NZ516521A

NZ516521A - Clear oil-containing pharmaceutical compositions

Clear oil-containing pharmaceutical compositions

Info

Publication number: NZ516521A
Authority: NZ; New Zealand
Prior art keywords: peg; oil; pharmaceutical composition; group; triglyceride
Prior art date: 1999-06-30

Application number

NZ516521A

Other languages

English (en)

Inventor

Feng-Jing Chen

Mahesh V Patel

Original Assignee

Lipocine Inc

Priority date

1999-06-30

Filing date

2000-06-02

Publication date

2003-11-28

2000-06-02 Application filed by Lipocine Inc filed Critical Lipocine Inc

2003-11-28 Publication of NZ516521A publication Critical patent/NZ516521A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 180
239000004094 surface-active agent Substances 0.000 claims abstract description 297
239000000203 mixture Substances 0.000 claims abstract description 220
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 152
239000003814 drug Substances 0.000 claims abstract description 118
229940124597 therapeutic agent Drugs 0.000 claims abstract description 96
238000000034 method Methods 0.000 claims abstract description 51
150000003626 triacylglycerols Chemical class 0.000 claims abstract description 51
239000006185 dispersion Substances 0.000 claims abstract description 48
-1 polyoxyethylene Polymers 0.000 claims description 239
239000000194 fatty acid Substances 0.000 claims description 211
235000014113 dietary fatty acids Nutrition 0.000 claims description 202
229930195729 fatty acid Natural products 0.000 claims description 202
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 137
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 109
229920001223 polyethylene glycol Polymers 0.000 claims description 102
239000004359 castor oil Substances 0.000 claims description 83
235000019438 castor oil Nutrition 0.000 claims description 83
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 83
239000002202 Polyethylene glycol Substances 0.000 claims description 82
125000005456 glyceride group Chemical group 0.000 claims description 78
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 74
230000002209 hydrophobic effect Effects 0.000 claims description 71
GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims description 69
229940049964 oleate Drugs 0.000 claims description 69
239000002552 dosage form Substances 0.000 claims description 64
150000004665 fatty acids Chemical class 0.000 claims description 62
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 60
IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 claims description 59
239000007864 aqueous solution Substances 0.000 claims description 48
235000015112 vegetable and seed oil Nutrition 0.000 claims description 48
229930182558 Sterol Natural products 0.000 claims description 46
239000003921 oil Substances 0.000 claims description 46
150000003432 sterols Chemical class 0.000 claims description 46
235000003702 sterols Nutrition 0.000 claims description 46
239000008158 vegetable oil Substances 0.000 claims description 46
235000019198 oils Nutrition 0.000 claims description 45
241000894007 species Species 0.000 claims description 45
239000008172 hydrogenated vegetable oil Substances 0.000 claims description 44
229920001983 poloxamer Polymers 0.000 claims description 43
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 42
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 42
150000002148 esters Chemical class 0.000 claims description 42
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 41
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 39
229940070765 laurate Drugs 0.000 claims description 38
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 37
235000019441 ethanol Nutrition 0.000 claims description 35
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 31
229920005862 polyol Polymers 0.000 claims description 29
150000003077 polyols Chemical class 0.000 claims description 29
229960000502 poloxamer Drugs 0.000 claims description 27
229920001451 polypropylene glycol Polymers 0.000 claims description 27
235000005687 corn oil Nutrition 0.000 claims description 26
239000002285 corn oil Substances 0.000 claims description 26
239000002563 ionic surfactant Substances 0.000 claims description 25
238000002156 mixing Methods 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims description 23
FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 claims description 22
229940079593 drug Drugs 0.000 claims description 22
239000000839 emulsion Substances 0.000 claims description 22
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 22
235000019483 Peanut oil Nutrition 0.000 claims description 21
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 21
235000012000 cholesterol Nutrition 0.000 claims description 21
229940107161 cholesterol Drugs 0.000 claims description 21
239000000312 peanut oil Substances 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 20
238000002835 absorbance Methods 0.000 claims description 19
239000003346 palm kernel oil Substances 0.000 claims description 19
235000019865 palm kernel oil Nutrition 0.000 claims description 19
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 18
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 18
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 18
235000019864 coconut oil Nutrition 0.000 claims description 18
239000003240 coconut oil Substances 0.000 claims description 18
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 18
235000010445 lecithin Nutrition 0.000 claims description 18
239000000787 lecithin Substances 0.000 claims description 18
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 18
239000000600 sorbitol Substances 0.000 claims description 18
KHICUSAUSRBPJT-UHFFFAOYSA-N 2-(2-octadecanoyloxypropanoyloxy)propanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C(O)=O KHICUSAUSRBPJT-UHFFFAOYSA-N 0.000 claims description 17
ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 claims description 17
CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims description 16
235000019489 Almond oil Nutrition 0.000 claims description 16
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 16
229920001214 Polysorbate 60 Polymers 0.000 claims description 16
239000008168 almond oil Substances 0.000 claims description 16
229920001400 block copolymer Polymers 0.000 claims description 16
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 16
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 16
229940093471 ethyl oleate Drugs 0.000 claims description 16
229940049918 linoleate Drugs 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 15
OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 claims description 15
235000010469 Glycine max Nutrition 0.000 claims description 15
239000001833 Succinylated monoglyceride Substances 0.000 claims description 15
235000008390 olive oil Nutrition 0.000 claims description 15
239000004006 olive oil Substances 0.000 claims description 15
239000002245 particle Substances 0.000 claims description 15
235000019327 succinylated monoglyceride Nutrition 0.000 claims description 15
150000003899 tartaric acid esters Chemical class 0.000 claims description 15
235000019482 Palm oil Nutrition 0.000 claims description 14
DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 claims description 14
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 14
239000008173 hydrogenated soybean oil Substances 0.000 claims description 14
239000002540 palm oil Substances 0.000 claims description 14
239000000047 product Substances 0.000 claims description 14
235000000346 sugar Nutrition 0.000 claims description 14
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims description 13
NKSOSPOXQKNIKJ-CLFAGFIQSA-N Polyoxyethylene dioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOC(=O)CCCCCCC\C=C/CCCCCCCC NKSOSPOXQKNIKJ-CLFAGFIQSA-N 0.000 claims description 13
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 13
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 13
ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims description 12
MQFYRUGXOJAUQK-UHFFFAOYSA-N 2-[2-[2-(2-octadecanoyloxyethoxy)ethoxy]ethoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCCCCCCCCCCCCC MQFYRUGXOJAUQK-UHFFFAOYSA-N 0.000 claims description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 12
229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic 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)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 12
229940074046 glyceryl laurate Drugs 0.000 claims description 12
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 12
LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 12
RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic 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)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims description 12
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 11
108010007979 Glycocholic Acid Proteins 0.000 claims description 11
235000012343 cottonseed oil Nutrition 0.000 claims description 11
239000002385 cottonseed oil Substances 0.000 claims description 11
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 11
229920000053 polysorbate 80 Polymers 0.000 claims description 11
108090000765 processed proteins & peptides Proteins 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
229940035044 sorbitan monolaurate Drugs 0.000 claims description 11
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 11
229940117972 triolein Drugs 0.000 claims description 11
HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 claims description 10
244000068988 Glycine max Species 0.000 claims description 10
229920001213 Polysorbate 20 Polymers 0.000 claims description 10
235000019485 Safflower oil Nutrition 0.000 claims description 10
150000005215 alkyl ethers Chemical class 0.000 claims description 10
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 10
239000003613 bile acid Substances 0.000 claims description 10
239000003833 bile salt Substances 0.000 claims description 10
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic 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)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 10
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic 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)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 10
229940018602 docusate Drugs 0.000 claims description 10
RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic 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)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 claims description 10
229920002523 polyethylene Glycol 1000 Polymers 0.000 claims description 10
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 10
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 10
235000005713 safflower oil Nutrition 0.000 claims description 10
239000003813 safflower oil Substances 0.000 claims description 10
235000012424 soybean oil Nutrition 0.000 claims description 10
239000003549 soybean oil Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 9
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 9
150000001298 alcohols Chemical class 0.000 claims description 9
LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 claims description 9
150000002170 ethers Chemical class 0.000 claims description 9
238000001727 in vivo Methods 0.000 claims description 9
150000003903 lactic acid esters Chemical class 0.000 claims description 9
229940067606 lecithin Drugs 0.000 claims description 9
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 9
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 9
229940068968 polysorbate 80 Drugs 0.000 claims description 9
102000004169 proteins and genes Human genes 0.000 claims description 9
108090000623 proteins and genes Proteins 0.000 claims description 9
235000011803 sesame oil Nutrition 0.000 claims description 9
239000008159 sesame oil Substances 0.000 claims description 9
VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims description 9
XOMRRQXKHMYMOC-NRFANRHFSA-N (3s)-3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C XOMRRQXKHMYMOC-NRFANRHFSA-N 0.000 claims description 8
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 8
AOWCOHYBGYRYGE-UHFFFAOYSA-N 1-[2,3-bis(2-oxopropoxy)propoxy]propan-2-one Chemical compound CC(=O)COCC(OCC(C)=O)COCC(C)=O AOWCOHYBGYRYGE-UHFFFAOYSA-N 0.000 claims description 8
OEZPKXDBWNXBRE-UHFFFAOYSA-N 2,3-bis(2-hydroxyethoxy)propyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(OCCO)COCCO OEZPKXDBWNXBRE-UHFFFAOYSA-N 0.000 claims description 8
FUJLYHJROOYKRA-QGZVFWFLSA-N O-lauroyl-L-carnitine Chemical compound CCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C FUJLYHJROOYKRA-QGZVFWFLSA-N 0.000 claims description 8
229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 8
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 8
229940093761 bile salts Drugs 0.000 claims description 8
229940009025 chenodeoxycholate Drugs 0.000 claims description 8
229940099371 diacetylated monoglycerides Drugs 0.000 claims description 8
229940068977 polysorbate 20 Drugs 0.000 claims description 8
235000011069 sorbitan monooleate Nutrition 0.000 claims description 8
239000001593 sorbitan monooleate Substances 0.000 claims description 8
229940035049 sorbitan monooleate Drugs 0.000 claims description 8
229940071209 stearoyl lactylate Drugs 0.000 claims description 8
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 8
238000005809 transesterification reaction Methods 0.000 claims description 8
229940014499 ursodeoxycholate Drugs 0.000 claims description 8
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 7
HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 claims description 7
RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims description 7
QIZPVNNYFKFJAD-UHFFFAOYSA-N 1-chloro-2-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1Cl QIZPVNNYFKFJAD-UHFFFAOYSA-N 0.000 claims description 7
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 7
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 7
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 7
239000005639 Lauric acid Substances 0.000 claims description 7
PSHXNVGSVNEJBD-LJQANCHMSA-N O-tetradecanoyl-L-carnitine Chemical compound CCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C PSHXNVGSVNEJBD-LJQANCHMSA-N 0.000 claims description 7
239000005642 Oleic acid Substances 0.000 claims description 7
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229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 claims description 7
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AAYACJGHNRIFCT-YRJJIGPTSA-M sodium glycochenodeoxycholate Chemical compound [Na+].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)NCC([O-])=O)C)[C@@]2(C)CC1 AAYACJGHNRIFCT-YRJJIGPTSA-M 0.000 description 1
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