NO124306B - - Google Patents
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- Publication number
- NO124306B NO124306B NO487569A NO487569A NO124306B NO 124306 B NO124306 B NO 124306B NO 487569 A NO487569 A NO 487569A NO 487569 A NO487569 A NO 487569A NO 124306 B NO124306 B NO 124306B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- alkali metal
- disulfonamide
- compounds
- metal salts
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- -1 alkali metal salts Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RJMGUEXGQXNUBI-UHFFFAOYSA-N 5-chloro-4-hydroxybenzene-1,3-disulfonyl chloride Chemical compound OC1=C(Cl)C=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O RJMGUEXGQXNUBI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GJQPMPFPNINLKP-UHFFFAOYSA-N diclofenamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 GJQPMPFPNINLKP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- DELKNGSNILXDSN-UHFFFAOYSA-N 4,5-dichlorobenzene-1,3-disulfonyl chloride Chemical compound ClC1=CC(S(Cl)(=O)=O)=CC(S(Cl)(=O)=O)=C1Cl DELKNGSNILXDSN-UHFFFAOYSA-N 0.000 description 1
- WKDNROIOJLGMTQ-UHFFFAOYSA-N 5-bromo-4-chlorobenzene-1,3-disulfonamide Chemical compound NS(=O)(=O)C1=CC(Br)=C(Cl)C(S(N)(=O)=O)=C1 WKDNROIOJLGMTQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
- D01F9/08—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments of inorganic material
- D01F9/12—Carbon filaments; Apparatus specially adapted for the manufacture thereof
- D01F9/14—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments
- D01F9/20—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products
- D01F9/21—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products from macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F9/22—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products from macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyacrylonitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Carbon And Carbon Compounds (AREA)
- Inorganic Fibers (AREA)
- Artificial Filaments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte til fremstilling av 4-klor-5-halogenbenzen-l,3-disulfonamider eller alkalimetallsalter av sådanne. Process for the production of 4-chloro-5-halobenzene-1,3-disulfonamides or alkali metal salts thereof.
Foreliggende oppfinnelse angår en The present invention relates to a
fremgangsmåte til fremstilling av nye 4-klor-5-halogen-benzen-l,3-disulfonamid-forbindelser med den generelle formel: process for the preparation of new 4-chloro-5-halo-benzene-1,3-disulfonamide compounds with the general formula:
samt alkalimetallsalter av sådanne forbindelser. I den ovenfor anførte formel be-tegner R et klor- eller bromatom. De nye forbindelser som fremstilles ved fremgangsmåten ifølge oppfinnelsen er for-delaktige kjemoterapeutiske forbindelser og har anvendelse bl. a. ved behandling av glaucoma (grønn stær). Forbindelsene har di-uretiske eller natriuretiske egenskaper. as well as alkali metal salts of such compounds. In the above-mentioned formula, R denotes a chlorine or bromine atom. The new compounds produced by the method according to the invention are advantageous chemotherapeutic compounds and are used, among other things, a. in the treatment of glaucoma (glaucoma). The compounds have diuretic or natriuretic properties.
Forbindelsene kan gis i terapeutiske doser The compounds may be administered in therapeutic doses
vanlige måter, f. eks. i form av tabletter. Forbindelsene er effektive ved oral anvendelse, såvel som ved injeksjon. Da for-bindelsenes alkalimetallsalter er lett opp-løselige i isotoniske, vandige midler, kan usual ways, e.g. in the form of tablets. The compounds are effective by oral application, as well as by injection. As the compounds' alkali metal salts are easily soluble in isotonic, aqueous media, can
injiserbare oppløsninger fremstilles ved å injectable solutions are prepared by
oppløse disse salter i det valgte medium dissolve these salts in the chosen medium
som, om ønskes, kan tilsettes konserve-ringsmidler. to which, if desired, preservatives can be added.
