NO161017B - Broennmotor for avviksboring. - Google Patents
Broennmotor for avviksboring. Download PDFInfo
- Publication number
- NO161017B NO161017B NO834173A NO834173A NO161017B NO 161017 B NO161017 B NO 161017B NO 834173 A NO834173 A NO 834173A NO 834173 A NO834173 A NO 834173A NO 161017 B NO161017 B NO 161017B
- Authority
- NO
- Norway
- Prior art keywords
- benzenesulfonyl
- acids
- semicarbazides
- drilling
- division
- Prior art date
Links
- 238000005553 drilling Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 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
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 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
- 239000000155 melt Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003178 anti-diabetic effect Effects 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
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B7/00—Special methods or apparatus for drilling
- E21B7/04—Directional drilling
- E21B7/06—Deflecting the direction of boreholes
- E21B7/068—Deflecting the direction of boreholes drilled by a down-hole drilling motor
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B4/00—Drives for drilling, used in the borehole
- E21B4/02—Fluid rotary type drives
Landscapes
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Mining & Mineral Resources (AREA)
- Physics & Mathematics (AREA)
- Environmental & Geological Engineering (AREA)
- Fluid Mechanics (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Mechanical Engineering (AREA)
- Earth Drilling (AREA)
- Drilling And Boring (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Permanent Field Magnets Of Synchronous Machinery (AREA)
- Hydraulic Motors (AREA)
- Perforating, Stamping-Out Or Severing By Means Other Than Cutting (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Cylinder Crankcases Of Internal Combustion Engines (AREA)
- Sheet Holders (AREA)
- Paper (AREA)
Description
Fremgangsmåte til fremstilling av benzolsulfonylsemikarbazider med blodsukkersenkende virkning.
Det er kjent at visse benzolsulfonyl-urinstoffderivater har blodsukkersenkende
egenskaper og er egnet 'som per os admi-nistrerbare antidiabetika (sammenlign f.
eks. Arzneimittelforschung, bind 8 (1958),
sidene 444—454).
Det er nu blitt funnet at benzolsulfonylsemikarbazider med den generelle formel
hvori X er en 1 til 6 karbonatomholdig
alkylrest i orto- eller meta-stilling, og Z-Z'-er en 5 karbonatomholdig alkylenkjede som
eventuelt kan være substituert med ytterligere lavmolekylære alkylrester, samt deres salter, har blodsukkersenkende egenskaper.
Oppfinnelsens gjenstand er en fremgangsmåte til fremstilling av slike benzolsulfonylsemikarbazider.
Ifølge oppfinnelsen fremstilles de fra l-benzolsulfonyl-3-alkylen-iminopara-bansyrer som spaltes hydrolytisk til de
ønskede fremgangsmåteprodukter.
Utgangsstoffene kan oppnås ved at det anvendes tilsvarende orto- og meta-alkyl-benzolsulfonylhalogenider som omsettes i
et egnet indifferent oppløsningsmiddel, eksempelvis benzol i nærvær av tertiære
baser som trietylamin med tilsvarende al-kyleniminoparabansyrer.
Utførelsesformen av fremgangsmåten ifølge oppfinnelsen er sterkt varierbare
med hensyn til reaksjonsbetingelser. Eksempelvis kan omsetningene gjennomføres under anvendelse av oppløsningsmidler med forhøyet temperatur.
Den hydrolytiske spaltning av de så-ledes dannede l-benzolsulfonyl-3-alkylen-iminoparabansyrer foregår hensiktsmessig ved kort oppvarmning med alkalilut, eksempelvis med natronlut.
De ved fremgangsmåten ifølge oppfinnelsen dannede benzolsulfonylsemikarbazider er verdifulle legemidler som spesielt utmerker seg ved god blodsukkersenkende virkning med liten toksisitet.
Som det fremgår av følgende tabell inntrer det allerede etter peroral admi-nistrering av det ifølge oppfinnelsen frem-stilte 4-(3-etyl-benzolsulfonyl)-l,l-penta-metylen-semikarbazid i mengder på 100 mg/kg etter 6 timer en 33 pst.-ig blod-sukkersenkning på kaniner.
Også det på samme måte i mengder på 400 mg/kg appliserte 4-(2-metyl-ben-zolsulf onyl) -1,1 -pentametylen-semikarba-zid utmerker seg ved en meget god blodsukkersenkende virkning:
Fremgangsmåteproduktene skal fortrinnsvis tjene til fremstilling av oralt ad-ministrerbare preparater med hypoglyke-misk virkning til behandling av diabetes mellitus, idet sulfonylsemikarbazidene 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 saltdannelse kan det eksempelvis anvendes: alkaliske midler som alkali- eller jordalkalihydroksyder, -kar-bonater, -bikarbonater, såvel som fysiolo-gisk tålbare organiske baser, videre syrer som klorhydrogensyre, bromhydrogensyre, svovelsyre og amidosulfonsyre.
Som medisinske preparater kommer det fortrinnsvis i betraktning tabletter som ved siden av de i mengder fra 0,05 til 0,5 g pr. administrerbarsenhet inneholdte fremgangsmåteprodukter inneholder de vanlige hjelpe- og bærestoffer som talkum, stivelse, melkesukker, tragant, magnesiumstearat.
Eksempel.
4-( 3- metyl- benzolsulfonyl)- l, l-pentametylen- semikarbazid.
a) 19,7 g pentametyleniminoparaban-syre (fremstillet ved omsetning av 1,1-pentametylensemikarbazid og oksalylklo-rid, smeltepunkt 136—138°C) suspenderes i 250 ml benzol og blandes med 10 g trietylamin. Det inntrer oppløsning. Deretter tilsetter man 19 g 3-metyl-benzolsulfoklo-rid og oppvarmer i 2 timer under tilbake-løp til koking. De utskilte krystaller av-suges etter lengere henstand, vaskes med vann og tørkes. l-(3-metyl-benzolsulfo-nyl)-3-pentametylen-iminoparabansyre
smelter ved 193—195°C. b) 3,5 g av det rå parabansyrederi-vat oppvarmes med 80 ml helnormal natronlut på dampbad. Etter kort tid inntrer oppløsning, deretter utskiller det seg krystaller. Man frasuger natriumsalt, vasker med aceton, oppløser i vann og feller ved surgjøring med eddiksyre. 4-(3-metyl-ben-zolsulfonyl)-l,l-pentametylen-semikarb-azid smelter etter omkrystallisering fra metanol ved 156—158°C.
Claims (1)
- Fremgangsmåte til fremstilling av blodsukkersenkende benzolsulfonylsemikarbazider med den generelle formelhvori X betyr en 1 til 6 karbonatomholdig alkylrest i orto- eller meta-stilling, og -Z-Z'- betyr en 5 karbonatomholdig alkylenkjede, som eventuelt kan være substituert med ytterligere lavmolekylære alkylrester, samt deres salter, karakterisert ved at man spalter hydrolytisk i benzolkjernen tilsvarende substituerte 1-benzolsulfonyl-3-alkylenimino-paraban-syrer, og behandler eventuelt de dannede benzolsulfonylsemikarbazider med fysiolo-gisk tålbare baser eller syrer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8232755 | 1982-11-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO834173L NO834173L (no) | 1984-05-18 |
| NO161017B true NO161017B (no) | 1989-03-13 |
| NO161017C NO161017C (no) | 1989-06-21 |
Family
ID=10534312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834173A NO161017C (no) | 1982-11-17 | 1983-11-15 | Broennmotor for avviksboring. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4492276A (no) |
| EP (1) | EP0109699B1 (no) |
| AT (1) | ATE23601T1 (no) |
| CA (1) | CA1212098A (no) |
| DE (1) | DE3367646D1 (no) |
| DK (1) | DK157251C (no) |
| NO (1) | NO161017C (no) |
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| USRE33751E (en) * | 1985-10-11 | 1991-11-26 | Smith International, Inc. | System and method for controlled directional drilling |
| GB8607701D0 (en) * | 1986-03-27 | 1986-04-30 | Shell Int Research | Rotary drill bit |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1954166A (en) * | 1931-07-31 | 1934-04-10 | Grant John | Rotary bit |
| US2336336A (en) * | 1942-08-13 | 1943-12-07 | John A Zublin | Rotary turbine bit |
| FR1252703A (fr) * | 1959-12-21 | 1961-02-03 | Neyrpic Ets | Raccord coudé à action hydraulique utilisable dans le forage du sol |
| SU1361283A1 (ru) * | 1960-05-09 | 1987-12-23 | С.Л. Залкин и М.Т. Гусман | Устройство дл ступенчатого вращательного бурени |
| US3260318A (en) * | 1963-11-12 | 1966-07-12 | Smith Ind International Inc | Well drilling apparatus |
| US3667556A (en) * | 1970-01-05 | 1972-06-06 | John Keller Henderson | Directional drilling apparatus |
| US4319649A (en) * | 1973-06-18 | 1982-03-16 | Jeter John D | Stabilizer |
| US3903974A (en) * | 1974-03-12 | 1975-09-09 | Roy H Cullen | Drilling assembly, deviation sub therewith, and method of using same |
| US4067404A (en) * | 1976-05-04 | 1978-01-10 | Smith International, Inc. | Angle adjustment sub |
| FR2369412A1 (fr) * | 1976-11-02 | 1978-05-26 | Alsthom Atlantique | Procede et dispositif de forage dirige |
| SE410753B (sv) * | 1978-03-06 | 1979-10-29 | Haglund Mats Torbjorn | Anordning for att styra en borrkrona i en bestemd bana |
| US4261425A (en) * | 1979-08-06 | 1981-04-14 | Bodine Albert G | Mechanically nutating drill driven by orbiting mass oscillator |
| US4271915A (en) * | 1979-08-06 | 1981-06-09 | Bodine Albert G | Elastically vibratory longitudinal jacketed drill |
| GB2059481B (en) * | 1979-09-21 | 1983-03-16 | Shell Int Research | Hydraulically powered drilling sub for deepwell drilling |
-
1983
- 1983-10-13 US US06/541,821 patent/US4492276A/en not_active Expired - Lifetime
- 1983-10-18 EP EP83201502A patent/EP0109699B1/en not_active Expired
- 1983-10-18 DE DE8383201502T patent/DE3367646D1/de not_active Expired
- 1983-10-18 AT AT83201502T patent/ATE23601T1/de not_active IP Right Cessation
- 1983-10-24 CA CA000439550A patent/CA1212098A/en not_active Expired
- 1983-11-15 NO NO834173A patent/NO161017C/no not_active IP Right Cessation
- 1983-11-15 DK DK520883A patent/DK157251C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3367646D1 (en) | 1987-01-02 |
| NO161017C (no) | 1989-06-21 |
| ATE23601T1 (de) | 1986-11-15 |
| DK157251C (da) | 1990-04-30 |
| EP0109699B1 (en) | 1986-11-12 |
| CA1212098A (en) | 1986-09-30 |
| DK157251B (da) | 1989-11-27 |
| DK520883D0 (da) | 1983-11-15 |
| US4492276A (en) | 1985-01-08 |
| EP0109699A2 (en) | 1984-05-30 |
| US4492276B1 (no) | 1991-07-30 |
| DK520883A (da) | 1984-05-18 |
| NO834173L (no) | 1984-05-18 |
| EP0109699A3 (en) | 1984-10-10 |
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| MM1K | Lapsed by not paying the annual fees |
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