DE2528070A1 - 9-thia-, 9-oxothia- und 9-dioxothia- 11,12-secoprostaglandine - Google Patents
9-thia-, 9-oxothia- und 9-dioxothia- 11,12-secoprostaglandineInfo
- Publication number
- DE2528070A1 DE2528070A1 DE19752528070 DE2528070A DE2528070A1 DE 2528070 A1 DE2528070 A1 DE 2528070A1 DE 19752528070 DE19752528070 DE 19752528070 DE 2528070 A DE2528070 A DE 2528070A DE 2528070 A1 DE2528070 A1 DE 2528070A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- acid
- methylsulfonyl
- hydroxy
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- -1 4,4,4-trifluorobutyl group Chemical group 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- GSLDYEUXPPAHCC-UHFFFAOYSA-N 12-hydroxy-8-methylsulfanylheptadecanoic acid Chemical compound CCCCCC(O)CCCC(SC)CCCCCCC(O)=O GSLDYEUXPPAHCC-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- JJUSAJSCYGSBSG-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonylheptadecanoic acid Chemical compound CCCCCC(O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O JJUSAJSCYGSBSG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- SRFGUIZCVKITPM-UHFFFAOYSA-N 12-hydroxy-8-methylsulfinylheptadecanoic acid Chemical compound CCCCCC(O)CCCC(S(C)=O)CCCCCCC(O)=O SRFGUIZCVKITPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- ZZZSNZRVMRWKCH-UHFFFAOYSA-N 12-hydroxy-13-(4-methylphenoxy)-8-methylsulfonyltridecanoic acid Chemical compound CC1=CC=C(OCC(O)CCCC(CCCCCCC(O)=O)S(C)(=O)=O)C=C1 ZZZSNZRVMRWKCH-UHFFFAOYSA-N 0.000 claims description 3
- RWCBBFGXZXCUJG-UHFFFAOYSA-N 12-hydroxy-8-(2-hydroxyethylsulfonyl)heptadecanoic acid Chemical compound CCCCCC(O)CCCC(S(=O)(=O)CCO)CCCCCCC(O)=O RWCBBFGXZXCUJG-UHFFFAOYSA-N 0.000 claims description 3
- FJGHLSVHGYSFIZ-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonyl-13-phenoxytridecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)COC1=CC=CC=C1 FJGHLSVHGYSFIZ-UHFFFAOYSA-N 0.000 claims description 3
- IKDJIINJTDAKDE-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonyl-13-propoxytridecanoic acid Chemical compound CCCOCC(O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O IKDJIINJTDAKDE-UHFFFAOYSA-N 0.000 claims description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- CLPHAYNBNTVRDI-UHFFFAOYSA-N ditert-butyl propanedioate Chemical compound CC(C)(C)OC(=O)CC(=O)OC(C)(C)C CLPHAYNBNTVRDI-UHFFFAOYSA-N 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- JJUSAJSCYGSBSG-TZHYSIJRSA-N (12r)-12-hydroxy-8-methylsulfonylheptadecanoic acid Chemical compound CCCCC[C@@H](O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O JJUSAJSCYGSBSG-TZHYSIJRSA-N 0.000 claims description 2
- JJUSAJSCYGSBSG-BHWOMJMDSA-N (12s)-12-hydroxy-8-methylsulfonylheptadecanoic acid Chemical compound CCCCC[C@H](O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O JJUSAJSCYGSBSG-BHWOMJMDSA-N 0.000 claims description 2
- VEGHWAOTBLBDGS-UHFFFAOYSA-N 11-(1-hydroxycyclohexyl)-8-methylsulfonylundecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC1(O)CCCCC1 VEGHWAOTBLBDGS-UHFFFAOYSA-N 0.000 claims description 2
- KWPLBRIONWZYFM-UHFFFAOYSA-N 12-hydroxy-12-methyl-8-methylsulfonylheptadecanoic acid Chemical compound CCCCCC(C)(O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O KWPLBRIONWZYFM-UHFFFAOYSA-N 0.000 claims description 2
- CHQQWSXEHAIOJB-UHFFFAOYSA-N 12-hydroxy-8-(2-hydroxyethylsulfanyl)heptadecanoic acid Chemical compound CCCCCC(O)CCCC(SCCO)CCCCCCC(O)=O CHQQWSXEHAIOJB-UHFFFAOYSA-N 0.000 claims description 2
- QSAMGQLMPGSZAN-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonylheptadec-10-enoic acid Chemical compound CCCCCC(O)C=CCC(S(C)(=O)=O)CCCCCCC(O)=O QSAMGQLMPGSZAN-UHFFFAOYSA-N 0.000 claims description 2
- BLULZTBNCMRZRI-UHFFFAOYSA-N 13-(4-fluorophenoxy)-12-hydroxy-8-methylsulfonyltridecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)COC1=CC=C(F)C=C1 BLULZTBNCMRZRI-UHFFFAOYSA-N 0.000 claims description 2
- DKVOMEQMMFQETR-UHFFFAOYSA-N 17,17,17-trifluoro-12-hydroxy-8-methylsulfonylheptadecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)CCCCC(F)(F)F DKVOMEQMMFQETR-UHFFFAOYSA-N 0.000 claims description 2
- SQOYVMIBHGPQIQ-UHFFFAOYSA-N 8-ethenylsulfonyl-12-hydroxyheptadecanoic acid Chemical compound CCCCCC(O)CCCC(S(=O)(=O)C=C)CCCCCCC(O)=O SQOYVMIBHGPQIQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- HJCPXJPQAKBWGB-UHFFFAOYSA-N methyl 12-hydroxy-8-methylsulfonylheptadecanoate Chemical compound CCCCCC(O)CCCC(S(C)(=O)=O)CCCCCCC(=O)OC HJCPXJPQAKBWGB-UHFFFAOYSA-N 0.000 claims description 2
- SGZPDMKAJLCBQF-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-12-hydroxy-8-methylsulfonylheptadecanamide Chemical compound CCCCCC(O)CCCC(S(C)(=O)=O)CCCCCCC(=O)NCCN(C)C SGZPDMKAJLCBQF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- MNDYENFOMQKZLW-UHFFFAOYSA-N 12-hydroxy-13-(4-methoxyphenoxy)-8-methylsulfonyltridecanoic acid Chemical compound COC1=CC=C(OCC(O)CCCC(CCCCCCC(O)=O)S(C)(=O)=O)C=C1 MNDYENFOMQKZLW-UHFFFAOYSA-N 0.000 claims 1
- QTWLBAJDOCPHTR-UHFFFAOYSA-N 12-hydroxy-16,16-dimethyl-8-methylsulfonylheptadecanoic acid Chemical compound CC(C)(C)CCCC(O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O QTWLBAJDOCPHTR-UHFFFAOYSA-N 0.000 claims 1
- CIDVJLAQRMKDHU-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonylheptadec-16-enoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)CCCC=C CIDVJLAQRMKDHU-UHFFFAOYSA-N 0.000 claims 1
- OVUIQBJOGRGROS-UHFFFAOYSA-N 2-(9-hydroxy-5-methylsulfonyltetradecoxy)acetic acid Chemical compound CCCCCC(O)CCCC(S(C)(=O)=O)CCCCOCC(O)=O OVUIQBJOGRGROS-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- UDNQSJWIMIYXTR-UHFFFAOYSA-N 8-ethylsulfonyl-12-hydroxyheptadecanoic acid Chemical compound CCCCCC(O)CCCC(S(=O)(=O)CC)CCCCCCC(O)=O UDNQSJWIMIYXTR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000003921 oil Substances 0.000 description 38
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 33
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- 235000011152 sodium sulphate Nutrition 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000013067 intermediate product Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- OALZIEQUXNGQMI-UHFFFAOYSA-N 1-chlorononan-4-ol Chemical compound CCCCCC(O)CCCCl OALZIEQUXNGQMI-UHFFFAOYSA-N 0.000 description 3
- ATKBLWQNGBIURV-UHFFFAOYSA-N 1-chlorononan-4-yl acetate Chemical compound CCCCCC(OC(C)=O)CCCCl ATKBLWQNGBIURV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 3
- OGEQZTWROZWKHT-UHFFFAOYSA-N ethyl 12-acetyloxy-8-bromoheptadecanoate Chemical compound CCCCCC(OC(C)=O)CCCC(Br)CCCCCCC(=O)OCC OGEQZTWROZWKHT-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- LRGSEZPULBLFOA-UHFFFAOYSA-N 1-bromonon-2-en-4-yl acetate Chemical compound CCCCCC(OC(C)=O)C=CCBr LRGSEZPULBLFOA-UHFFFAOYSA-N 0.000 description 2
- ZCTKTQUONMEFHR-UHFFFAOYSA-N 1-chlorononan-4-one Chemical compound CCCCCC(=O)CCCCl ZCTKTQUONMEFHR-UHFFFAOYSA-N 0.000 description 2
- XKIJCFBYODRSFS-UHFFFAOYSA-N 1-iodononan-4-yl acetate Chemical compound CCCCCC(OC(C)=O)CCCI XKIJCFBYODRSFS-UHFFFAOYSA-N 0.000 description 2
- NIGIPTBWXNZEGF-UHFFFAOYSA-N 12-acetyloxy-8-methylsulfonylheptadecanoic acid Chemical compound CCCCCC(OC(C)=O)CCCC(S(C)(=O)=O)CCCCCCC(O)=O NIGIPTBWXNZEGF-UHFFFAOYSA-N 0.000 description 2
- IMUXADADEUUEFK-UHFFFAOYSA-N 12-hydroxy-8-methylsulfonyl-13-pyridin-3-yloxytridecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)COC1=CC=CN=C1 IMUXADADEUUEFK-UHFFFAOYSA-N 0.000 description 2
- NGIFESNJOFINQX-UHFFFAOYSA-N 13-(2,4-dichlorophenoxy)-12-hydroxy-8-methylsulfonyltridecanoic acid Chemical compound OC(=O)CCCCCCC(S(=O)(=O)C)CCCC(O)COC1=CC=C(Cl)C=C1Cl NGIFESNJOFINQX-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 102000018997 Growth Hormone Human genes 0.000 description 2
- 108010051696 Growth Hormone Proteins 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
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- BRCNMBUJVWBFKB-UHFFFAOYSA-N dimethyl 2-methylsulfonyl-2-(5-phenoxy-4-phenylmethoxypentyl)nonanedioate Chemical compound C=1C=CC=CC=1COC(CCCC(CCCCCCC(=O)OC)(C(=O)OC)S(C)(=O)=O)COC1=CC=CC=C1 BRCNMBUJVWBFKB-UHFFFAOYSA-N 0.000 description 1
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- GAOQPPTZKQPRGZ-UHFFFAOYSA-N ethyl 12-acetyloxy-8-bromo-17,17,17-trifluoroheptadecanoate Chemical compound CCOC(=O)CCCCCCC(Br)CCCC(OC(C)=O)CCCCC(F)(F)F GAOQPPTZKQPRGZ-UHFFFAOYSA-N 0.000 description 1
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- OCCWQCYBCZADCE-UHFFFAOYSA-N ethyl 2-methylsulfonylacetate Chemical compound CCOC(=O)CS(C)(=O)=O OCCWQCYBCZADCE-UHFFFAOYSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 1
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- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
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- RMMQXTIADMYYMS-UHFFFAOYSA-N methyl 12-acetyloxy-8-methylsulfonylheptadecanoate Chemical compound CCCCCC(OC(C)=O)CCCC(S(C)(=O)=O)CCCCCCC(=O)OC RMMQXTIADMYYMS-UHFFFAOYSA-N 0.000 description 1
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- AWEBKESJHBEPQL-UHFFFAOYSA-N methyl 9-methoxy-8-methyl-9-sulfanylidenenonanoate Chemical compound COC(=O)CCCCCCC(C)C(=S)OC AWEBKESJHBEPQL-UHFFFAOYSA-N 0.000 description 1
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- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
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- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 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
- 238000000935 solvent evaporation Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000036561 sun exposure Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
-
- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48317874A | 1974-06-25 | 1974-06-25 | |
| US56656675A | 1975-04-09 | 1975-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2528070A1 true DE2528070A1 (de) | 1976-01-08 |
Family
ID=27047557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528070 Withdrawn DE2528070A1 (de) | 1974-06-25 | 1975-06-24 | 9-thia-, 9-oxothia- und 9-dioxothia- 11,12-secoprostaglandine |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS51125020A (en, 2012) |
| CA (1) | CA1064961A (en, 2012) |
| CH (1) | CH614935A5 (en, 2012) |
| DE (1) | DE2528070A1 (en, 2012) |
| DK (1) | DK263775A (en, 2012) |
| ES (1) | ES438765A1 (en, 2012) |
| FI (1) | FI751730A7 (en, 2012) |
| FR (1) | FR2276037A1 (en, 2012) |
| GB (1) | GB1476262A (en, 2012) |
| IE (1) | IE41258B1 (en, 2012) |
| IL (1) | IL47487A (en, 2012) |
| LU (1) | LU72797A1 (en, 2012) |
| NL (1) | NL7507020A (en, 2012) |
| NO (1) | NO142219C (en, 2012) |
| NZ (1) | NZ177843A (en, 2012) |
| SE (1) | SE7506804L (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008098077A2 (en) | 2007-02-06 | 2008-08-14 | University Of Louisville Research Foundation | Substituted alkine derivatives as anti-cancer agents |
| CA2865487A1 (en) | 2011-03-07 | 2012-09-13 | Paula J. Bates | Predictive marker of dnmt1 inhibitor therapeutic efficacy and methods of using the marker |
| WO2014039860A2 (en) | 2012-09-07 | 2014-03-13 | University Of Louisville Research Foundation, Inc. | Compositions and methods for modulating dnmt1 inhibitor activity |
-
1975
- 1975-06-10 FI FI751730A patent/FI751730A7/fi not_active Application Discontinuation
- 1975-06-11 DK DK263775A patent/DK263775A/da unknown
- 1975-06-12 NO NO752091A patent/NO142219C/no unknown
- 1975-06-12 NL NL7507020A patent/NL7507020A/xx not_active Application Discontinuation
- 1975-06-13 SE SE7506804A patent/SE7506804L/xx unknown
- 1975-06-16 NZ NZ177843A patent/NZ177843A/xx unknown
- 1975-06-16 IL IL47487A patent/IL47487A/xx unknown
- 1975-06-17 GB GB2579775A patent/GB1476262A/en not_active Expired
- 1975-06-18 CA CA229,586A patent/CA1064961A/en not_active Expired
- 1975-06-18 FR FR7519087A patent/FR2276037A1/fr active Granted
- 1975-06-19 IE IE1371/75A patent/IE41258B1/xx unknown
- 1975-06-20 ES ES438765A patent/ES438765A1/es not_active Expired
- 1975-06-24 CH CH820875A patent/CH614935A5/xx not_active IP Right Cessation
- 1975-06-24 DE DE19752528070 patent/DE2528070A1/de not_active Withdrawn
- 1975-06-24 LU LU72797A patent/LU72797A1/xx unknown
- 1975-06-25 JP JP50077579A patent/JPS51125020A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2276037B1 (en, 2012) | 1979-03-02 |
| DK263775A (da) | 1975-12-26 |
| IE41258L (en) | 1975-12-25 |
| SE7506804L (sv) | 1975-12-29 |
| LU72797A1 (en, 2012) | 1976-04-13 |
| NO142219C (no) | 1980-07-16 |
| IL47487A (en) | 1979-05-31 |
| IL47487A0 (en) | 1975-08-31 |
| AU8221675A (en) | 1976-12-23 |
| CA1064961A (en) | 1979-10-23 |
| NZ177843A (en) | 1978-04-03 |
| IE41258B1 (en) | 1979-11-21 |
| ES438765A1 (es) | 1977-07-01 |
| NO752091L (en, 2012) | 1975-12-30 |
| GB1476262A (en) | 1977-06-10 |
| FR2276037A1 (fr) | 1976-01-23 |
| NL7507020A (nl) | 1975-12-30 |
| JPS51125020A (en) | 1976-11-01 |
| NO142219B (no) | 1980-04-08 |
| CH614935A5 (en) | 1979-12-28 |
| FI751730A7 (en, 2012) | 1975-12-26 |
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