FI64578C - Foerfarande foer framstaellning av nya farmakologiskt aktiva prostaglandin-analoger - Google Patents

Foerfarande foer framstaellning av nya farmakologiskt aktiva prostaglandin-analoger Download PDF

Info

Publication number: FI64578C
Authority: FI; Finland
Prior art keywords: methyl; group; hydrogen; formula; hydroxy
Prior art date: 1975-01-24

Application number

FI760002A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI760002A (xx

FI64578B (fi

Inventor

Umberto Guzzi

Romeo Ciabatti

Original Assignee

Lepetit Spa

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.)

1975-01-24

Filing date

1976-01-05

Publication date

1983-12-12

1976-01-05 Application filed by Lepetit Spa filed Critical Lepetit Spa

1976-07-25 Publication of FI760002A publication Critical patent/FI760002A/fi

1983-08-31 Application granted granted Critical

1983-08-31 Publication of FI64578B publication Critical patent/FI64578B/fi

1983-12-12 Publication of FI64578C publication Critical patent/FI64578C/fi

Links

238000002360 preparation method Methods 0.000 title claims description 7
230000000144 pharmacologic effect Effects 0.000 title 1
239000000203 mixture Substances 0.000 claims description 39
238000000034 method Methods 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000004043 oxo group Chemical group O=* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000003180 prostaglandins Chemical class 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 claims description 2
VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 claims description 2
ZKCZXVODRKOWIY-UHFFFAOYSA-N diphenylstannane Chemical compound C=1C=CC=CC=1[SnH2]C1=CC=CC=C1 ZKCZXVODRKOWIY-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000000047 product Substances 0.000 description 59
239000002253 acid Substances 0.000 description 56
238000010521 absorption reaction Methods 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
150000004702 methyl esters Chemical class 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 30
-1 alkyl radical Chemical class 0.000 description 27
239000003921 oil Substances 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 17
239000007858 starting material Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000000862 absorption spectrum Methods 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000002243 precursor Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
238000013375 chromatographic separation Methods 0.000 description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
CKGAPNASZQDWOE-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methoxyheptan-2-one Chemical compound CCCCC(OC)C(=O)CP(=O)(OC)OC CKGAPNASZQDWOE-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000012027 Collins reagent Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 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
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
230000007017 scission Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WZAWFKKYWRMNLU-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methoxy-3-methylheptan-2-one Chemical compound CCCCC(C)(OC)C(=O)CP(=O)(OC)OC WZAWFKKYWRMNLU-UHFFFAOYSA-N 0.000 description 1
QFLUTIBQKCBLNG-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenoxyheptan-2-one Chemical compound COP(=O)(OC)CC(=O)C(CCCC)OC1=CC=CC=C1 QFLUTIBQKCBLNG-UHFFFAOYSA-N 0.000 description 1
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
206010000234 Abortion spontaneous Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
MKJQIOMCOYQKNP-UHFFFAOYSA-N bromomethane;magnesium Chemical compound [Mg].BrC MKJQIOMCOYQKNP-UHFFFAOYSA-N 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000003529 luteolytic effect Effects 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
208000015994 miscarriage Diseases 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
UKVVPDHLUHAJNZ-PMACEKPBSA-N prostane Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC UKVVPDHLUHAJNZ-PMACEKPBSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
125000001424 substituent group Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Pyrane Compounds (AREA)

FI760002A 1975-01-24 1976-01-05 Foerfarande foer framstaellning av nya farmakologiskt aktiva prostaglandin-analoger FI64578C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3248/75A GB1538871A (en)	1975-01-24	1975-01-24	Prostaglandins
GB324875		1975-01-24

Publications (3)

Publication Number	Publication Date
FI760002A FI760002A (xx)	1976-07-25
FI64578B FI64578B (fi)	1983-08-31
FI64578C true FI64578C (fi)	1983-12-12

Family

ID=9754749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI760002A FI64578C (fi)	1975-01-24	1976-01-05	Foerfarande foer framstaellning av nya farmakologiskt aktiva prostaglandin-analoger

Country Status (28)

Country	Link
JP (1)	JPS6024098B2 (xx)
AR (1)	AR212328A1 (xx)
AT (1)	AT351186B (xx)
BE (1)	BE837865A (xx)
CA (1)	CA1076569A (xx)
CH (1)	CH609682A5 (xx)
CS (1)	CS187333B2 (xx)
DD (1)	DD122517A5 (xx)
DE (1)	DE2601646A1 (xx)
DK (1)	DK27376A (xx)
FI (1)	FI64578C (xx)
FR (1)	FR2298322A1 (xx)
GB (1)	GB1538871A (xx)
GR (1)	GR58537B (xx)
HU (1)	HU174185B (xx)
IE (1)	IE43821B1 (xx)
IL (1)	IL48870A (xx)
LU (1)	LU74240A1 (xx)
NL (1)	NL185203C (xx)
NO (1)	NO147714C (xx)
NZ (1)	NZ179816A (xx)
PH (1)	PH14040A (xx)
PT (1)	PT64737B (xx)
RO (1)	RO71901A (xx)
SE (1)	SE446726B (xx)
SU (1)	SU607550A3 (xx)
YU (1)	YU40805B (xx)
ZA (1)	ZA7681B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4064350A (en) *	1976-11-22	1977-12-20	G. D. Searle & Co.	15,16-Dihydroxyprostaglandins
US4194055A (en) *	1976-03-03	1980-03-18	American Cyanamid Company	15,16-dioxy prostenoic acids and esters
IT1162731B (it) *	1979-04-10	1987-04-01	Lepetit Spa	16-metil-16-metossi-5,6-diidro-prosta-glandine della serie e1 ad attivita'antisecretoria
JPS56162014A (en) *	1980-05-16	1981-12-12	Nippon Denso Co Ltd	Measuring device for flow rate of gas

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1392716A (en) *	1971-05-11	1975-04-30	Ici Ltd	Moulding
US4304907A (en) *	1972-05-10	1981-12-08	The Upjohn Company	Bicyclo lactone intermediates for prostaglandin analogs

1975
- 1975-01-24 GB GB3248/75A patent/GB1538871A/en not_active Expired
1976
- 1976-01-05 FI FI760002A patent/FI64578C/fi not_active IP Right Cessation
- 1976-01-07 ZA ZA00760081A patent/ZA7681B/xx unknown
- 1976-01-09 GR GR49742A patent/GR58537B/el unknown
- 1976-01-15 YU YU111/76A patent/YU40805B/xx unknown
- 1976-01-16 CS CS76305A patent/CS187333B2/cs unknown
- 1976-01-17 DE DE19762601646 patent/DE2601646A1/de active Granted
- 1976-01-19 IL IL48870A patent/IL48870A/xx unknown
- 1976-01-21 AT AT36776A patent/AT351186B/de not_active IP Right Cessation
- 1976-01-21 RO RO7684563A patent/RO71901A/ro unknown
- 1976-01-22 IE IE120/76A patent/IE43821B1/en unknown
- 1976-01-22 PH PH18006A patent/PH14040A/en unknown
- 1976-01-22 DD DD190915A patent/DD122517A5/xx unknown
- 1976-01-22 FR FR7601707A patent/FR2298322A1/fr active Granted
- 1976-01-23 BE BE163765A patent/BE837865A/xx not_active IP Right Cessation
- 1976-01-23 CH CH83176A patent/CH609682A5/xx not_active IP Right Cessation
- 1976-01-23 PT PT64737A patent/PT64737B/pt unknown
- 1976-01-23 CA CA244,132A patent/CA1076569A/en not_active Expired
- 1976-01-23 NZ NZ179816A patent/NZ179816A/xx unknown
- 1976-01-23 JP JP51006567A patent/JPS6024098B2/ja not_active Expired
- 1976-01-23 SE SE7600729A patent/SE446726B/xx not_active IP Right Cessation
- 1976-01-23 NL NLAANVRAGE7600696,A patent/NL185203C/xx not_active IP Right Cessation
- 1976-01-23 DK DK27376*#A patent/DK27376A/da not_active Application Discontinuation
- 1976-01-23 AR AR262009A patent/AR212328A1/es active
- 1976-01-23 HU HU76LE788A patent/HU174185B/hu not_active IP Right Cessation
- 1976-01-23 SU SU762311606A patent/SU607550A3/ru active
- 1976-01-23 LU LU74240A patent/LU74240A1/xx unknown
- 1976-01-23 NO NO760214A patent/NO147714C/no unknown

Also Published As

Publication number	Publication date
IE43821B1 (en)	1981-06-03
GR58537B (en)	1977-10-31
IL48870A0 (en)	1976-03-31
GB1538871A (en)	1979-01-24
PT64737B (fr)	1977-08-12
NO147714B (no)	1983-02-21
PH14040A (en)	1980-12-12
LU74240A1 (xx)	1976-07-23
SU607550A3 (ru)	1978-05-15
NO760214L (xx)	1976-07-27
NL7600696A (nl)	1976-07-27
JPS5198249A (xx)	1976-08-30
AR212328A1 (es)	1978-06-30
CS187333B2 (en)	1979-01-31
FI760002A (xx)	1976-07-25
NL185203C (nl)	1990-02-16
IL48870A (en)	1979-11-30
SE7600729L (sv)	1976-07-25
ZA7681B (en)	1976-12-29
JPS6024098B2 (ja)	1985-06-11
YU11176A (en)	1982-10-31
DK27376A (da)	1976-07-25
BE837865A (fr)	1976-07-23
FI64578B (fi)	1983-08-31
ATA36776A (de)	1978-12-15
DD122517A5 (xx)	1976-10-12
IE43821L (en)	1976-07-24
HU174185B (hu)	1979-11-28
CA1076569A (en)	1980-04-29
AT351186B (de)	1979-07-10
DE2601646C2 (xx)	1987-07-02
FR2298322B1 (xx)	1979-09-21
NO147714C (no)	1983-06-01
YU40805B (en)	1986-06-30
FR2298322A1 (fr)	1976-08-20
DE2601646A1 (de)	1976-07-29
PT64737A (fr)	1976-02-01
CH609682A5 (en)	1979-03-15
SE446726B (sv)	1986-10-06
RO71901A (ro)	1982-02-26
NZ179816A (en)	1978-04-03
NL185203B (nl)	1989-09-18

Legal Events

Date	Code	Title	Description
1994-08-05	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: GRUPPO LEPETIT S.P.A.

Publication	Publication Date	Title
US4020097A (en)	1977-04-26	Bicyclo [3.1.0]hexane-3-one derivatives of 11-deoxy PGE
US20040176645A1 (en)	2004-09-09	Process for stereoselective synthesis of prostacyclin derivatives
CN104350035A (zh)	2015-02-11	制备曲前列环素及其衍生物的方法
DE69008851T2 (de)	1994-08-18	VERFAHREN ZUR HERSTELLUNG VON 5,6,7, -TRINOR- 4,8,-INTER-m-PHENYLEN PGI,2 Abkömmlingen.
EP3556743B1 (en)	2020-12-09	Process for preparing (9e,11z)-9, 11-hexadecadienal
FI64578C (fi)	1983-12-12	Foerfarande foer framstaellning av nya farmakologiskt aktiva prostaglandin-analoger
US4169895A (en)	1979-10-02	Antisecretory 16,16-dimethyl-17-oxaprostaglandins
GB2030144A (en)	1980-04-02	Keto-bicyclooctanes
US4000305A (en)	1976-12-28	15-, 16- AND 17-Indolyl or indolinyl nor prostanoic acid derivatives
Banwell et al.	1998	Diastereoselective synthesis of the tetrahydropyranoid core of the polyketide herbicide herboxidiene and model studies pertaining to attachment of the side-chain
Harashima et al.	1991	Sodium bis (2-methoxyethoxy)(1, 1, 1, 3, 3, 3-hexafluoro-2-propoxy) aluminum hydride, a new stereoselective reducing agent in a carbacyclin synthesis
US4918202A (en)	1990-04-17	Precursor of prostaglandin
US4041064A (en)	1977-08-09	16-Methyl prost-5-en-13-ynoic acid derivatives
US4170596A (en)	1979-10-09	Novel monoesters of cis-cyclopentenediol, process for preparation thereof, and process for preparation of lactones from the monoesters
NO146280B (no)	1982-05-24	Bis-tetrahydropyranyleter for anvendelse som mellomprodukt for fremstilling av en fysiologisk aktiv p-bifenylester av en prostaglandinanalog av e- eller f-serien
CA1254577A (en)	1989-05-23	7-oxabicycloheptane prostaglandin intermediates and method for preparing same
KR810001216B1 (ko)	1981-09-29	프로스타글란딘계 화합물의 제조방법
Leppard et al.	1976	Preparation of 4‐(4′‐Methyl‐2′‐oxo‐cyclohex‐3′‐en‐1′‐yl)‐pentan‐1‐ol and Derivatives of 3‐(4′‐Methyl‐2′‐oxo‐cyclohex‐3′‐en‐1′‐yl)‐butan‐1‐ol
US4499292A (en)	1985-02-12	7-Oxabicycloheptane prostaglandin intermediates and method for preparing same
US4213907A (en)	1980-07-22	Prostaglandin intermediates
JPS5921864B2 (ja)	1984-05-22	フルオロプロスタグランジン及びその製造法
JP2788333B2 (ja)	1998-08-20	シクロペンタノール類の製造法
SU1291587A1 (ru)	1987-02-23	Способ получени простагландина @ 2 @ или его аналогов
US3912725A (en)	1975-10-14	Process for converting a type prostaglandins to E type prostaglandins
US4309351A (en)	1982-01-05	Chemical synthesis