NO874892L - Analogifremgangsmaate for fremstilling av terapeutisk aktive 3-(omega-(3,5-di-t-butyl-4-hydroxyfenyl)-alkanoyl)-pyrroler og deres deoxy-analoger. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive 3-(omega-(3,5-di-t-butyl-4-hydroxyfenyl)-alkanoyl)-pyrroler og deres deoxy-analoger.Info
- Publication number
- NO874892L NO874892L NO874892A NO874892A NO874892L NO 874892 L NO874892 L NO 874892L NO 874892 A NO874892 A NO 874892A NO 874892 A NO874892 A NO 874892A NO 874892 L NO874892 L NO 874892L
- Authority
- NO
- Norway
- Prior art keywords
- butyl
- pyrrole
- formula
- compound
- hydroxybenzoyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 110
- 238000002360 preparation method Methods 0.000 title claims description 62
- -1 3,5-DI-T-BUTYL-4-HYDROXYPHENYL Chemical class 0.000 title claims description 46
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 367
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000000460 chlorine Substances 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 52
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- 150000002431 hydrogen Chemical group 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- 230000002140 halogenating effect Effects 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 208000031225 myocardial ischemia Diseases 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 206010037660 Pyrexia Diseases 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000027950 fever generation Effects 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 5
- 230000036407 pain Effects 0.000 claims description 5
- 206010027654 Allergic conditions Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 206010031264 Osteonecrosis Diseases 0.000 claims 1
- 208000024884 ischemic bone disease Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 152
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000007858 starting material Substances 0.000 description 82
- 239000000243 solution Substances 0.000 description 74
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 238000012360 testing method Methods 0.000 description 65
- AZQAMZGMCZXTFA-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)-(1h-pyrrol-3-yl)methanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C2=CNC=C2)=C1 AZQAMZGMCZXTFA-UHFFFAOYSA-N 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 53
- 229910001868 water Inorganic materials 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 230000005764 inhibitory process Effects 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XQXORENQJNIVBQ-UHFFFAOYSA-N [4-(3,5-ditert-butyl-4-hydroxybenzoyl)-1h-pyrrol-2-yl] thiocyanate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C=2C=C(SC#N)NC=2)=C1 XQXORENQJNIVBQ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 21
- 210000000988 bone and bone Anatomy 0.000 description 21
- 241000700159 Rattus Species 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 18
- LDSGTEZWZAYGOW-UHFFFAOYSA-N (5-chloro-1h-pyrrol-3-yl)-(3,5-ditert-butyl-4-hydroxyphenyl)methanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C=2C=C(Cl)NC=2)=C1 LDSGTEZWZAYGOW-UHFFFAOYSA-N 0.000 description 17
- 150000003233 pyrroles Chemical class 0.000 description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 208000006386 Bone Resorption Diseases 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 15
- 239000011575 calcium Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- GOQZFAPMKZNPQM-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)-(2,4,5-trichloro-1h-pyrrol-3-yl)methanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C=2C(=C(Cl)NC=2Cl)Cl)=C1 GOQZFAPMKZNPQM-UHFFFAOYSA-N 0.000 description 14
- ADJZFLZPQWLUKH-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)-(5-methylsulfanyl-1h-pyrrol-3-yl)methanone Chemical compound N1C(SC)=CC(C(=O)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ADJZFLZPQWLUKH-UHFFFAOYSA-N 0.000 description 14
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
- 239000002609 medium Substances 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 14
- 230000024279 bone resorption Effects 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- VBUTUGMXCRBUJV-UHFFFAOYSA-N (1-benzylpyrrol-3-yl)-(3,5-ditert-butyl-4-hydroxyphenyl)methanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C2=CN(CC=3C=CC=CC=3)C=C2)=C1 VBUTUGMXCRBUJV-UHFFFAOYSA-N 0.000 description 11
- SJECIVUDRRWBPK-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)-(1-methylpyrrol-3-yl)methanone Chemical compound CN1C=CC(C(=O)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 SJECIVUDRRWBPK-UHFFFAOYSA-N 0.000 description 11
- XCSVMPPZPRTOMC-UHFFFAOYSA-N 2,6-ditert-butyl-4-(1h-pyrrol-3-ylmethyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC2=CNC=C2)=C1 XCSVMPPZPRTOMC-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 230000003110 anti-inflammatory effect Effects 0.000 description 10
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- 238000000338 in vitro Methods 0.000 description 10
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- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 238000010998 test method Methods 0.000 description 10
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- CIKDJALNJWPKQL-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)-(1-ethylpyrrol-3-yl)methanone Chemical compound CCN1C=CC(C(=O)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 CIKDJALNJWPKQL-UHFFFAOYSA-N 0.000 description 9
- WNKWMUVETZJDSH-UHFFFAOYSA-N [1-(benzenesulfonyl)pyrrol-3-yl]-(3,5-ditert-butyl-4-hydroxyphenyl)methanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)C2=CN(C=C2)S(=O)(=O)C=2C=CC=CC=2)=C1 WNKWMUVETZJDSH-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
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- 230000004054 inflammatory process Effects 0.000 description 9
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- 230000002269 spontaneous effect Effects 0.000 description 9
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 8
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 8
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- 239000001963 growth medium Substances 0.000 description 8
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- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 6
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- 206010011086 Coronary artery occlusion Diseases 0.000 description 6
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- 239000008346 aqueous phase Substances 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
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- 238000004587 chromatography analysis Methods 0.000 description 6
- 229960002390 flurbiprofen Drugs 0.000 description 6
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/936,551 US4833155A (en) | 1986-11-25 | 1986-11-25 | 3-(ω-(3,5,-di-t-butyl-4-hydroxyphenyl)-alkanoyl)pyrroles, and anti-inflammatory uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
NO874892D0 NO874892D0 (no) | 1987-11-24 |
NO874892L true NO874892L (no) | 1988-06-17 |
Family
ID=25468795
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO874892A NO874892L (no) | 1986-11-25 | 1987-11-24 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 3-(omega-(3,5-di-t-butyl-4-hydroxyfenyl)-alkanoyl)-pyrroler og deres deoxy-analoger. |
Country Status (13)
Country | Link |
---|---|
US (1) | US4833155A (fr) |
EP (1) | EP0269981A1 (fr) |
JP (1) | JPS63154658A (fr) |
KR (1) | KR880006191A (fr) |
AU (1) | AU8164287A (fr) |
DK (1) | DK617487A (fr) |
FI (1) | FI875184A (fr) |
HU (2) | HU201010B (fr) |
IL (1) | IL84577A0 (fr) |
NO (1) | NO874892L (fr) |
PH (1) | PH24245A (fr) |
PT (1) | PT86205B (fr) |
ZA (1) | ZA878812B (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5234937A (en) * | 1990-03-27 | 1993-08-10 | Warner-Lambert Company | 3,5-di-tertiary-butyl-4-hydroxphenyl oxazolyl methanones and related compounds as antiinflammatory agents |
US5086064A (en) * | 1990-03-27 | 1992-02-04 | Warner-Lambert Company | 3,5-di-tertiary-butyl-4-hydroxyphenyl thiazolyl, oxazolyl, and imidazolyl methanones and related compounds as antiinflammatory agents |
US5102897A (en) * | 1990-03-27 | 1992-04-07 | Warner-Lambert Company | 3,5-ditertiarybutyl-4-hydroxyphenyl, 1,3,4-thiadiazoles and oxadiazoles linked by carbon, oxygen, and sulfur residues |
US5234939A (en) * | 1990-03-27 | 1993-08-10 | Warner-Lambert Company | 3,5-di-tertiary-butyl-4-hydroxyphenyl imidazolyl methanones and related compounds as antiinflammatory agents |
FR2669029B1 (fr) * | 1990-11-14 | 1994-09-02 | Adir | Nouveaux derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
US5684204A (en) * | 1995-11-15 | 1997-11-04 | The Procter & Gamble Company | Sulfur containing di-tert-butylphenol compounds useful as anti-inflammatory agents |
MY128323A (en) * | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
AP1390A (en) * | 1996-11-27 | 2005-04-15 | Aventis Pharmaceuticals Products Inc | Pharmaceutical composition comprising a compound having anti-Xa activity and a platelet aggregation antagonist compound. |
US7479507B2 (en) * | 2003-01-14 | 2009-01-20 | Adam Heller | Anti-inflammatory substituted phenols and elastomeric compositions for oral delivery of drugs |
EP1582531A1 (fr) | 2004-03-24 | 2005-10-05 | Aventis Pharma S.A. | Procédé d'oxydation d'héparines non-fractionnées et la détection de la présence ou de l'absence de glycosérine dans l'héparine et les produits dérivés de l'héparine. |
EP2084142B1 (fr) | 2006-10-17 | 2016-03-23 | SI Group, Inc. | Produits de réaction hétérocycliques alkylés convenant comme anti-oxydants |
FR2934998B1 (fr) * | 2008-08-12 | 2010-09-03 | Robert Vachy | Nouveaux derives de glucopyranose, leur preparation et leurs applications biologiques |
BR112022000255A8 (pt) | 2019-07-09 | 2022-03-22 | Optimvia Llc | Métodos para sintetizar polissacarídeos anticoagulantes |
EP4182452A4 (fr) | 2020-07-14 | 2024-07-31 | Optimvia Llc | Procédés de synthèse de sulfate d'héparane non anticoagulant |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3644631A (en) * | 1969-05-13 | 1972-02-22 | Endo Lab | Therapeutic methods utilizing aryl pyrrol-3-yl ketones |
US4000160A (en) * | 1973-04-11 | 1976-12-28 | Sterling Drug Inc. | Pyrrolyl oxyphenyl ketones |
US4124725A (en) * | 1977-05-16 | 1978-11-07 | Riker Laboratories, Inc. | Anti-inflammatory method |
US4418074A (en) * | 1981-11-23 | 1983-11-29 | Riker Laboratories, Inc. | 2,6 Di(t-butyl)-4-(2'-pyrrol)-phenol and anti-inflammatory use thereof |
-
1986
- 1986-11-25 US US06/936,551 patent/US4833155A/en not_active Expired - Fee Related
-
1987
- 1987-11-24 JP JP62295916A patent/JPS63154658A/ja active Pending
- 1987-11-24 EP EP87117332A patent/EP0269981A1/fr not_active Withdrawn
- 1987-11-24 DK DK617487A patent/DK617487A/da not_active Application Discontinuation
- 1987-11-24 NO NO874892A patent/NO874892L/no unknown
- 1987-11-24 AU AU81642/87A patent/AU8164287A/en not_active Abandoned
- 1987-11-24 HU HU884130A patent/HU201010B/hu not_active IP Right Cessation
- 1987-11-24 FI FI875184A patent/FI875184A/fi not_active IP Right Cessation
- 1987-11-24 IL IL84577A patent/IL84577A0/xx unknown
- 1987-11-24 PT PT86205A patent/PT86205B/pt not_active IP Right Cessation
- 1987-11-24 HU HU875244A patent/HUT46303A/hu unknown
- 1987-11-24 ZA ZA878812A patent/ZA878812B/xx unknown
- 1987-11-24 PH PH36112A patent/PH24245A/en unknown
- 1987-11-24 KR KR870013217A patent/KR880006191A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
ZA878812B (en) | 1989-06-28 |
PT86205B (pt) | 1990-11-07 |
US4833155A (en) | 1989-05-23 |
DK617487A (da) | 1988-05-26 |
FI875184A (fi) | 1988-05-26 |
IL84577A0 (en) | 1988-04-29 |
KR880006191A (ko) | 1988-07-22 |
FI875184A0 (fi) | 1987-11-24 |
AU8164287A (en) | 1988-05-26 |
NO874892D0 (no) | 1987-11-24 |
PT86205A (en) | 1987-12-01 |
EP0269981A1 (fr) | 1988-06-08 |
HU201010B (en) | 1990-09-28 |
PH24245A (en) | 1990-05-04 |
HUT47904A (en) | 1989-04-28 |
JPS63154658A (ja) | 1988-06-27 |
DK617487D0 (da) | 1987-11-24 |
HUT46303A (en) | 1988-10-28 |
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