CA1135689A - Substituted phenol ester containing compounds - Google Patents
Substituted phenol ester containing compoundsInfo
- Publication number
- CA1135689A CA1135689A CA000345303A CA345303A CA1135689A CA 1135689 A CA1135689 A CA 1135689A CA 000345303 A CA000345303 A CA 000345303A CA 345303 A CA345303 A CA 345303A CA 1135689 A CA1135689 A CA 1135689A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- nicotinate
- binding substance
- compound
- prepared according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 phenol ester Chemical class 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 53
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 29
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000011664 nicotinic acid Substances 0.000 claims abstract description 15
- 235000001968 nicotinic acid Nutrition 0.000 claims abstract description 14
- 229960003512 nicotinic acid Drugs 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 22
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 claims description 16
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 claims description 8
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims description 6
- UHMDBYRPFFWVIH-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-yl pyridine-3-carboxylate Chemical compound C=1C=CC=2CCCCC=2C=1OC(=O)C1=CC=CN=C1 UHMDBYRPFFWVIH-UHFFFAOYSA-N 0.000 claims description 5
- GKUHMJCSBVHYAY-UHFFFAOYSA-N (2-benzoyl-4-chlorophenyl) pyridine-3-carboxylate Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1OC(=O)C1=CC=CN=C1 GKUHMJCSBVHYAY-UHFFFAOYSA-N 0.000 claims description 3
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- KDWWTXCFEYTIEL-UHFFFAOYSA-N (2-cyclohexylphenyl) pyridine-3-carboxylate;hydron;chloride Chemical compound Cl.C=1C=CN=CC=1C(=O)OC1=CC=CC=C1C1CCCCC1 KDWWTXCFEYTIEL-UHFFFAOYSA-N 0.000 claims description 2
- YUJPABSYWMRDOH-UHFFFAOYSA-N (4-cyclododecylphenyl) pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C=C1)=CC=C1C1CCCCCCCCCCC1 YUJPABSYWMRDOH-UHFFFAOYSA-N 0.000 claims description 2
- WZPVEPWPLQMODU-UHFFFAOYSA-N (4-cyclohexylphenyl) pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C=C1)=CC=C1C1CCCCC1 WZPVEPWPLQMODU-UHFFFAOYSA-N 0.000 claims description 2
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-UHFFFAOYSA-N 0.000 claims description 2
- KZMYFIUFUAOZHP-UHFFFAOYSA-N 4-(1-adamantyl)phenol Chemical compound C1=CC(O)=CC=C1C1(C2)CC(C3)CC2CC3C1 KZMYFIUFUAOZHP-UHFFFAOYSA-N 0.000 claims description 2
- JNAUIOQFUDVUJP-UHFFFAOYSA-N 4-cyclododecylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCCCCCCCC1 JNAUIOQFUDVUJP-UHFFFAOYSA-N 0.000 claims description 2
- SCWNNOCLLOHZIG-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1-naphthol Chemical compound C1CCCC2=C1C=CC=C2O SCWNNOCLLOHZIG-UHFFFAOYSA-N 0.000 claims description 2
- DQFQTZGYPLXEDG-UHFFFAOYSA-N [4-(2-cyclohexylacetyl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(OC(=O)C=2C=NC=CC=2)C=CC=1C(=O)CC1CCCCC1 DQFQTZGYPLXEDG-UHFFFAOYSA-N 0.000 claims description 2
- HBKRFGSYVQCWSJ-UHFFFAOYSA-N [4-(2-phenylpropan-2-yl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(OC(=O)C=2C=NC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 HBKRFGSYVQCWSJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 2
- JLYDPEZMYMABFQ-UHFFFAOYSA-N 6-cyclohexyl-2-phenylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(C2CCCCC2)N=C1C1=CC=CC=C1 JLYDPEZMYMABFQ-UHFFFAOYSA-N 0.000 claims 5
- GQNIODHYMWTPEU-UHFFFAOYSA-N 6-(2-cyclohexylacetyl)-2-phenylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(C(=O)CC2CCCCC2)N=C1C1=CC=CC=C1 GQNIODHYMWTPEU-UHFFFAOYSA-N 0.000 claims 4
- AVBIPSXXCFDJIO-UHFFFAOYSA-N 6-cyclododecyl-2-phenylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(C2CCCCCCCCCCC2)N=C1C1=CC=CC=C1 AVBIPSXXCFDJIO-UHFFFAOYSA-N 0.000 claims 4
- VIRHPUXFJHWRER-UHFFFAOYSA-N [2-(1-adamantyl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=CC=C(C23CC4CC(CC(C4)C2)C3)C=1OC(=O)C1=CC=CN=C1 VIRHPUXFJHWRER-UHFFFAOYSA-N 0.000 claims 4
- IKARRQFFZRTPEB-UHFFFAOYSA-N (2-tert-butyl-4-cyclohexylphenyl) pyridine-3-carboxylate Chemical compound CC(C)(C)C1=CC(C2CCCCC2)=CC=C1OC(=O)C1=CC=CN=C1 IKARRQFFZRTPEB-UHFFFAOYSA-N 0.000 claims 2
- JNYASUANIQIFHA-UHFFFAOYSA-N (4-cyclohexylphenyl) 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(C2CCCCC2)C=CC=1OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JNYASUANIQIFHA-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- ODJPWXGMNLXNCU-UHFFFAOYSA-N 2-(1-adamantyl)phenol Chemical compound OC1=CC=CC=C1C1(C2)CC(C3)CC2CC3C1 ODJPWXGMNLXNCU-UHFFFAOYSA-N 0.000 claims 1
- IHRMORKSPQLLPZ-UHFFFAOYSA-N 2-cyclododecylphenol Chemical compound OC1=CC=CC=C1C1CCCCCCCCCCC1 IHRMORKSPQLLPZ-UHFFFAOYSA-N 0.000 claims 1
- MTZCULKBCXZEHR-UHFFFAOYSA-N 2-cyclohexyl-1-(2-hydroxyphenyl)ethanone Chemical compound OC1=CC=CC=C1C(=O)CC1CCCCC1 MTZCULKBCXZEHR-UHFFFAOYSA-N 0.000 claims 1
- OZUQBIVVKGATPZ-UHFFFAOYSA-N 2-cyclohexyl-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1CCCCC1 OZUQBIVVKGATPZ-UHFFFAOYSA-N 0.000 claims 1
- PJNMKAQCMGXVNI-UHFFFAOYSA-N 2-tert-butyl-4-cyclohexylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2CCCCC2)=C1 PJNMKAQCMGXVNI-UHFFFAOYSA-N 0.000 claims 1
- KQALADCYUHGQHC-UHFFFAOYSA-N 6-cyclohexyl-2-phenylpyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C(C2CCCCC2)N=C1C1=CC=CC=C1 KQALADCYUHGQHC-UHFFFAOYSA-N 0.000 claims 1
- DBKLIGHGFZVBFK-UHFFFAOYSA-N [4-(1-adamantyl)phenyl] pyridine-3-carboxylate Chemical compound C=1C=C(C23CC4CC(CC(C4)C2)C3)C=CC=1OC(=O)C1=CC=CN=C1 DBKLIGHGFZVBFK-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 abstract description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 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 description 28
- 230000009467 reduction Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 235000012000 cholesterol Nutrition 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
- 229960001214 clofibrate Drugs 0.000 description 3
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 206010014476 Elevated cholesterol Diseases 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- HTXIBSPLKGAJRX-UHFFFAOYSA-N 2-(1-adamantyl)-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1(C2)CC(C3)CC2CC3C1 HTXIBSPLKGAJRX-UHFFFAOYSA-N 0.000 description 1
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 description 1
- VVMQAIJCWNJCMK-UHFFFAOYSA-N 2-chloro-4-cyclohexylphenol Chemical compound C1=C(Cl)C(O)=CC=C1C1CCCCC1 VVMQAIJCWNJCMK-UHFFFAOYSA-N 0.000 description 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
- YUQPJMAOUVWWOM-UHFFFAOYSA-N 4-cyclohexyl-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1CCCCC1 YUQPJMAOUVWWOM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010014486 Elevated triglycerides Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- CUZYGTJIGATQSB-UHFFFAOYSA-N [4-[2-(1-adamantyl)acetyl]phenyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(C(=O)CC23CC4CC(CC(C4)C2)C3)C=CC=1OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 CUZYGTJIGATQSB-UHFFFAOYSA-N 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229950008441 clofibric acid Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2904757.2-44 | 1979-02-08 | ||
| DE2904757 | 1979-02-08 | ||
| US222,679 | 1981-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1135689A true CA1135689A (en) | 1982-11-16 |
Family
ID=6062456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345303A Expired CA1135689A (en) | 1979-02-08 | 1980-02-08 | Substituted phenol ester containing compounds |
Country Status (22)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3891219T1 (de) * | 1988-01-22 | 1990-02-01 | Kh Nii Endokrinologii I Chimii | P-chlorphenoxysobuttersaeureundezylester und arzneimittel auf dessen grundlage zur behandlung der hyperlipidaemie |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3175M (fr) * | 1963-06-25 | 1965-03-08 | Analyses Et De Rech S Biolog M | Nouveaux composés chimiques a action vaso-dilatatrice périphérique. |
| DE2352012A1 (de) * | 1972-11-01 | 1974-05-09 | Ciba Geigy Ag | Neue aliphatisch substituierte arylchalkogeno-kohlenwasserstoffderivate und verfahren zu ihrer herstellung |
| ES438246A1 (es) * | 1975-06-04 | 1977-01-16 | Alter Sa | Un procedimiento de preparacion del glicol 2-(p-clorofenoci)-2-metilpropinato nicotinato. |
| JPS57102866A (en) * | 1980-12-19 | 1982-06-26 | Kyorin Pharmaceut Co Ltd | Nicotinic acid derivative and its preparation |
-
1980
- 1980-02-06 SE SE8000962A patent/SE450381B/sv not_active IP Right Cessation
- 1980-02-07 IL IL59337A patent/IL59337A/xx not_active IP Right Cessation
- 1980-02-07 DK DK053680A patent/DK152360C/da not_active IP Right Cessation
- 1980-02-07 MX MX808635U patent/MX6377E/es unknown
- 1980-02-07 ES ES488345A patent/ES488345A0/es active Granted
- 1980-02-07 IE IE236/80A patent/IE49385B1/en not_active IP Right Cessation
- 1980-02-08 PL PL1980221888A patent/PL123379B1/pl unknown
- 1980-02-08 CH CH106380A patent/CH644092A5/de not_active IP Right Cessation
- 1980-02-08 IT IT19782/80A patent/IT1141197B/it active
- 1980-02-08 GB GB8004310A patent/GB2041937B/en not_active Expired
- 1980-02-08 FR FR8002783A patent/FR2448532A1/fr active Granted
- 1980-02-08 AR AR279916A patent/AR228251A1/es active
- 1980-02-08 AU AU55355/80A patent/AU532208B2/en not_active Ceased
- 1980-02-08 AT AT0070380A patent/AT374797B/de not_active IP Right Cessation
- 1980-02-08 CA CA000345303A patent/CA1135689A/en not_active Expired
- 1980-02-08 BE BE0/199326A patent/BE881626A/fr not_active IP Right Cessation
- 1980-02-08 NL NL8000826A patent/NL8000826A/nl not_active Application Discontinuation
- 1980-02-08 JP JP1374980A patent/JPS55129245A/ja active Granted
- 1980-02-08 YU YU00338/80A patent/YU33880A/xx unknown
- 1980-02-08 GR GR61163A patent/GR73905B/el unknown
- 1980-02-08 HU HU80289A patent/HU182099B/hu not_active IP Right Cessation
-
1985
- 1985-06-27 SG SG511/85A patent/SG51185G/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |