IL49285A - The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one - Google Patents
The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-oneInfo
- Publication number
- IL49285A IL49285A IL49285A IL4928573A IL49285A IL 49285 A IL49285 A IL 49285A IL 49285 A IL49285 A IL 49285A IL 4928573 A IL4928573 A IL 4928573A IL 49285 A IL49285 A IL 49285A
- Authority
- IL
- Israel
- Prior art keywords
- trans
- iodo
- cyclopentene
- och
- cyclohexyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 5
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- IJAISRYWNXYCTM-UHFFFAOYSA-N 7-(5-oxocyclopenten-1-yl)heptanal Chemical compound O=CCCCCCCC1=CCCC1=O IJAISRYWNXYCTM-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims 1
- 229910001641 magnesium iodide Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 19
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 4
- 150000003180 prostaglandins Chemical class 0.000 abstract description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 125000006239 protecting group Chemical group 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- SJZDDNSUIVLYIN-BQYQJAHWSA-N (e)-1-iodooct-1-ene Chemical compound CCCCCC\C=C\I SJZDDNSUIVLYIN-BQYQJAHWSA-N 0.000 abstract 1
- KTBUGNSRUZRREG-MDZDMXLPSA-N (e)-3-(1-ethoxyethoxy)-1-iodooct-1-ene Chemical compound CCCCCC(\C=C\I)OC(C)OCC KTBUGNSRUZRREG-MDZDMXLPSA-N 0.000 abstract 1
- -1 2-tetrahydropyranyloxy Chemical group 0.000 abstract 1
- BJSLPGNZBIRLNV-UHFFFAOYSA-N C(C)C1=CC(CC1O)=O.OC1C=C(C(C1)=O)CCCCCCC(=O)OCC Chemical compound C(C)C1=CC(CC1O)=O.OC1C=C(C(C1)=O)CCCCCCC(=O)OCC BJSLPGNZBIRLNV-UHFFFAOYSA-N 0.000 abstract 1
- NSMHRVMZHYOGSZ-UHFFFAOYSA-N IC=CCCCCCCCC1=CC=CC=C1 Chemical compound IC=CCCCCCCCC1=CC=CC=C1 NSMHRVMZHYOGSZ-UHFFFAOYSA-N 0.000 abstract 1
- IRHYASGSXKKCEL-WEVVVXLNSA-N [(e)-4-iodobut-3-enyl]cyclohexane Chemical compound I\C=C\CCC1CCCCC1 IRHYASGSXKKCEL-WEVVVXLNSA-N 0.000 abstract 1
- BQZXRDJKRSBDST-UXBLZVDNSA-N [(e)-5-iodopent-4-enyl]benzene Chemical compound I\C=C\CCCC1=CC=CC=C1 BQZXRDJKRSBDST-UXBLZVDNSA-N 0.000 abstract 1
- JMVFMMPRPBSDCU-UXBLZVDNSA-N [(e)-5-iodopent-4-enyl]cyclohexane Chemical compound I\C=C\CCCC1CCCCC1 JMVFMMPRPBSDCU-UXBLZVDNSA-N 0.000 abstract 1
- SOHOKGYYESQMHN-YRNVUSSQSA-N [(e)-6-iodohex-5-enyl]benzene Chemical compound I\C=C\CCCCC1=CC=CC=C1 SOHOKGYYESQMHN-YRNVUSSQSA-N 0.000 abstract 1
- ZZMATCATVCPAJU-YRNVUSSQSA-N [(e)-6-iodohex-5-enyl]cyclohexane Chemical compound I\C=C\CCCCC1CCCCC1 ZZMATCATVCPAJU-YRNVUSSQSA-N 0.000 abstract 1
- MCHZXWNMHQWPQP-XYOKQWHBSA-N [(e)-7-iodohept-6-enyl]benzene Chemical compound I\C=C\CCCCCC1=CC=CC=C1 MCHZXWNMHQWPQP-XYOKQWHBSA-N 0.000 abstract 1
- YOMBYYPUZBOVOW-XYOKQWHBSA-N [(e)-7-iodohept-6-enyl]cyclohexane Chemical compound I\C=C\CCCCCC1CCCCC1 YOMBYYPUZBOVOW-XYOKQWHBSA-N 0.000 abstract 1
- AHXDFLPEQWTXGJ-UKTHLTGXSA-N [(e)-8-iodooct-7-enyl]benzene Chemical compound I\C=C\CCCCCCC1=CC=CC=C1 AHXDFLPEQWTXGJ-UKTHLTGXSA-N 0.000 abstract 1
- ZLHUULZTFOPFCM-UKTHLTGXSA-N [(e)-8-iodooct-7-enyl]cyclohexane Chemical compound I\C=C\CCCCCCC1CCCCC1 ZLHUULZTFOPFCM-UKTHLTGXSA-N 0.000 abstract 1
- AGAUJJYFWPKQAT-UHFFFAOYSA-N [Li]C=CC(CCCCC)OC(C)OCC Chemical compound [Li]C=CC(CCCCC)OC(C)OCC AGAUJJYFWPKQAT-UHFFFAOYSA-N 0.000 abstract 1
- PXPDRDIQJMSQFQ-UHFFFAOYSA-N [Li]\C=C\CCCCCC Chemical compound [Li]\C=C\CCCCCC PXPDRDIQJMSQFQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- UOINAUPBIJRWIS-UHFFFAOYSA-N ethyl 7-(3,5-dioxocyclopenten-1-yl)heptanoate Chemical compound CCOC(=O)CCCCCCC1=CC(=O)CC1=O UOINAUPBIJRWIS-UHFFFAOYSA-N 0.000 abstract 1
- NOYKGOKFCDFQJT-UHFFFAOYSA-N ethyl 7-cyclopenta-1,3-dien-1-ylheptanoate Chemical compound CCOC(=O)CCCCCCC1=CC=CC1 NOYKGOKFCDFQJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000006038 hexenyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- PPTCQVOXIJIQIE-UHFFFAOYSA-N propan-2-yl 7-(3-hydroxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound CC(C)OC(=O)CCCCCCC1=CC(O)CC1=O PPTCQVOXIJIQIE-UHFFFAOYSA-N 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- 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
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Materials Engineering (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/221,058 US4031129A (en) | 1972-01-26 | 1972-01-26 | 15-Deoxy-PGE1 and method for preparing same |
| US25572872A | 1972-05-22 | 1972-05-22 | |
| US29344272A | 1972-09-29 | 1972-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL49285A true IL49285A (en) | 1977-10-31 |
Family
ID=27396893
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49286A IL49286A (en) | 1972-01-26 | 1973-01-17 | 1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing them |
| IL41305A IL41305A (en) | 1972-01-26 | 1973-01-17 | Method for preparing prosta-glandins of the a,e,f and 11-deoxy-e series and certain novel 15-deoxoprostaglandins |
| IL49285A IL49285A (en) | 1972-01-26 | 1973-01-17 | The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one |
| IL49286A IL49286A0 (en) | 1972-01-26 | 1976-03-25 | Novel 1-iodo-1-trans-alkenes,their preparation and pharmaceutical compositions containing them |
| IL49285A IL49285A0 (en) | 1972-01-26 | 1976-03-25 | The preparation of 2'-(6-alkoxycarbonylhexyl)-2-cyclopenten-1-one |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49286A IL49286A (en) | 1972-01-26 | 1973-01-17 | 1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing them |
| IL41305A IL41305A (en) | 1972-01-26 | 1973-01-17 | Method for preparing prosta-glandins of the a,e,f and 11-deoxy-e series and certain novel 15-deoxoprostaglandins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL49286A IL49286A0 (en) | 1972-01-26 | 1976-03-25 | Novel 1-iodo-1-trans-alkenes,their preparation and pharmaceutical compositions containing them |
| IL49285A IL49285A0 (en) | 1972-01-26 | 1976-03-25 | The preparation of 2'-(6-alkoxycarbonylhexyl)-2-cyclopenten-1-one |
Country Status (17)
| Country | Link |
|---|---|
| JP (3) | JPS5333583B2 (es) |
| AR (2) | AR199893A1 (es) |
| AU (1) | AU452896B2 (es) |
| BE (1) | BE794516A (es) |
| BG (3) | BG25206A3 (es) |
| CA (1) | CA1014092A (es) |
| CH (3) | CH580046A5 (es) |
| DD (3) | DD112750A5 (es) |
| DE (2) | DE2365927A1 (es) |
| ES (3) | ES410962A1 (es) |
| FR (3) | FR2181693B1 (es) |
| GB (3) | GB1419181A (es) |
| IE (2) | IE37106B1 (es) |
| IL (5) | IL49286A (es) |
| NL (2) | NL153514B (es) |
| RO (1) | RO71588A (es) |
| SE (3) | SE7600888L (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1018970A (en) * | 1972-10-27 | 1977-10-11 | American Home Products Corporation | 15-substituted prostanoic acids |
| JPS5720305B2 (es) * | 1973-02-28 | 1982-04-27 | ||
| US4029693A (en) * | 1975-01-20 | 1977-06-14 | The Upjohn Company | 2A,2B-Dihomo-11-deoxy-17(substituted phenyl)-18,19,20-trinor-PGE2 compounds and their corresponding esters |
| US4032561A (en) * | 1975-05-27 | 1977-06-28 | The Upjohn Company | 17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGF1.sub.α compounds |
| US4016184A (en) * | 1975-09-17 | 1977-04-05 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD1 compounds |
| US4365075A (en) * | 1975-09-17 | 1982-12-21 | The Upjohn Company | ω-Aryl-PGD compounds |
| US4029814A (en) * | 1975-12-29 | 1977-06-14 | The Upjohn Company | Phenyl-substituted prostaglandin-e type analogs |
| US4219662A (en) * | 1977-02-28 | 1980-08-26 | The Upjohn Company | 11-Deoxy-17-phenyl-PGE1 analogs |
| AU529883B2 (en) * | 1978-09-04 | 1983-06-23 | Australian National University, The | Substituted cyclopentenones |
-
0
- BE BE794516D patent/BE794516A/xx unknown
-
1973
- 1973-01-15 AU AU51081/73A patent/AU452896B2/en not_active Expired
- 1973-01-15 IE IE57/73A patent/IE37106B1/xx unknown
- 1973-01-15 CA CA161,270A patent/CA1014092A/en not_active Expired
- 1973-01-15 IE IE599/76A patent/IE37108B1/xx unknown
- 1973-01-17 IL IL49286A patent/IL49286A/en unknown
- 1973-01-17 IL IL41305A patent/IL41305A/en unknown
- 1973-01-17 IL IL49285A patent/IL49285A/en unknown
- 1973-01-24 GB GB366073A patent/GB1419181A/en not_active Expired
- 1973-01-24 GB GB4753874A patent/GB1419182A/en not_active Expired
- 1973-01-24 GB GB4753974A patent/GB1419183A/en not_active Expired
- 1973-01-25 NL NL737301094A patent/NL153514B/xx unknown
- 1973-01-25 BG BG022528A patent/BG25206A3/xx unknown
- 1973-01-25 CH CH270376A patent/CH580046A5/xx not_active IP Right Cessation
- 1973-01-25 ES ES410962A patent/ES410962A1/es not_active Expired
- 1973-01-25 BG BG032229A patent/BG25207A3/xx unknown
- 1973-01-25 CH CH105573A patent/CH590834A5/xx not_active IP Right Cessation
- 1973-01-25 JP JP999673A patent/JPS5333583B2/ja not_active Expired
- 1973-01-25 DE DE2365927*A patent/DE2365927A1/de active Pending
- 1973-01-25 CH CH270276A patent/CH578502A5/xx not_active IP Right Cessation
- 1973-01-25 DD DD179628*A patent/DD112750A5/xx unknown
- 1973-01-25 BG BG7300032232A patent/BG25208A3/xx unknown
- 1973-01-25 DD DD179629*A patent/DD113214A5/xx unknown
- 1973-01-25 DD DD168453A patent/DD108069A5/xx unknown
- 1973-01-25 AR AR246283A patent/AR199893A1/es active
- 1973-01-25 FR FR7302607A patent/FR2181693B1/fr not_active Expired
- 1973-01-25 RO RO197391055A patent/RO71588A/ro unknown
- 1973-01-25 DE DE2365513A patent/DE2365513C3/de not_active Expired
-
1974
- 1974-09-18 AR AR255637A patent/AR200537A1/es active
-
1975
- 1975-01-17 FR FR7501567A patent/FR2257567B1/fr not_active Expired
- 1975-01-17 FR FR7501566A patent/FR2272642B1/fr not_active Expired
- 1975-06-16 ES ES438595A patent/ES438595A1/es not_active Expired
- 1975-06-16 ES ES438594A patent/ES438594A1/es not_active Expired
-
1976
- 1976-01-26 SE SE7600888A patent/SE7600888L/xx unknown
- 1976-01-28 SE SE7600889A patent/SE7600889L/xx unknown
- 1976-01-28 SE SE7600890A patent/SE7600890L/xx unknown
- 1976-03-25 IL IL49286A patent/IL49286A0/xx unknown
- 1976-03-25 IL IL49285A patent/IL49285A0/xx unknown
- 1976-10-08 JP JP51120458A patent/JPS5253840A/ja active Pending
- 1976-10-08 JP JP51120459A patent/JPS5253801A/ja active Pending
-
1977
- 1977-07-20 NL NL7708070A patent/NL7708070A/xx not_active Application Discontinuation
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