JPH0529226B2 - - Google Patents
Info
- Publication number
- JPH0529226B2 JPH0529226B2 JP60285857A JP28585785A JPH0529226B2 JP H0529226 B2 JPH0529226 B2 JP H0529226B2 JP 60285857 A JP60285857 A JP 60285857A JP 28585785 A JP28585785 A JP 28585785A JP H0529226 B2 JPH0529226 B2 JP H0529226B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hexyl
- hydrogen
- formyl
- 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.)
- Expired - Lifetime
Links
- -1 carbamoylmethyl Chemical group 0.000 claims description 144
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 77
- HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 150000002148 esters Chemical class 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical group O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 229910052786 argon Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 102000019280 Pancreatic lipases Human genes 0.000 claims description 4
- 108050006759 Pancreatic lipases Proteins 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229940116369 pancreatic lipase Drugs 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- ACLRSQBAOVWZKR-GXYFIZJQSA-N [(z,2s)-1-[(2s,3s)-3-ethyl-4-oxooxetan-2-yl]nonadec-10-en-2-yl] (2s)-2-formamido-4-methylpentanoate Chemical compound CCCCCCCC\C=C/CCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CC ACLRSQBAOVWZKR-GXYFIZJQSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 2
- XCLQOWPJMRZANV-FRBYDGBNSA-N [(2S,10Z,13Z)-1-[(2S,3S)-3-ethyl-4-oxooxetan-2-yl]nonadeca-10,13-dien-2-yl] (2S)-2-formamido-4-methylpentanoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CC XCLQOWPJMRZANV-FRBYDGBNSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 82
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- 239000000741 silica gel Substances 0.000 description 44
- 229910002027 silica gel Inorganic materials 0.000 description 44
- 239000000243 solution Substances 0.000 description 39
- 229960000380 propiolactone Drugs 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- FGRMZDNDNMUTII-RDBSUJKOSA-N (3s,4s)-3-hexyl-4-[(2r)-2-hydroxyhex-5-enyl]oxetan-2-one Chemical compound CCCCCC[C@H]1[C@H](C[C@H](O)CCC=C)OC1=O FGRMZDNDNMUTII-RDBSUJKOSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007903 gelatin capsule Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- RSOUWOFYULUWNE-UHFFFAOYSA-N 3-hexyl-4-(2-hydroxytridecyl)oxetan-2-one Chemical compound CCCCCCCCCCCC(O)CC1OC(=O)C1CCCCCC RSOUWOFYULUWNE-UHFFFAOYSA-N 0.000 description 5
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 5
- 235000021314 Palmitic acid Nutrition 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 229960003136 leucine Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- HFBHOAHFRNLZGN-ZCFIWIBFSA-N (2r)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)NC=O HFBHOAHFRNLZGN-ZCFIWIBFSA-N 0.000 description 4
- SRBATDDRZARFDZ-VKHMYHEASA-N (2s)-2-formamidopropanoic acid Chemical compound OC(=O)[C@H](C)NC=O SRBATDDRZARFDZ-VKHMYHEASA-N 0.000 description 4
- RSOUWOFYULUWNE-AKQSQHNNSA-N (3s,4s)-3-hexyl-4-(2-hydroxytridecyl)oxetan-2-one Chemical compound CCCCCCCCCCCC(O)C[C@@H]1OC(=O)[C@H]1CCCCCC RSOUWOFYULUWNE-AKQSQHNNSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- CKEVMZSLVHLLBF-UHFFFAOYSA-N benzyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1=CC=CC=C1 CKEVMZSLVHLLBF-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229960002446 octanoic acid Drugs 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229940070710 valerate Drugs 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 3
- 239000004395 L-leucine Substances 0.000 description 3
- NSTPXGARCQOSAU-VIFPVBQESA-N N-formyl-L-phenylalanine Chemical compound O=CN[C@H](C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-VIFPVBQESA-N 0.000 description 3
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- GXLZCXZLVDUDHP-OAQYLSRUSA-N [(1r)-2-hydroxy-1,2,2-triphenylethyl] acetate Chemical compound C1([C@@H](OC(=O)C)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=CC=C1 GXLZCXZLVDUDHP-OAQYLSRUSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- LEAJNQBUKCXJJK-HZJYTTRNSA-N (13z,16z)-2-benzyl-3-hydroxy-5-(oxan-2-yloxy)docosa-13,16-dienoic acid Chemical compound C1CCCOC1OC(CCCCCCC\C=C/C\C=C/CCCCC)CC(O)C(C(O)=O)CC1=CC=CC=C1 LEAJNQBUKCXJJK-HZJYTTRNSA-N 0.000 description 2
- KQKLSTVZQMEMMO-MURFETPASA-N (13z,16z)-2-ethyl-3-hydroxy-5-(oxan-2-yloxy)docosa-13,16-dienoic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(CC(O)C(CC)C(O)=O)OC1CCCCO1 KQKLSTVZQMEMMO-MURFETPASA-N 0.000 description 2
- IBNYAIKYXDLAGF-PYEOEOCKSA-N (2r)-2-[1-hydroxy-3-(oxan-2-yloxy)butyl]octanoic acid Chemical compound CCCCCC[C@@H](C(O)=O)C(O)CC(C)OC1CCCCO1 IBNYAIKYXDLAGF-PYEOEOCKSA-N 0.000 description 2
- QBYYLBWFBPAOKU-YFKPBYRVSA-N (2s)-2-formamido-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC=O QBYYLBWFBPAOKU-YFKPBYRVSA-N 0.000 description 2
- TYBPYMSSRRRYRQ-GFOWMXPYSA-N (3r)-3-hexyl-6-undecyloxane-2,4-dione Chemical compound CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1 TYBPYMSSRRRYRQ-GFOWMXPYSA-N 0.000 description 2
- CVQQWXHQVCRSJO-PIXUNUMVSA-N (3s,4s)-3-benzyl-4-[(2r,10z,13z)-2-hydroxynonadeca-10,13-dienyl]oxetan-2-one Chemical compound CCCCC\C=C/C\C=C/CCCCCCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CC1=CC=CC=C1 CVQQWXHQVCRSJO-PIXUNUMVSA-N 0.000 description 2
- VSDRCEGPJDXVCK-FDWBJODVSA-N (3s,4s)-3-ethyl-4-[(2s)-2-(oxan-2-yloxy)-2-(4-phenoxyphenyl)ethyl]oxetan-2-one Chemical compound O1C(=O)[C@@H](CC)[C@@H]1C[C@@H](C=1C=CC(OC=2C=CC=CC=2)=CC=1)OC1OCCCC1 VSDRCEGPJDXVCK-FDWBJODVSA-N 0.000 description 2
- FGRMZDNDNMUTII-TTZKSVMKSA-N (3s,4s)-3-hexyl-4-(2-hydroxyhex-5-enyl)oxetan-2-one Chemical compound CCCCCC[C@H]1[C@H](CC(O)CCC=C)OC1=O FGRMZDNDNMUTII-TTZKSVMKSA-N 0.000 description 2
- RSOUWOFYULUWNE-HKBOAZHASA-N (3s,4s)-3-hexyl-4-[(2r)-2-hydroxytridecyl]oxetan-2-one Chemical compound CCCCCCCCCCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CCCCCC RSOUWOFYULUWNE-HKBOAZHASA-N 0.000 description 2
- UBDDSAOCYALIQA-FKBYEOEOSA-N (3s,4s)-3-hexyl-4-[(2s)-2-hydroxy-2-(4-phenoxyphenyl)ethyl]oxetan-2-one Chemical compound O1C(=O)[C@@H](CCCCCC)[C@@H]1C[C@H](O)C(C=C1)=CC=C1OC1=CC=CC=C1 UBDDSAOCYALIQA-FKBYEOEOSA-N 0.000 description 2
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- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 WBWWGRHZICKQGZ-HZAMXZRMSA-N 0.000 description 1
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- YYZKKCVNAPQHEP-OTDUKCBNSA-N tert-butyl (z,3r)-3-hydroxyicos-11-enoate Chemical compound CCCCCCCC\C=C/CCCCCCC[C@@H](O)CC(=O)OC(C)(C)C YYZKKCVNAPQHEP-OTDUKCBNSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-M tetradecanoate Chemical compound CCCCCCCCCCCCCC([O-])=O TUNFSRHWOTWDNC-UHFFFAOYSA-M 0.000 description 1
- 101150054171 thf1 gene Proteins 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH06102/84-5 | 1984-12-21 | ||
| CH610284 | 1984-12-21 | ||
| CH03934/85-9 | 1985-09-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61152663A JPS61152663A (ja) | 1986-07-11 |
| JPH0529226B2 true JPH0529226B2 (es) | 1993-04-28 |
Family
ID=4304303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60285857A Granted JPS61152663A (ja) | 1984-12-21 | 1985-12-20 | オキセタノン類 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS61152663A (es) |
| KR (1) | KR950008310B1 (es) |
| ES (1) | ES9100003A1 (es) |
| GR (1) | GR853048B (es) |
| ZA (1) | ZA859575B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013249293A (ja) * | 2012-06-04 | 2013-12-12 | Kao Corp | リパーゼ活性阻害剤、抗真菌剤、及びフケ抑制剤 |
| KR102528984B1 (ko) * | 2013-04-04 | 2023-05-08 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 매크롤라이드 그리고 그의 제조방법 및 용도 |
| CN106998685A (zh) | 2014-10-08 | 2017-08-01 | 哈佛大学的校长及成员们 | 14‑元酮内酯及其制备和使用方法 |
| CA2980315A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| JP7224331B2 (ja) * | 2017-07-12 | 2023-02-17 | メイヨ・ファウンデーション・フォー・メディカル・エデュケーション・アンド・リサーチ | 脂肪毒性損傷の低減のための化合物 |
-
1985
- 1985-12-13 ZA ZA859575A patent/ZA859575B/xx unknown
- 1985-12-18 GR GR853048A patent/GR853048B/el not_active IP Right Cessation
- 1985-12-20 JP JP60285857A patent/JPS61152663A/ja active Granted
- 1985-12-21 KR KR1019850009683A patent/KR950008310B1/ko not_active IP Right Cessation
-
1986
- 1986-07-15 ES ES556896A patent/ES9100003A1/es not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES9100003A1 (es) | 1991-01-01 |
| KR950008310B1 (ko) | 1995-07-27 |
| KR860004865A (ko) | 1986-07-14 |
| GR853048B (es) | 1986-04-22 |
| ZA859575B (en) | 1986-08-27 |
| JPS61152663A (ja) | 1986-07-11 |
| ES556896A0 (es) | 1991-01-01 |
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