IL97148A - Oxetanones a process for their manufacture and pharmaceutical compositions containing them - Google Patents

Oxetanones a process for their manufacture and pharmaceutical compositions containing them

Info

Publication number: IL97148A
Authority: IL; Israel
Prior art keywords: methyl; oxo; oxetanyl; group; alkyl
Prior art date: 1990-02-26

Application number

IL9714891A

Other languages

English (en)

Other versions

IL97148A0 (en

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-02-26

Filing date

1991-02-05

Publication date

1996-11-14

1991-02-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1992-05-25 Publication of IL97148A0 publication Critical patent/IL97148A0/xx

1996-11-14 Publication of IL97148A publication Critical patent/IL97148A/en

Links

238000004519 manufacturing process Methods 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 8
239000008194 pharmaceutical composition Substances 0.000 title description 2
239000002253 acid Substances 0.000 claims abstract description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 134
-1 sulphinyl Chemical group 0.000 claims description 97
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 79
239000000203 mixture Substances 0.000 claims description 52
125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
125000004434 sulfur atom Chemical group 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
NEBHNFJAFFHYGN-BYPYZUCNSA-N (2s)-2-carbamoyl-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(N)=O)C(O)=O NEBHNFJAFFHYGN-BYPYZUCNSA-N 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
125000004430 oxygen atom Chemical group O* 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 11
125000004079 stearyl 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])C([H])([H])[H] 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 7
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 7
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 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 5
239000005977 Ethylene Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
206010003210 Arteriosclerosis Diseases 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
DMYQVZFQHRNQJD-KCHLEUMXSA-N [(2s)-1-[(2s,3s)-3-ethyl-4-oxooxetan-2-yl]nonadecan-2-yl] 1-carbamoylcyclohexane-1-carboxylate Chemical compound C([C@H](CCCCCCCCCCCCCCCCC)OC(=O)C1(CCCCC1)C(N)=O)[C@@H]1OC(=O)[C@H]1CC DMYQVZFQHRNQJD-KCHLEUMXSA-N 0.000 claims description 3
WMIAOJGLNFEFNR-CNTOOOFYSA-N [(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] 2-carbamoylbutanoate Chemical compound CCCCCCCCCCC[C@H](OC(=O)C(CC)C(N)=O)C[C@@H]1OC(=O)[C@H]1CCCCCC WMIAOJGLNFEFNR-CNTOOOFYSA-N 0.000 claims description 3
208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
201000005577 familial hyperlipidemia Diseases 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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 3
235000020824 obesity Nutrition 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
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
ALANGIWUSWGPFZ-SSUZURRFSA-N [(2s)-1-[(2s,3s)-3-ethyl-4-oxooxetan-2-yl]nonadecan-2-yl] (2r)-5-oxopyrrolidine-2-carboxylate Chemical compound C([C@H](CCCCCCCCCCCCCCCCC)OC(=O)[C@@H]1NC(=O)CC1)[C@@H]1OC(=O)[C@H]1CC ALANGIWUSWGPFZ-SSUZURRFSA-N 0.000 claims description 2
COGKGUUMTRBTTQ-QKDODKLFSA-N [(2s)-1-[(2s,3s)-3-ethyl-4-oxooxetan-2-yl]nonadecan-2-yl] 1-carbamoylcyclopentane-1-carboxylate Chemical compound C([C@H](CCCCCCCCCCCCCCCCC)OC(=O)C1(CCCC1)C(N)=O)[C@@H]1OC(=O)[C@H]1CC COGKGUUMTRBTTQ-QKDODKLFSA-N 0.000 claims description 2
CLYUMKOZZIGLAV-GSDHBNRESA-N [(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] 1-carbamoylcyclohexane-1-carboxylate Chemical compound C([C@H](CCCCCCCCCCC)OC(=O)C1(CCCCC1)C(N)=O)[C@@H]1OC(=O)[C@H]1CCCCCC CLYUMKOZZIGLAV-GSDHBNRESA-N 0.000 claims description 2
ATSSPNQNBOHRKT-MCSJAMFESA-N [(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] 2-carbamoylhexanoate Chemical compound CCCCCCCCCCC[C@H](OC(=O)C(CCCC)C(N)=O)C[C@@H]1OC(=O)[C@H]1CCCCCC ATSSPNQNBOHRKT-MCSJAMFESA-N 0.000 claims description 2
XEWNCNQXDXKJMH-KVROEHFOSA-N [(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] 3-amino-2-methyl-3-oxopropanoate Chemical compound CCCCCCCCCCC[C@H](OC(=O)C(C)C(N)=O)C[C@@H]1OC(=O)[C@H]1CCCCCC XEWNCNQXDXKJMH-KVROEHFOSA-N 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000005505 thiomorpholino group Chemical group 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
JQSYIBJVIXNPLU-QORCZRPOSA-N [(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2s)-2-carbamoyl-3-methylbutanoate Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@@H](C(C)C)C(N)=O)C[C@@H]1OC(=O)[C@H]1CCCCCC JQSYIBJVIXNPLU-QORCZRPOSA-N 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
239000012876 carrier material Substances 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 7
102000019280 Pancreatic lipases Human genes 0.000 abstract 1
108050006759 Pancreatic lipases Proteins 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
229940116369 pancreatic lipase Drugs 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 201
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 192
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 146
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
239000000243 solution Substances 0.000 description 108
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
229960000380 propiolactone Drugs 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
229910001868 water Inorganic materials 0.000 description 47
235000019439 ethyl acetate Nutrition 0.000 description 46
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
238000003756 stirring Methods 0.000 description 43
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 36
229910002027 silica gel Inorganic materials 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
239000007858 starting material Substances 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
239000012071 phase Substances 0.000 description 30
239000000047 product Substances 0.000 description 25
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 15
NEBHNFJAFFHYGN-UHFFFAOYSA-N 2-carbamoyl-3-methylbutanoic acid Chemical compound CC(C)C(C(N)=O)C(O)=O NEBHNFJAFFHYGN-UHFFFAOYSA-N 0.000 description 14
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
239000002808 molecular sieve Substances 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 12
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 12
229910052786 argon Inorganic materials 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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 10
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 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 9
239000001120 potassium sulphate Substances 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
229960001407 sodium bicarbonate Drugs 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
239000013078 crystal Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
PIQPQYDHYCTWIZ-LJQANCHMSA-N (3r)-3-[tert-butyl(dimethyl)silyl]oxytetradecanal Chemical compound CCCCCCCCCCC[C@H](CC=O)O[Si](C)(C)C(C)(C)C PIQPQYDHYCTWIZ-LJQANCHMSA-N 0.000 description 6
LGCOYXMRBUYHMO-VJBWXMMDSA-N (3s,4s)-3-ethyl-4-[(2r)-2-hydroxynonadecyl]oxetan-2-one Chemical compound CCCCCCCCCCCCCCCCC[C@@H](O)C[C@@H]1OC(=O)[C@H]1CC LGCOYXMRBUYHMO-VJBWXMMDSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229940043279 diisopropylamine Drugs 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
239000001828 Gelatine Substances 0.000 description 5
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 5
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000000969 carrier Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
NEBHNFJAFFHYGN-SCSAIBSYSA-N (2r)-2-carbamoyl-3-methylbutanoic acid Chemical compound CC(C)[C@H](C(N)=O)C(O)=O NEBHNFJAFFHYGN-SCSAIBSYSA-N 0.000 description 4
QOEAGDYTCLPUEA-NGDRWEMDSA-N (2s,3s,5r)-2-ethyl-3-hydroxy-5-phenylmethoxydocosanoic acid Chemical compound CCCCCCCCCCCCCCCCC[C@H](C[C@H](O)[C@H](CC)C(O)=O)OCC1=CC=CC=C1 QOEAGDYTCLPUEA-NGDRWEMDSA-N 0.000 description 4
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
MCANQXNXHKXBML-UHFFFAOYSA-N 2-carbamoylpentanoic acid Chemical compound CCCC(C(N)=O)C(O)=O MCANQXNXHKXBML-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
239000004367 Lipase Substances 0.000 description 4
102000004882 Lipase Human genes 0.000 description 4
108090001060 Lipase Proteins 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
235000019421 lipase Nutrition 0.000 description 4
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 4
210000000496 pancreas Anatomy 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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235000010357 aspartame Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
HUZCTWYDQIQZPM-UHFFFAOYSA-N benzyl 2,2,2-trichloroethanimidate Chemical compound ClC(Cl)(Cl)C(=N)OCC1=CC=CC=C1 HUZCTWYDQIQZPM-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
IICZCZBCNYFZKN-FKDZAPPDSA-N benzyl n-[2-[(2r)-2-[tert-butyl(dimethyl)silyl]oxytridecyl]-4-oxooxetan-3-yl]carbamate Chemical compound CCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)CC1OC(=O)C1NC(=O)OCC1=CC=CC=C1 IICZCZBCNYFZKN-FKDZAPPDSA-N 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
HLLYSYPNVSEVGY-UHFFFAOYSA-N carbamoyl pentanoate Chemical compound CCCCC(=O)OC(N)=O HLLYSYPNVSEVGY-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
235000019219 chocolate Nutrition 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
IERCWZWOKCAFTO-MRXNPFEDSA-N dodecyl (2r)-2-carbamoyl-3-methylbutanoate Chemical compound CCCCCCCCCCCCOC(=O)[C@H](C(C)C)C(N)=O IERCWZWOKCAFTO-MRXNPFEDSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000008344 egg yolk phospholipid Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
WJGXVEKBRCNUIY-UHFFFAOYSA-N ethyl 2-carbamoyl-4-phenylbutanoate Chemical compound CCOC(=O)C(C(N)=O)CCC1=CC=CC=C1 WJGXVEKBRCNUIY-UHFFFAOYSA-N 0.000 description 1
VSWFEQKBQLKDSE-UHFFFAOYSA-N ethyl 2-carbamoylpentanoate Chemical compound CCCC(C(N)=O)C(=O)OCC VSWFEQKBQLKDSE-UHFFFAOYSA-N 0.000 description 1
229940073505 ethyl vanillin Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
GTFMAONWNTUZEW-UHFFFAOYSA-N glutaramic acid Chemical compound NC(=O)CCCC(O)=O GTFMAONWNTUZEW-UHFFFAOYSA-N 0.000 description 1
MSJCGIOEMICSIR-UHFFFAOYSA-N heptanethioic s-acid Chemical compound CCCCCCC(S)=O MSJCGIOEMICSIR-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
235000019626 lipase activity Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
FODOUIXGKGNSMR-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O FODOUIXGKGNSMR-UHFFFAOYSA-L 0.000 description 1
CGJMROBVSBIBKP-UHFFFAOYSA-M malonamate Chemical compound NC(=O)CC([O-])=O CGJMROBVSBIBKP-UHFFFAOYSA-M 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
BJDOHPOZGXIYPX-JCYYIGJDSA-N methyl (2r,3r,5r)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-methyldocosanoate Chemical compound CCCCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](C)C(=O)OC BJDOHPOZGXIYPX-JCYYIGJDSA-N 0.000 description 1
APVBZFBSOZYETA-IDZRBWSNSA-N methyl (2r,3r,5r)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-prop-2-ynyldocosanoate Chemical compound CCCCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](CC#C)C(=O)OC APVBZFBSOZYETA-IDZRBWSNSA-N 0.000 description 1
VLXRAZVRPKRTER-KLJDGLGGSA-N methyl (2s,3s,5s)-5-(2-carbamoylphenoxy)-2-hexyl-3-hydroxyhexadecanoate Chemical compound CCCCCCCCCCC[C@@H](C[C@H](O)[C@H](CCCCCC)C(=O)OC)OC1=CC=CC=C1C(N)=O VLXRAZVRPKRTER-KLJDGLGGSA-N 0.000 description 1
AUEZSDRLGPFCCH-RUZDIDTESA-N methyl (3r)-3-[tert-butyl(dimethyl)silyl]oxyicosanoate Chemical compound CCCCCCCCCCCCCCCCC[C@H](CC(=O)OC)O[Si](C)(C)C(C)(C)C AUEZSDRLGPFCCH-RUZDIDTESA-N 0.000 description 1
RVKKWZPQRLLBMT-HXUWFJFHSA-N methyl (3r)-3-hydroxyicosanoate Chemical compound CCCCCCCCCCCCCCCCC[C@@H](O)CC(=O)OC RVKKWZPQRLLBMT-HXUWFJFHSA-N 0.000 description 1
UOZZAMWODZQSOA-CQSZACIVSA-N methyl (3r)-3-hydroxytetradecanoate Chemical compound CCCCCCCCCCC[C@@H](O)CC(=O)OC UOZZAMWODZQSOA-CQSZACIVSA-N 0.000 description 1
INURHLMYHGYYDX-DRRMNDGNSA-N methyl (e)-3-[(2s)-1-[(2s,3s)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl]oxyprop-2-enoate Chemical compound CCCCCCCCCCC[C@H](O\C=C\C(=O)OC)C[C@@H]1OC(=O)[C@H]1CCCCCC INURHLMYHGYYDX-DRRMNDGNSA-N 0.000 description 1
YWFMUUIJORXGQT-UHFFFAOYSA-N methyl 1-carbamoylcyclopentane-1-carboxylate Chemical compound COC(=O)C1(C(N)=O)CCCC1 YWFMUUIJORXGQT-UHFFFAOYSA-N 0.000 description 1
IZHYBGITNQKGKF-UHFFFAOYSA-N methyl 2-(n-benzylanilino)acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OC)CC1=CC=CC=C1 IZHYBGITNQKGKF-UHFFFAOYSA-N 0.000 description 1
YXLVLOWNJCOOAU-UHFFFAOYSA-N methyl 2-ethyl-3-oxobutanoate Chemical compound CCC(C(C)=O)C(=O)OC YXLVLOWNJCOOAU-UHFFFAOYSA-N 0.000 description 1
SMCVPMKCDDNUCQ-UHFFFAOYSA-N methyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OC SMCVPMKCDDNUCQ-UHFFFAOYSA-N 0.000 description 1
ZHYWEHNCZJJFQZ-UHFFFAOYSA-N methyl 3-oxoicosanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)CC(=O)OC ZHYWEHNCZJJFQZ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
125000001421 myristyl 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])[H] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001196 nonadecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
NOPZJEGEHWRZSE-UHFFFAOYSA-N octadecyl formate Chemical compound CCCCCCCCCCCCCCCCCCOC=O NOPZJEGEHWRZSE-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001253 polyvinylpolypyrrolidone Substances 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 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
229960001404 quinidine Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
DTXSRICYVCKUME-UHFFFAOYSA-L ruthenium(2+);diacetate Chemical compound [Ru+2].CC([O-])=O.CC([O-])=O DTXSRICYVCKUME-UHFFFAOYSA-L 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000758 substrate Substances 0.000 description 1
JDVPQXZIJDEHAN-UHFFFAOYSA-M succinamate Chemical compound NC(=O)CCC([O-])=O JDVPQXZIJDEHAN-UHFFFAOYSA-M 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
229960004793 sucrose Drugs 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
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
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Obesity (AREA)
Hematology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Polyesters Or Polycarbonates (AREA)

IL9714891A 1990-02-26 1991-02-05 Oxetanones a process for their manufacture and pharmaceutical compositions containing them IL97148A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH60490		1990-02-26
CH400590		1990-12-17

Publications (2)

Publication Number	Publication Date
IL97148A0 IL97148A0 (en)	1992-05-25
IL97148A true IL97148A (en)	1996-11-14

Family

ID=25685091

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9714891A IL97148A (en)	1990-02-26	1991-02-05	Oxetanones a process for their manufacture and pharmaceutical compositions containing them

Country Status (18)

Country	Link
EP (1)	EP0444482B1 (pt)
JP (1)	JP2753403B2 (pt)
KR (1)	KR0183036B1 (pt)
AT (1)	ATE133167T1 (pt)
AU (1)	AU645291B2 (pt)
CA (1)	CA2035967C (pt)
DE (1)	DE59107262D1 (pt)
DK (1)	DK0444482T3 (pt)
ES (1)	ES2082869T3 (pt)
FI (1)	FI115054B (pt)
GR (1)	GR3019618T3 (pt)
HU (1)	HU218272B (pt)
IE (1)	IE72196B1 (pt)
IL (1)	IL97148A (pt)
MC (1)	MC2226A1 (pt)
NO (1)	NO177055C (pt)
NZ (1)	NZ237170A (pt)
PT (1)	PT96887B (pt)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2035972C (en) *	1990-02-23	2006-07-11	Martin Karpf	Process for the preparation of oxetanones
CA2098167C (en) *	1992-06-24	2006-12-19	Dorothea Isler	Foodstuffs and feedstuffs containing a lipase inhibitor
NL1004559C2 (nl) *	1996-11-18	1998-05-19	Unilife	Boter.
WO2001032670A1 (en) *	1999-10-29	2001-05-10	John Jason Gentry Mullins	Oxetanone derivatives
US6348492B1 (en) *	1999-10-29	2002-02-19	2Pro Chemical	Oxetanone derivatives
US6342519B2 (en) *	1999-10-29	2002-01-29	2 Pro Chemical	Oxetanone derivatives
US7074822B2 (en)	2004-02-23	2006-07-11	Solvay Pharmaceuticals Gmbh	Alkyl carbamate-substituted β-lactones, process for their preparation, and pharmaceutical compositions containing them
DE102004009076A1 (de) *	2004-02-23	2005-10-27	Solvay Pharmaceuticals Gmbh	Alkylcarbamat-substituierte β-Lactone, Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US8258321B2 (en)	2007-10-31	2012-09-04	Burnham Institute For Medical Research	Beta-lactone compounds
EP3651784B1 (en) *	2017-07-12	2022-09-28	Mayo Foundation for Medical Education and Research	Compounds for the reducing lipotoxic damage

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS608117B2 (ja) *	1977-02-08	1985-02-28	財団法人微生物化学研究会	新生理活性物質エステラスチンおよびその製造法
GB2023604B (en) *	1978-05-25	1982-07-28	Microbial Chem Res Found	Physiologically active derivatives of esterastin and production thereof
JPH0669130B2 (ja) *	1984-08-09	1994-08-31	三菱電機株式会社	遅延線

1991
- 1991-02-05 IL IL9714891A patent/IL97148A/en active IP Right Grant
- 1991-02-07 CA CA002035967A patent/CA2035967C/en not_active Expired - Fee Related
- 1991-02-15 ES ES91102151T patent/ES2082869T3/es not_active Expired - Lifetime
- 1991-02-15 EP EP91102151A patent/EP0444482B1/de not_active Expired - Lifetime
- 1991-02-15 AT AT91102151T patent/ATE133167T1/de not_active IP Right Cessation
- 1991-02-15 DK DK91102151.7T patent/DK0444482T3/da not_active Application Discontinuation
- 1991-02-15 DE DE59107262T patent/DE59107262D1/de not_active Expired - Fee Related
- 1991-02-20 HU HU61/91A patent/HU218272B/hu not_active IP Right Cessation
- 1991-02-20 AU AU71228/91A patent/AU645291B2/en not_active Ceased
- 1991-02-20 NZ NZ237170A patent/NZ237170A/en unknown
- 1991-02-21 MC MC912172A patent/MC2226A1/fr unknown
- 1991-02-22 JP JP3131730A patent/JP2753403B2/ja not_active Expired - Fee Related
- 1991-02-25 NO NO910729A patent/NO177055C/no unknown
- 1991-02-25 IE IE63191A patent/IE72196B1/en not_active IP Right Cessation
- 1991-02-26 PT PT96887A patent/PT96887B/pt not_active IP Right Cessation
- 1991-02-26 KR KR1019910003075A patent/KR0183036B1/ko not_active Expired - Fee Related
- 1991-02-26 FI FI910925A patent/FI115054B/fi not_active IP Right Cessation
1996
- 1996-04-09 GR GR960401013T patent/GR3019618T3/el unknown

Also Published As

Publication number	Publication date
PT96887B (pt)	1998-09-30
HUT56557A (en)	1991-09-30
FI910925L (fi)	1991-08-27
NO177055B (no)	1995-04-03
NO910729D0 (no)	1991-02-25
JPH0770099A (ja)	1995-03-14
ATE133167T1 (de)	1996-02-15
FI910925A0 (fi)	1991-02-26
PT96887A (pt)	1991-10-31
EP0444482A3 (en)	1991-12-04
KR0183036B1 (ko)	1999-05-01
AU7122891A (en)	1991-08-29
CA2035967A1 (en)	1991-08-27
ES2082869T3 (es)	1996-04-01
CA2035967C (en)	2001-10-16
IE910631A1 (en)	1991-08-28
AU645291B2 (en)	1994-01-13
FI115054B (fi)	2005-02-28
IE72196B1 (en)	1997-03-26
DK0444482T3 (da)	1996-05-06
JP2753403B2 (ja)	1998-05-20
IL97148A0 (en)	1992-05-25
GR3019618T3 (en)	1996-07-31
KR910021391A (ko)	1991-12-20
MC2226A1 (fr)	1993-02-02
NO177055C (no)	1995-07-12
EP0444482A2 (de)	1991-09-04
DE59107262D1 (de)	1996-02-29
HU218272B (en)	2000-07-28
NO910729L (no)	1991-08-27
NZ237170A (en)	1993-12-23
EP0444482B1 (de)	1996-01-17

Legal Events

Date	Code	Title
1997-04-15	FF	Patent granted
1997-07-13	KB	Patent renewed
2001-06-14	KB	Patent renewed
2005-03-20	KB	Patent renewed

Publication	Publication Date	Title
US5260310A (en)	1993-11-09	Oxetanone compounds and pharmaceutical compositions containing them
RU2108322C1 (ru)	1998-04-10	Производные циклоалкилзамещенного глутарамида и фармацевтическая композиция на их основе
EP0525420B1 (en)	1999-05-12	Pseudopeptides and dipeptides characterised by a substituted methyl ketone moiety at the C-terminus as thiol protease inhibitors
DE69432614T2 (de)	2004-02-26	Alkohol und Aldehyde Derivate als Cathepsin L Inhibitore und als Inhibitore der Knochenresorption
HUT74511A (en)	1997-01-28	Metalloproteinase inhibitors, pharmaceutical compns. contg. them and process to prepare the said compds.
IE910631A1 (en)	1991-08-28	Oxetanones
CA1130800A (en)	1982-08-31	N-SUBSTITUTED .omega.-AMINOALKANOYL-.omega.-AMINOALKANOIC ACIDS, THEIR USE AND PROCESS FOR THEIR PRODUCTION AS WELL AS PHARMACEUTICAL PRODUCTS CONTAINING THESE COMPOUNDS
HRP980096A2 (en)	1998-12-31	Reverse hydroxamate derivatives as matrix metalloprotease inhibitors, metalloprotease inhibitors, and tnf alpha inhibitors
US6444849B1 (en)	2002-09-03	Amide derivatives
EP0520427B1 (en)	1994-12-14	Cyclopropenone derivatives
HUT57705A (en)	1991-12-30	Process for producing acat-inhibitors
FR2640971A1 (pt)	1990-06-29
NO178546B (no)	1996-01-08	Analogifremgangsmåte for fremstilling av terapeutisk aktive ACE-hemmere med nootrop virkning
EP0848957A1 (en)	1998-06-24	Fas LIGAND SOLUBILIZATION INHIBITOR
WO1995019959A1 (en)	1995-07-27	Amino acid derivatives and their use as phospholipase a2 inhibitors
US4594443A (en)	1986-06-10	Derivatives of 4-phenyl-4-oxo-buten-2-oic acid and therapeutic use thereof
CZ281839B6 (cs)	1997-02-12	Derivát aminokyseliny, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
JPH0925235A (ja)	1997-01-28	１−ｏ−アシルグリセロール−２，３−ホスフェート誘導体を有効成分とするがん転移抑制剤
CZ298048B6 (cs)	2007-06-06	Farmaceutický prostredek a deriváty kyseliny hydroxamové
US5438046A (en)	1995-08-01	N-heteroaryl substituted derivatives of propanamide useful in the treatment of cardiovascular diseases
EP0925786A1 (en)	1999-06-30	Remedies for ischemic diseases
JPH09188631A (ja)	1997-07-22	Ｆａｓリガンド可溶化抑制薬
JPH09249628A (ja)	1997-09-22	フェノール誘導体
JPH11171881A (ja)	1999-06-29	含酸素複素環誘導体
JP2000086611A (ja)	2000-03-28	新規なメタロプロテイナ―ゼ阻害剤