BE889905A - Derives d'heteroprostaglandines ainsi que leurs procedes de preparation - Google Patents
Derives d'heteroprostaglandines ainsi que leurs procedes de preparation Download PDFInfo
- Publication number
- BE889905A BE889905A BE0/205621A BE205621A BE889905A BE 889905 A BE889905 A BE 889905A BE 0/205621 A BE0/205621 A BE 0/205621A BE 205621 A BE205621 A BE 205621A BE 889905 A BE889905 A BE 889905A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- derivatives
- heteroprostaglandin
- preparation methods
- represents hydrogen
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salts Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- NCHPDGCQTUJYKK-UHFFFAOYSA-N pyrrolidin-1-ium;acetate Chemical compound CC(O)=O.C1CCNC1 NCHPDGCQTUJYKK-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Description
<EMI ID=1.1>
DE PREPARATION
<EMI ID=2.1>
La présente invention se rapporte d'une manière générale à des dérivée do prostaglandines et plus particulièrement à de nouveaux composée de etruc-
<EMI ID=3.1>
<EMI ID=4.1>
<EMI ID=5.1>
dé la manière suivante :
<EMI ID=6.1>
<EMI ID=7.1>
<EMI ID=8.1>
<EMI ID=9.1>
<EMI ID=10.1>
que l'hydroxyde de sodium.
<EMI ID=11.1>
<EMI ID=12.1>
<EMI ID=13.1>
<EMI ID=14.1>
<EMI ID=15.1>
<EMI ID=16.1>
<EMI ID=17.1> <EMI ID=18.1>
<EMI ID=19.1>
<EMI ID=20.1>
<EMI ID=21.1>
<EMI ID=22.1> <EMI ID=23.1>
<EMI ID=24.1>
<EMI ID=25.1>
<EMI ID=26.1>
<EMI ID=27.1>
<EMI ID=28.1> <EMI ID=29.1>
<EMI ID=30.1>
<EMI ID=31.1>
<EMI ID=32.1>
et à température ambiante, pour obtenir les dérivés oxoéthylènedithio-
<EMI ID=33.1>
<EMI ID=34.1>
dana laquelle R a la même signification que précédemment.
<EMI ID=35.1>
<EMI ID=36.1>
<EMI ID=37.1>
<EMI ID=38.1>
<EMI ID=39.1>
A
B. Pr�prration du Synthon B
<EMI ID=40.1>
<EMI ID=41.1>
<EMI ID=42.1>
<EMI ID=43.1>
<EMI ID=44.1>
C. Préparation du Synthon C
<EMI ID=45.1>
de formule générale :
<EMI ID=46.1>
<EMI ID=47.1>
L
<EMI ID=48.1>
<EMI ID=49.1>
formule générale :
<EMI ID=50.1>
<EMI ID=51.1> <EMI ID=52.1> <EMI ID=53.1>
<EMI ID=54.1>
<EMI ID=55.1>
<EMI ID=56.1>
<EMI ID=57.1>
<EMI ID=58.1>
<EMI ID=59.1>
<EMI ID=60.1>
<EMI ID=61.1> inerte avec l'acétate de pyrrolidine ou l'acétate de pipéridine dans un oolvant approprié, tel que le toluène et à une température allant:
<EMI ID=62.1>
<EMI ID=63.1>
<EMI ID=64.1>
<EMI ID=65.1>
F. Préparation du Synthon F
<EMI ID=66.1>
<EMI ID=67.1>
<EMI ID=68.1>
<EMI ID=69.1>
<EMI ID=70.1>
.
(finirai"
<EMI ID=71.1>
<EMI ID=72.1>
<EMI ID=73.1>
<EMI ID=74.1>
<EMI ID=75.1>
<EMI ID=76.1>
<EMI ID=77.1>
<EMI ID=78.1>
<EMI ID=79.1>
<EMI ID=80.1>
<EMI ID=81.1>
gtoéralo :
<EMI ID=82.1>
<EMI ID=83.1>
<EMI ID=84.1>
<EMI ID=85.1>
<EMI ID=86.1>
<EMI ID=87.1>
<EMI ID=88.1>
<EMI ID=89.1>
<EMI ID=90.1>
<EMI ID=91.1>
<EMI ID=92.1>
<EMI ID=93.1>
ce mélange étant par la ('mite hydrogène à pression atmosphérique sur
<EMI ID=94.1>
ci-dessus, <EMI ID=95.1> <EMI ID=96.1>
<EMI ID=97.1>
<EMI ID=98.1>
<EMI ID=99.1>
<EMI ID=100.1>
<EMI ID=101.1>
<EMI ID=102.1>
<EMI ID=103.1>
<EMI ID=104.1>
<EMI ID=105.1>
<EMI ID=106.1>
<EMI ID=107.1>
acétal-2 (R)-heptyloxy-3 cyclopentane de formule générale :
<EMI ID=108.1>
<EMI ID=109.1>
<EMI ID=110.1>
Mit
<EMI ID=111.1>
<EMI ID=112.1>
<EMI ID=113.1>
<EMI ID=114.1>
<EMI ID=115.1>
<EMI ID=116.1>
<EMI ID=117.1>
<EMI ID=118.1>
<EMI ID=119.1>
soit
<EMI ID=120.1> <EMI ID=121.1>
<EMI ID=122.1>
<EMI ID=123.1>
<EMI ID=124.1>
<EMI ID=125.1>
<EMI ID=126.1>
t�nul8 ....&18
<EMI ID=127.1>
<EMI ID=128.1>
<EMI ID=129.1>
<EMI ID=130.1>
'W8w ,-".iy
<EMI ID=131.1>
<EMI ID=132.1> <EMI ID=133.1>
<EMI ID=134.1>
<EMI ID=135.1>
P.F. : 129-130[deg.]C
<EMI ID=136.1>
<EMI ID=137.1>
form4 au cours de la réaction et ce au moyen d'une trompe à eau de façon
<EMI ID=138.1>
<EMI ID=139.1>
<EMI ID=140.1>
<EMI ID=141.1>
<EMI ID=142.1>
<EMI ID=143.1>
noua pression réduite.
De cette manière, on obtient le composé IV après cristallisation dama l'éther de pétrole.
<EMI ID=144.1>
<EMI ID=145.1>
<EMI ID=146.1>
ajouta 9g de comparé IV pain lorsque le solide est dissous, on introduit
<EMI ID=147.1>
<EMI ID=148.1>
<EMI ID=149.1>
sur couche mince (solvant : chloroforme/ether éthylique 3/1). On détruit
<EMI ID=150.1>
<EMI ID=151.1>
Après évaporation des solvants, on récupère une huile Jaune.
<EMI ID=152.1>
dans l'éthanol aqueux.
<EMI ID=153.1>
<EMI ID=154.1>
<EMI ID=155.1>
<EMI ID=156.1>
<EMI ID=157.1>
<EMI ID=158.1>
<EMI ID=159.1>
<EMI ID=160.1>
<EMI ID=161.1>
<EMI ID=162.1>
<EMI ID=163.1>
<EMI ID=164.1> Coeme ce composé est particulièrement instable, il est réduit en (R)-
<EMI ID=165.1>
risât Ion"
<EMI ID=166.1>
<EMI ID=167.1>
<EMI ID=168.1>
<EMI ID=169.1>
<EMI ID=170.1>
<EMI ID=171.1>
<EMI ID=172.1>
R-
<EMI ID=173.1>
<EMI ID=174.1>
<EMI ID=175.1>
<EMI ID=176.1>
<EMI ID=177.1>
<EMI ID=178.1>
<EMI ID=179.1>
<EMI ID=180.1>
<EMI ID=181.1>
<EMI ID=182.1>
S.M.
<EMI ID=183.1>
EXEMPLE 5
<EMI ID=184.1>
<EMI ID=185.1>
<EMI ID=186.1>
<EMI ID=187.1>
<EMI ID=188.1>
<EMI ID=189.1>
produit désiré cristallise dans l'éther de petrole.
De cette manière, on obtient le composé XII souhaité avec un rendement
<EMI ID=190.1>
<EMI ID=191.1>
<EMI ID=192.1>
<EMI ID=193.1>
<EMI ID=194.1>
Lorsque la solution est devenue claire, on la reprend dama du dichloro-
<EMI ID=195.1>
<EMI ID=196.1>
<EMI ID=197.1>
<EMI ID=198.1>
<EMI ID=199.1> <EMI ID=200.1>
solution benzénique 2N en acétate de pyrrolidine.
On abandonne le milieu réactionnel durant environ 8 heures à OOC puis on
<EMI ID=201.1>
la phase organique et on la concentre soue pression réduite. L'aldéhyde
<EMI ID=202.1>
<EMI ID=203.1>
l'étape suivante.
Do cette manière, on obtient le compose XIV souhaité ou Synthon E. R.M.N. à 60 MHz
<EMI ID=204.1>
<EMI ID=205.1> <EMI ID=206.1>
<EMI ID=207.1>
<EMI ID=208.1>
Aprèr, 30 minutes d'agitation à température ambiante, on filtre la solu-
<EMI ID=209.1>
<EMI ID=210.1>
réduite pour obtenir une huile foncée que l'on purifie par chromatographie
<EMI ID=211.1>
<EMI ID=212.1>
forae d'une huile incolore.
<EMI ID=213.1>
<EMI ID=214.1>
<EMI ID=215.1>
<EMI ID=216.1>
esbi�te.
<EMI ID=217.1>
<EMI ID=218.1> <EMI ID=219.1>
<EMI ID=220.1>
<EMI ID=221.1>
<EMI ID=222.1>
<EMI ID=223.1>
<EMI ID=224.1>
<EMI ID=225.1>
<EMI ID=226.1>
<EMI ID=227.1>
<EMI ID=228.1>
<EMI ID=229.1>
<EMI ID=230.1>
<EMI ID=231.1>
<EMI ID=232.1>
<EMI ID=233.1>
<EMI ID=234.1> <EMI ID=235.1>
<EMI ID=236.1>
<EMI ID=237.1>
<EMI ID=238.1>
<EMI ID=239.1> <EMI ID=240.1>
<EMI ID=241.1>
<EMI ID=242.1>
<EMI ID=243.1>
8IIl4J
<EMI ID=244.1>
<EMI ID=245.1>
<EMI ID=246.1>
<EMI ID=247.1>
<EMI ID=248.1>
<EMI ID=249.1>
<EMI ID=250.1>
<EMI ID=251.1>
<EMI ID=252.1>
<EMI ID=253.1>
<EMI ID=254.1>
SJ4.
<EMI ID=255.1> <EMI ID=256.1>
<EMI ID=257.1>
on reprend par le chlorure de méthylène.
<EMI ID=258.1>
sodiua et on concentre. On sépare alorn par chromatographie aur couche mince l'huile résultante (solvant: éther éthylique/éther de pétrole 1/1).
<EMI ID=259.1> .noua forme d'une huile incolore.
<EMI ID=260.1>
<EMI ID=261.1>
<EMI ID=262.1>
<EMI ID=263.1>
<EMI ID=264.1>
<EMI ID=265.1>
<EMI ID=266.1>
<EMI ID=267.1>
<EMI ID=268.1>
<EMI ID=269.1>
1
<EMI ID=270.1>
compooé.
<EMI ID=271.1>
<EMI ID=272.1>
<EMI ID=273.1>
S. H.
<EMI ID=274.1>
<EMI ID=275.1>
<EMI ID=276.1>
<EMI ID=277.1>
<EMI ID=278.1>
<EMI ID=279.1>
<EMI ID=280.1>
<EMI ID=281.1> <EMI ID=282.1>
<EMI ID=283.1>
<EMI ID=284.1>
<EMI ID=285.1>
<EMI ID=286.1>
<EMI ID=287.1>
<EMI ID=288.1>
<EMI ID=289.1>
cT<l�p<eKc*.
<EMI ID=290.1>
<EMI ID=291.1>
Eg�t :.."':)1
<EMI ID=292.1>
<EMI ID=293.1>
<EMI ID=294.1>
<EMI ID=295.1> Ce composé a été obtenu colon la méthode décrite à l'Exemple 7d) cideasua.
<EMI ID=296.1>
<EMI ID=297.1>
pentane.
<EMI ID=298.1>
<EMI ID=299.1>
<EMI ID=300.1>
<EMI ID=301.1>
<EMI ID=302.1>
<EMI ID=303.1>
Claims (1)
- Revendications <EMI ID=304.1><EMI ID=305.1><EMI ID=306.1><EMI ID=307.1>auquel ils août attachée, représentent un groupement carbonyle et Z représente hydrogène ou hydroxy ainsi que les sels de métaux alcalins<EMI ID=308.1><EMI ID=309.1><EMI ID=310.1><EMI ID=311.1><EMI ID=312.1><EMI ID=313.1><EMI ID=314.1> <EMI ID=315.1><EMI ID=316.1><EMI ID=317.1>et Z' représente hydrogène ou un radical 0-R,<EMI ID=318.1>pour obtenir :<EMI ID=319.1>lesquelles X représente hydrogène ou hydroxyliait<EMI ID=320.1><EMI ID=321.1>dans laquelle Z représente hydrogène ou hydroxy, dérivé@ que l'on<EMI ID=322.1> <EMI ID=323.1><EMI ID=324.1><EMI ID=325.1>w<EMI ID=326.1><EMI ID=327.1>et A est tel que : <EMI ID=328.1><EMI ID=329.1> - lorsque B représente <EMI ID=330.1> , A représente<EMI ID=331.1><EMI ID=332.1><EMI ID=333.1> <EMI ID=334.1> <EMI ID=335.1><EMI ID=336.1>Ir "JI lL"*<EMI ID=337.1><EMI ID=338.1><EMI ID=339.1>rqw6omlu<EMI ID=340.1><EMI ID=341.1>..I.HW <EMI ID=342.1> <EMI ID=343.1> <EMI ID=344.1> <EMI ID=345.1> <EMI ID=346.1> <EMI ID=347.1><EMI ID=348.1><EMI ID=349.1><EMI ID=350.1><EMI ID=351.1> <EMI ID=352.1>- . w...b....<EMI ID=353.1><EMI ID=354.1><EMI ID=355.1><EMI ID=356.1><EMI ID=357.1><EMI ID=358.1><EMI ID=359.1> <EMI ID=360.1><EMI ID=361.1><EMI ID=362.1> <EMI ID=363.1><EMI ID=364.1>'Wa 9 futà" l�e<EMI ID=365.1><EMI ID=366.1><EMI ID=367.1><EMI ID=368.1><EMI ID=369.1><EMI ID=370.1><EMI ID=371.1><EMI ID=372.1><EMI ID=373.1><EMI ID=374.1><EMI ID=375.1><EMI ID=376.1><EMI ID=377.1>"en<EMI ID=378.1> <EMI ID=379.1>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8026240 | 1980-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE889905A true BE889905A (fr) | 1982-02-10 |
Family
ID=10515399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/205621A BE889905A (fr) | 1980-08-12 | 1981-08-10 | Derives d'heteroprostaglandines ainsi que leurs procedes de preparation |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5754141A (fr) |
| KR (2) | KR840002175B1 (fr) |
| AT (1) | AT378179B (fr) |
| BE (1) | BE889905A (fr) |
| HU (1) | HU185645B (fr) |
| MA (1) | MA19238A1 (fr) |
| SU (1) | SU1145925A3 (fr) |
| ZA (1) | ZA814947B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3346657C1 (de) * | 1983-12-23 | 1985-01-24 | Braun Ag, 6000 Frankfurt | Schwinghebelantrieb fuer elektrische Kleingeraete |
| DE3346655C1 (de) * | 1983-12-23 | 1985-01-24 | Braun Ag, 6000 Frankfurt | Vorrichtung zur Umwandlung der Drehbewegung eines Exzenters in eine hin- und hergehende Bewegung |
-
1981
- 1981-07-20 ZA ZA814947A patent/ZA814947B/xx unknown
- 1981-08-04 KR KR1019810002839A patent/KR840002175B1/ko active IP Right Grant
- 1981-08-05 MA MA19438A patent/MA19238A1/fr unknown
- 1981-08-10 BE BE0/205621A patent/BE889905A/fr not_active IP Right Cessation
- 1981-08-11 JP JP56126548A patent/JPS5754141A/ja active Pending
- 1981-08-11 HU HU812316A patent/HU185645B/hu unknown
- 1981-08-12 SU SU813320103A patent/SU1145925A3/ru active
- 1981-08-12 AT AT0354581A patent/AT378179B/de active
-
1984
- 1984-09-21 KR KR1019840005809A patent/KR850000670B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ATA354581A (de) | 1984-11-15 |
| ZA814947B (en) | 1982-07-28 |
| MA19238A1 (fr) | 1982-04-01 |
| JPS5754141A (fr) | 1982-03-31 |
| KR840002175B1 (ko) | 1984-11-26 |
| KR830006158A (ko) | 1983-09-17 |
| AT378179B (de) | 1985-06-25 |
| KR850000670B1 (ko) | 1985-05-09 |
| KR850002757A (ko) | 1985-05-15 |
| HU185645B (en) | 1985-03-28 |
| SU1145925A3 (ru) | 1985-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: SANOFI Effective date: 19870831 |