GB2285805A - Esters - Google Patents
Esters Download PDFInfo
- Publication number
- GB2285805A GB2285805A GB9400882A GB9400882A GB2285805A GB 2285805 A GB2285805 A GB 2285805A GB 9400882 A GB9400882 A GB 9400882A GB 9400882 A GB9400882 A GB 9400882A GB 2285805 A GB2285805 A GB 2285805A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- formulae
- acid bis
- bis
- stigmasteryiester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000002148 esters Chemical class 0.000 title claims description 34
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 93
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 58
- -1 vitamin-E compound Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 27
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 25
- 239000012141 concentrate Substances 0.000 claims description 24
- 239000004491 dispersible concentrate Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 239000001530 fumaric acid Substances 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229930182558 Sterol Natural products 0.000 claims description 11
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 235000003702 sterols Nutrition 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229930003316 Vitamin D Natural products 0.000 claims description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 10
- 150000003432 sterols Chemical class 0.000 claims description 10
- 235000019166 vitamin D Nutrition 0.000 claims description 10
- 239000011710 vitamin D Substances 0.000 claims description 10
- 229940046008 vitamin d Drugs 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
- 239000011976 maleic acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000000259 anti-tumor effect Effects 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 7
- 239000008187 granular material Substances 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229930003427 Vitamin E Natural products 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 239000008188 pellet Substances 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000011709 vitamin E Substances 0.000 claims description 6
- 235000019165 vitamin E Nutrition 0.000 claims description 6
- 229940046009 vitamin E Drugs 0.000 claims description 6
- 239000001361 adipic acid Substances 0.000 claims description 5
- 235000011037 adipic acid Nutrition 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000007957 coemulsifier Substances 0.000 claims description 3
- 239000011162 core material Substances 0.000 claims description 3
- 235000021588 free fatty acids Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
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- 235000013343 vitamin Nutrition 0.000 claims description 3
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- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003165 hydrotropic effect Effects 0.000 claims description 2
- 150000007928 imidazolide derivatives Chemical class 0.000 claims description 2
- 239000008180 pharmaceutical surfactant Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 18
- 210000004369 blood Anatomy 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000008280 blood Substances 0.000 description 15
- 235000008504 concentrate Nutrition 0.000 description 15
- 238000009792 diffusion process Methods 0.000 description 15
- 239000004530 micro-emulsion Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 210000004881 tumor cell Anatomy 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000011732 tocopherol Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
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- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229960001295 tocopherol Drugs 0.000 description 6
- 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 description 5
- 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 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 210000002950 fibroblast Anatomy 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
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- 150000003839 salts Chemical class 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000011647 vitamin D3 Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
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- 229960002061 ergocalciferol Drugs 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
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- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
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- 235000001892 vitamin D2 Nutrition 0.000 description 4
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- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 4
- 235000005282 vitamin D3 Nutrition 0.000 description 4
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 4
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- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
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- 244000060011 Cocos nucifera Species 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001505332 Polyomavirus sp. Species 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
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- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
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- BUNBVCKYYMRTNS-UHFFFAOYSA-N tachysterol Natural products C=1CCC2(C)C(C(C)CCC(C)C(C)C)CCC2C=1C=CC1=C(C)CCC(O)C1 BUNBVCKYYMRTNS-UHFFFAOYSA-N 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-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
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3159/91A CH681891A5 (enrdf_load_stackoverflow) | 1992-10-09 | 1992-10-09 | |
| DE4319492A DE4319492A1 (de) | 1992-10-09 | 1993-06-11 | Dicarbonsäureester |
| GB9400882A GB2285805A (en) | 1992-10-09 | 1994-01-18 | Esters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3159/91A CH681891A5 (enrdf_load_stackoverflow) | 1992-10-09 | 1992-10-09 | |
| GB9400882A GB2285805A (en) | 1992-10-09 | 1994-01-18 | Esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9400882D0 GB9400882D0 (en) | 1994-03-16 |
| GB2285805A true GB2285805A (en) | 1995-07-26 |
Family
ID=25692340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9400882A Withdrawn GB2285805A (en) | 1992-10-09 | 1994-01-18 | Esters |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH681891A5 (enrdf_load_stackoverflow) |
| DE (1) | DE4319492A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2285805A (enrdf_load_stackoverflow) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
| EP0946485A4 (en) * | 1996-11-12 | 2000-01-19 | Tamarkin Pharmaceutical Innova | METHOD FOR TREATING DERMATOLOGICAL DISEASES |
| EP1045641A4 (en) * | 1997-12-16 | 2003-03-19 | Cognis Corp | STEROLESTER AS A FOOD ADDITIVE |
