FI71138C - Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner Download PDF

Info

Publication number: FI71138C
Authority: FI; Finland
Prior art keywords: oxide; formula; compound; acid; hydroxy
Prior art date: 1976-12-31

Application number

FI773757A

Other languages

English (en)

Finnish (fi)

Other versions

FI773757A (fi

FI71138B (fi

Inventor

Carmelo Gandolfi

Carlo Passarotti

Alessandro Andr-Oni

Angelo Fumagalli

Franco Faustini

Roberto Ceserani

Maria Maddalena Usardi

Original Assignee

Erba Farmitalia

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.)

1976-12-31

Filing date

1977-12-13

Publication date

1986-11-24

1976-12-31 Priority claimed from IT3104176A external-priority patent/IT1072541B/it

1977-01-14 Priority claimed from IT1928377A external-priority patent/IT1079103B/it

1977-03-14 Priority claimed from IT2117177A external-priority patent/IT1085878B/it

1977-03-21 Priority claimed from IT2141277A external-priority patent/IT1075678B/it

1977-03-31 Priority claimed from IT2186377A external-priority patent/IT1115636B/it

1977-12-13 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1978-07-01 Publication of FI773757A publication Critical patent/FI773757A/fi

1986-08-14 Publication of FI71138B publication Critical patent/FI71138B/fi

1986-11-24 Application granted granted Critical

1986-11-24 Publication of FI71138C publication Critical patent/FI71138C/fi

Links

239000002253 acid Substances 0.000 claims description 356
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 291
150000001875 compounds Chemical class 0.000 claims description 260
239000000203 mixture Substances 0.000 claims description 87
229910052739 hydrogen Inorganic materials 0.000 claims description 51
238000000034 method Methods 0.000 claims description 51
239000001257 hydrogen Substances 0.000 claims description 49
-1 bicyclic prostaglandins Chemical class 0.000 claims description 45
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical class 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
125000004043 oxo group Chemical group O=* 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
230000009467 reduction Effects 0.000 claims description 15
125000006239 protecting group Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004423 acyloxy group Chemical group 0.000 claims description 11
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
238000006266 etherification reaction Methods 0.000 claims description 6
125000000129 anionic group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229940094443 oxytocics prostaglandins Drugs 0.000 claims description 5
230000001603 reducing effect Effects 0.000 claims description 5
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 claims description 4
230000008569 process Effects 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
239000000571 coke Substances 0.000 claims description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
RYXPMWYHEBGTRV-UHFFFAOYSA-N Omeprazole sodium Chemical compound [Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RYXPMWYHEBGTRV-UHFFFAOYSA-N 0.000 claims 1
229940049964 oleate Drugs 0.000 claims 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 207
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 170
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 157
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
150000004702 methyl esters Chemical class 0.000 description 147
LQMPUMZAMJWOIC-UHFFFAOYSA-N 6-bromo-3-(5-chloro-2-ethylsulfonylanilino)-7-[(4-cyclopentylpiperazin-1-yl)methyl]quinazolin-4-one Chemical compound BrC=1C=C2C(N(C=NC2=CC=1CN1CCN(CC1)C1CCCC1)NC1=C(C=CC(=C1)Cl)S(=O)(=O)CC)=O LQMPUMZAMJWOIC-UHFFFAOYSA-N 0.000 description 127
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 64
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
239000002904 solvent Substances 0.000 description 62
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 59
238000003756 stirring Methods 0.000 description 56
239000012074 organic phase Substances 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
239000000741 silica gel Substances 0.000 description 53
229910002027 silica gel Inorganic materials 0.000 description 53
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
238000001819 mass spectrum Methods 0.000 description 48
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 41
230000007935 neutral effect Effects 0.000 description 37
229910052799 carbon Inorganic materials 0.000 description 33
125000001246 bromo group Chemical group Br* 0.000 description 32
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 23
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
239000000460 chlorine Substances 0.000 description 19
229910000403 monosodium phosphate Inorganic materials 0.000 description 19
235000019799 monosodium phosphate Nutrition 0.000 description 19
239000000725 suspension Substances 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
150000002148 esters Chemical class 0.000 description 18
230000002829 reductive effect Effects 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 16
238000006722 reduction reaction Methods 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
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230000000694 effects Effects 0.000 description 15
239000011630 iodine Substances 0.000 description 15
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
150000001298 alcohols Chemical class 0.000 description 12
239000002585 base Substances 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000012279 sodium borohydride Substances 0.000 description 12
229910000033 sodium borohydride Inorganic materials 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
235000011181 potassium carbonates Nutrition 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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230000008020 evaporation Effects 0.000 description 9
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 9
235000006408 oxalic acid Nutrition 0.000 description 9
238000007363 ring formation reaction Methods 0.000 description 9
239000011734 sodium Substances 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 8
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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
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239000012442 inert solvent Substances 0.000 description 8
HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 8
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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 7
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230000002744 anti-aggregatory effect Effects 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
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239000002244 precipitate Substances 0.000 description 7
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KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 7
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229910052708 sodium Inorganic materials 0.000 description 7
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
238000005406 washing Methods 0.000 description 7
229910052725 zinc Inorganic materials 0.000 description 7
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
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238000009835 boiling Methods 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
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HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
238000005903 acid hydrolysis reaction Methods 0.000 description 4
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230000003276 anti-hypertensive effect Effects 0.000 description 4
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
238000013375 chromatographic separation Methods 0.000 description 4
150000004292 cyclic ethers Chemical class 0.000 description 4
YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 4
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 4
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ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
230000010287 polarization Effects 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000003405 preventing effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000000328 pro-aggregatory effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003815 prostacyclins Chemical class 0.000 description 1
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
PXGPLTODNUVGFL-JZFBHDEDSA-N prostaglandin F2beta Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-JZFBHDEDSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
RFIZPYFNEYSHKG-UHFFFAOYSA-N pyrrolidine-2,5-dione;sodium Chemical compound [Na].O=C1CCC(=O)N1 RFIZPYFNEYSHKG-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
239000006215 rectal suppository Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000002731 stomach secretion inhibitor Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
239000000003 vaginal tablet Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical 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)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)

FI773757A 1976-12-31 1977-12-13 Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner FI71138C (fi)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
IT3104176A IT1072541B (it)	1976-12-31	1976-12-31	6(9)-ossido-prostenoici acidi
IT3104176		1976-12-31
IT1928377A IT1079103B (it)	1977-01-14	1977-01-14	Derivati del 9-ossido-alo-prostanoico acido
IT1928377		1977-01-14
IT2117177A IT1085878B (it)	1977-03-14	1977-03-14	Bicilicli ossiranici 15-cheto-prostenoici acidi
IT2117177		1977-03-14
IT2141277A IT1075678B (it)	1977-03-21	1977-03-21	15-idrossi-bicicliche prostaglandine
IT2141277		1977-03-21
IT2186377		1977-03-31
IT2186377A IT1115636B (it)	1977-03-31	1977-03-31	13,14-deidro-bicicliche prostaglandine

Publications (3)

Publication Number	Publication Date
FI773757A FI773757A (fi)	1978-07-01
FI71138B FI71138B (fi)	1986-08-14
FI71138C true FI71138C (fi)	1986-11-24

Family

ID=27517783

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI773757A FI71138C (fi)	1976-12-31	1977-12-13	Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner

Country Status (19)

Country	Link
US (9)	US4297368A (xx)
JP (1)	JPS5384959A (xx)
BE (1)	BE862514A (xx)
CH (1)	CH636096A5 (xx)
DE (1)	DE2757919A1 (xx)
DK (1)	DK586077A (xx)
FI (1)	FI71138C (xx)
FR (1)	FR2376147A1 (xx)
GB (1)	GB1599280A (xx)
GR (1)	GR66057B (xx)
HU (1)	HU182725B (xx)
IL (1)	IL53630A0 (xx)
KE (1)	KE3196A (xx)
MY (1)	MY8200265A (xx)
NL (1)	NL7714613A (xx)
NO (1)	NO153689C (xx)
NZ (1)	NZ185986A (xx)
SE (1)	SE437268B (xx)
YU (1)	YU316677A (xx)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1053781B (it) *	1974-09-25	1981-10-10	Erba C S P A Ora Farmitalia	Omega nor cicloalcil 13.14 deidro prostaglandine
US4178367A (en) *	1977-02-21	1979-12-11	Ono Pharmaceutical Co. Ltd.	Prostaglandin I2 analogues
HU182583B (en) *	1977-03-01	1984-02-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing prostacyclin and analogues thereof
AU524786B2 (en) *	1977-03-07	1982-10-07	The Upjohn Company	Prostacyclins
IT1088966B (it) *	1977-11-15	1985-06-10	Erba Carlo Spa	13,14-dideidro-prostaglandine
US4206127A (en) *	1977-11-23	1980-06-03	Miles Laboratories, Inc.	5,6-Dihydro analogues of prostaglandin I2
BE871209R (fr) *	1977-12-05	1979-04-12	Upjohn Co	Analogues de 5,6-dihydro-prostacycline et leur preparation
IL58384A0 (en)	1978-10-14	1980-01-31	Beecham Group Ltd	12-aza analogues of prostcyclin their preparation and pharmaceutical composition containing them
DE2947526A1 (de) *	1978-11-29	1980-06-12	Ono Pharmaceutical Co	Prostacyclin-analoge
US4237060A (en)	1979-03-23	1980-12-02	Hoffmann-La Roche Inc.	Prostacyclin analogs
US4235924A (en)	1979-06-07	1980-11-25	American Cyanamid Company	Prostacyclin analogs of the 1 series and related analogs wherein the carboxylic acid function has been replaced
US4328156A (en) *	1979-07-05	1982-05-04	The Upjohn Company	19-Hydroxy-19-methyl-7α-homo-PGI1 compounds
US4301079A (en) *	1979-07-05	1981-11-17	The Upjohn Company	19-Hydroxy-19-methyl-PGI1 compounds
US4273718A (en) *	1979-07-05	1981-06-16	The Upjohn Company	2-Decarboxy-2-hydroxymethyl-9-deoxy-6ε,9αepoxy-16,16-difluoro-19-hydroxy-PGF1
US4321203A (en) *	1979-07-05	1982-03-23	The Upjohn Company	19-Hydroxy-7a-homo-PGI1 compounds
US4474966A (en) *	1980-03-03	1984-10-02	The Upjohn Company	19-Hydroxy-7a-homo-PGI1 and 19-hydroxy-19-methyl-7a-homo-PGI1 compounds
DE3035713A1 (de) *	1980-09-22	1982-04-29	F. Hoffmann-La Roche & Co. AG, 4002 Basel	Prostacycline
EP0059307A1 (de)	1981-02-26	1982-09-08	Grünenthal GmbH	Verfahren zur Herstellung von 2-Oxabicyclo(3.3.0)octanderivaten und danach erhältliche Produkte
US4543353A (en) *	1981-11-27	1985-09-24	Farmitalia Carlo Erba S.P.A.	Ester and amide derivatives of 13,14-didehydro prostaglandins
EP0108451A3 (en) *	1982-11-05	1985-04-10	The Procter & Gamble Company	Novel prostaglandin analogues
US4576962A (en) *	1983-10-19	1986-03-18	The Procter & Gamble Company	Prostaglandin analogues
US5153174A (en) *	1989-10-30	1992-10-06	Union Carbide Chemicals & Plastics Inc.	Polymer mixtures useful in skin care
WO1999012899A1 (en) *	1997-09-09	1999-03-18	The Procter & Gamble Company	A process for making prostaglandin f analogs
EP1615881A2 (en) *	2003-04-01	2006-01-18	Theravance, Inc.	Diarylmethyl and related compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
HUE028874T2 (en)	2009-07-28	2017-01-30	Ono Pharmaceutical Co	Bicyclic compound and its use for medical purposes
US9150537B2 (en)	2011-01-27	2015-10-06	Ono Pharmaceutical Co., Ltd.	Bicyclic compound and use thereof for medical purposes
WO2012102357A1 (ja)	2011-01-27	2012-08-02	小野薬品工業株式会社	二環式化合物およびその医薬用途
WO2018003945A1 (ja)	2016-06-30	2018-01-04	小野薬品工業株式会社	二環式化合物の製造方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL51189A (en) *	1976-02-04	1985-08-30	Upjohn Co	Prostaglandin analogs
GB1583961A (en) *	1976-05-11	1981-02-04	Wellcome Found	Prostacyclin and derivatives thereof
JPS537665A (en) *	1976-05-11	1978-01-24	Wellcome Found	Novel ether* its preparation and its use
MX4813E (es) *	1976-06-01	1982-10-19	Upjohn Co	Procedimiento para preparar analogos de prostaglandinas
US4125712A (en) *	1976-06-01	1978-11-14	The Upjohn Company	Certain 5,6-dihydro-prostacyclin analogs
US4123441A (en) *	1976-09-22	1978-10-31	The Upjohn Company	Enlarged-hetero-ring prostacyclin analogs
GB1595056A (en) *	1976-10-12	1981-08-05	Wellcome Found	Pharmaceutical combination
AU511711B2 (en) *	1976-12-30	1980-09-04	Upjohn Company, The	6-Oxo and 5, 6-Dihalo prostaglandin analogues
HU182583B (en)	1977-03-01	1984-02-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing prostacyclin and analogues thereof
AU524786B2 (en) *	1977-03-07	1982-10-07	The Upjohn Company	Prostacyclins
GB2002363B (en) *	1977-08-03	1982-03-24	Upjohn Co	Prostacyclin analogues
US4206127A (en) *	1977-11-23	1980-06-03	Miles Laboratories, Inc.	5,6-Dihydro analogues of prostaglandin I2

1977
- 1977-12-13 FI FI773757A patent/FI71138C/fi not_active IP Right Cessation
- 1977-12-15 NZ NZ185986A patent/NZ185986A/xx unknown
- 1977-12-18 IL IL53630A patent/IL53630A0/xx unknown
- 1977-12-21 GB GB53226/77A patent/GB1599280A/en not_active Expired
- 1977-12-22 GR GR55028A patent/GR66057B/el unknown
- 1977-12-24 DE DE19772757919 patent/DE2757919A1/de not_active Withdrawn
- 1977-12-28 JP JP15758977A patent/JPS5384959A/ja active Pending
- 1977-12-29 DK DK586077A patent/DK586077A/da not_active Application Discontinuation
- 1977-12-30 NO NO774524A patent/NO153689C/no unknown
- 1977-12-30 HU HU77EA181A patent/HU182725B/hu unknown
- 1977-12-30 BE BE183997A patent/BE862514A/xx not_active IP Right Cessation
- 1977-12-30 YU YU03166/77A patent/YU316677A/xx unknown
- 1977-12-30 SE SE7714948A patent/SE437268B/sv unknown
- 1977-12-30 FR FR7739879A patent/FR2376147A1/fr active Granted
- 1977-12-30 NL NL7714613A patent/NL7714613A/xx not_active Application Discontinuation
1978
- 1978-01-03 CH CH4978A patent/CH636096A5/de not_active IP Right Cessation
- 1978-06-29 US US05/920,166 patent/US4297368A/en not_active Expired - Lifetime
- 1978-07-28 US US05/928,809 patent/US4328240A/en not_active Expired - Lifetime
- 1978-12-01 US US05/965,267 patent/US4277491A/en not_active Expired - Lifetime
1979
- 1979-02-26 US US05/015,148 patent/US4230721A/en not_active Expired - Lifetime
- 1979-04-13 US US06/029,925 patent/US4303670A/en not_active Expired - Lifetime
- 1979-06-18 US US06/049,118 patent/US4254137A/en not_active Expired - Lifetime
- 1979-06-18 US US06/049,326 patent/US4262016A/en not_active Expired - Lifetime
- 1979-11-01 US US06/090,305 patent/US4250188A/en not_active Expired - Lifetime
- 1979-11-30 US US06/098,963 patent/US4271184A/en not_active Expired - Lifetime
1982
- 1982-03-17 KE KE3196A patent/KE3196A/xx unknown
- 1982-12-30 MY MY265/82A patent/MY8200265A/xx unknown

Also Published As

Publication number	Publication date
KE3196A (en)	1982-04-02
US4303670A (en)	1981-12-01
NZ185986A (en)	1979-12-11
FR2376147B1 (xx)	1982-01-08
FR2376147A1 (fr)	1978-07-28
US4262016A (en)	1981-04-14
DK586077A (da)	1978-07-01
GR66057B (xx)	1981-01-14
YU316677A (en)	1984-02-29
NL7714613A (nl)	1978-07-04
GB1599280A (en)	1981-09-30
FI773757A (fi)	1978-07-01
FI71138B (fi)	1986-08-14
US4250188A (en)	1981-02-10
US4254137A (en)	1981-03-03
DE2757919A1 (de)	1978-07-13
US4297368A (en)	1981-10-27
US4271184A (en)	1981-06-02
US4328240A (en)	1982-05-04
US4230721A (en)	1980-10-28
CH636096A5 (de)	1983-05-13
NO774524L (no)	1978-07-03
MY8200265A (en)	1982-12-31
BE862514A (fr)	1978-04-14
HU182725B (en)	1984-03-28
SE7714948L (sv)	1978-07-01
IL53630A0 (en)	1978-03-10
NO153689C (no)	1986-05-07
US4277491A (en)	1981-07-07
JPS5384959A (en)	1978-07-26
SE437268B (sv)	1985-02-18
NO153689B (no)	1986-01-27

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: FARMITALIA CARLO ERBA S.P.A

Publication	Publication Date	Title
FI71138C (fi)	1986-11-24	Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner
FI72509B (fi)	1987-02-27	Foerfarande foer framstaellning av 9-deoxi-9a-metylen-isosterer av pgi2.
FI77645C (fi)	1989-04-10	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1a,1b-dihomo-3-oxakarbacyklinderivat.
US4490537A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
US3835179A (en)	1974-09-10	Novel 15-substituted prostanoic acids and esters
JPS6140662B2 (xx)	1986-09-10
US4000305A (en)	1976-12-28	15-, 16- AND 17-Indolyl or indolinyl nor prostanoic acid derivatives
IE45604B1 (en)	1982-10-06	Prostacyclin derivatives
US4241215A (en)	1980-12-23	Prostane derivatives
US4490549A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
FI78064B (fi)	1989-02-28	Foerfarande foer framstaellning av terapeutiskt anvaendbara karbacyklinderivat.
DE2606051A1 (de)	1976-09-02	2,2-difluor-prostaglandin-e, -f tief alpha, -f tief beta, -a und -b-analoga und verfahren zu deren herstellung
KR840000948B1 (ko)	1984-07-01	PGI_2의 9-데옥시-9a-메틸렌 등배전자체의 제조방법
US4259244A (en)	1981-03-31	Certain 13,14-didehydro-PGI1 compounds
US3935241A (en)	1976-01-27	11α-METHYLSUBSTITUTED PROSTAGLANDIN DERIVATIVES
CA1183842A (en)	1985-03-12	Bicyclic prostaglandins and process for their preparation
CS216842B2 (cs)	1982-11-26	Způsob výroby 2-oxabicyklických prostaglandinů
CA1060006A (en)	1979-08-07	15-SUBSTITUTED 11.alpha.-CYANO PROSTAGLANDINS AND RELATED COMPOUNDS
CA1209134A (en)	1986-08-05	9-deoxy-9a-methylene isosteres of pgi.sub.2 and process for their preparation
US4046787A (en)	1977-09-06	Novel 15-substituted prostanoic acids and esters
US4100343A (en)	1978-07-11	11-Deoxyprostaglandin derivatives
CA1183841A (en)	1985-03-12	Bicyclic prostaglandins and process for their preparation
Gandolfi et al.	1981	Certain 13, 14-didehydro-PGI 1 compounds
Abraham et al.	1979	11 Hydroxy methyl 11-deoxyprostaglandin E 1
Smith et al.	1978	6-Hydroxy-PGE 1 compounds