NO833092L - Fremgangsmaate for fremstilling av arachidonsyre-analoger med anti-inflammatorisk og anti-allergisk aktivitet - Google Patents
Fremgangsmaate for fremstilling av arachidonsyre-analoger med anti-inflammatorisk og anti-allergisk aktivitetInfo
- Publication number
- NO833092L NO833092L NO833092A NO833092A NO833092L NO 833092 L NO833092 L NO 833092L NO 833092 A NO833092 A NO 833092A NO 833092 A NO833092 A NO 833092A NO 833092 L NO833092 L NO 833092L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- compound
- eicosa
- formula
- hydroxylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 title description 17
- 230000003266 anti-allergic effect Effects 0.000 title description 2
- 230000003110 anti-inflammatory effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 87
- 229910052799 carbon Inorganic materials 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 66
- 238000002360 preparation method Methods 0.000 claims description 46
- -1 1-H-tetrazole compound Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 24
- 231100000252 nontoxic Toxicity 0.000 claims description 14
- 230000003000 nontoxic effect Effects 0.000 claims description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 150000002825 nitriles Chemical group 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical group [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 2
- ADEFMCVVKBCPRI-UHFFFAOYSA-N n-hydroxydocosa-5,8,11,14-tetraynamide Chemical compound CCCCCCCC#CCC#CCC#CCC#CCCCC(=O)NO ADEFMCVVKBCPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 208000035196 congenital hypomyelinating 2 neuropathy Diseases 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 39
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000003960 organic solvent Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000003536 tetrazoles Chemical class 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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- 229940114079 arachidonic acid Drugs 0.000 description 8
- 235000021342 arachidonic acid Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
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- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 108090000128 Lipoxygenases Proteins 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
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- 239000000047 product Substances 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
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- 239000007788 liquid Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 229910002027 silica gel Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 5
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- 125000005907 alkyl ester group Chemical group 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- UEJNSDDZSLEWPA-UHFFFAOYSA-N henicosa-5,8,11,14-tetraynoic acid Chemical compound CCCCCCC#CCC#CCC#CCC#CCCCC(O)=O UEJNSDDZSLEWPA-UHFFFAOYSA-N 0.000 description 4
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- 238000011534 incubation Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 150000002617 leukotrienes Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 210000004623 platelet-rich plasma Anatomy 0.000 description 4
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- 239000000829 suppository Substances 0.000 description 4
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 238000004090 dissolution Methods 0.000 description 1
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- 150000004668 long chain fatty acids Chemical class 0.000 description 1
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- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
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- MZDAJXUFNLJJHZ-UHFFFAOYSA-N n-hydroxydocosa-4,7,10,13-tetraynamide Chemical compound CCCCCCCCC#CCC#CCC#CCC#CCCC(=O)NO MZDAJXUFNLJJHZ-UHFFFAOYSA-N 0.000 description 1
- URADWRHWKKSUBD-UHFFFAOYSA-N n-hydroxydocosa-7,10,13,16-tetraynamide Chemical compound CCCCCC#CCC#CCC#CCC#CCCCCCC(=O)NO URADWRHWKKSUBD-UHFFFAOYSA-N 0.000 description 1
- HVQRSZNMPFQAMF-UHFFFAOYSA-N n-hydroxynonadeca-5,8,11,14-tetraynamide Chemical compound CCCCC#CCC#CCC#CCC#CCCCC(=O)NO HVQRSZNMPFQAMF-UHFFFAOYSA-N 0.000 description 1
- RSGAYCJJMINBGQ-UHFFFAOYSA-N n-hydroxynonadeca-8,11,14-triynamide Chemical compound CCCCC#CCC#CCC#CCCCCCCC(=O)NO RSGAYCJJMINBGQ-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- KRBPLTWIUFFEMM-UHFFFAOYSA-N nonadeca-3,6,9,12-tetraynoic acid Chemical compound CCCCCCC#CCC#CCC#CCC#CCC(O)=O KRBPLTWIUFFEMM-UHFFFAOYSA-N 0.000 description 1
- NIZLDBUNROLUSY-UHFFFAOYSA-N octadeca-4,7,10,13-tetraynoic acid Chemical compound CCCCC#CCC#CCC#CCC#CCCC(O)=O NIZLDBUNROLUSY-UHFFFAOYSA-N 0.000 description 1
- DGWUMEQJYAUDBT-UHFFFAOYSA-N octadeca-7,10,13-trienoic acid Chemical compound CCCCC=CCC=CCC=CCCCCCC(O)=O DGWUMEQJYAUDBT-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
- 230000003287 optical effect Effects 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 230000037361 pathway Effects 0.000 description 1
- MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960000580 terconazole Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/048—Acyclic alcohols with carbon-to-carbon triple bonds with double and triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/18—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/412,477 US4497827A (en) | 1982-08-30 | 1982-08-30 | Arachidonic acid analogues as anti-inflammatory and anti-allergic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO833092L true NO833092L (no) | 1984-03-01 |
Family
ID=23633154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO833092A NO833092L (no) | 1982-08-30 | 1983-08-29 | Fremgangsmaate for fremstilling av arachidonsyre-analoger med anti-inflammatorisk og anti-allergisk aktivitet |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4497827A (fr) |
| EP (1) | EP0104468B1 (fr) |
| JP (1) | JPS5965036A (fr) |
| KR (1) | KR840005722A (fr) |
| AT (1) | ATE20885T1 (fr) |
| AU (1) | AU1852083A (fr) |
| CA (1) | CA1209578A (fr) |
| DE (1) | DE3364718D1 (fr) |
| DK (1) | DK393583A (fr) |
| ES (4) | ES8603807A1 (fr) |
| FI (1) | FI833062A (fr) |
| IE (1) | IE55902B1 (fr) |
| NO (1) | NO833092L (fr) |
| NZ (1) | NZ205403A (fr) |
| ZA (1) | ZA836395B (fr) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604407A (en) * | 1985-04-04 | 1986-08-05 | E. R. Squibb & Sons, Inc. | Hydroxamates |
| DE3518655A1 (de) * | 1985-05-24 | 1986-11-27 | Grünenthal GmbH, 5190 Stolberg | Neue phenolderivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel |
| FR2584400B1 (fr) * | 1985-07-05 | 1988-02-19 | Cird | Esters et amides de l'acide eicosatriynoique et leur application en pharmacie et en cosmetique |
| DE3604050A1 (de) * | 1986-02-08 | 1987-08-13 | Boehringer Mannheim Gmbh | Thioether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| US4761403A (en) * | 1986-04-09 | 1988-08-02 | Abbott Laboratories | Lipoxygenase inhibiting compounds |
| US4707494A (en) * | 1986-08-26 | 1987-11-17 | E. R. Squibb & Sons, Inc. | 7-oxabicyclo(2.2.1)heptane compounds useful in the treatment of inflammation |
| US4672075A (en) * | 1986-08-26 | 1987-06-09 | E. R. Squibb & Sons | 7-Oxabicyclo(2.2.1)heptane hydroxamic acid derivatives useful as antiinflammatory, antiasthma and antipsoriatic agents |
| US4908384A (en) * | 1986-08-29 | 1990-03-13 | Mcneilab, Inc. | Fatty acid leukotriene synthesis inhibitors |
| FR2609026B1 (fr) * | 1986-12-31 | 1989-03-31 | Cird | Amides de l'acide eicosatetraynoique et leur application en pharmacie et en cosmetique |
| US5145861A (en) * | 1987-11-04 | 1992-09-08 | Merrell Dow Pharmaceuticals Inc. | Fluorinated arachidonic acid derivatives |
| US4963541A (en) * | 1989-02-22 | 1990-10-16 | Abbott Laboratories | Pyrimido-pyrimidine lipoxygenase inhibiting compounds |
| US5225429A (en) * | 1989-05-02 | 1993-07-06 | Merrell Dow Pharmaceuticals Inc. | Fluorinated arachidonic acid derivatives |
| ATE101114T1 (de) * | 1989-05-02 | 1994-02-15 | Merrell Dow Pharma | Flourierte abkoemmlinge von archidsaeuren. |
| WO1999057106A1 (fr) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Nouveaux cannabinoides analgesiques et immunomodulateurs |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| IL125731A (en) | 1998-08-11 | 2004-06-20 | Zvi Yehuda | Acylates which are products of neurotransmitters and essential fatty acids, pharmaceutical compositions containing them, use of such acylates in the manufacture of medicaments, and method for treating nervous diseases in non-human animals |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| CA2387764A1 (fr) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Ligands selectifs de recepteurs (cb2) de cannabinoides peripheriques |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6943266B1 (en) | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| JP2004532185A (ja) * | 2001-01-26 | 2004-10-21 | ユニバーシティ オブ コネチカット | 新規なカンナビミメティックリガンド |
| CA2436133A1 (fr) | 2001-01-29 | 2002-08-08 | University Of Connecticut | Aminoalkylindoles cannabimimetiques selectifs d'un recepteur |
| US7057076B2 (en) * | 2001-07-13 | 2006-06-06 | University Of Connecticut | Bicyclic and tricyclic cannabinoids |
| EP1448557A4 (fr) * | 2001-10-26 | 2005-02-02 | Univ Connecticut | Heteroindanes: nouvelle classe de ligands cannabimimetiques efficaces |
| CA2496097A1 (fr) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Ceto-cannabinoides possedant des indications therapeutiques |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE319677B (fr) * | 1965-03-27 | 1970-01-19 | Sumitomo Chemical Co | |
| GB1074693A (en) * | 1966-01-03 | 1967-07-05 | Sumitomo Chemical Co | Purification of fatty acid amide derivatives |
| US3427316A (en) * | 1966-05-02 | 1969-02-11 | Millmaster Onyx Corp | Quaternary ammonium hydroxamates |
| US3995059A (en) * | 1966-10-04 | 1976-11-30 | Sumitomo Chemical Company, Limited | Pharmaceutical compositions containing fatty acid amide derivatives |
| FR2140369A1 (en) * | 1971-06-11 | 1973-01-19 | Ceskoslovenska Akademie Ved | Ethanol palmitamide - for treatment of upper respiratory infections and for detoxication |
| BE788209A (fr) * | 1971-09-01 | 1973-02-28 | Pfizer | Derives tetrazoyliques des prostaglandines naturelles |
| NL7208324A (en) * | 1972-06-19 | 1973-12-21 | Animal feed supplement - consisting of long chain acylhydroxyamide | |
| DE2256347C3 (de) * | 1972-11-17 | 1982-01-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von α,β -ungestättigten Ketonen |
| DE2343055A1 (de) * | 1973-08-25 | 1975-03-06 | Basf Ag | Ungesaettigte nitrile |
| FR2264522A1 (en) * | 1974-03-22 | 1975-10-17 | Rouchy Maurice | Vitamin F cpds having surface active properties - comprise linoleic, linolenic and arachidonic acid radical joined via O or N to polyalcohols |
| JPS601283B2 (ja) * | 1976-06-08 | 1985-01-14 | 帝人株式会社 | 包接化合物並びにその製造法 |
| NL7614113A (nl) * | 1976-12-18 | 1978-06-20 | Akzo Nv | Hydroxamzuren. |
| US4336372A (en) * | 1979-04-02 | 1982-06-22 | The Upjohn Company | 2-Decarboxy-2-tetrazolyl-PG2 compounds |
| US4277410A (en) * | 1980-05-02 | 1981-07-07 | Emery Industries, Inc. | Process for the production of carboxylic amides using alkyltin catalysts |
-
1982
- 1982-08-30 US US06/412,477 patent/US4497827A/en not_active Expired - Fee Related
-
1983
- 1983-08-29 IE IE2016/83A patent/IE55902B1/xx unknown
- 1983-08-29 ES ES525219A patent/ES8603807A1/es not_active Expired
- 1983-08-29 FI FI833062A patent/FI833062A/fi not_active Application Discontinuation
- 1983-08-29 AU AU18520/83A patent/AU1852083A/en not_active Abandoned
- 1983-08-29 JP JP58156560A patent/JPS5965036A/ja active Pending
- 1983-08-29 KR KR1019830004026A patent/KR840005722A/ko not_active Application Discontinuation
- 1983-08-29 DK DK393583A patent/DK393583A/da not_active Application Discontinuation
- 1983-08-29 DE DE8383108499T patent/DE3364718D1/de not_active Expired
- 1983-08-29 ZA ZA836395A patent/ZA836395B/xx unknown
- 1983-08-29 NZ NZ205403A patent/NZ205403A/en unknown
- 1983-08-29 NO NO833092A patent/NO833092L/no unknown
- 1983-08-29 CA CA000435535A patent/CA1209578A/fr not_active Expired
- 1983-08-29 AT AT83108499T patent/ATE20885T1/de active
- 1983-08-29 EP EP83108499A patent/EP0104468B1/fr not_active Expired
-
1985
- 1985-03-01 ES ES540854A patent/ES8704878A1/es not_active Expired
- 1985-03-01 ES ES540853A patent/ES8606235A1/es not_active Expired
- 1985-03-01 ES ES540855A patent/ES8607955A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES525219A0 (es) | 1986-01-16 |
| FI833062A0 (fi) | 1983-08-29 |
| ZA836395B (en) | 1985-04-24 |
| JPS5965036A (ja) | 1984-04-13 |
| ES8606235A1 (es) | 1986-04-16 |
| DK393583D0 (da) | 1983-08-29 |
| ES8704878A1 (es) | 1987-05-01 |
| IE55902B1 (en) | 1991-02-14 |
| NZ205403A (en) | 1986-10-08 |
| ES540855A0 (es) | 1986-06-16 |
| DE3364718D1 (en) | 1986-08-28 |
| EP0104468B1 (fr) | 1986-07-23 |
| EP0104468A1 (fr) | 1984-04-04 |
| AU1852083A (en) | 1984-03-08 |
| DK393583A (da) | 1984-03-01 |
| KR840005722A (ko) | 1984-11-16 |
| ES540854A0 (es) | 1987-05-01 |
| ES540853A0 (es) | 1986-04-16 |
| ES8607955A1 (es) | 1986-06-16 |
| ES8603807A1 (es) | 1986-01-16 |
| US4497827A (en) | 1985-02-05 |
| ATE20885T1 (de) | 1986-08-15 |
| CA1209578A (fr) | 1986-08-12 |
| IE832016L (en) | 1984-02-29 |
| FI833062A (fi) | 1984-03-01 |
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