSAZFRKEFQPOIS-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
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 241001539019 Monolene Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 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 1
- UMURZOABHVOJFS-UHFFFAOYSA-N OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O.C1(=CC=CC=C1)N.C1(=CC=CC=C1)N Chemical compound OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O.C1(=CC=CC=C1)N.C1(=CC=CC=C1)N UMURZOABHVOJFS-UHFFFAOYSA-N 0.000 description 1
- HUKRXGSYMIJOBG-UHFFFAOYSA-N OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O.CN.CN Chemical compound OC1(C(C=C(C=C1)O)S(=O)(=O)O)S(=O)(=O)O.CN.CN HUKRXGSYMIJOBG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009441 vascular protection Effects 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| 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. |
| CH115473A CH558340A (en) | 1973-01-26 | 1973-01-26 | Dihydroxybenzenedisulphonic acid derivs - prepd from dihydroxybenzene - disulphonic acid and base |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2323723A1 DE2323723A1 (de) | 1973-11-29 |
| DE2323723C2 true DE2323723C2 (enExample) | 1987-08-13 |
Family
ID=25686824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2323723A Granted DE2323723A1 (de) | 1972-05-17 | 1973-05-10 | Verfahren zur herstellung von neuen derivaten der p-dihydroxybenzoldisulfonsaeure |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5716982B2 (enExample) |
| AR (1) | AR204506A1 (enExample) |
| CA (1) | CA1024146A (enExample) |
| CS (1) | CS194162B2 (enExample) |
| DD (1) | DD107025A5 (enExample) |
| DE (1) | DE2323723A1 (enExample) |
| ES (1) | ES414365A1 (enExample) |
| FR (1) | FR2201888B1 (enExample) |
| GB (1) | GB1419995A (enExample) |
| HU (1) | HU169471B (enExample) |
| NL (1) | NL179186C (enExample) |
| PL (1) | PL93785B1 (enExample) |
| RO (2) | RO72544A (enExample) |
| SE (1) | SE416729B (enExample) |
| YU (1) | YU41547B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH550148A (fr) * | 1972-05-17 | 1974-06-14 | Esteve Lab Del Dr Sa | Procede de preparation de sels d'acides p-dihydroxybenzenedisulfoniques. |
| CH591437A5 (enExample) * | 1974-05-08 | 1977-09-15 | Esteve Dr Lab Del Sa | |
| ZA745083B (en) * | 1973-09-11 | 1975-08-27 | Esteve Labor Dr | Process for the preparation of monoesters and diesters of 2,5-dihydroxy-benzene-sulphonic acid |
| CH591438A5 (enExample) * | 1975-05-16 | 1977-09-15 | Esteve Dr Lab Del Sa | |
| ES2015433A6 (es) * | 1989-08-03 | 1990-08-16 | Esteve Quimica Sa | Procedimientos de preparacion de la sal de piperacina del monotosilato del acido 2,5-dihidroxibencenosulfonico |
| AU715600B2 (en) * | 1996-04-03 | 2000-02-03 | Laboratorios Del Dr. Esteve, S.A. | Use of 2,5-dihydroxybenzenesulfonic derivatives for the manufacture of medicaments intended for the normalization of the endothelial function, for the treatment of sexual dysfunction and vascular complications of diabetes, as well as vascular disorders of endothelial origin |
| FR2747040B1 (fr) * | 1996-04-03 | 1998-06-26 | Esteve Labor Dr | Derives 2,5-dihydroxybenzenesulfoniques comme medicaments pour normaliser la fonction endotheliale et la fonction sexuelle, et traiter les troubles vasculaires d'origine diabetique ou endotheliale |
| LT5475B (lt) | 2006-04-12 | 2008-02-25 | Laboratorios Del Dr. Esteve, S. A. | 2,5-dihidroksibenzensulfoninių junginių panaudojimas sutrikimų, paremtų no produkcijos susilpnėjimu, gydymui ir/arba edhf funkcijos reguliavimo pablogėjimui |
| EP2313366A2 (en) | 2008-01-03 | 2011-04-27 | Action Medicines, S.L. | Processes for the preparation of 2,5-dihydroxybenzenesulfonic acid salts |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547988A (en) * | 1968-02-05 | 1970-12-15 | Eastman Kodak Co | Process for the preparation of dialkali dihydroxybenzene disulfonates |
-
1973
- 1973-01-01 AR AR247787A patent/AR204506A1/es active
- 1973-04-07 ES ES414365A patent/ES414365A1/es not_active Expired
- 1973-05-03 GB GB2114173A patent/GB1419995A/en not_active Expired
- 1973-05-10 CA CA170,960A patent/CA1024146A/en not_active Expired
- 1973-05-10 DE DE2323723A patent/DE2323723A1/de active Granted
- 1973-05-14 YU YU1264/73A patent/YU41547B/xx unknown
- 1973-05-15 RO RO7383592A patent/RO72544A/ro unknown
- 1973-05-15 DD DD170840A patent/DD107025A5/xx unknown
- 1973-05-15 RO RO7300074783A patent/RO62887A/ro unknown
- 1973-05-15 SE SE7306845A patent/SE416729B/xx unknown
- 1973-05-15 NL NLAANVRAGE7306734,A patent/NL179186C/xx active Search and Examination
- 1973-05-15 PL PL1973162553A patent/PL93785B1/pl unknown
- 1973-05-16 FR FR7317709A patent/FR2201888B1/fr not_active Expired
- 1973-05-17 CS CS733534A patent/CS194162B2/cs unknown
- 1973-05-17 JP JP5419273A patent/JPS5716982B2/ja not_active Expired
- 1973-05-17 HU HUEE2140A patent/HU169471B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS194162B2 (en) | 1979-11-30 |
| CA1024146A (en) | 1978-01-10 |
| YU126473A (en) | 1982-02-28 |
| JPS4941518A (enExample) | 1974-04-18 |
| DE2323723A1 (de) | 1973-11-29 |
| AR204506A1 (es) | 1976-02-12 |
| RO72544A (ro) | 1981-06-30 |
| FR2201888A1 (enExample) | 1974-05-03 |
| ES414365A1 (es) | 1976-02-01 |
| HU169471B (enExample) | 1976-11-28 |
| SE416729B (sv) | 1981-02-02 |
| FR2201888B1 (enExample) | 1977-01-21 |
| RO62887A (fr) | 1978-02-15 |
| DD107025A5 (enExample) | 1974-07-12 |
| JPS5716982B2 (enExample) | 1982-04-08 |
| NL179186C (nl) | 1986-08-01 |
| GB1419995A (en) | 1976-01-07 |
| NL7306734A (enExample) | 1973-11-20 |
| PL93785B1 (en) | 1977-06-30 |
| YU41547B (en) | 1987-10-31 |
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