NO143795B - CHEMICAL INTERMEDIATE FOR USE IN THE PREPARATION OF THERAPEUTIC ACTIVE 2,6-METHAN-3-BENZAZOSINES - Google Patents
CHEMICAL INTERMEDIATE FOR USE IN THE PREPARATION OF THERAPEUTIC ACTIVE 2,6-METHAN-3-BENZAZOSINES Download PDFInfo
- Publication number
- NO143795B NO143795B NO742973A NO742973A NO143795B NO 143795 B NO143795 B NO 143795B NO 742973 A NO742973 A NO 742973A NO 742973 A NO742973 A NO 742973A NO 143795 B NO143795 B NO 143795B
- Authority
- NO
- Norway
- Prior art keywords
- used according
- benzazosines
- methan
- preparation
- compounds used
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000126 substance Substances 0.000 title description 4
- 230000001225 therapeutic effect Effects 0.000 title 1
- 241000238631 Hexapoda Species 0.000 claims description 10
- 241000238876 Acari Species 0.000 claims description 7
- 230000000590 parasiticidal effect Effects 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002297 parasiticide Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- 241001124076 Aphididae Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- -1 alkyl radical Chemical class 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XXDAXUSYDPWTPK-UHFFFAOYSA-N 2-(oxo-lambda5-phosphanylidyne)acetic acid Chemical class P(=O)#CC(=O)O XXDAXUSYDPWTPK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 241001600407 Aphis <genus> Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Conveying And Assembling Of Building Elements In Situ (AREA)
Description
Insekticide og acaricide preparater. Insecticide and acaricide preparations.
Foreliggende oppfinnelse angår insekticide og acaricide preparater som inneholder visse derivater av fosforyleddiksyre, enten som eneste aktive bestanddel eller sammen med andre stoffer med parasiticid virkning. The present invention relates to insecticidal and acaricidal preparations containing certain derivatives of phosphorylacetic acid, either as the only active ingredient or together with other substances with parasiticidal action.
Det er tidligere angitt (i norsk patentskrift nr. 80 467) at forbindelser med den generelle formel It has previously been stated (in Norwegian patent document no. 80 467) that compounds with the general formula
(hvor R, og R, er alkyl-, aralkyl- eller arylradikaler, R.t og R, er vannstoff eller alkyl-, hydroksyalkyl-, aryl- eller nitro-arylradikaler, X,, XL, og X;! er svovel eller oxygen, og m et helt lite tall) er egnet til bekjempelse av skadedyr, inkl. insekter gnagere og sopparter. (where R, and R, are alkyl, aralkyl or aryl radicals, R.t and R, are hydrogen or alkyl, hydroxyalkyl, aryl or nitro-aryl radicals, X,, XL, and X;! is sulfur or oxygen, and with a very small number) are suitable for combating pests, including insects, rodents and fungal species.
Det er nu funnet at alkyl-merkapto-metylenamider av 0,0-dialkyl-tio- eller ditio-fosforyleddiksyrer, med den generelle formel: It has now been found that alkyl-mercapto-methylene amides of 0,0-dialkyl-thio- or dithio-phosphoryl diacids, with the general formula:
(i hvilken R betegner et uforgrenet eller forgrenet, mettet lavere alkylradikal, R' betegner et lavere alkylradikal, og X betegner oxygen eller svovel), har en sterk insekticid og acaricid virkning, men er meget lite giftig overfor varmblodige dyr. Disse derivater er derfor godt egnet til anvendel- (in which R denotes an unbranched or branched, saturated lower alkyl radical, R' denotes a lower alkyl radical, and X denotes oxygen or sulphur), has a strong insecticidal and acaricidal effect, but is very little toxic to warm-blooded animals. These derivatives are therefore well suited for application
se i preparater for bekjempelse av insek- see in preparations for combating insects
ter og midd. mites and mites.
Disse forbindelser er krystallinske stof- These compounds are crystalline substances
fer med lavt smeltepunkt, eller væsker. De er oppløselige i de fleste organiske oppløs-ningsmidler, men i alminnelighet uopplø-selige i vann. En fremgangsmåte til frem-stilling av forbindelsene er beskrevet i pa-tentinnehaverens østerrikske patent nr. 206 446. fer with a low melting point, or liquids. They are soluble in most organic solvents, but generally insoluble in water. A method for producing the compounds is described in the patent holder's Austrian patent no. 206 446.
De insekticide og acaricide preparater ifølge oppfinnelsen er følgelig karakterisert ved at de fnneholder et eller flere 0,0-dialkyl-tio- eller ditio-fosforyleddiksyre-alkyl-metylenamider med den ovenfor angitte generelle formel. The insecticidal and acaricidal preparations according to the invention are consequently characterized in that they contain one or more 0,0-dialkyl-thio- or dithio-phosphorylacetic acid-alkyl-methylene amides with the above-mentioned general formula.
Disse preparater kan foreligge enten som eneste aktive bestanddel eller sammen med et eller flere andre parasiticide stoffer, som insekticider og/eller fungicider. Preparatene kan foreligge som oppløsnin-ger i passende oppløsningsmidler, som sus-pensjoner i vann og/eller andre væsker og/ eller i blanding med inerte faste bærere eller fortynningsmidler og/eller et eller flere gjødningsstoffer. These preparations can be present either as the only active ingredient or together with one or more other parasiticidal substances, such as insecticides and/or fungicides. The preparations can be present as solutions in suitable solvents, as suspensions in water and/or other liquids and/or in admixture with inert solid carriers or diluents and/or one or more fertilisers.
Følgende forbindelser har vist seg å ha en særlig sterk insekticid og acaricid virkning: The following compounds have been shown to have a particularly strong insecticidal and acaricidal effect:
Som det fremgår av nedenstående tabeller i hvilke virkningen mot afider og midd av forbindelser som anvendes ifølge foreliggende oppfinnelse, sammenlignes med sådan virkning av forbindelser soni anvendes ifølge det foran nevnte norske patentskrift 80 467, er forbindelser som anvendes ifølge oppfinnelsen, betydelig bedre egnet til bekjempelse av nevnte skadedyr enn forbindelsene som anvendes iføl-ge det norske patentskrift: As can be seen from the tables below, in which the effect against aphids and mites of compounds used according to the present invention is compared with such effect of compounds used according to the above-mentioned Norwegian patent document 80 467, compounds used according to the invention are significantly better suited for combating of said pests than the compounds used according to the Norwegian patent document:
De ovenfor angitte data gir som midlere dose som frembringer 95 pst.'s dødelig-het (LD 95) for forbindelsene som anvendes ifølge oppfinnelsen, en verdi på 0,00332, mens de for forbindelsene som anvendes ifølge norsk patent 80 467, gir en midlere LD 95-dose på 0,00633, med andre ord aktiviteten av forbindelsene • som anvendes ifølge foreliggende oppfinnelse, er nær den dobbelte av aktiviteten av forbindelsene som anvendes ifølge det norske patentskrift. The above-mentioned data gives as average dose which produces 95 percent mortality (LD 95) for the compounds used according to the invention, a value of 0.00332, while for the compounds used according to Norwegian patent 80 467, they give a average LD 95 dose of 0.00633, in other words the activity of the compounds used according to the present invention is close to double the activity of the compounds used according to the Norwegian patent document.
Hva særlig angår virkningen mot afider ved lokal rotabsorpsjon henholdsvis virkningen mot midd ved kontakt, gir tabellen en midlere LD 95-verdi for forbindelsene som anvendes ifølge oppfinnelsen, mot afider på 27,4, og for forbindelsene som anvendes ifølge patentet, på 40, mens LD 95-verdiene for virkningen mot midd er 0,0028 for forbindelsene som anvendes ifølge oppfinnelsen, og 0,017 for forbindelsene som anvendes ifølge patentet. With particular regard to the effect against aphids by local root absorption and the effect against mites by contact, the table gives an average LD 95 value for the compounds used according to the invention against aphids of 27.4, and for the compounds used according to the patent, of 40, while The LD 95 values for the action against mites are 0.0028 for the compounds used according to the invention, and 0.017 for the compounds used according to the patent.
Også forholdet insekticid aktivitet : Also the ratio insecticidal activity :
giftighet overfor varmblodige dyr er større for forbindelsene som anvendes, ifølge oppfinnelsen enn for forbindelsene som anvendes ifølge norsk patent 80 467, som det fremgår av nedenstående tabell: toxicity towards warm-blooded animals is greater for the compounds used according to the invention than for the compounds used according to Norwegian patent 80 467, as can be seen from the table below:
I det følgende beskrives metoder til bestemmelse av den parasiticide virkning av fosforyleddiksyrederivatene som anvendes ifølge oppfinnelsen og angis resultatene av sådanne bestemmelser, samt av bestemmelser av disse derivaters giftighet overfor varmblodige dyr. In the following, methods for determining the parasiticidal effect of the phosphorylacetic acid derivatives used according to the invention are described and the results of such determinations are given, as well as of determinations of the toxicity of these derivatives towards warm-blooded animals.
Forsøksmetoder. Experimental methods.
1) Virkning mot afider: Unge bønneplan-ter som er infisert med afider (Aphis tabae Scop) dyppes i noen få sekunder ned i på passende måte sammensatte vandige dispersjoner av det produkt som skal under-søkes. De holdes derpå under kontrollerte betingelser som er skikket for insektene (med hensyn til lys, temperatur og fuktig-het). 24 timer efter behandlingen bestem-mes dødeligheten blant insektene ved anvendelse av forskjellige doser av produktet, under et binokulært mikroskop. 2) Virkning mot midd: Undersøkelsen ut-føres således som angitt ovenfor under 1, men under anvendelse som forsøksdyr av Tetranychus telarius som vokser på unge bønneplanter. 3) Ovicid virkning: Voksne hundyr av ar-ten T. telarius L. anbringes i 24 timer på unge bønneplanter som bare har spirende («cotyledon») blader, for egglegging. De voksne insekter fjernes derpå med en luft-strøm og plantene behandles som angitt ovenfor under 1. Antallet av drepte egg telles efter 6 døgn under et binokulært mikroskop. 4) Systemisk virkning ved absorbsjon i røtter: De deler av unge bønneplanter som ligger under jorden og som er infisert med afider (Aphis fabae Scop) føres inn i små forvede glassbeholdere inneholdende vandige dispersjoner av de produkter som skal prøves. Disse små glassbeholdere oppbevares 8 døgn i et rom som er egnet for insektene, idet dødeligheten blant de afider som lever på plantenes underjordiske deler observeres daglig. 5) Insekticid virkning mot fluer ved lokal påføring: Ved hjelp av en mikrosprøyte «Agla» påføres en dråpe (1 mm^) av en oppløsning i aceton av det produkt som skal prøves på ryggpartiet av 4 døgn gamle fluer av hunnkjønn (Musea domestica L). Der ble brukt en stamme som man hadde latt vokse i laboratoriet, og som var føl-somme overfor klorerte, organiske forbindelser og overfor andre insekticider. Insektene holdes under observasjon i passende små metallbur og dødeligheten observeres efter 24 timer. 6) Insekticid virkning på fluer ved ab-sorosjon i fotsålen, ( torsal absorbsjon) : Husfluer (Musea domestica L) av hunn-kjønn lignende dem som brukes i den under 5 ovenfor angitte metode føres inn i 1000 1) Action against aphids: Young bean plants infected with aphids (Aphis tabae Scop) are dipped for a few seconds into suitably composed aqueous dispersions of the product to be examined. They are then kept under controlled conditions that are suitable for the insects (with regard to light, temperature and humidity). 24 hours after the treatment, the mortality among the insects is determined using different doses of the product, under a binocular microscope. 2) Effect against mites: The investigation is thus carried out as stated above under 1, but using Tetranychus telarius which grows on young bean plants as experimental animals. 3) Ovicidal effect: Adult females of the species T. telarius L. are placed for 24 hours on young bean plants that only have budding ("cotyledon") leaves, for egg-laying. The adult insects are then removed with an air stream and the plants are treated as indicated above under 1. The number of killed eggs is counted after 6 days under a binocular microscope. 4) Systemic effect by absorption in roots: The parts of young bean plants that lie underground and are infected with aphids (Aphis fabae Scop) are introduced into small glass containers containing aqueous dispersions of the products to be tested. These small glass containers are kept for 8 days in a room suitable for the insects, as the mortality among the aphids that live on the underground parts of the plants is observed daily. 5) Insecticidal effect against flies by local application: Using an "Agla" microsyringe, a drop (1 mm^) of a solution in acetone of the product to be tested is applied to the back of 4-day-old female flies (Musea domestica L ). A strain was used which had been allowed to grow in the laboratory and which was sensitive to chlorinated organic compounds and to other insecticides. The insects are kept under observation in suitable small metal cages and mortality is observed after 24 hours. 6) Insecticidal effect on flies by absorption in the sole of the foot, (torsal absorption): Female houseflies (Musea domestica L) similar to those used in the method specified under 5 above are introduced into 1000
ml's begerglass hvis innervegger er over-trukket med en jevn hinne av det produkt som skal undersøkes. Begerglassene luk-kes med gas og oppbevares i et rom hvor temperaturen og fuktighetsbetingelsene er passende for insektene. Man observerer antallet av insekter som er slått ned efter de første to timer og dødeligheten efter 20 timer. ml's beaker whose inner walls are coated with an even film of the product to be examined. The beakers are sealed with gas and stored in a room where the temperature and humidity conditions are suitable for the insects. One observes the number of insects that have been knocked down after the first two hours and the mortality after 20 hours.
Resultater av bestemmelser utført efter disse metoder er oppført i tabeller I og II i det følgende. Results of determinations carried out according to these methods are listed in Tables I and II below.
Bestemmelse av akutt giftighet overfor Determination of acute toxicity towards
varmblodige dyr ved oral og intravenøs anvendelse av merkapto- etylenamider av 0, 0-dialkyl- tio- og ditio- fosforyl- eddiksyre. warm-blooded animals by oral and intravenous application of mercapto-ethylene amides of 0,0-dialkyl-thio- and dithio-phosphoryl-acetic acid.
Den akutte giftighet av de aktive forbindelser i preparatene ifølge oppfinnelsen The acute toxicity of the active compounds in the preparations according to the invention
på varmblodige dyr ble utført under anvendelse som forsøksdyr av små hvite rotter on warm-blooded animals was carried out using small white rats as experimental animals
med vekt 18—20 g. En oppløsning av dimetylacetamid av de produkter som skal weighing 18-20 g. A solution of dimethylacetamide of the products to be
undersøkes, ble ved hjelp av mavesonder examined, was by means of stomach probes
innført i dyrene. Oppløsningsmidlets inn- introduced into the animals. The solvent's in-
flytelse på giftvirkningene kan betraktes som ubetydelig. influence on the toxic effects can be considered negligible.
Ved bestemmelsen av akutt giftighet ved intravenøs anvendelse ble der likeledes brukt små hvite rotter med vekt 18—20 g som forsøksdyr, og oppløsningen av pro-duktene av dimetylacetamid. In the determination of acute toxicity by intravenous application, small white rats weighing 18-20 g were also used as experimental animals, and the solution of the products of dimethylacetamide.
Resultatene angis i nedenstående tabell II og er uttrykt som den dose i mg pr. kg legemsvekt som gir en dødelighet på 50 pst. (LD 50). The results are shown in table II below and are expressed as the dose in mg per kg body weight which gives a mortality of 50 per cent (LD 50).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4355670A | 1970-06-04 | 1970-06-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO742973L NO742973L (en) | 1971-12-07 |
| NO143795B true NO143795B (en) | 1981-01-05 |
| NO143795C NO143795C (en) | 1981-04-22 |
Family
ID=21927757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2092/71A NO134867C (en) | 1970-06-04 | 1971-06-03 | |
| NO742973A NO143795C (en) | 1970-06-04 | 1974-08-19 | CHEMICAL INTERMEDIATE FOR USE IN THE PREPARATION OF THERAPEUTIC ACTIVE 2,6-METHAN-3-BENZAZOSINES |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2092/71A NO134867C (en) | 1970-06-04 | 1971-06-03 |
Country Status (17)
| Country | Link |
|---|---|
| AR (3) | AR202774A1 (en) |
| BE (1) | BE768084A (en) |
| CA (1) | CA926396A (en) |
| CH (2) | CH555830A (en) |
| DE (2) | DE2166115A1 (en) |
| DK (1) | DK137925B (en) |
| ES (2) | ES391890A1 (en) |
| FI (1) | FI54109C (en) |
| FR (1) | FR2100721B1 (en) |
| GB (1) | GB1323491A (en) |
| HK (1) | HK61578A (en) |
| IL (1) | IL36977A (en) |
| NL (1) | NL7107745A (en) |
| NO (2) | NO134867C (en) |
| PH (3) | PH12851A (en) |
| SE (1) | SE401366B (en) |
| ZA (1) | ZA713617B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US9688638B2 (en) | 2013-11-27 | 2017-06-27 | Nektar Therapeutics | Opioid agonists and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1478851A (en) * | 1965-05-05 | 1967-04-28 | Geigy Ag J R | New methano-benzazocines and their preparation |
-
1971
- 1971-05-31 CA CA114432A patent/CA926396A/en not_active Expired
- 1971-06-03 SE SE7107208A patent/SE401366B/en unknown
- 1971-06-03 IL IL36977A patent/IL36977A/en unknown
- 1971-06-03 ES ES391890A patent/ES391890A1/en not_active Expired
- 1971-06-03 GB GB1889771*[A patent/GB1323491A/en not_active Expired
- 1971-06-03 NO NO2092/71A patent/NO134867C/no unknown
- 1971-06-03 DK DK269871AA patent/DK137925B/en unknown
- 1971-06-03 ZA ZA713617A patent/ZA713617B/en unknown
- 1971-06-03 FI FI1548/71A patent/FI54109C/en active
- 1971-06-04 DE DE19712166115 patent/DE2166115A1/en active Pending
- 1971-06-04 PH PH12520A patent/PH12851A/en unknown
- 1971-06-04 DE DE19712127819 patent/DE2127819A1/en not_active Ceased
- 1971-06-04 NL NL7107745A patent/NL7107745A/xx not_active Application Discontinuation
- 1971-06-04 CH CH203973A patent/CH555830A/en not_active IP Right Cessation
- 1971-06-04 FR FR7120353A patent/FR2100721B1/fr not_active Expired
- 1971-06-04 AR AR235981A patent/AR202774A1/en active
- 1971-06-04 CH CH813671A patent/CH556339A/en not_active IP Right Cessation
- 1971-06-04 BE BE768084A patent/BE768084A/en unknown
-
1972
- 1972-12-28 AR AR245888A patent/AR197694A1/en active
-
1973
- 1973-08-20 ES ES418038A patent/ES418038A1/en not_active Expired
- 1973-10-22 PH PH15136A patent/PH13928A/en unknown
- 1973-10-22 PH PH15137A patent/PH13014A/en unknown
-
1974
- 1974-06-14 AR AR254189A patent/AR214033A1/en active
- 1974-08-19 NO NO742973A patent/NO143795C/en unknown
-
1978
- 1978-10-19 HK HK615/78A patent/HK61578A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1323491A (en) | 1973-07-18 |
| ES418038A1 (en) | 1976-02-16 |
| NO143795C (en) | 1981-04-22 |
| AR214033A1 (en) | 1979-04-30 |
| FI54109C (en) | 1978-10-10 |
| AR197694A1 (en) | 1974-04-30 |
| PH12851A (en) | 1979-09-12 |
| PH13014A (en) | 1979-11-09 |
| IL36977A (en) | 1975-10-15 |
| NO134867C (en) | 1976-12-29 |
| FI54109B (en) | 1978-06-30 |
| CA926396A (en) | 1973-05-15 |
| HK61578A (en) | 1978-10-27 |
| BE768084A (en) | 1971-12-06 |
| ES391890A1 (en) | 1974-08-01 |
| CH555830A (en) | 1974-11-15 |
| SE401366B (en) | 1978-05-02 |
| FR2100721B1 (en) | 1975-01-17 |
| NL7107745A (en) | 1971-12-07 |
| NO134867B (en) | 1976-09-20 |
| NO742973L (en) | 1971-12-07 |
| PH13928A (en) | 1980-11-04 |
| AR202774A1 (en) | 1975-07-24 |
| ZA713617B (en) | 1972-01-26 |
| FR2100721A1 (en) | 1972-03-24 |
| DK137925C (en) | 1978-10-30 |
| CH556339A (en) | 1974-11-29 |
| DE2127819A1 (en) | 1972-01-13 |
| IL36977A0 (en) | 1971-08-25 |
| DE2166115A1 (en) | 1972-12-14 |
| DK137925B (en) | 1978-06-05 |
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