NL8005876A - Alkylfenyl-5z,8z,11z,14z,17z-eicosapentaenoaten en geneesmiddelen, die deze verbindingen als actief bestanddeel bevatten. - Google Patents
Alkylfenyl-5z,8z,11z,14z,17z-eicosapentaenoaten en geneesmiddelen, die deze verbindingen als actief bestanddeel bevatten. Download PDFInfo
- Publication number
- NL8005876A NL8005876A NL8005876A NL8005876A NL8005876A NL 8005876 A NL8005876 A NL 8005876A NL 8005876 A NL8005876 A NL 8005876A NL 8005876 A NL8005876 A NL 8005876A NL 8005876 A NL8005876 A NL 8005876A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- parts
- methyl
- compound
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 33
- 239000004480 active ingredient Substances 0.000 title claims description 4
- 229940126601 medicinal product Drugs 0.000 title 1
- 229940066279 eicosapentaenoate Drugs 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- -1 1- (1,1-dimethylethyl) phenyl Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000001262 anti-secretory effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229940127218 antiplatelet drug Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- SBHCLVQMTBWHCD-YECCEMIOSA-N (2z)-icosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCC=CC=CC=CC=C\C=C/C(O)=O SBHCLVQMTBWHCD-YECCEMIOSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 150000007930 O-acyl isoureas Chemical class 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- STXYWYJRHVLJET-UHFFFAOYSA-N [Se]=[SeH2](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Se]=[SeH2](C1=CC=CC=C1)C1=CC=CC=C1 STXYWYJRHVLJET-UHFFFAOYSA-N 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 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
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/088,502 US4264517A (en) | 1978-12-11 | 1979-10-26 | Alkylphenyl 5Z,8Z,11Z,14Z,17Z-eicosapentaenoates |
| US8850279 | 1979-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8005876A true NL8005876A (nl) | 1981-04-28 |
Family
ID=22211743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8005876A NL8005876A (nl) | 1979-10-26 | 1980-10-24 | Alkylfenyl-5z,8z,11z,14z,17z-eicosapentaenoaten en geneesmiddelen, die deze verbindingen als actief bestanddeel bevatten. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4264517A (es) |
| JP (1) | JPS5686134A (es) |
| BE (1) | BE885890A (es) |
| CA (1) | CA1140576A (es) |
| DE (1) | DE3039960A1 (es) |
| DK (1) | DK452380A (es) |
| ES (3) | ES8202781A1 (es) |
| FR (1) | FR2468577A1 (es) |
| GB (1) | GB2061277B (es) |
| IT (1) | IT1133047B (es) |
| NL (1) | NL8005876A (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4576758A (en) * | 1984-06-01 | 1986-03-18 | The Upjohn Company | Anti-inflammatory lipoxin B analogs |
| JP2008540394A (ja) | 2005-05-04 | 2008-11-20 | プロノヴァ バイオファーマ ノルゲ アクティーゼルスカブ | 脂肪酸組成物、即ち、ｄｈａ誘導体の医薬としての使用 |
| GB0605900D0 (en) * | 2006-03-23 | 2006-05-03 | Lipigen As | Modulators of nuclear receptors |
| RU2507193C2 (ru) * | 2006-11-01 | 2014-02-20 | Пронова Биофарма Норге А/С | Альфа-замещенные омега-3 липиды, которые являются активаторами или модуляторами рецептора, активируемого пролифераторами пероксисом (ppar) |
| CN101631757A (zh) * | 2006-11-01 | 2010-01-20 | 普罗诺瓦生物医药挪威公司 | ω-3脂质化合物 |
| MX2009004336A (es) * | 2006-11-01 | 2009-05-22 | Pronova Biopharma Norge As | Lipidos omega-3 alfa-sustituidos que son activadores o moduladores del receptor activado por proliferadores de peroxisoma (ppar). |
| EP2102139A2 (en) * | 2006-11-01 | 2009-09-23 | Pronova Biopharma Norge AS | Omega-3 lipid compounds |
| US20100267828A1 (en) * | 2007-10-31 | 2010-10-21 | Anne Kristin Holmeide | dha derivatives and their use as medicaments |
| US8108517B2 (en) * | 2007-11-27 | 2012-01-31 | Umber Systems | System and method for collecting, reporting and analyzing data on application-level activity and other user information on a mobile data network |
| US9085527B2 (en) | 2008-07-08 | 2015-07-21 | Catabasis Pharmaceuticals, Inc. | Fatty acid acylated salicylates and their uses |
| PL2315740T3 (pl) | 2008-07-08 | 2018-05-30 | Catabasis Pharmaceuticals, Inc. | Salicylany acetylowane kwasem tłuszczowym i ich zastosowania |
| BR112012004677A2 (pt) | 2009-09-01 | 2020-11-03 | Catabasis Pharmaceuticals, Inc. | conjugados de ácido graxo niacina e seus usos |
| USRE46608E1 (en) | 2009-09-01 | 2017-11-14 | Catabasis Pharmaceuticals, Inc. | Fatty acid niacin conjugates and their uses |
| US20130046013A1 (en) * | 2010-01-20 | 2013-02-21 | Ragnar Hovland | Salicylate fatty acid derivatives |
| CN114853627B (zh) * | 2022-04-26 | 2023-06-20 | 自然资源部第三海洋研究所 | 一种取代苯甲酸二十二碳六烯酰胺乙基酯衍生物及其制备方法与应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181670A (en) * | 1978-12-11 | 1980-01-01 | G. D. Searle & Co. | Phenyl 5Z,8Z,11Z,14Z-eicosatetraenoate and congeners |
-
1979
- 1979-10-26 US US06/088,502 patent/US4264517A/en not_active Expired - Lifetime
-
1980
- 1980-10-23 DE DE19803039960 patent/DE3039960A1/de not_active Withdrawn
- 1980-10-24 FR FR8022869A patent/FR2468577A1/fr not_active Withdrawn
- 1980-10-24 ES ES496248A patent/ES8202781A1/es not_active Expired
- 1980-10-24 DK DK452380A patent/DK452380A/da not_active Application Discontinuation
- 1980-10-24 NL NL8005876A patent/NL8005876A/nl not_active Application Discontinuation
- 1980-10-24 GB GB8034380A patent/GB2061277B/en not_active Expired
- 1980-10-27 BE BE0/202604A patent/BE885890A/fr unknown
- 1980-10-27 IT IT50013/80A patent/IT1133047B/it active
- 1980-10-27 CA CA000363359A patent/CA1140576A/en not_active Expired
- 1980-10-27 JP JP15057880A patent/JPS5686134A/ja active Pending
-
1981
- 1981-11-13 ES ES507122A patent/ES8206429A1/es not_active Expired
- 1981-11-13 ES ES507123A patent/ES8206430A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES507122A0 (es) | 1982-08-16 |
| ES8206429A1 (es) | 1982-08-16 |
| DE3039960A1 (de) | 1981-05-07 |
| CA1140576A (en) | 1983-02-01 |
| BE885890A (fr) | 1981-04-27 |
| FR2468577A1 (fr) | 1981-05-08 |
| ES507123A0 (es) | 1982-08-16 |
| ES8206430A1 (es) | 1982-08-16 |
| IT1133047B (it) | 1986-07-09 |
| ES496248A0 (es) | 1982-02-16 |
| JPS5686134A (en) | 1981-07-13 |
| ES8202781A1 (es) | 1982-02-16 |
| GB2061277B (en) | 1983-11-16 |
| US4264517A (en) | 1981-04-28 |
| DK452380A (da) | 1981-04-27 |
| IT8050013A0 (it) | 1980-10-27 |
| GB2061277A (en) | 1981-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8005876A (nl) | Alkylfenyl-5z,8z,11z,14z,17z-eicosapentaenoaten en geneesmiddelen, die deze verbindingen als actief bestanddeel bevatten. | |
| EP0098591B1 (de) | Neue heterocyclische Verbindungen und diese enthaltende Rodentizide | |
| WO2003051820A1 (de) | Verfahren zur herstellung von 2-halogenacyl-3-amino-acrylsäure- derivaten | |
| EP0568898A1 (de) | Benzothiepin-, Benzothiopyran- und Benzothiophenderivate, deren Herstellung und Verwendung als Heilmittel | |
| CH624936A5 (es) | ||
| EP0176035B1 (de) | 1-substituierte Tetralinderivate, ihre Herstellung und Verwendung | |
| EP0496238A1 (de) | Substituierte Benzoxazepine und Benzthiazepine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln | |
| DE2814321A1 (de) | Interphenylen-8-aza-9-dioxothia- 11,12-secoprostaglandine | |
| DE2519480A1 (de) | Aryl-oxo-heptensaeuren | |
| US4027031A (en) | 2-Cyclopropanecarboxamido-S-halothiazole as anti-inflammatory agents | |
| Buckler et al. | Synthesis and antiinflammatory activity of some aryltetrazolylalkanoic acids | |
| US4181670A (en) | Phenyl 5Z,8Z,11Z,14Z-eicosatetraenoate and congeners | |
| EP0184981B1 (de) | Neue Pyrrolinone und deren Zwischenprodukte | |
| DE3302814C2 (es) | ||
| DE2633992C2 (es) | ||
| DE2449928A1 (de) | Verfahren zur herstellung neuer carbocyclischer verbindungen | |
| US3870751A (en) | Substituted phenyl acetic acids | |
| EP0109381B1 (de) | Thiophen-2-carbonsäurederivate und Verfahren zu deren Herstellung | |
| DE60204681T2 (de) | Verfahren zur herstellung von 2-[4-(2,2,-dihalocyclopropyl)phenoxy]-alkansäuren und ihre estern | |
| DE69021162T2 (de) | Substituierte Dibenzonfurane und ihre Verwendung. | |
| EP0056617B1 (de) | Cycloheptenderivate, Verfahren und Zwischenprodukte für ihre Herstellung, sowie diese enthaltende Arzneimittel | |
| EP0104483A2 (de) | Sulfamoylbenzophenon-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen | |
| US3642869A (en) | 5 8-dihydronaphthyloxy acetic acids | |
| DE2934398A1 (de) | Hydroxyalkansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen | |
| CH620893A5 (es) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |