DE1806926A1 - Lithiumsalz der Hydrochinonsulfonsaeure - Google Patents
Lithiumsalz der HydrochinonsulfonsaeureInfo
- Publication number
- DE1806926A1 DE1806926A1 DE19681806926 DE1806926A DE1806926A1 DE 1806926 A1 DE1806926 A1 DE 1806926A1 DE 19681806926 DE19681806926 DE 19681806926 DE 1806926 A DE1806926 A DE 1806926A DE 1806926 A1 DE1806926 A1 DE 1806926A1
- Authority
- DE
- Germany
- Prior art keywords
- lithium
- lithium salt
- hydroquinone
- sulfonic acid
- alcohol
- 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.)
- Withdrawn
Links
- 229910003002 lithium salt Inorganic materials 0.000 title claims description 28
- 159000000002 lithium salts Chemical class 0.000 title claims description 28
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 title claims description 17
- 230000000740 bleeding effect Effects 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- RSAUPWATSUEKCJ-UHFFFAOYSA-M lithium;2,5-dihydroxybenzenesulfonate Chemical compound [Li+].OC1=CC=C(O)C(S([O-])(=O)=O)=C1 RSAUPWATSUEKCJ-UHFFFAOYSA-M 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 230000002159 abnormal effect Effects 0.000 claims description 3
- SUPUVLWGKPVHBQ-UHFFFAOYSA-M lithium sulfite Chemical compound [Li+].OS([O-])=O SUPUVLWGKPVHBQ-UHFFFAOYSA-M 0.000 claims description 3
- 230000035699 permeability Effects 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- VKDSBABHIXQFKH-UHFFFAOYSA-M potassium;4-hydroxy-3-sulfophenolate Chemical compound [K+].OC1=CC=C(O)C(S([O-])(=O)=O)=C1 VKDSBABHIXQFKH-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
- 208000032843 Hemorrhage Diseases 0.000 description 11
- 208000034158 bleeding Diseases 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000282376 Panthera tigris Species 0.000 description 2
- 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 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 230000002168 angioprotective effect Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000000245 forearm Anatomy 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229940081543 potassium bitartrate Drugs 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
- 208000036981 active tuberculosis Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003481 dermatitic effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000544 hyperemic effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZPPPLBXXTCVBNC-UHFFFAOYSA-M lithium;2,3-dihydroxybutanedioate;hydron Chemical compound [H+].[Li+].[O-]C(=O)C(O)C(O)C([O-])=O ZPPPLBXXTCVBNC-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1569267A CH464953A (fr) | 1966-06-08 | 1967-11-09 | Procédé de préparation du sel de lithium de l'acide para-dihydroxy-benzène-sulfonique |
| CH1569367A CH467757A (fr) | 1967-11-09 | 1967-11-09 | Procédé de préparation du sel de lithium de l'acide p-dihydroxy-benzène-sulfonique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1806926A1 true DE1806926A1 (de) | 1969-07-03 |
Family
ID=25716854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681806926 Withdrawn DE1806926A1 (de) | 1967-11-09 | 1968-10-29 | Lithiumsalz der Hydrochinonsulfonsaeure |
Country Status (5)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038390A (en) * | 1972-05-17 | 1977-07-26 | Laboratorios Del Dr. Esteve, S.A. | Salts of p-dihydroxybenzene disulfonic acids for combatting hemorrhages and fragility of the capillaries |
| US3947448A (en) * | 1972-05-17 | 1976-03-30 | Laboratorios Del Dr. Esteve Sa | Salts of novel p-dihydroxybenezene disulfonic acids |
| US4005220A (en) * | 1973-02-20 | 1977-01-25 | Laboratorios Del Dr. Esteve, S.A. | Hemostatic compositions comprising salts of substituted hydroquinone sulfonic acid |
| US4513007A (en) * | 1983-05-03 | 1985-04-23 | Laboratoires Om Sa | Method for treating heart disease |
| EP0677171B1 (en) * | 1993-11-04 | 2000-03-29 | Dade Behring Inc. | Tetrahydroxyquinone as an activator component for activated partial thromboplastine time test of blood coagulation and as a detector of blood coagulation disorders |
| US9012692B2 (en) | 2008-01-03 | 2015-04-21 | AmDerma Pharmaceuticals, LLC | Processes for the preparation of 2,5-dihydroxybenzenesulfonic acid salts |
| EP2745914A3 (en) | 2012-12-24 | 2015-03-25 | Université de Mons | Process for desulphurization of gases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043866A (en) * | 1958-12-05 | 1962-07-10 | Dow Chemical Co | Chloropyrocatechol sulfonic acid compounds |
| CH363033A (fr) * | 1959-01-28 | 1962-07-15 | Om Lab Sa | Procédé de préparation de dérivés sulfonés, thérapeutiquement actifs, du p-dihydroxy-benzène |
-
1968
- 1968-10-23 BE BE722746D patent/BE722746A/xx unknown
- 1968-10-29 GB GB1233798D patent/GB1233798A/en not_active Expired
- 1968-10-29 DE DE19681806926 patent/DE1806926A1/de not_active Withdrawn
- 1968-10-30 US US771977A patent/US3629327A/en not_active Expired - Lifetime
- 1968-11-07 FR FR1590923D patent/FR1590923A/fr not_active Expired
- 1968-11-07 FR FR172904A patent/FR8285M/fr not_active Expired
-
1971
- 1971-03-29 US US00129154A patent/US3764700A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR1590923A (US08063081-20111122-C00044.png) | 1970-04-20 |
| US3629327A (en) | 1971-12-21 |
| BE722746A (US08063081-20111122-C00044.png) | 1969-04-01 |
| US3764700A (en) | 1973-10-09 |
| GB1233798A (US08063081-20111122-C00044.png) | 1971-05-26 |
| FR8285M (US08063081-20111122-C00044.png) | 1970-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |