CH498134A - Pharmaceutical furazan deriv prodn - Google Patents
Pharmaceutical furazan deriv prodnInfo
- Publication number
- CH498134A CH498134A CH1479370A CH1479370A CH498134A CH 498134 A CH498134 A CH 498134A CH 1479370 A CH1479370 A CH 1479370A CH 1479370 A CH1479370 A CH 1479370A CH 498134 A CH498134 A CH 498134A
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- general formula
- furazan
- deriv
- prodn
- Prior art date
Links
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 2
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- HJUUDZMTOBNFHQ-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-1,2,5-oxadiazol-3-amine Chemical compound C1=C(C)C(C)=CC=C1C1=NON=C1N HJUUDZMTOBNFHQ-UHFFFAOYSA-N 0.000 description 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical group N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000001640 Fibromyalgia Diseases 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
- 208000018650 Intervertebral disc disease Diseases 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 206010044074 Torticollis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- -1 alkyl nitrite Chemical compound 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 208000018197 inherited torticollis Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Pharmaceutical furazan deriv. prodn. Compounds possessing depressant, anticonvulsive and muscle-relaxing properties, have the general formula: (where R1 is H or a lower alkyl, and R2 is a lower alkyl occupying the m- or o-position). These compounds are produced by reacting hydroxylamine hydrochloride with (where R3 is H or lower alkyl).
Description
Verfahren zur Herstellung von neuen Furazanderivaten
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Furazanderivate.
Verbindungen der allgemeinen Formel I,
EMI1.1
in welcher Rt Wasserstoff oder eine niedere Alkylgruppe und R2 eine niedere Alkylgruppe, welche die o- oder m-Stellung einnimmt, bedeutet, sind bisher nicht bekannt geworden.
Wie nun gefunden wurde, besitzen diese Verbndungen wertvolle pharmakologische Eigenschaften. Sie wirken zentraldämpfend, antikonvulsiv und muskelrelaxierend.
Die neuen Verbindungen der allgemeinen Formel I können zur Beruhigung von schwachen Erregungszuständen und zur Behebung der Muskelsteife, z. B. bei rheumatischen Erkrankungen, Fibrositis, Bursitis, Myositis, Spondylitis, Discopathien und Torticollis, verwendet werden.
In den Verbindungen der allgemeinen Formel I können Rt und R2 als niedere Alkylgruppen beispielsweise die Methyl-, Athyl-, Propyl-, Isopropyl-, Butyl-, Isobutyl-, sek. Butyl-, tert. Butyl-, Pentyl-, Isopentyloder die 2,2-Dimethylpropylgruppen sein, Rt kann die o-, m- oder p-Stellung einnehmen.
Verbindungen der allgemeinen Formel I werden hergestellt, indem man eine Verbindung der allgemeinen Formel II,
EMI1.2
in welcher R, und R2 die unter Formel I angegebene Bedeutung haben und R3 Wasserstoff oder einen niederen Alkylrest bedeutet, durch Umsetzen mit Hydroxylamin-hydrochlorid in eine Verbindung der allgemeinen Formel 1 überführt.
Die Umsetzung wird vorzugsweise in einem Lösungsmittel und in Gegenwart von basischen Stoffen vorgenommen. Als Lösungsmittel eignen sich insbesondere hydroxylgruppenhaltige Lösungsmittel, wie z.B.
niedere Alkanole und Wasser. Geeignete basische Stoffe sind z. B. Alkalimetallhydroxide wie Natriumoder Kaliumhydroxid, ferner auch Erdalkalimetallhydroxide, wie z. B. Calcium- oder Bariumhydroxid, oder Carbonate, die den genannten Alkalihydroxiden entsprechen. Vorzugsweise wird das Hydroxylamin im Überschuss als mineralsaures Salz, z. B. als Hydrochlorid, eingesetzt und die Base durch überschüssiges Alkali in Freiheit gesetzt.
Die Ausgangsverbindungen der allgemeinen Formel ii können durch Reaktion von im Benzolkern gemäss der Definition für R1 und R2 substituierten 4-Phenylimidazolen mit einem niederen Alkylnitrit (oder mit salpetriger Säure) zur entsprechenden Verbindung der allgemeinen Formel II übergeführt werden.
Die neuen Wirkstoffe (I) können peroral, rektal oder parenteral verabreicht werden. Die täglichen Dosen bewegen sich zwischen 5060(x) mg.
Das nachfolgende Beispiel erläutert die Herstellung der neuen Verbindungen der allgemeinen Formel I und von bisher nicht beschriebenen Zwischenprodukten näher, soll jedoch den Umfang der Erfindung in keiner Weise beschränken. Die Temperaturen sind in Celsiusgraden angegeben.
Beispiel
Man suspendiert 0,5 g 2-Methyl-4-nitroso-5-(otolyl)-imidazol in 4 ml Äthanol und versetzt diese Suspension mit einer Lösung von 0,3 g Hydroxylaminhydrochlorid in 2 ml Wasser. Das Gemisch wird 5 Minuten im Wasserbad auf 900 erwärmt, wobei das grüne Nitrosoderivat in Lösung geht. Der braunen Lösung gibt man 0,3 ml konzentrierter wässriger Salz .säure zu und kocht l Stunde am Rückfluss. Nach dem Abkühlen wird der Alkohol abgedampft und der Rückstand mit Wasser und Äther extrahiert. Die organische Phase wird mit Wasser gewaschen, mit Natriumsulfat getrocknet, mit Aktivkohle entfärbt, filtriert und eingedampft. Die zurückbleibenden Kristalle werden aus Isopropanol umkristallisiert. Man erhält so 3-Amino 4-(oWtolyl)-furazan vom Smp. 888o.