| US7084172B2 (en) * | 2001-09-17 | 2006-08-01 | Pierre Fabre Dermo-Cosmetique | Bioprecursors for percutaneous application |
| US8148414B2 (en) | 2008-08-19 | 2012-04-03 | Xenoport, Inc. | Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US9302977B2 (en) | 2013-06-07 | 2016-04-05 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9416096B2 (en) | 2013-09-06 | 2016-08-16 | Xenoport, Inc. | Crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, methods of synthesis and use |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| US9505776B2 (en) | 2013-03-14 | 2016-11-29 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US9597292B2 (en) | 2012-08-22 | 2017-03-21 | Xenoport, Inc. | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| US9604922B2 (en) | 2014-02-24 | 2017-03-28 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
| US10179118B2 (en) | 2013-03-24 | 2019-01-15 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of dimethyl fumarate |
| US10222388B2 (en) | 2013-08-07 | 2019-03-05 | Orgentec Diagnostika Gmbh | 25-OH vitamin D derivatives for determining vitamin D metabolites |
| US10945984B2 (en) | 2012-08-22 | 2021-03-16 | Arbor Pharmaceuticals, Llc | Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH681891A5 (enrdf_load_stackoverflow) * | 1992-10-09 | 1993-06-15 | Marigen Sa | |
| US5593691A (en) * | 1993-06-03 | 1997-01-14 | Marigen S.A. | Biotenside solvents for pharmaceuticals and cosmetics |
| FI974648A7 (fi) * | 1997-09-09 | 1999-05-06 | Raisio Benecol Oy | Hydroksihappo-, maitohappo- ja hydroksialkanoaattiesterit ja niiden käyttö |
| CN104434927A (zh) * | 2014-12-16 | 2015-03-25 | 吉林农业大学 | 丙二酸双环戊烷并多氢菲酯b在制备降血压药物中的应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB760346A (en) * | 1952-12-18 | 1956-10-31 | Roche Products Ltd | Novel esters of bixins and norbixins and process for the manufacture thereof |
| EP0195311A2 (en) * | 1985-03-06 | 1986-09-24 | Nippon Fine Chemical Co., Ltd. | Process for preparing fatty acid esters |
| US5198432A (en) * | 1988-01-29 | 1993-03-30 | Center For Innovative Technology | Method of preventing chlorohydrocarbon toxicity using sterol derivatives |
| CH681891A5 (enrdf_load_stackoverflow) * | 1992-10-09 | 1993-06-15 | Marigen Sa |
-
1992
- 1992-10-09 CH CH3159/91A patent/CH681891A5/de not_active IP Right Cessation
-
1993
- 1993-06-11 DE DE4319492A patent/DE4319492A1/de not_active Withdrawn
-
1994
- 1994-01-18 GB GB9400882A patent/GB2285805A/en not_active Withdrawn
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Cited By (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946485A4 (en) * | 1996-11-12 | 2000-01-19 | Tamarkin Pharmaceutical Innova | METHOD FOR TREATING DERMATOLOGICAL DISEASES |
| US6180669B1 (en) | 1996-11-12 | 2001-01-30 | Tamarkin Pharmaceutical Innovation Ltd. | Method for treatment of dermatological disorders |
| EP1045641A4 (en) * | 1997-12-16 | 2003-03-19 | Cognis Corp | STEROLESTER AS A FOOD ADDITIVE |
| US6713466B2 (en) | 1997-12-16 | 2004-03-30 | Cognis Corporation | Processes for preparing sterol esters |
| US6147236A (en) * | 1998-08-25 | 2000-11-14 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
| US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
| US7084172B2 (en) * | 2001-09-17 | 2006-08-01 | Pierre Fabre Dermo-Cosmetique | Bioprecursors for percutaneous application |
| US9452972B2 (en) | 2008-08-19 | 2016-09-27 | Xenoport, Inc. | Methods of using prodrugs of methyl hydrogen fumarate and pharmaceutical compositions thereof |
| US8148414B2 (en) | 2008-08-19 | 2012-04-03 | Xenoport, Inc. | Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use |
| US8778991B2 (en) | 2008-08-19 | 2014-07-15 | Xenoport, Inc. | Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use |
| US8785443B2 (en) | 2008-08-19 | 2014-07-22 | Xenoport, Inc. | Methods of using prodrugs of methyl hydrogen fumarate and pharmaceutical compositions thereof |
| US10945984B2 (en) | 2012-08-22 | 2021-03-16 | Arbor Pharmaceuticals, Llc | Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects |
| US9597292B2 (en) | 2012-08-22 | 2017-03-21 | Xenoport, Inc. | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| US10940117B2 (en) | 2012-08-22 | 2021-03-09 | Arbor Pharmaceuticals, Llc | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| US10716760B2 (en) | 2012-08-22 | 2020-07-21 | Arbor Pharmaceuticals, Llc | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| US11679092B2 (en) | 2013-03-14 | 2023-06-20 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US11230548B2 (en) | 2013-03-14 | 2022-01-25 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US9090558B2 (en) | 2013-03-14 | 2015-07-28 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US11083703B2 (en) | 2013-03-14 | 2021-08-10 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US11905298B2 (en) | 2013-03-14 | 2024-02-20 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US12076306B2 (en) | 2013-03-14 | 2024-09-03 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US9505776B2 (en) | 2013-03-14 | 2016-11-29 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US10406133B2 (en) | 2013-03-14 | 2019-09-10 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US10596140B2 (en) | 2013-03-14 | 2020-03-24 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US10179118B2 (en) | 2013-03-24 | 2019-01-15 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of dimethyl fumarate |
| US11938111B2 (en) | 2013-03-24 | 2024-03-26 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of dimethyl fumarate |
| US9302977B2 (en) | 2013-06-07 | 2016-04-05 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| US11199553B2 (en) | 2013-08-07 | 2021-12-14 | Orgentec Diagnostika Gmbh | 25-OH vitamin D derivatives for determining vitamin D metabolites |
| US10222388B2 (en) | 2013-08-07 | 2019-03-05 | Orgentec Diagnostika Gmbh | 25-OH vitamin D derivatives for determining vitamin D metabolites |
| US9682057B2 (en) | 2013-09-06 | 2017-06-20 | Xenoport, Inc. | Crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, methods of synthesis and use |
| US9416096B2 (en) | 2013-09-06 | 2016-08-16 | Xenoport, Inc. | Crystalline forms of (N,N-Diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, methods of synthesis and use |
| US9604922B2 (en) | 2014-02-24 | 2017-03-28 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| US11135296B2 (en) | 2014-03-24 | 2021-10-05 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of fumaric acid esters |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9400882D0 (en) | 1994-03-16 |
| DE4319492A1 (de) | 1994-04-14 |
| CH681891A5 (enrdf_load_stackoverflow) | 1993-06-15 |
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| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |