NO140422B - PROSTAGLAND COUNTRIES FOR USE IN PREGNANCY PREVENTION / PREGNANCY - Google Patents
PROSTAGLAND COUNTRIES FOR USE IN PREGNANCY PREVENTION / PREGNANCY Download PDFInfo
- Publication number
- NO140422B NO140422B NO2080/72A NO208072A NO140422B NO 140422 B NO140422 B NO 140422B NO 2080/72 A NO2080/72 A NO 2080/72A NO 208072 A NO208072 A NO 208072A NO 140422 B NO140422 B NO 140422B
- Authority
- NO
- Norway
- Prior art keywords
- pregnancy
- prostaglandin
- methyl
- pge
- prostagland
- Prior art date
Links
- 230000035935 pregnancy Effects 0.000 title description 6
- 230000002265 prevention Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 Prostaglandin compound Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 description 21
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003433 contraceptive agent Substances 0.000 description 4
- 229940124558 contraceptive agent Drugs 0.000 description 4
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000699673 Mesocricetus auratus Species 0.000 description 2
- 239000004015 abortifacient agent Substances 0.000 description 2
- 229960000711 alprostadil Drugs 0.000 description 2
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000009597 pregnancy test Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Foreliggende oppfinnelse angår nye prostaglandinforbindelser for anvendelse i svangerskapsforebyggende/svangerskaps avbryt-ende midler.Prostansyre har følgende struktur og atomnummering: The present invention relates to new prostaglandin compounds for use in contraceptives/termination agents. Prostanic acid has the following structure and atomic numbering:
Forskjellige derivater av prostansyre er kjent innen faget. Various derivatives of prostanic acid are known in the art.
Disse kalles prostaglandiner. Se for eksempel Bergstrom et sl., Pharmacol. Rev. 20, 1 (1968), og henvisninger angitt der. Eksempelvis har prostaglandin E1 (PGE^) følgende struktur: These are called prostaglandins. See, for example, Bergstrom et al., Pharmacol. Fox. 20, 1 (1968), and references therein. For example, prostaglandin E1 (PGE^) has the following structure:
Prostaglandin E2(PGE2) har følgende struktur: Prostaglandin E2 (PGE2) has the following structure:
Prostaglandin E^(PGE^) har følgende struktur: Prostaglandin E^(PGE^) has the following structure:
Dihyciroprostaglandin E1(dihydro-PGE1) har følgende struktur: Dihyciroprostaglandin E1 (dihydro-PGE1) has the following structure:
Prostaglandiner med en sekundær a- eller B-hydroxyl istedenfor oxogruppen i ringen til prostaglandin E er også kjent. Disse kalles prostaglandin F. For eksempel har prostaglandin R2q (PGF2a) følgende struktur: Prostaglandins with a secondary α- or β-hydroxyl instead of the oxo group in the ring of prostaglandin E are also known. These are called prostaglandin F. For example, prostaglandin R2q (PGF2a) has the following structure:
Prostaglandin F2^(PGF2g ) har følgende struktur: Prostaglandin F2^(PGF2g) has the following structure:
Prostaglandin F og FD tilsvarende PGE-, PGE_, PGE-. og dihydro- Prostaglandin F and FD corresponding to PGE-, PGE_, PGE-. and dihydro-
Oi CS \Z 3Oh CS \Z 3
PGE^er også kjent. PGE^ is also known.
I formlene II og VII, angir stiplete linjer til cyclopentanringen substituenter i ct-konf igurasjon, det vil si under cyclo- . pentanringens plan. Heltrukne linjer til cyclopentanringen angir substituenter i B-konfigurasjon, det vil si over cyclopentanringens plan» Den sidekjedete hydroxyl ved C-15 i formlene II og VII er i S-konfigurasjon. Se Nature, 212, 38(1966) hvor prostaglandinenes stereokjemi er diskutert. In formulas II and VII, dashed lines to the cyclopentane ring indicate substituents in the ct configuration, that is, under cyclo- . plane of the pentane ring. Solid lines to the cyclopentane ring indicate substituents in B configuration, that is above the plane of the cyclopentane ring» The side chain hydroxyl at C-15 in formulas II and VII is in S configuration. See Nature, 212, 38(1966) where the stereochemistry of the prostaglandins is discussed.
De kjente prostaglandinmolekyler har hver flere assymetriske sentra, og kan foreligge i den racemiske form og i hver av de to enantiomere former, det vil si den høyredreiende og venstredreiende form. Som angitt i de opptrukne formler, representerer hver av formlene II og VII den spesielle optisk aktive form av den prostaglandin som erholdes fra visse pattedyrvev, for eksempel fra saue- blærekjertler, svinelunger, eller menneskelig sædplasma, eller ved carbonylreduksjon og/eller dobbeltbinding-reduksjon av et således erholdt prostaglandin. Se for eksempelBergstom et al., som angitt overfor. Speilbilde av hver av formlene II og VII vil følgelig representere den andre enantiomer av prostaglahdinet. Den racemiske form av et prostaglandin kan inneholde likt antall av begge de enantiomere molekyler, og en av formlene II og VII The known prostaglandin molecules each have several asymmetric centers, and can exist in the racemic form and in each of the two enantiomeric forms, i.e. the dextrorotatory and levorotatory form. As indicated in the above formulas, each of formulas II and VII represents the particular optically active form of the prostaglandin obtained from certain mammalian tissues, for example from ovine bladder glands, porcine lungs, or human seminal plasma, or by carbonyl reduction and/or double bond reduction of a prostaglandin thus obtained. See, for example, Bergstom et al., as noted above. The mirror image of each of formulas II and VII will therefore represent the other enantiomer of the prostaglandin. The racemic form of a prostaglandin may contain equal numbers of both enantiomeric molecules, and one of the formulas II and VII
og speilbilde av denne formel er nødvendig for å angi korrekt den. tilsvarende racemiske prostaglandin. For letthet angir uttrykkene PGE.PGE-, PGE-,, dihydro-PGE, , PGF. , PGF- , PGF-. , dihydro-1 2 3 1 1a 2a 3a and the mirror image of this formula is necessary to correctly state it. equivalent to racemic prostaglandin. For convenience, the terms PGE.PGE-, PGE-,, dihydro-PGE, , PGF. , PGF- , PGF-. , dihydro-1 2 3 1 1a 2a 3a
PGF. , PGF1D, PGFOD, PGF,Q og dihydro-PGF.0den optisk aktive form PGF. , PGF1D, PGFOD, PGF,Q and dihydro-PGF.0 the optically active form
1 Cl. lp Zp JB lp 1 Cl. lp Zp JB lp
av dette prostaglandin med den samme absolutte konfigurasjon som PGE.J erholdt fra pattedyrvev. Når det henvises til den racemiske form av en av disse prostaglandiner er ordet "racemisk" plassert foran prostaglandinnavnet, eksempelvis racemisk PGE2eller racemisk PGF_ . of this prostaglandin with the same absolute configuration as PGE.J obtained from mammalian tissue. When referring to the racemic form of one of these prostaglandins, the word "racemic" is placed before the prostaglandin name, for example racemic PGE2 or racemic PGF_ .
De nye prostaglandinforbindelser for anvendelse i svanger-skapsforebyggende/svangerskapsavbrytende midler er kjennetegnet vet at de er en optisk aktiv forbindelse av generell formel: The new prostaglandin compounds for use in contraceptives/abortion agents are characterized by the fact that they are an optically active compound of the general formula:
eller speilbildet av denne, eller en racemisk blanding derav, hvor R.j er hydrogen, alkyl med 1-8 carbonatomer, eller et farma-kologisk akseptabelt kation, hvor R2er methyl eller ethyl, A er og hvor x er trans-CH=CH-, Y er cis-CH=CH-, og hvor bindingene ved C-15 har ct,B- eller 3,a-konfigurasjon, unntatt 1 5 (S) -raethyl-PGE., og 1 5 (S)-1 5-methyl-PGF1 a, og deres alkylestere. Et markant kjennetegn til alle de kjente prostaglandiner er den sekundære hydroxylgruppe ved C-15, det vil si atomgrupperingen Prostaglandiner som erholdes fra dyrevev inneholder alltid denne atomgruppering. I motsetning inneholder hver av de nye prostaglandinsyrederivater som anvendes ifølge denne oppfinnelse en tertiær hydroxylgruppe ved C-15, det vil si atomgrupperingen eller den tilsvarende R-konfigurasjon or the mirror image thereof, or a racemic mixture thereof, where R.j is hydrogen, alkyl with 1-8 carbon atoms, or a pharmacologically acceptable cation, where R.sup.2 is methyl or ethyl, A is and where x is trans-CH=CH-, Y is cis-CH=CH-, and where the bonds at C-15 have ct,B- or 3,a-configuration, except 1 5 (S)-raethyl-PGE., and 1 5 (S)-1 5- methyl-PGF1 a, and their alkyl esters. A marked characteristic of all the known prostaglandins is the secondary hydroxyl group at C-15, that is the atomic grouping Prostaglandins obtained from animal tissue always contain this atomic grouping. In contrast, each of the new prostaglandin acid derivatives used according to this invention contains a tertiary hydroxyl group at C-15, i.e. the atomic grouping or the corresponding R configuration
hvor er methyl eller ethyl. Disse nye prostansyrederivater kan følgelig for letthets skyld betegnes 15-methyl-prostaglandiner eller 15-ethyl-prostaglandiner, for eksempel 15-methyl-PGE2, 15-ethyl-PGF2aog 15-methyl-15(R)-PGF2g. where is methyl or ethyl. These new prostanic acid derivatives can therefore, for the sake of simplicity, be termed 15-methyl-prostaglandins or 15-ethyl-prostaglandins, for example 15-methyl-PGE2, 15-ethyl-PGF2a and 15-methyl-15(R)-PGF2g.
PGFa~ PGFg og PGE-forbindelsene er nyttige i svangerskapsfore-byggende/svangerskapsavbrytendemidler for eggløsende hunpatte-dyr, innbefattet mennesker og dyr, slike som aper, rotter, kaniner, hunder, kveg og lignende. For det formål administreres eksempelvis PGE_ eller PGF» systemisk, det vil si intravenøst, subcutant og intravaginalt, med en dose på ca. 0,001 mg til ca. 20 mg pr. kg kroppsvekt av hunpattedyret, fortrinnsvis under et tidsrom som starter tilnærmet ved eggløsningen og slutter tilnærmet ved den neste ventede menstruasjon eller like før dette tidspunkt. I tillegg fullføres en utstøtelse av fosteret i tidlig eller se-nere stadium av tilsvarende administrering av forbindelsene under den første tredjedel av den normale svangerskapsperiode. PGFa~ PGFg and the PGE compounds are useful in contraceptives/abortion agents for ovulating female mammals, including humans and animals such as monkeys, rats, rabbits, dogs, cattle and the like. For that purpose, for example, PGE_ or PGF" is administered systemically, i.e. intravenously, subcutaneously and intravaginally, with a dose of approx. 0.001 mg to approx. 20 mg per kg body weight of the female mammal, preferably during a period starting approximately at ovulation and ending approximately at the next expected menstruation or just before this time. In addition, expulsion of the fetus at an early or later stage is completed by corresponding administration of the compounds during the first third of the normal gestation period.
De nye 15-methyl og 15-ethyl prostaglandinanaloge omfattet av formel VIII frembringer de samme biologiske reaksjoner som ovenfor beskrevet for de tilsvarende kjente prostaglandiner. Hver av disse 15-methyl og 15-ethyl-forbindelser er følgelig nyttige for de ovenfor beskrevne formål, og benyttes for disse formål som ovenfor beskrevet. Imidlertid er hver av disse 15-methyl og 15- ethyl-prostaglandinanaloge ganske overraskende og uventet mer nyttige enn det tilsvarende kjente prostaglandin på grunn av at analogen er kraftigere og har en vesentlig virketid. Av den grunn trenges færre og mindre doser av disse prostaglandinanaloge for å nå de ønskede resultater. The new 15-methyl and 15-ethyl prostaglandin analogues included in formula VIII produce the same biological reactions as described above for the corresponding known prostaglandins. Each of these 15-methyl and 15-ethyl compounds is consequently useful for the purposes described above, and is used for these purposes as described above. However, each of these 15-methyl and 15-ethyl prostaglandin analogs is quite surprisingly and unexpectedly more useful than the corresponding known prostaglandin because the analog is more potent and has a substantial duration of action. For that reason, fewer and smaller doses of these prostaglandin analogues are needed to achieve the desired results.
Anti- graviditetstest Anti-pregnancy test
Drektige Golden hamstere ble subcutant gitt en oppløs-ning av testforbindelsen. Pregnant Golden hamsters were subcutaneously given a solution of the test compound.
Oppløsninger av testforbindelsene ble fremstillet ved at hver forbindelse ble oppløst i ethanol (0,05 ml ethanol pr. mg forbindelse), hvorefter oppløsningen ble fortynnet med fysiolo-gisk saltvann inntil 0,5 ml av den resulterende oppløsning inne-holdt den ønskede mengde av forbindelsen. Solutions of the test compounds were prepared by dissolving each compound in ethanol (0.05 ml of ethanol per mg of compound), after which the solution was diluted with physiological saline until 0.5 ml of the resulting solution contained the desired amount of the connection.
Hver oppløsning ble administrert subcutant i en enkei 0,5 ml injeksjon til hver av 6 eller 8 drektige Golden hamstere ved 4.dag i drektighetsperioden. På den 8.dag ble hver av de 6 eller 8 dyr avlivet, uterus ble åpnet, og nærvær eller fravær av implantasjonssteder ble observert. Ved denne prosedyre utviste kontrolldyrene (som bare mottok bærer) vanligvis 12 - 14 implan-tas jonssteder . Each solution was administered subcutaneously in a single 0.5 ml injection to each of 6 or 8 pregnant Golden hamsters on day 4 of the gestation period. On the 8th day, each of the 6 or 8 animals was sacrificed, the uterus was opened, and the presence or absence of implantation sites was observed. By this procedure, the control animals (which received only vehicle) typically exhibited 12-14 implantation sites.
De erholdte anti-graviditetsdata er uttrykt som den mi-nimale effektive dose av forbindelsen som fullstendig inhiberer graviditet i hamsteren MED). Resultatene er angitt i den etter-følgende tabell: The anti-pregnancy data obtained are expressed as the minimum effective dose of the compound which completely inhibits pregnancy in the hamster MED). The results are indicated in the following table:
Anti- graviditetsdata ( hamster) Anti-pregnancy data (hamster)
Som det fremgår av ovenstående tabell er alle forbindelser som anvendes i foreliggende svangerskapsforebyggende/svangerskaps-avbrytende midler betydelig mer aktive enn de kjente prostaglan-dinderivater. As can be seen from the above table, all compounds used in the present contraceptives/termination agents are significantly more active than the known prostaglandin derivatives.
De prostaglandinforbindelser som anvendes i foreliggende svangerskapsforebyggende/svangerskapsavbrytendemidler er de-taljert beskrevet og eksemplifisert i Norsk patent 135.935. The prostaglandin compounds used in the present pregnancy prevention/termination agents are described in detail and exemplified in Norwegian patent 135,935.
Claims (1)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3451870A | 1970-05-04 | 1970-05-04 | |
| US3454970A | 1970-05-04 | 1970-05-04 | |
| US3730770A | 1970-05-14 | 1970-05-14 | |
| US3730870A | 1970-05-14 | 1970-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO140422B true NO140422B (en) | 1979-05-21 |
| NO140422C NO140422C (en) | 1979-08-29 |
Family
ID=27488226
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1638/71A NO135935C (en) | 1970-05-04 | 1971-05-03 | |
| NO2080/72A NO140422C (en) | 1970-05-04 | 1972-06-13 | PROSTAGLAND COUNTRIES FOR USE IN PREGNANCY PREVENTION / PREGNANCY |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1638/71A NO135935C (en) | 1970-05-04 | 1971-05-03 |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA959485A (en) |
| DE (2) | DE2121980C3 (en) |
| FR (1) | FR2100627B1 (en) |
| GB (2) | GB1314293A (en) |
| IL (1) | IL36682A (en) |
| MY (1) | MY7400305A (en) |
| NL (1) | NL154729B (en) |
| NO (2) | NO135935C (en) |
| SE (1) | SE388852B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2258668C3 (en) * | 1971-12-03 | 1981-08-06 | Syntex Corp., Panama-City | New prostaglandins, processes for their production and pharmaceuticals containing them |
| US3887587A (en) * | 1972-04-17 | 1975-06-03 | Pfizer | Synthesis of prostaglandins of the one-series |
-
1971
- 1971-04-15 CA CA110,447A patent/CA959485A/en not_active Expired
- 1971-04-21 IL IL36682A patent/IL36682A/en unknown
- 1971-04-29 SE SE7105577A patent/SE388852B/en unknown
- 1971-05-03 NO NO1638/71A patent/NO135935C/no unknown
- 1971-05-03 FR FR7115790A patent/FR2100627B1/fr not_active Expired
- 1971-05-03 NL NL717105999A patent/NL154729B/en not_active IP Right Cessation
- 1971-05-04 GB GB4292972A patent/GB1314293A/en not_active Expired
- 1971-05-04 DE DE2121980A patent/DE2121980C3/en not_active Expired
- 1971-05-04 DE DE2166630A patent/DE2166630C3/en not_active Expired
- 1971-05-04 GB GB1289871*[A patent/GB1314291A/en not_active Expired
-
1972
- 1972-06-13 NO NO2080/72A patent/NO140422C/en unknown
-
1974
- 1974-12-30 MY MY305/74A patent/MY7400305A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2121980C3 (en) | 1980-02-14 |
| SE388852B (en) | 1976-10-18 |
| IL36682A0 (en) | 1971-06-23 |
| DE2166630B2 (en) | 1979-02-22 |
| IL36682A (en) | 1976-04-30 |
| NL154729B (en) | 1977-10-17 |
| DE2166630A1 (en) | 1974-12-12 |
| GB1314293A (en) | 1973-04-18 |
| GB1314291A (en) | 1973-04-18 |
| NO135935B (en) | 1977-03-21 |
| DE2121980B2 (en) | 1979-06-07 |
| FR2100627B1 (en) | 1981-12-18 |
| NO135935C (en) | 1977-06-29 |
| DE2166630C3 (en) | 1979-10-11 |
| NL7105999A (en) | 1971-11-08 |
| NO140422C (en) | 1979-08-29 |
| CA959485A (en) | 1974-12-17 |
| FR2100627A1 (en) | 1972-03-24 |
| DE2121980A1 (en) | 1971-11-25 |
| MY7400305A (en) | 1974-12-31 |
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