Dosene av 4-klorbenzen-l,3-disulfonamid-forbindelsen som fremstilles ved The doses of the 4-chlorobenzene-1,3-disulfonamide compound produced by
fremgangsmåten ifølge foreliggende oppfinnelse kan varieres innen et stort områ- the method according to the present invention can be varied within a large area
de. Av denne grunn kan tabletter inne-holdende 100, 150, 250 eller 500 mg av den aktive bestanddel gjøres tilgjengelig for legene for symptomatisk innstilling av do-sen etter den enkelte pasient. De nevnte doser ligger godt under den giftige eller dødelige dose for forbindelsene. Studier av kronisk giftighet med hunder som for-søksdyr og under ani? ;ndelse av 4,5-diklor-benzen-l,3-disulfonar"aid viser at 20 mg pr. kg pr. døgn tåles godt i lange tidsrom uten noen uønskede toksiske virkninger. Ved for-søk med mus ble den dose som fremkalte en dødelighet på 50 % (LD50) funnet å være 703 mg pr. kg ved intravenøs anvendelse, og 1710 mg pr. kg ved oral anvendelse. the. For this reason, tablets containing 100, 150, 250 or 500 mg of the active ingredient can be made available to doctors for symptomatic adjustment of the dose according to the individual patient. The mentioned doses are well below the toxic or lethal dose for the compounds. Studies of chronic toxicity with dogs as test animals and during ani? A study of 4,5-dichloro-benzene-1,3-disulfonamide shows that 20 mg per kg per day is well tolerated for long periods of time without any unwanted toxic effects. In experiments with mice, the dose that induced a 50% lethality (LD50) found to be 703 mg per kg by intravenous application, and 1710 mg per kg by oral application.
Fremgangsmåten ifølge oppfinnelsen til fremstilling av 4-klor-5-halogenbenzen-1,3-disulfonamid-forbindelser er karakterisert ved at man omsetter et 5-halogen-4-hydroxybenzen-l,3-disulfonylklorid med fosforpentaklorid, hvorved der dannes det tilsvarende 4-klor-5-halogenbenzen-l,3-disulfonylklorid, som man på kj ent måte overfører til det tilsvarende 4-klor-5-halo-genbenzen-l,3-d'isulfonamid, i hvilket 5-halogensubstituenten er et kloratom eller et bromatom, og eventuelt på kjent måte danner de tilsvarende alkalimetallsalter. The process according to the invention for the production of 4-chloro-5-halobenzene-1,3-disulfonamide compounds is characterized by reacting a 5-halo-4-hydroxybenzene-1,3-disulfonyl chloride with phosphorus pentachloride, whereby the corresponding 4 -chloro-5-halobenzene-1,3-disulfonyl chloride, which is transferred in a known manner to the corresponding 4-chloro-5-halobenzene-1,3-disulfonamide, in which the 5-halogen substituent is a chlorine atom or a bromine atom, and possibly in a known manner they form the corresponding alkali metal salts.
Fortrinnsvis bruker man 2,5 mol fosforpentaklorid pr. mol disulfonylklorid. Preferably, 2.5 mol of phosphorus pentachloride is used per moles of disulfonyl chloride.
Alkalimetallsaltene av 4-klor-5-halo-genbenzen-l,3-disulfonamid-forbindelsene fremstillet ved fremgangsmåten ifølge oppfinnelsen kan fremstilles ved å oppløse vedkommende forbindelse i en vandig eller en alkoholisk oppløsning av vedkommende al-kalimetallhydroksyd, og om ønskes å iso- eller ved hjelp av andre metoder som er lere saltet ved fordampning av oppløsnings- kjent for fagfolk i den organiske kjemi, midlet. Et hvilket som helst alkalimetall- I det følgende beskrives som eksempler salt som natrium, kalium eller litiumsalter noen utførelsesformer for fremgangsmåten kan fremstilles ved hjelp av denne metode, ifølge oppfinnelsen. The alkali metal salts of the 4-chloro-5-halo-benzene-1,3-disulfonamide compounds produced by the method according to the invention can be prepared by dissolving the compound in question in an aqueous or an alcoholic solution of the alkali metal hydroxide in question, and if desired to iso- or by means of other methods which are clay salted by evaporation of solvent- known to those skilled in organic chemistry, the agent. Any alkali metal - In the following, salt such as sodium, potassium or lithium salts are described as examples, some embodiments of the method can be prepared using this method, according to the invention.
En blanding av 5-klor-4-hydroksyben-zen-l,3-disulfonylklorid (omkring 302 g tilsvarende 0,92 mol) og 480 g (2,3 mol) fosforpentaklorid oppvarmes i en time til 120— 140° C i en to liters rundkolbe. Den herved erholdte klare oppløsning helles på is, hvorved 4,5-diklorbenzen-l,3-disulfonyl-klorid øyeblikkelig skiller seg ut som et fast stoff. Dette faste stoff oppsamles ved filtrering og vaskes med vann. Mens det ennå er i fuktig tilstand tilsettes det i porsjoner og i løpet av 20 minutter til en liter konsentrert ammoniakkvann i et 3 liters beger-glass omgitt av et koldt vannbad. Man lar derpå reaksjonsblandingen stå i en time uten avkjøling, hvorpå den oppvarmes på dampbad i omkring 30 minutter mens luft bobles gjennom den for å fjerne noe av overskuddet av ammoniakk. Reaksjonsblandingen filtreres derpå, surgjøres med konsentrert saltsyre og avkjøles. Produktet skiller seg ut som et gummiaktig stoff fra hvilket den overliggende væske dekanteres. Det gummiaktige stoff tritureres derpå med 250 ml vann for å frembringe krystallisa-sjon. Det således erholdte rå produkt om-krystalliseres fra 3200 ml kokende vann og derpå fra 40 %'s vandig isopropylalkohol, hvorpå man får 4,5-diklorbenzen-l,3-disulfonamid som et hvitt fast stoff med sm.p. 228,5—229,0° C. Eksempel 2: 5- brom- 4- klort>enzen- l, 3- disulfonamid. A mixture of 5-chloro-4-hydroxybenzene-1,3-disulfonyl chloride (about 302 g corresponding to 0.92 mol) and 480 g (2.3 mol) phosphorus pentachloride is heated for one hour to 120-140° C in a two liter round flask. The clear solution thus obtained is poured onto ice, whereby 4,5-dichlorobenzene-1,3-disulfonyl chloride immediately separates out as a solid. This solid is collected by filtration and washed with water. While still moist, it is added in portions and over 20 minutes to one liter of concentrated ammonia water in a 3 liter beaker surrounded by a cold water bath. The reaction mixture is then allowed to stand for one hour without cooling, after which it is heated on a steam bath for about 30 minutes while air is bubbled through it to remove some of the excess ammonia. The reaction mixture is then filtered, acidified with concentrated hydrochloric acid and cooled. The product separates as a gummy substance from which the overlying liquid is decanted. The gummy substance is then triturated with 250 ml of water to produce crystallization. The crude product thus obtained is recrystallized from 3200 ml of boiling water and then from 40% aqueous isopropyl alcohol, whereupon 4,5-dichlorobenzene-1,3-disulfonamide is obtained as a white solid with m.p. 228.5—229.0° C. Example 2: 5-bromo-4-chlorotriene-1,3-disulfonamide.
Ved i stedet for det i eksempel 1 an-vendte 5-klor-4-hydroksybenzen-l,3-disulfonylklorid å bruke en ekvimolar mengde 5-brom-4-hydrofcsyibenzen-l,3-disulfonid-klorid og forøvrig igå frem således som beskrevet i eksempel 1 får man 5-brom-4-klorbenzen-l,3-disulfonamid. By instead of the 5-chloro-4-hydroxybenzene-1,3-disulfonyl chloride used in example 1, using an equimolar amount of 5-bromo-4-hydroxybenzene-1,3-disulfonide chloride and otherwise proceeding as follows described in example 1, 5-bromo-4-chlorobenzene-1,3-disulfonamide is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681816170 DE1816170A1 (en) | 1968-12-20 | 1968-12-20 | Process for the production of carbon or graphite fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124306B true NO124306B (en) | 1972-04-04 |
Family
ID=5716975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO487569A NO124306B (en) | 1968-12-20 | 1969-12-10 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT295023B (en) |
| BE (1) | BE743458A (en) |
| CH (1) | CH515853A (en) |
| DE (1) | DE1816170A1 (en) |
| FR (1) | FR2026637A1 (en) |
| GB (1) | GB1232186A (en) |
| NL (1) | NL6918783A (en) |
| NO (1) | NO124306B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS602408B2 (en) * | 1977-08-17 | 1985-01-21 | 東邦ベスロン株式会社 | Carbon fiber with excellent heat and oxidation resistance |
-
1968
- 1968-12-20 DE DE19681816170 patent/DE1816170A1/en not_active Withdrawn
-
1969
- 1969-12-09 CH CH1828369A patent/CH515853A/en not_active IP Right Cessation
- 1969-12-10 NO NO487569A patent/NO124306B/no unknown
- 1969-12-10 AT AT1149969A patent/AT295023B/en not_active IP Right Cessation
- 1969-12-11 FR FR6942969A patent/FR2026637A1/fr not_active Withdrawn
- 1969-12-15 NL NL6918783A patent/NL6918783A/xx unknown
- 1969-12-19 BE BE743458D patent/BE743458A/xx unknown
- 1969-12-19 GB GB1232186D patent/GB1232186A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2026637A1 (en) | 1970-09-18 |
| BE743458A (en) | 1970-06-19 |
| CH515853A (en) | 1971-11-30 |
| AT295023B (en) | 1971-12-27 |
| DE1816170A1 (en) | 1970-09-17 |
| NL6918783A (en) | 1970-06-23 |
| GB1232186A (en) | 1971-05-19 |
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