In analoger Weise erhält man das 3-Amino-4-(3,4xylyl)-furazan, Smp. 111-113 .
Process for the production of new furazan derivatives
The invention relates to a process for the preparation of new furazan derivatives.
Compounds of general formula I,
EMI1.1
in which Rt is hydrogen or a lower alkyl group and R2 is a lower alkyl group which is in the o- or m-position, have not yet become known.
As has now been found, these compounds have valuable pharmacological properties. They have a central damping, anticonvulsant and muscle relaxant effect.
The new compounds of general formula I can be used to calm weak states of excitement and to relieve muscle stiffness, e.g. B. in rheumatic diseases, fibrositis, bursitis, myositis, spondylitis, discopathies and torticollis can be used.
In the compounds of general formula I, Rt and R2 can be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec. Butyl, tert. Butyl, pentyl, isopentyl or the 2,2-dimethylpropyl groups, Rt can be in the o-, m- or p-position.
Compounds of general formula I are prepared by adding a compound of general formula II,
EMI1.2
in which R and R2 have the meaning given under formula I and R3 denotes hydrogen or a lower alkyl radical, converted into a compound of general formula 1 by reaction with hydroxylamine hydrochloride.
The reaction is preferably carried out in a solvent and in the presence of basic substances. Particularly suitable solvents are solvents containing hydroxyl groups, such as e.g.
lower alkanols and water. Suitable basic substances are, for. B. alkali metal hydroxides such as sodium or potassium hydroxide, and also alkaline earth metal hydroxides such. B. calcium or barium hydroxide, or carbonates, which correspond to the alkali hydroxides mentioned. Preferably the hydroxylamine is used in excess as a mineral acid salt, e.g. B. as the hydrochloride, and the base is set free by excess alkali.
The starting compounds of general formula ii can be converted to the corresponding compound of general formula II by reacting 4-phenylimidazoles substituted in the benzene nucleus according to the definition for R1 and R2 with a lower alkyl nitrite (or with nitrous acid).
The new active ingredients (I) can be administered orally, rectally or parenterally. The daily doses range between 5060 (x) mg.
The following example explains the preparation of the new compounds of the general formula I and of intermediates not previously described, but is not intended to restrict the scope of the invention in any way. The temperatures are given in degrees Celsius.
example
0.5 g of 2-methyl-4-nitroso-5- (otolyl) imidazole is suspended in 4 ml of ethanol, and a solution of 0.3 g of hydroxylamine hydrochloride in 2 ml of water is added to this suspension. The mixture is heated to 900 in a water bath for 5 minutes, the green nitroso derivative going into solution. 0.3 ml of concentrated aqueous hydrochloric acid are added to the brown solution and the mixture is refluxed for 1 hour. After cooling, the alcohol is evaporated and the residue is extracted with water and ether. The organic phase is washed with water, dried with sodium sulfate, decolorized with activated charcoal, filtered and evaporated. The remaining crystals are recrystallized from isopropanol. This gives 3-amino 4- (oWtolyl) -furazan with a melting point of 888o.
3-Amino-4- (3,4xylyl) furazan, melting point 111-113, is obtained in an analogous manner.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1479370A CH498134A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan deriv prodn |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH167568A CH508650A (en) | 1968-02-06 | 1968-02-06 | Process for the production of new furazan derivatives |
| CH1479370A CH498134A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan deriv prodn |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH498134A true CH498134A (en) | 1970-10-31 |
Family
ID=4215963
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1479470A CH498135A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
| CH167568A CH508650A (en) | 1968-02-06 | 1968-02-06 | Process for the production of new furazan derivatives |
| CH1479370A CH498134A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan deriv prodn |
| CH1479570A CH498136A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
| CH1479670A CH498137A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1479470A CH498135A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
| CH167568A CH508650A (en) | 1968-02-06 | 1968-02-06 | Process for the production of new furazan derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1479570A CH498136A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
| CH1479670A CH498137A (en) | 1968-02-06 | 1968-02-06 | Pharmaceutical furazan derivs prodn |
Country Status (1)
| Country | Link |
|---|---|
| CH (5) | CH498135A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132680B1 (en) * | 1983-07-22 | 1987-01-28 | Bayer Ag | Substituted furazans |
| IT1196237B (en) * | 1984-08-29 | 1988-11-16 | Enichimica Secondaria | HEROCICLIC COMPOUNDS WITH HERBICIDE ACTIVITY |
| DE4217794A1 (en) * | 1992-05-29 | 1993-12-02 | Cassella Ag | Phenylfuroxane |
| DE4218582A1 (en) * | 1992-06-05 | 1993-12-09 | Cassella Ag | Pyridyl-1,2,5-oxadiazole-carbonamide-2-oxides |
| DE4220264A1 (en) * | 1992-06-20 | 1993-12-23 | Cassella Ag | Phenyl-1,2,5-oxadiazole-carbonamide-2-oxide |
| US5763457A (en) * | 1995-11-13 | 1998-06-09 | Eli Lilly And Company | Method for treating anxiety |
-
1968
- 1968-02-06 CH CH1479470A patent/CH498135A/en not_active IP Right Cessation
- 1968-02-06 CH CH167568A patent/CH508650A/en not_active IP Right Cessation
- 1968-02-06 CH CH1479370A patent/CH498134A/en not_active IP Right Cessation
- 1968-02-06 CH CH1479570A patent/CH498136A/en not_active IP Right Cessation
- 1968-02-06 CH CH1479670A patent/CH498137A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH498137A (en) | 1970-10-31 |
| CH498136A (en) | 1970-10-31 |
| CH508650A (en) | 1971-06-15 |
| CH498135A (en) | 1970-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |