NO116117B - - Google Patents
Info
- Publication number
- NO116117B NO116117B NO16777567A NO16777567A NO116117B NO 116117 B NO116117 B NO 116117B NO 16777567 A NO16777567 A NO 16777567A NO 16777567 A NO16777567 A NO 16777567A NO 116117 B NO116117 B NO 116117B
- Authority
- NO
- Norway
- Prior art keywords
- blood sugar
- production
- carbon atoms
- formula
- salts
- Prior art date
Links
- 239000008280 blood Substances 0.000 claims description 9
- 210000004369 blood Anatomy 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 244000265913 Crataegus laevigata Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- JWPWVPPTDSULMI-UHFFFAOYSA-N benzenesulfonamidothiourea Chemical class NC(=S)NNS(=O)(=O)C1=CC=CC=C1 JWPWVPPTDSULMI-UHFFFAOYSA-N 0.000 description 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- -1 traHigant Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Fremgangsmåte til fremstilling av nye benzolsulfonylsemikarbazider med blodsukkersenkende virkning. Process for the production of new benzenesulfonyl semicarbazides with blood sugar-lowering action.
Det er kjent at visse benzolsulfonylurinstoffderivater har blodsukkersenkende egenskaper og er egnet som per os administrerbare antidiabetika (sammenlikn f.eks. "Arzneimittelforschung", bind 8 It is known that certain benzenesulfonylurea derivatives have blood sugar-lowering properties and are suitable as per os administrable antidiabetics (compare e.g. "Arzneimittelforschung", vol. 8
(<1>95<8>) side 444-454). (<1>95<8>) pages 444-454).
Oppfinnelsens gjenstand er en fremgangsmåte til fremstilling av benzolsulfonyl-semikarbazider med den generelle formel The object of the invention is a process for the preparation of benzenesulfonyl semicarbazides with the general formula
hvori X betyr en alkylrest med 1 til 6 karbonatomer og -Z-Z'- betyr en alkylenkjede med 3 til 4 karbonatomer som eventuelt er substituert in which X means an alkyl residue with 1 to 6 carbon atoms and -Z-Z'- means an alkylene chain with 3 to 4 carbon atoms which is optionally substituted
med ytterligere lavmolekylære alkylrester, samt fremstilling av deres salter som er verdifulle legemidler og har gode blodsukkersenkende egenskaper. with additional low-molecular alkyl residues, as well as the production of their salts, which are valuable pharmaceuticals and have good blood sugar-lowering properties.
Man får fremgangsmåteproduktene ifølge oppfinnelsen fra de tilsvarende benzolsulfonyl-tiosemikarbazider ved avsvovling, eksempelvis ved hjelp av oksyder eller salter av tungmetaller eller også The process products according to the invention are obtained from the corresponding benzenesulfonyl-thiosemicarbazides by desulphurisation, for example with the help of oxides or salts of heavy metals or also
ved anvendelse av oksydasjonsmidler som hydrogenperoksyd, natriumper-oksyd og salpetersyrling. by using oxidizing agents such as hydrogen peroxide, sodium peroxide and nitric acid.
I utgangsstoffene kan substituenten X eksempelvis ha følgende betydning: o,m,p-metyl, o,m,p-etyl, o,m,p-(n)-propyl, o,m,p-isopropyl, o,m,p-n-butyl, o,m,p-isobutyl, o,m,p-tert. butyl, p-pentyl-(3)»p-isoamyl, p-tert.-amyl, p-n-heksyl. In the starting materials, the substituent X can for example have the following meaning: o,m,p-methyl, o,m,p-ethyl, o,m,p-(n)-propyl, o,m,p-isopropyl, o,m, p-n-butyl, o,m,p-isobutyl, o,m,p-tert. butyl, p-pentyl-(3)»p-isoamyl, p-tert-amyl, p-n-hexyl.
Substituenten -Z-Z'- betyr en 3-4 karbonatomholdig alkylenkjede som eventuelt er substituert med ytterligere lavmolekylære alkylrester, eksempelvis a,a-dimetyltrimetylen, tetrametylen, a,a-dimetyltetråmetylen. The substituent -Z-Z'- means a 3-4 carbon-containing alkylene chain which is optionally substituted with further low molecular weight alkyl residues, for example a,a-dimethyltrimethylene, tetramethylene, a,a-dimethyltetramethylene.
De ved fremgangsmåten ifølge oppfinnelsen oppnåelige benzolsulfonyl-semikarbazider, er verdifulle legemidler som spesielt utmerker seg ved en god blodsukkersenkende virkning med lav toksisitet. The benzenesulfonyl-semicarbazides obtainable by the method according to the invention are valuable drugs which are particularly distinguished by a good blood sugar-lowering effect with low toxicity.
Således kunne det med det ifølge oppfinnelsen fremstilte 4-(4-metylbenzolsulfonyl)-l,1-tetrametylen-semikarbazid ved kaniner allerede ved en applikasjon på 100 mg/kg kroppsvekt iakttas en 30%-ig blodsukkersenkning etter 6 timer. Blodsukkerverdien ble bestemt på vanlig måte etter Hagedorn/Jensen. Spesielt tydelig fremkom den gode virkning av forbindelsen ifølge oppfinnelsen ved en utprøvning i "terskeldosis-området". Ved "terskeldosis" forstår man da den minste virksomme stoffmengde i milligram pr. kg kroppsvekt av forsøksdyret som må tilføres intravenøst eller peroralt for å frembringe en markert blodsukkersenkning i sammenlikning med kontrolldyr som er holdt på samme måte. Det har nå vist seg at terskeldosen for benzolsulfonyl-semikarbazidene ifølge oppfinnelsen ligger meget lavt. Således er for kaniner en dosering på 1,25 til 2,5 mg av 4-(4-metylbenzolsulfonyl)-1,1-tetrametylen-semikarbazid ved intravenøs administrering og på 5 mg/kg ved. peroral applikasjon allerede tilstrekkelig for å frembringe en blodsukkersenkning. De under samme betingelser fastslåtte sammen-liknings-terskeldosisverdier for det kjente N-(4-metylbenzolsulfonyl)-N'-n-butyl-urinstoff, utgjør for kaniner ved peroral administrering Thus, with the 4-(4-methylbenzenesulfonyl)-1,1-tetramethylene-semicarbazide produced according to the invention, a 30% drop in blood sugar could be observed in rabbits already at an application of 100 mg/kg body weight after 6 hours. The blood sugar value was determined in the usual way according to Hagedorn/Jensen. The good effect of the compound according to the invention emerged particularly clearly in a test in the "threshold dose range". By "threshold dose" is meant the smallest effective amount of substance in milligrams per kg body weight of the experimental animal that must be administered intravenously or perorally to produce a marked lowering of blood sugar in comparison with control animals kept in the same way. It has now been shown that the threshold dose for the benzenesulfonyl semicarbazides according to the invention is very low. Thus, for rabbits a dosage of 1.25 to 2.5 mg of 4-(4-methylbenzenesulfonyl)-1,1-tetramethylene-semicarbazide by intravenous administration and of 5 mg/kg by. oral application is already sufficient to produce a lowering of blood sugar. The comparative threshold dose values determined under the same conditions for the known N-(4-methylbenzenesulfonyl)-N'-n-butyl urea for rabbits by oral administration amount to
35 mg/kg og ved intravenøs applikasjon 20 mg/kg. Dermed er altså 4-(4-metylbenzolsulfonyl )-l,1-tetrametylen-semikarbazid ved per os administrering syv ganger og ved intravenøs administrering åtte til seks ganger så virksom som den kjente sammenlikningsforbinctelse. 35 mg/kg and by intravenous application 20 mg/kg. Thus, 4-(4-methylbenzenesulfonyl)-1,1-tetramethylene-semicarbazide is seven times more effective when administered per os and eight to six times more effective when administered intravenously than the known comparative compound.
Fremgangsmåteproduktene viser på grunn av mangel påThe procedure products show due to lack of
en p-aminogruppe i benzolkjernen ingen effekt som kan sammenliknes med effekten av sulfonamidene (terapeutisk anvendt ved infeksjons-sykdommer) og ved årelang medikasjon er det derfor ikke å frykte for noen resistensforeteelse. Av samme grunn opptrer det heller ikke bi-virkninger som er å tilbakeføre på en ødeleggelse av tarmflora. a p-amino group in the benzene nucleus no effect that can be compared to the effect of the sulphonamides (therapeutically used in infectious diseases) and with years of medication there is therefore no fear of any resistance phenomenon. For the same reason, there are also no side effects that can be attributed to a destruction of intestinal flora.
Fremgangsmåteproduktene skal derfor fortrinnsvis tjene til fremstilling av oralt administrerbare preparater med hypoglykemisk virkning til behandling av diabetes mellitus, idet sulfonyl-semi-karbazidene kan anvendes såvel som sådanne eller i form av deres salter med baser eller syrer eller i nærvær av stoffer som fører til en saltdannelse. Til saltdannelsen kan det eksempelvis anvendes: alkaliske midler som alkali- eller jordalkalihydroksyder, -karbonater, -bikarbonater såvel som fysiologisk tålbare organiske baser; videre syrer som klorhydrogensyre, bromhydrogensyre, svovelsyre og amido-sulfonsyre. The process products should therefore preferably be used for the production of orally administrable preparations with hypoglycemic action for the treatment of diabetes mellitus, as the sulfonyl-semi-carbazides can be used as such or in the form of their salts with bases or acids or in the presence of substances that lead to a salt formation. For salt formation, for example, alkaline agents such as alkali or alkaline earth hydroxides, carbonates, bicarbonates as well as physiologically tolerable organic bases can be used; further acids such as hydrochloric acid, hydrobromic acid, sulfuric acid and amidosulfonic acid.
Som medisinske preparater kommer det fortrinnsvis i betraktning tabletter som ved siden av de i mengder på ca. 0,05 til 0,5 g pr. administreringsenhet inneholdte fremgangsmåteprodukter, inneholder de vanlige hjelpe- og bærestoffer som talkum, stivelse, melkesukker, traHigant, magnesiumstearat. As medicinal preparations, tablets are preferably taken into account which, in addition to those in quantities of approx. 0.05 to 0.5 g per administration unit contained process products, they contain the usual auxiliary and carrier substances such as talc, starch, milk sugar, traHigant, magnesium stearate.
Eksempel.Example.
4- ( 4- metylbenzolsulfonyl )- l, l- tetrametylen- semikarbazid.4-(4-methylbenzenesulfonyl)-l,l-tetramethylene-semicarbazide.
6,8 g kvikksølvklorid oppløses i 100 ml vann. Under omrøring tildrypper man 25 ml 2-n natronlut. Man får en fin suspensjon av kvikksølvoksyd. Under omrøring setter man til denne suspensjon 6 g 4-(4-metylbenzolsulfonyl)-l,l-:tetrametylen-tiosemikarbazid, smeltepunkt l87-l88°cf under spaltning^som man har oppløst i den beregnede mengde fortynnet natronlut. Etter 2 1/2 timers omrøring frafiltrerer man det dannede kvikksølvsulfid, klargjør filtratet med kull og surgjør med eddiksyre. Man får 3»4g 4-(4-metylbenzolsulfonyl)-l,l-tetrametylen-semikarbazid med smeltepunkt l80-l82°C etter omkrystallisering fra metanol/dimetylformamid. Dissolve 6.8 g of mercuric chloride in 100 ml of water. While stirring, add 25 ml of 2-n caustic soda. You get a fine suspension of mercuric oxide. While stirring, 6 g of 4-(4-methylbenzenesulfonyl)-1,1-:tetramethylene-thiosemicarbazide, melting point 187-188°c during cleavage, which has been dissolved in the calculated amount of dilute caustic soda, is added to this suspension. After stirring for 2 1/2 hours, the mercury sulphide formed is filtered off, the filtrate clarified with charcoal and acidified with acetic acid. 3.4 g of 4-(4-methylbenzenesulfonyl)-1,1-tetramethylene-semicarbazide with melting point 180-182°C is obtained after recrystallization from methanol/dimethylformamide.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34956A DE1204675B (en) | 1961-09-20 | 1961-09-20 | Process for the production of benzenesulfonyl-semicarbazides and their salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116117B true NO116117B (en) | 1969-02-03 |
Family
ID=7095793
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16777467A NO116116B (en) | 1961-09-20 | 1967-04-18 | |
| NO16777567A NO116117B (en) | 1961-09-20 | 1967-04-18 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16777467A NO116116B (en) | 1961-09-20 | 1967-04-18 |
Country Status (5)
| Country | Link |
|---|---|
| CH (3) | CH427799A (en) |
| DE (1) | DE1204675B (en) |
| FR (2) | FR2267M (en) |
| GB (1) | GB1010566A (en) |
| NO (2) | NO116116B (en) |
-
1961
- 1961-09-20 DE DEF34956A patent/DE1204675B/en active Pending
-
1962
- 1962-09-18 CH CH1101762A patent/CH427799A/en unknown
- 1962-09-18 CH CH1800066A patent/CH438312A/en unknown
- 1962-09-18 CH CH1800166A patent/CH438313A/en unknown
- 1962-09-20 GB GB35872/62A patent/GB1010566A/en not_active Expired
- 1962-12-18 FR FR918959A patent/FR2267M/en active Active
- 1962-12-18 FR FR918958A patent/FR2266M/en active Active
-
1967
- 1967-04-18 NO NO16777467A patent/NO116116B/no unknown
- 1967-04-18 NO NO16777567A patent/NO116117B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1204675B (en) | 1965-11-11 |
| CH427799A (en) | 1967-01-15 |
| CH438313A (en) | 1967-06-30 |
| FR2266M (en) | 1964-01-13 |
| FR2267M (en) | 1964-01-13 |
| GB1010566A (en) | 1965-11-17 |
| NO116116B (en) | 1969-02-03 |
| CH438312A (en) | 1967-06-30 |
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