NO155315B - PROCEDURE FOR THE COLLECTION AND EXAMINATION OF GASES DISSOLVED IN SEAWATER IN SMALL CONCENTRATIONS FOR THE PURPOSE AA FORECASTING THE HYDROCARBON POTENTIAL OF A FORM WHICH GIVES HYDROCARBONES. - Google Patents
PROCEDURE FOR THE COLLECTION AND EXAMINATION OF GASES DISSOLVED IN SEAWATER IN SMALL CONCENTRATIONS FOR THE PURPOSE AA FORECASTING THE HYDROCARBON POTENTIAL OF A FORM WHICH GIVES HYDROCARBONES. Download PDFInfo
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- NO155315B NO155315B NO811063A NO811063A NO155315B NO 155315 B NO155315 B NO 155315B NO 811063 A NO811063 A NO 811063A NO 811063 A NO811063 A NO 811063A NO 155315 B NO155315 B NO 155315B
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- hydrocarbones
- forecasting
- seawater
- examination
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- 238000000034 method Methods 0.000 title claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 title 1
- 239000007789 gas Substances 0.000 title 1
- 229930195733 hydrocarbon Natural products 0.000 title 1
- 150000002430 hydrocarbons Chemical class 0.000 title 1
- 239000013535 sea water Substances 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 5
- 150000005309 metal halides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 7
- -1 alkanoyl halide Chemical class 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003216 chloruretic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01V—GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS
- G01V9/00—Prospecting or detecting by methods not provided for in groups G01V1/00 - G01V8/00
- G01V9/007—Prospecting or detecting by methods not provided for in groups G01V1/00 - G01V8/00 by detecting gases or particles representative of underground layers at or near the surface
Landscapes
- Engineering & Computer Science (AREA)
- Remote Sensing (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Geophysics (AREA)
- Sampling And Sample Adjustment (AREA)
- Investigating Or Analyzing Materials By The Use Of Electric Means (AREA)
Description
Fremgangsmåte ved fremstilling av terapeutisk virksomme alkylidensubstituerte carboxylsyrer. Process for the production of therapeutically effective alkylidene-substituted carboxylic acids.
Foreliggende oppfinnelse angår en ny fremgangsmåte ved fremstilling av en klasse kjernesubstituerte fenoxyeddiksyrer med sterkt aktive diuretiske egenskaper. The present invention relates to a new process for the production of a class of core-substituted phenoxyacetic acids with highly active diuretic properties.
Farmakologiske studier av produktene Pharmacological studies of the products
fremstilt ifølge foreliggende oppfinnelse vi-ser at i mange tilfelle har de den ene-stående egenskap at de bevirker utskillelse av mere elektrolytt enn kan bevirkes utskilt av kjente diuretika. På grunn av denne egenskap er de nyttige ved terapi for behandling av tilstander som skyldes en ual-mindelig høy tilbakeholdelse av elektrolytt eller væske i legemet, såsom ved behandling av vatersott-tilstander som skyldes for eksempel congenstiv hjertefeil. produced according to the present invention shows that in many cases they have the unique property that they cause excretion of more electrolyte than can be caused to be excreted by known diuretics. Because of this property, they are useful in therapy for the treatment of conditions due to an unusually high retention of electrolyte or fluid in the body, such as in the treatment of dropsy conditions due to, for example, congestive heart failure.
Produktene som fremstilles ved foreliggende fremgangsmåte er [4-(2-alkylidenalkanoyl)-fenoxy]-eddiksyrer med føl-gende strukturformel I: The products produced by the present process are [4-(2-alkylidenealkanoyl)-phenoxy]-acetic acids with the following structural formula I:
hvor where
R er ethyl, og X2 og X3 er enten begge methyl, eller den ene er halogen og den R is ethyl, and X2 and X3 are either both methyl, or one is halogen and the
annen methyl, eller R er isopropyl og X* og X» er begge klor, og disse forbindelsers syreaddisjonssalter. Disse forbindelser oppviser særlig gode diuretiske, natriure-tiske og kloruretiske egenskaper og er således særlig nyttige midler ved behandling av tilstander forbundet med elektrolytt- og væskeretensjon. other methyl, or R is isopropyl and X* and X» are both chlorine, and the acid addition salts of these compounds. These compounds exhibit particularly good diuretic, natriuretic and chloruretic properties and are thus particularly useful agents in the treatment of conditions associated with electrolyte and fluid retention.
Ved foreliggende fremgangsmåte fremstilles ovenstående forbindelser ved å omsette en forbindelse av formelen II: In the present method, the above compounds are prepared by reacting a compound of the formula II:
hvor R er som ovenfor angitt, og X er where R is as above, and X is
halogen, med en forbindelse av formelen halogen, with a compound of the formula
III: III:
hvor X2 og X3 er som ovenfor angitt, i nærvær av et metallhalogenid, og om ønskes, fremstilles syreaddisjonssaltene på i og for seg kjent vis. Den følgende ligning illustrerer reaksjonen: hvor R, X^ og X<3> er som ovenfor angitt, X er halogen, f. eks. klor, brom, etc., og MX er et metallhalogenid. Metallhalogenidene virker som katalysatorer ved å fremme kondensasjonen av alkanoylhalogenidreak-tanten med fenoxy-eddiksyre-forbindelsen. Katalysatorer som har vist seg å være særlig egnet for dette formål innbefatter vannfritt aluminiumklorid og bortrifluorid. where X2 and X3 are as indicated above, in the presence of a metal halide, and if desired, the acid addition salts are prepared in a manner known per se. The following equation illustrates the reaction: where R, X^ and X<3> are as indicated above, X is halogen, e.g. chlorine, bromine, etc., and MX is a metal halide. The metal halides act as catalysts by promoting the condensation of the alkanoyl halide reactant with the phenoxy-acetic acid compound. Catalysts which have been found to be particularly suitable for this purpose include anhydrous aluminum chloride and boron trifluoride.
Reaksjonsoppløsningsmidlet og tempe-raturen ved hvilken reaksjonen utføres, er ikke særlig kritiske forhold ved oppfinnelsen da et hvilket som helst oppløs-ningsmiddel som er inert overfor syrehalo-genidene og fenoxyeddiksyrereaktantene og metallhalogenidkatalysatoren kan anvendes med godt resultat, og reaksjons-temperaturen kan varieres for å få den ønskede reaksjonshastighet. Det har imid-lertid vist seg at carbondisulfid og petrol-ether er særlig egnede oppløsningsmidler i hvilke reaksjonen kan utføres og at reaksjonen foregår mest fordelaktig ved svak oppvarmning som f. eks. ved tilbakeløps-temperaturene ved oppvarmning på dampbad. The reaction solvent and the temperature at which the reaction is carried out are not particularly critical aspects of the invention as any solvent which is inert to the acid halides and the phenoxyacetic acid reactants and the metal halide catalyst can be used with good results, and the reaction temperature can be varied to get the desired reaction rate. However, it has been shown that carbon disulphide and petrol ether are particularly suitable solvents in which the reaction can be carried out and that the reaction takes place most advantageously with mild heating such as e.g. at the return temperatures when heating in a steam bath.
[4 (2-alkylidenalkanoyl) -f enoxy] -eddik-syreforbindelsene som fremstilles ved foreliggende fremgangsmåte fåes i alminnelig-het som krystallinske faste stoffer og om ønskes kan de renses ved omkrystallisasjon fra et oppløsningsmiddel. Egnede oppløs-ningsmidler innbefatter f. eks. methylcyclohexan, n-butyl-klorid og en blanding av benzen og cyclohexan. The [4(2-alkylidenealkanoyl)-phenoxy]-acetic acid compounds produced by the present process are generally obtained as crystalline solids and, if desired, they can be purified by recrystallization from a solvent. Suitable solvents include e.g. methylcyclohexane, n-butyl chloride and a mixture of benzene and cyclohexane.
Syrehalogenidreaktantene i fremgangsmåten fremstilles lett ved konvensjonelle metoder. Eksempelvis reagerer de tilsvarende syrer av 2-alkyliden-alkansyrehalo-genidene med fosfortriklorid eller thionyl-klorid under dannelse av det ønskede 2-alkyliden-substituerte alkanoylklorid. En modifikasjon av denne syrehalogenidsyn-tese består først i å danne det tilsvarende natriumsalt av alkansyren og omsette dette salt med fosforoxyklorid eller thio-nylklorid for å danne det ønskede 2-alkyli-den-substituerte alkanoylklorid. The acid halide reactants in the process are easily prepared by conventional methods. For example, the corresponding acids of the 2-alkylidene-alkanoyl halides react with phosphorus trichloride or thionyl chloride to form the desired 2-alkylidene-substituted alkanoyl chloride. A modification of this acid halide synthesis consists first in forming the corresponding sodium salt of the alkanoic acid and reacting this salt with phosphorus oxychloride or thionyl chloride to form the desired 2-alkylidene-substituted alkanoyl chloride.
Følgende eksempler vil belyse foreliggende fremgangsmåte. The following examples will illustrate the present method.
Eksempel 1. Example 1.
[ 2, 3- dimethyl- 4- ( 2- methylenbutyryl) - [ 2, 3- dimethyl- 4-( 2- methylenebutyryl)-
f enoxy]- eddiksyre. f enoxy]- acetic acid.
Til en oppløsning av 18 g (0,1 mol) 2,3-dimetyl-fenoxy)-eddiksyre og 11,8 g (0,1 mol) 2-ethylacryloylklorid i 200 ml carbondisulfid, tilsettes 39,9 g (0,3 mol) aluminiumklorid i små porsjoner under vannfrie betingelser under omrøring. Efter alt aluminiumklorid er tilsatt, oppvarmes blandingen på dampbad i 3 timer eller inntil utvikling av hydrogenklorid opp-hører. Blandingen avkjøles så, carbondi-sulfidet dekanteres og is og konsentrert saltsyre tilsettes til residuet. Det organiske skikt ekstraheres med ether. Etheroppløs-ningen ekstraheres så med natriumbicar-bonatoppløsning og etheren kastes. Bicar-bonatekstraktet syres og det faste stoff som skilles ut, samles opp, tørkes og kry-stalliseres fra methylcyclohexan for å få rent [2,3-dimethyl-4- (2-methylenbutytyl) - fenoxy]-eddiksyre med smeltepunkt 83,5 — 84,5°C (korrigert). 39.9 g (0.3 mol) of aluminum chloride in small portions under anhydrous conditions with stirring. After all the aluminum chloride has been added, the mixture is heated on a steam bath for 3 hours or until the evolution of hydrogen chloride ceases. The mixture is then cooled, the carbon disulfide is decanted and ice and concentrated hydrochloric acid are added to the residue. The organic layer is extracted with ether. The ether solution is then extracted with sodium bicarbonate solution and the ether is discarded. The bicarbonate extract is acidified and the solid which separates out is collected, dried and crystallized from methylcyclohexane to obtain pure [2,3-dimethyl-4-(2-methylenebutylethyl)-phenoxy]-acetic acid of melting point 83.5 — 84.5°C (corrected).
Ved å følge praktisk talt samme fremgangsmåte som beskrevet i eksempel 1 ble også [4-(2-alkyliden-alkanoyl)-fenoxy] - eddiksyreforbindelsene angitt i tabell 1, fremstilt. Ligningen foran tabellen illustrerer fremgangsmåten i eksempel 1: By following practically the same procedure as described in example 1, the [4-(2-alkylidene-alkanoyl)-phenoxy]-acetic acid compounds indicated in table 1 were also prepared. The equation in front of the table illustrates the procedure in example 1:
Oppfinnelsen angår også syreaddisjonssalter av disse fenoxyeddiksyrer som fremstilles ved omsetning av disse syrer med en base med en ikke-giftig farmako-logisk mottagbar kation. I almindelighet vil en hvilken som helst base som danner et syreaddisjonssalt med en carboxylsyre og hvis farmakologiske egenskaper ikke vil ha noen uheldig fysiologisk virkning når den opptaes av legemet, komme innenfor rammen av foreliggende oppfinnelse. Egnede baser innbefatter således f. eks. al-kalimetall- og jordalkalimetallhydroxyder, The invention also relates to acid addition salts of these phenoxyacetic acids which are prepared by reacting these acids with a base with a non-toxic pharmacologically acceptable cation. In general, any base which forms an acid addition salt with a carboxylic acid and whose pharmacological properties will not have any adverse physiological effect when absorbed by the body will come within the scope of the present invention. Suitable bases thus include e.g. alkali metal and alkaline earth metal hydroxides,
-carbonater, etc., ammoniakk, primære, sekundære og tertiære aminer, såsom mo-noalkylaminer, dialkylaminer, trialkyl- -carbonates, etc., ammonia, primary, secondary and tertiary amines, such as monoalkylamines, dialkylamines, trialkyl-
aminer, nitrogenholdige heterocykliske amines, nitrogen-containing heterocyclic
aminer, f. eks. piperidin, etc. De således amines, e.g. piperidine, etc. They thus
fremstilte syreaddisjonssalter er de funk-sjonelle ekvivalenter av de tilsvarende fenoxyeddiksyrer, og en fagmann vil innse at acid addition salts prepared are the functional equivalents of the corresponding phenoxyacetic acids, and one skilled in the art will recognize that
i den utstrekning fenoxyeddiksyrene ifølge to the extent that the phenoxyacetic acids according
oppfinnelsen er nyttige i terapi, vil de for-skjellige syreaddisjonssalter som omfattes invention are useful in therapy, the various acid addition salts which are included
av foreliggende oppfinnelse, bare begrenset of the present invention, limited only
av det kriterium at basene som anvendes of the criterion that the bases used
ved fremstilling av saltene, må være så vel in the preparation of the salts, must be as well
ikke-giftige som fysiologisk godtagbare. non-toxic as physiologically acceptable.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13502680A | 1980-03-28 | 1980-03-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO811063L NO811063L (en) | 1981-09-29 |
| NO155315B true NO155315B (en) | 1986-12-01 |
| NO155315C NO155315C (en) | 1987-03-11 |
Family
ID=22466164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811063A NO155315C (en) | 1980-03-28 | 1981-03-27 | PROCEDURE FOR THE COLLECTION AND EXAMINATION OF GASES DISSOLVED IN SEAWATER IN SMALL CONCENTRATIONS FOR THE PURPOSE AA FORECASTING THE HYDROCARBON POTENTIAL OF A FORM WHICH GIVES HYDROCARBONES. |
Country Status (5)
| Country | Link |
|---|---|
| BR (1) | BR8101849A (en) |
| GB (2) | GB2074726B (en) |
| IT (1) | IT1137438B (en) |
| MX (1) | MX7351E (en) |
| NO (1) | NO155315C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792526A (en) * | 1982-12-21 | 1988-12-20 | Union Oil Company Of California | Method for collecting and analyzing hydrocarbons |
| DE4021465A1 (en) * | 1990-07-05 | 1992-01-16 | Kettel Dirk | METHOD FOR DETECTING THE NATURAL GAS POTENTIAL IN SEDIMENT POOLS AND DERIVING THE PETROLEUM POTENTIAL THEREOF |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB585322A (en) * | 1945-02-21 | 1947-02-04 | John David Main Smith | Improvements in or relating to apparatus for colorimetric gas investigation |
-
1981
- 1981-03-26 GB GB8109591A patent/GB2074726B/en not_active Expired
- 1981-03-27 MX MX819376U patent/MX7351E/en unknown
- 1981-03-27 BR BR8101849A patent/BR8101849A/en not_active IP Right Cessation
- 1981-03-27 NO NO811063A patent/NO155315C/en unknown
- 1981-03-27 IT IT20771/81A patent/IT1137438B/en active
-
1983
- 1983-09-15 GB GB08324733A patent/GB2137339B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2137339A (en) | 1984-10-03 |
| GB2074726B (en) | 1984-10-24 |
| GB2074726A (en) | 1981-11-04 |
| NO811063L (en) | 1981-09-29 |
| GB2137339B (en) | 1985-05-01 |
| IT8120771A0 (en) | 1981-03-27 |
| GB8324733D0 (en) | 1983-10-19 |
| BR8101849A (en) | 1981-09-29 |
| IT1137438B (en) | 1986-09-10 |
| NO155315C (en) | 1987-03-11 |
| MX7351E (en) | 1988-07-19 |
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