IL49286A - 1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing them - Google Patents
1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL49286A IL49286A IL49286A IL4928673A IL49286A IL 49286 A IL49286 A IL 49286A IL 49286 A IL49286 A IL 49286A IL 4928673 A IL4928673 A IL 4928673A IL 49286 A IL49286 A IL 49286A
- Authority
- IL
- Israel
- Prior art keywords
- iodo
- trans
- hydroxy
- octene
- cyclohexyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000003085 diluting agent Substances 0.000 claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 63
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 22
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000010666 hydroalumination reaction Methods 0.000 claims description 7
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 230000026045 iodination Effects 0.000 claims description 3
- 238000006192 iodination reaction Methods 0.000 claims description 3
- KQDYMAYUKUZGDA-VOTSOKGWSA-N (e)-1-iodooct-1-en-3-ol Chemical compound CCCCCC(O)\C=C\I KQDYMAYUKUZGDA-VOTSOKGWSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000002083 iodinating effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 18
- -1 2-tetrahydropyranyloxy Chemical group 0.000 abstract description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052744 lithium Inorganic materials 0.000 abstract description 5
- 150000003180 prostaglandins Chemical class 0.000 abstract description 5
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 4
- 239000007858 starting material Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- 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
- 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
- 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
- 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
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 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
- 125000006239 protecting group Chemical group 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 86
- 239000000243 solution Substances 0.000 description 65
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 44
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 35
- 229910052740 iodine Inorganic materials 0.000 description 35
- 239000011630 iodine Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- 239000000284 extract Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 235000019345 sodium thiosulphate Nutrition 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000001282 iso-butane Substances 0.000 description 10
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 230000003292 diminished effect Effects 0.000 description 6
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- 229910000086 alane Inorganic materials 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 150000004694 iodide salts Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- RZZWGTYQTFSVPY-AATRIKPKSA-N (e)-1-iodohept-1-en-3-ol Chemical compound CCCCC(O)\C=C\I RZZWGTYQTFSVPY-AATRIKPKSA-N 0.000 description 3
- CPZXMHHQFPHMKW-SNAWJCMRSA-N (e)-1-iodohex-1-en-3-ol Chemical compound CCCC(O)\C=C\I CPZXMHHQFPHMKW-SNAWJCMRSA-N 0.000 description 3
- VAVSCVJYAOHETD-ONEGZZNKSA-N (e)-1-iodopent-1-en-3-ol Chemical compound CCC(O)\C=C\I VAVSCVJYAOHETD-ONEGZZNKSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 3
- HZXROYNWUJPHAP-UHFFFAOYSA-N 1-iodoheptan-3-ol Chemical compound CCCCC(O)CCI HZXROYNWUJPHAP-UHFFFAOYSA-N 0.000 description 2
- CIMVABGOEOUEFN-UHFFFAOYSA-N 1-iodohexan-3-ol Chemical compound CCCC(O)CCI CIMVABGOEOUEFN-UHFFFAOYSA-N 0.000 description 2
- PTZXILRKRVNNBV-UHFFFAOYSA-N 1-iodopentan-3-ol Chemical compound CCC(O)CCI PTZXILRKRVNNBV-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 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 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003385 sodium Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YQQADCAOENMNMI-AATRIKPKSA-N (E)-1-iodo-4-methylhept-1-en-3-ol Chemical compound CCCC(C)C(O)\C=C\I YQQADCAOENMNMI-AATRIKPKSA-N 0.000 description 1
- BSVXXKZWQSPZFV-CMDGGOBGSA-N (e)-3-(2-ethoxyethoxy)-1-iodooct-1-ene Chemical compound CCCCCC(\C=C\I)OCCOCC BSVXXKZWQSPZFV-CMDGGOBGSA-N 0.000 description 1
- QPQXCZGFJJMKHH-OWOJBTEDSA-N (e)-3-iodoprop-2-en-1-ol Chemical compound OC\C=C\I QPQXCZGFJJMKHH-OWOJBTEDSA-N 0.000 description 1
- PRRWCKUDFDIEOH-UHFFFAOYSA-N 1,1-diiodooctan-3-ol Chemical compound CCCCCC(O)CC(I)I PRRWCKUDFDIEOH-UHFFFAOYSA-N 0.000 description 1
- RAJKWQFELNIZPN-UHFFFAOYSA-N 1-iodooctan-3-ol Chemical compound CCCCCC(O)CCI RAJKWQFELNIZPN-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 101100388509 Caenorhabditis elegans che-3 gene Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical class [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QCQALVMFTWRCFI-UHFFFAOYSA-N oct-2-yne Chemical compound CCCCCC#CC QCQALVMFTWRCFI-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
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- 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
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- 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
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- 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
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- 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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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (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 |
|---|---|
| IL49286A true IL49286A (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 |
| IL49285A IL49285A0 (en) | 1972-01-26 | 1976-03-25 | The preparation of 2'-(6-alkoxycarbonylhexyl)-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 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| IL49285A IL49285A0 (en) | 1972-01-26 | 1976-03-25 | The preparation of 2'-(6-alkoxycarbonylhexyl)-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 |
Country Status (17)
| Country | Link |
|---|---|
| JP (3) | JPS5333583B2 (fr) |
| AR (2) | AR199893A1 (fr) |
| AU (1) | AU452896B2 (fr) |
| BE (1) | BE794516A (fr) |
| BG (3) | BG25207A3 (fr) |
| CA (1) | CA1014092A (fr) |
| CH (3) | CH590834A5 (fr) |
| DD (3) | DD113214A5 (fr) |
| DE (2) | DE2365513C3 (fr) |
| ES (3) | ES410962A1 (fr) |
| FR (3) | FR2181693B1 (fr) |
| GB (3) | GB1419182A (fr) |
| IE (2) | IE37106B1 (fr) |
| IL (5) | IL49286A (fr) |
| NL (2) | NL153514B (fr) |
| RO (1) | RO71588A (fr) |
| SE (3) | SE7600888L (fr) |
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 (fr) * | 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/fr 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 GB4753874A patent/GB1419182A/en not_active Expired
- 1973-01-24 GB GB4753974A patent/GB1419183A/en not_active Expired
- 1973-01-24 GB GB366073A patent/GB1419181A/en not_active Expired
- 1973-01-25 NL NL737301094A patent/NL153514B/xx unknown
- 1973-01-25 DE DE2365513A patent/DE2365513C3/de not_active Expired
- 1973-01-25 DD DD179629*A patent/DD113214A5/xx unknown
- 1973-01-25 RO RO197391055A patent/RO71588A/fr unknown
- 1973-01-25 DD DD179628*A patent/DD112750A5/xx unknown
- 1973-01-25 ES ES410962A patent/ES410962A1/es not_active Expired
- 1973-01-25 DD DD168453A patent/DD108069A5/xx unknown
- 1973-01-25 CH CH105573A patent/CH590834A5/xx not_active IP Right Cessation
- 1973-01-25 AR AR246283A patent/AR199893A1/es active
- 1973-01-25 DE DE2365927*A patent/DE2365927A1/de active Pending
- 1973-01-25 JP JP999673A patent/JPS5333583B2/ja not_active Expired
- 1973-01-25 CH CH270276A patent/CH578502A5/xx not_active IP Right Cessation
- 1973-01-25 FR FR7302607A patent/FR2181693B1/fr not_active Expired
- 1973-01-25 BG BG032229A patent/BG25207A3/xx unknown
- 1973-01-25 CH CH270376A patent/CH580046A5/xx not_active IP Right Cessation
- 1973-01-25 BG BG7300032232A patent/BG25208A3/xx unknown
- 1973-01-25 BG BG022528A patent/BG25206A3/xx unknown
-
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 ES438594A patent/ES438594A1/es not_active Expired
- 1975-06-16 ES ES438595A patent/ES438595A1/es not_active Expired
-
1976
- 1976-01-26 SE SE7600888A patent/SE7600888L/xx unknown
- 1976-01-28 SE SE7600890A patent/SE7600890L/xx unknown
- 1976-01-28 SE SE7600889A patent/SE7600889L/xx unknown
- 1976-03-25 IL IL49285A patent/IL49285A0/xx unknown
- 1976-03-25 IL IL49286A patent/IL49286A0/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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