FI71308C - Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara (13e)-(8r,11r,12r)-11,15-dihydroxi-16,19-dimetyl-9-oxo-13,18-prostadiensyraderivat och av deras salter - Google Patents

Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara (13e)-(8r,11r,12r)-11,15-dihydroxi-16,19-dimetyl-9-oxo-13,18-prostadiensyraderivat och av deras salter Download PDF

Info

Publication number: FI71308C
Authority: FI; Finland
Prior art keywords: solution; acid; dimethyl; oxo; ether
Prior art date: 1981-02-13

Application number

FI820422A

Other languages

English (en)

Finnish (fi)

Other versions

FI71308B (fi

FI820422L (fi

Inventor

Helmut Vorbrueggen

Norbert Schwarz

Walter Elger

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-02-13

Filing date

1982-02-10

Publication date

1986-12-19

1981-02-13 Priority claimed from DE19813106149 external-priority patent/DE3106149A1/de

1982-01-22 Priority claimed from DE19823202457 external-priority patent/DE3202457A1/de

1982-02-10 Application filed by Schering Ag filed Critical Schering Ag

1982-08-14 Publication of FI820422L publication Critical patent/FI820422L/fi

1986-09-09 Publication of FI71308B publication Critical patent/FI71308B/fi

1986-12-19 Application granted granted Critical

1986-12-19 Publication of FI71308C publication Critical patent/FI71308C/fi

Links

238000004458 analytical method Methods 0.000 title description 3
230000001225 therapeutic effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 73
-1 tetrahydropyran-2-yloxy Chemical group 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 3
VXBBXTLIXJOCET-UHFFFAOYSA-N (3,6-dimethyl-2-oxohept-5-enyl)phosphonic acid Chemical compound CC(C)=CCC(C)C(=O)CP(O)(O)=O VXBBXTLIXJOCET-UHFFFAOYSA-N 0.000 claims 1
KPKGFLKJYICXGM-ROUUACIJSA-N 7-[(1S,2S)-2-octa-1,6-dienylcyclopentyl]-2-oxoheptanoic acid Chemical class O=C(C(=O)O)CCCCC[C@H]1CCC[C@@H]1C=CCCCC=CC KPKGFLKJYICXGM-ROUUACIJSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 124
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
238000006243 chemical reaction Methods 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
229910052943 magnesium sulfate Inorganic materials 0.000 description 33
235000019341 magnesium sulphate Nutrition 0.000 description 33
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 27
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
239000002904 solvent Substances 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 23
238000001704 evaporation Methods 0.000 description 21
230000008020 evaporation Effects 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
238000004440 column chromatography Methods 0.000 description 18
229910052786 argon Inorganic materials 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
229960001760 dimethyl sulfoxide Drugs 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
150000004702 methyl esters Chemical class 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
239000012223 aqueous fraction Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000007787 solid Substances 0.000 description 5
206010000234 Abortion spontaneous Diseases 0.000 description 4
241000700198 Cavia Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012267 brine Substances 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
150000004679 hydroxides Chemical class 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
208000015994 miscarriage Diseases 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000035935 pregnancy Effects 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
208000000995 spontaneous abortion Diseases 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
VAVRJAFIQXYMTN-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,3,6-trimethylhept-5-en-2-one Chemical compound COP(=O)(OC)CC(=O)C(C)(C)CC=C(C)C VAVRJAFIQXYMTN-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
239000003810 Jones reagent Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000000463 material Substances 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
238000002390 rotary evaporation Methods 0.000 description 3
150000003385 sodium Chemical class 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
OIGRHMGALPXFHI-UHFFFAOYSA-N (sulfamoylamino)ethane Chemical compound CCNS(N)(=O)=O OIGRHMGALPXFHI-UHFFFAOYSA-N 0.000 description 2
NOXPGSDFQWSNSW-UHFFFAOYSA-N (sulfamoylamino)methane Chemical compound CNS(N)(=O)=O NOXPGSDFQWSNSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 2
FPRITVHPAICIAA-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,6-dimethylhept-5-en-2-one Chemical compound COP(=O)(OC)CC(=O)C(C)CC=C(C)C FPRITVHPAICIAA-UHFFFAOYSA-N 0.000 description 2
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 2
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
ZWPIIIVBTUUSPK-VQTJNVASSA-N CC(C=CCCCC=C[C@H]1CCC([C@@H]1CCCCCCC(=O)O)=O)(C)C Chemical compound CC(C=CCCCC=C[C@H]1CCC([C@@H]1CCCCCCC(=O)O)=O)(C)C ZWPIIIVBTUUSPK-VQTJNVASSA-N 0.000 description 2
LKPISDZBKWCNPJ-WOLZVPSQSA-N CC=CCCCC=C[C@@H]1[C@@H](CCCCCC(C(O)=O)OC2OCCCC2)CCC1 Chemical compound CC=CCCCC=C[C@@H]1[C@@H](CCCCCC(C(O)=O)OC2OCCCC2)CCC1 LKPISDZBKWCNPJ-WOLZVPSQSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000012027 Collins reagent Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
206010000210 abortion Diseases 0.000 description 2
231100000176 abortion Toxicity 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
NNIOYZMQTMUSGH-UHFFFAOYSA-N ethyl 2,5-dimethylhex-4-enoate Chemical compound CCOC(=O)C(C)CC=C(C)C NNIOYZMQTMUSGH-UHFFFAOYSA-N 0.000 description 2
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000005187 foaming Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
229910000342 sodium bisulfate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
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CUGFPUPVVPERHH-DYAFIPEPSA-N [(1S,2R,3R,4R)-2-(7-methoxy-7-oxoheptyl)-4-(oxan-2-yloxy)-3-[(1E)-4,4,7-trimethyl-3-oxoocta-1,6-dienyl]cyclopentyl] benzoate Chemical compound O([C@@H]1C[C@@H]([C@@H]([C@H]1\C=C\C(=O)C(C)(C)CC=C(C)C)CCCCCCC(=O)OC)OC(=O)C=1C=CC=CC=1)C1CCCCO1 CUGFPUPVVPERHH-DYAFIPEPSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
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HJWOVKIAELHYCD-UHFFFAOYSA-N diethyl 2-methyl-2-(3-methylbut-2-enyl)propanedioate Chemical compound CCOC(=O)C(C)(CC=C(C)C)C(=O)OCC HJWOVKIAELHYCD-UHFFFAOYSA-N 0.000 description 1
UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
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GHXNOADWTDSHDJ-UHFFFAOYSA-N ethyl 2,2,5-trimethylhex-4-enoate Chemical compound CCOC(=O)C(C)(C)CC=C(C)C GHXNOADWTDSHDJ-UHFFFAOYSA-N 0.000 description 1
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125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
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UKYRRLFLRTXZEV-UHFFFAOYSA-N methyl 2,2,5-trimethylhex-4-enoate Chemical compound COC(=O)C(C)(C)CC=C(C)C UKYRRLFLRTXZEV-UHFFFAOYSA-N 0.000 description 1
VBIYLIKAHBXBJY-UHFFFAOYSA-N methyl 2,5-dimethylhex-4-enoate Chemical compound COC(=O)C(C)CC=C(C)C VBIYLIKAHBXBJY-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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UQZVCDCIMBLVNR-TWYODKAFSA-N sulprostone Chemical compound O[C@@H]1CC(=O)[C@H](C\C=C/CCCC(=O)NS(=O)(=O)C)[C@H]1\C=C\[C@@H](O)COC1=CC=CC=C1 UQZVCDCIMBLVNR-TWYODKAFSA-N 0.000 description 1
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125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
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239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- 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
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- 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
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI820422A 1981-02-13 1982-02-10 Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara (13e)-(8r,11r,12r)-11,15-dihydroxi-16,19-dimetyl-9-oxo-13,18-prostadiensyraderivat och av deras salter FI71308C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE3106149		1981-02-13
DE19813106149 DE3106149A1 (de)	1981-02-13	1981-02-13	(13e)-(8r,11r,12r,15s,16rs)-11,15-dihydroxy-16,19-dimethyl-9-oxo-13,18-prostadiensaeure sowie deren salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE19823202457 DE3202457A1 (de)	1982-01-22	1982-01-22	(13e)-(8r,11r,12r,15r)-11,15-dihydroxy-16,16,19-trimethyl-9-oxo-13,18-prostadiensaeure sowie deren salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE3202457		1982-01-22

Publications (3)

Publication Number	Publication Date
FI820422L FI820422L (fi)	1982-08-14
FI71308B FI71308B (fi)	1986-09-09
FI71308C true FI71308C (fi)	1986-12-19

Family

ID=25791276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI820422A FI71308C (fi)	1981-02-13	1982-02-10	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara (13e)-(8r,11r,12r)-11,15-dihydroxi-16,19-dimetyl-9-oxo-13,18-prostadiensyraderivat och av deras salter

Country Status (18)

Country	Link
EP (1)	EP0058632B1 (el)
AU (1)	AU543274B2 (el)
CA (1)	CA1205469A (el)
CS (1)	CS228915B2 (el)
DD (1)	DD202287A5 (el)
DE (1)	DE3260101D1 (el)
DK (1)	DK62082A (el)
ES (1)	ES509558A0 (el)
FI (1)	FI71308C (el)
GR (1)	GR78239B (el)
HU (1)	HU187643B (el)
IE (1)	IE52600B1 (el)
IL (1)	IL64994A (el)
NO (1)	NO158298C (el)
NZ (1)	NZ199729A (el)
PH (1)	PH18579A (el)
SU (1)	SU1218925A3 (el)
YU (1)	YU30582A (el)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2635985A1 (de) *	1976-08-06	1978-02-09	Schering Ag	Prostansaeurederivat und verfahren zu ihrer herstellung

1982
- 1982-02-10 FI FI820422A patent/FI71308C/fi not_active IP Right Cessation
- 1982-02-11 GR GR67289A patent/GR78239B/el unknown
- 1982-02-11 CA CA000396022A patent/CA1205469A/en not_active Expired
- 1982-02-12 IE IE316/82A patent/IE52600B1/en unknown
- 1982-02-12 YU YU00305/82A patent/YU30582A/xx unknown
- 1982-02-12 EP EP82730013A patent/EP0058632B1/de not_active Expired
- 1982-02-12 AU AU80419/82A patent/AU543274B2/en not_active Ceased
- 1982-02-12 HU HU82446A patent/HU187643B/hu unknown
- 1982-02-12 NZ NZ199729A patent/NZ199729A/en unknown
- 1982-02-12 ES ES509558A patent/ES509558A0/es active Granted
- 1982-02-12 DK DK62082A patent/DK62082A/da not_active Application Discontinuation
- 1982-02-12 NO NO820419A patent/NO158298C/no unknown
- 1982-02-12 IL IL64994A patent/IL64994A/xx unknown
- 1982-02-12 DE DE8282730013T patent/DE3260101D1/de not_active Expired
- 1982-02-12 CS CS82984A patent/CS228915B2/cs unknown
- 1982-02-12 SU SU823394400A patent/SU1218925A3/ru active
- 1982-02-15 DD DD82237418A patent/DD202287A5/de unknown
- 1982-02-15 PH PH26869A patent/PH18579A/en unknown

Also Published As

Publication number	Publication date
ES8301913A1 (es)	1983-02-01
IE820316L (en)	1982-08-13
NO820419L (no)	1982-08-16
GR78239B (el)	1984-09-26
ES509558A0 (es)	1983-02-01
AU8041982A (en)	1982-08-19
EP0058632A1 (de)	1982-08-25
NO158298B (no)	1988-05-09
CS228915B2 (en)	1984-05-14
PH18579A (en)	1985-08-12
DE3260101D1 (en)	1984-05-17
IL64994A (en)	1985-05-31
FI71308B (fi)	1986-09-09
DD202287A5 (de)	1983-09-07
SU1218925A3 (ru)	1986-03-15
NO158298C (no)	1988-08-17
YU30582A (en)	1984-12-31
EP0058632B1 (de)	1984-04-11
IL64994A0 (en)	1982-04-30
AU543274B2 (en)	1985-04-18
CA1205469A (en)	1986-06-03
FI820422L (fi)	1982-08-14
DK62082A (da)	1982-08-14
IE52600B1 (en)	1987-12-23
HU187643B (en)	1986-02-28
NZ199729A (en)	1985-07-12

Publication	Publication Date	Title
EP0783308B1 (en)	2001-07-04	Use of 9-deoxy prostaglandin derivatives to treat glaucoma
US4446147A (en)	1984-05-01	Azaprostacyclins, their preparation and pharmaceutical use
IE45863B1 (en)	1982-12-15	Prostanoic acid derivatives and process for their preparation
US7674921B2 (en)	2010-03-09	Internal 1,15-lactones of fluprostenol and related prostaglandin F2α analogs and their use in the treatment of glaucoma and intraocular hypertension
NO155537B (no)	1987-01-05	Analogifremgangsmaate ved fremstilling av terapeutisk aktive, nye carbacycliner.
FI77645B (fi)	1988-12-30	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1a,1b-dihomo-3-oxakarbacyklinderivat.
US4217360A (en)	1980-08-12	Novel 1,3-benzodioxaneprostanoic acid derivatives and process for the preparation thereof
US4004020A (en)	1977-01-18	Novel prostanoic acid derivatives and process for the preparation thereof
CA1091664A (en)	1980-12-16	Prostaglandin derivatives
FI71308B (fi)	1986-09-09	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara (13e)-(8r,11r,12r)-11,15-dihydroxi-16,19-dimetyl-9-oxo-13,18-prostadiensyraderivat och av deras salter
FI66367B (fi)	1984-06-29	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 7-oxoprostacyklinderivat
US4532236A (en)	1985-07-30	Certain prostacyclins and their blood-pressure-lowering and thrombocyte-aggregation-inhibiting compositions and methods
IE51308B1 (en)	1986-11-26	Heterocyclic compounds,medicaments containing them and processes for preparing them
CS235307B2 (en)	1985-05-15	Method of 6a-carbaprostaglandine -12 derivatives production
US4006136A (en)	1977-02-01	Prostaglandin intermediates
US4161608A (en)	1979-07-17	11 Hydroxy methyl 11-deoxyprostaglandin E1
US4234720A (en)	1980-11-18	Prostaglandin derivatives
US4089898A (en)	1978-05-16	11-Deoxyprostaglandin derivatives
US4188331A (en)	1980-02-12	Prostaglandin derivatives
HU207715B (en)	1993-05-28	Process for producing 9-substituted carbacyclin derivatives and pharmaceutical compositions containing them as active components
CS252481B2 (en)	1987-09-17	Method of new carbacyclines production
US4036856A (en)	1977-07-19	Cyclopentanone derivatives
Abraham et al.	1979	11 Hydroxy methyl 11-deoxyprostaglandin E 1
DE3106149A1 (de)	1982-09-09	(13e)-(8r,11r,12r,15s,16rs)-11,15-dihydroxy-16,19-dimethyl-9-oxo-13,18-prostadiensaeure sowie deren salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen
CA2201294A1 (en)	1996-04-11	Use of 9-deoxy prostaglandin derivatives to treat glaucoma

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: SCHERING AKTIENGESELLSCHAFT