NO132989B - - Google Patents
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- Publication number
- NO132989B NO132989B NO980/71A NO98071A NO132989B NO 132989 B NO132989 B NO 132989B NO 980/71 A NO980/71 A NO 980/71A NO 98071 A NO98071 A NO 98071A NO 132989 B NO132989 B NO 132989B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- compound
- acid
- compounds
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- -1 cyano, carbamoyl Chemical group 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 210000004209 hair Anatomy 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- 206010003246 arthritis Diseases 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- OYZNWOYTLBHRSA-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(Cl)C=C1 OYZNWOYTLBHRSA-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XYOCCJDQAKGZCD-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(F)C=C1 XYOCCJDQAKGZCD-UHFFFAOYSA-N 0.000 description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YFVOFFKNHQTQQE-UHFFFAOYSA-N 1-(4-bromo-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C([N+]([O-])=O)=C1 YFVOFFKNHQTQQE-UHFFFAOYSA-N 0.000 description 2
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 2
- GBSUBBOECZHZBD-UHFFFAOYSA-N 3-ethoxy-2-[4-(4-fluorophenoxy)phenyl]-2-methyl-3-oxopropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C(=O)OCC)=CC=C1OC1=CC=C(F)C=C1 GBSUBBOECZHZBD-UHFFFAOYSA-N 0.000 description 2
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GNIZAEYOWHQLKF-UHFFFAOYSA-N 1-[3-amino-4-(4-fluorophenoxy)phenyl]ethanone Chemical compound NC1=CC(C(=O)C)=CC=C1OC1=CC=C(F)C=C1 GNIZAEYOWHQLKF-UHFFFAOYSA-N 0.000 description 1
- QAXHXNYRVSPOEJ-UHFFFAOYSA-N 1-[3-chloro-4-(4-fluorophenoxy)phenyl]ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1OC1=CC=C(F)C=C1 QAXHXNYRVSPOEJ-UHFFFAOYSA-N 0.000 description 1
- KLQBBOAJYBGKHM-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=C(Cl)C=C1 KLQBBOAJYBGKHM-UHFFFAOYSA-N 0.000 description 1
- HXFDKYCCCPFDSF-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)-3-nitrophenyl]ethanone Chemical compound [O-][N+](=O)C1=CC(C(=O)C)=CC=C1OC1=CC=C(F)C=C1 HXFDKYCCCPFDSF-UHFFFAOYSA-N 0.000 description 1
- NVWVWEWVLBKPSM-UHFFFAOYSA-N 2,4-difluorophenol Chemical compound OC1=CC=C(F)C=C1F NVWVWEWVLBKPSM-UHFFFAOYSA-N 0.000 description 1
- UHFQWDFIFPURHI-UHFFFAOYSA-N 2-[3-chloro-4-(4-fluorophenoxy)phenyl]-3-ethoxy-2-methyl-3-oxopropanoic acid Chemical compound CCOC(=O)C(C)(C1=CC(=C(C=C1)OC2=CC=C(C=C2)F)Cl)C(=O)O UHFQWDFIFPURHI-UHFFFAOYSA-N 0.000 description 1
- QODCOZLKTXFAAT-UHFFFAOYSA-N 2-[3-chloro-4-(4-fluorophenoxy)phenyl]propanoic acid Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(F)C=C1 QODCOZLKTXFAAT-UHFFFAOYSA-N 0.000 description 1
- OJDHMLBZLAWEKS-UHFFFAOYSA-N 2-[4-(2,4-difluorophenoxy)phenyl]propanamide Chemical compound C1=CC(C(C(N)=O)C)=CC=C1OC1=CC=C(F)C=C1F OJDHMLBZLAWEKS-UHFFFAOYSA-N 0.000 description 1
- PLZSRQWNBANPAL-UHFFFAOYSA-N 2-[4-(2,4-difluorophenoxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(F)C=C1F PLZSRQWNBANPAL-UHFFFAOYSA-N 0.000 description 1
- ZAEBZFDADJZUIH-UHFFFAOYSA-N 2-[4-(4-chloro-2-fluorophenoxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(Cl)C=C1F ZAEBZFDADJZUIH-UHFFFAOYSA-N 0.000 description 1
- VZDYFOVBQBKBDC-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-3-ethoxy-2-methyl-3-oxopropanoic acid Chemical compound CCOC(=O)C(C)(C1=CC=C(C=C1)OC2=CC=C(C=C2)Cl)C(=O)O VZDYFOVBQBKBDC-UHFFFAOYSA-N 0.000 description 1
- JEWMYTWSCLIAMM-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-2-methylpropanedioic acid Chemical compound C1=CC(C(C(O)=O)(C(O)=O)C)=CC=C1OC1=CC=C(F)C=C1 JEWMYTWSCLIAMM-UHFFFAOYSA-N 0.000 description 1
- VMMSFFIABDLZIP-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC1=CC=C(F)C=C1 VMMSFFIABDLZIP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MJXXROBCOJLPMM-UHFFFAOYSA-N ethyl 2-[4-(4-chlorophenoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 MJXXROBCOJLPMM-UHFFFAOYSA-N 0.000 description 1
- LHQPIHZJRIQDIZ-UHFFFAOYSA-N ethyl 2-[4-(4-fluorophenoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(F)C=C1 LHQPIHZJRIQDIZ-UHFFFAOYSA-N 0.000 description 1
- ROVVUKNBYULXFJ-UHFFFAOYSA-N ethyl 2-[4-(4-fluorophenoxy)phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1OC1=CC=C(F)C=C1 ROVVUKNBYULXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000001047 pyretic effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1257070 | 1970-03-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132989B true NO132989B (cs) | 1975-11-10 |
| NO132989C NO132989C (cs) | 1976-02-18 |
Family
ID=10007088
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO71980A NO132989C (cs) | 1970-03-16 | 1971-03-15 | |
| NO71981A NO131507C (cs) | 1970-03-16 | 1971-03-15 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO71981A NO131507C (cs) | 1970-03-16 | 1971-03-15 |
Country Status (18)
| Country | Link |
|---|---|
| AT (4) | AT318577B (cs) |
| BE (2) | BE764257A (cs) |
| CA (2) | CA925520A (cs) |
| CH (2) | CH532010A (cs) |
| CS (4) | CS169813B2 (cs) |
| DE (2) | DE2112322A1 (cs) |
| DK (1) | DK139673B (cs) |
| ES (4) | ES389252A1 (cs) |
| FR (2) | FR2085712B1 (cs) |
| GB (1) | GB1307284A (cs) |
| IE (2) | IE35234B1 (cs) |
| IL (2) | IL36394A (cs) |
| NL (2) | NL7103404A (cs) |
| NO (2) | NO132989C (cs) |
| PL (4) | PL94403B1 (cs) |
| RO (4) | RO61058A (cs) |
| SE (2) | SE366732B (cs) |
| ZA (2) | ZA711644B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2837525A1 (de) * | 1978-08-28 | 1980-03-20 | Bayer Ag | Verfahren zur herstellung von 4- fluoro-3-phenoxy-toluol |
| SE8400239D0 (sv) * | 1984-01-19 | 1984-01-19 | Pharmacia Ab | Nya arylettiksyraderivat |
| WO1989006227A1 (en) * | 1987-12-28 | 1989-07-13 | The Dow Chemical Company | Phenoxyphenoxypropionates, intermediates thereof and methods of preparation |
| ES2163986B1 (es) * | 1999-07-13 | 2003-02-16 | Menarini Lab | Acidos-alfa-arilpropionicos y arilaceticos como inhibidores de la ciclooxigenasa-ii. |
| FR2862964B1 (fr) * | 2003-11-27 | 2006-12-29 | Merck Sante Sas | Derives de la diphenylamine. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE363818B (cs) * | 1968-08-15 | 1974-02-04 | Lilly Co Eli |
-
1970
- 1970-03-16 GB GB1257070A patent/GB1307284A/en not_active Expired
-
1971
- 1971-03-04 CA CA106861A patent/CA925520A/en not_active Expired
- 1971-03-04 CA CA106862A patent/CA925878A/en not_active Expired
- 1971-03-05 NL NL7103404A patent/NL7103404A/xx not_active Application Discontinuation
- 1971-03-10 IE IE302/71A patent/IE35234B1/xx unknown
- 1971-03-10 IE IE301/71A patent/IE35109B1/xx unknown
- 1971-03-11 IL IL36394A patent/IL36394A/en unknown
- 1971-03-11 IL IL36395A patent/IL36395A/xx unknown
- 1971-03-12 ZA ZA711644A patent/ZA711644B/xx unknown
- 1971-03-12 ZA ZA711643A patent/ZA711643B/xx unknown
- 1971-03-15 DK DK120971AA patent/DK139673B/da unknown
- 1971-03-15 FR FR7108942A patent/FR2085712B1/fr not_active Expired
- 1971-03-15 NO NO71980A patent/NO132989C/no unknown
- 1971-03-15 SE SE03327/71A patent/SE366732B/xx unknown
- 1971-03-15 PL PL1971182996A patent/PL94403B1/pl unknown
- 1971-03-15 ES ES389252A patent/ES389252A1/es not_active Expired
- 1971-03-15 NL NL7103403A patent/NL7103403A/xx unknown
- 1971-03-15 BE BE764257A patent/BE764257A/xx unknown
- 1971-03-15 CS CS1864A patent/CS169813B2/cs unknown
- 1971-03-15 FR FR7108943A patent/FR2085713B1/fr not_active Expired
- 1971-03-15 SE SE03328/71A patent/SE366733B/xx unknown
- 1971-03-15 PL PL1971146906A patent/PL72430B1/pl unknown
- 1971-03-15 BE BE764258A patent/BE764258A/xx unknown
- 1971-03-15 PL PL1971146901A patent/PL70292B1/pl unknown
- 1971-03-15 CS CS3910*A patent/CS170543B2/cs unknown
- 1971-03-15 NO NO71981A patent/NO131507C/no unknown
- 1971-03-15 CS CS6523*A patent/CS169814B2/cs unknown
- 1971-03-15 ES ES389253A patent/ES389253A1/es not_active Expired
- 1971-03-15 PL PL1971182995A patent/PL94402B1/pl unknown
- 1971-03-15 DE DE19712112322 patent/DE2112322A1/de active Pending
- 1971-03-15 DE DE19712112323 patent/DE2112323A1/de active Pending
- 1971-03-15 CS CS1863A patent/CS170542B2/cs unknown
- 1971-03-16 RO RO66285A patent/RO61058A/ro unknown
- 1971-03-16 AT AT1065472A patent/AT318577B/de not_active IP Right Cessation
- 1971-03-16 CH CH378771A patent/CH532010A/fr not_active IP Right Cessation
- 1971-03-16 AT AT226971A patent/AT318574B/de active
- 1971-03-16 RO RO68711A patent/RO61065A/ro unknown
- 1971-03-16 AT AT227071A patent/AT318575B/de active
- 1971-03-16 RO RO68712A patent/RO62254A/ro unknown
- 1971-03-16 CH CH378871A patent/CH530363A/fr not_active IP Right Cessation
- 1971-03-16 RO RO66280A patent/RO61093A/ro unknown
- 1971-03-16 AT AT1065372A patent/AT318576B/de not_active IP Right Cessation
-
1972
- 1972-01-12 ES ES398802A patent/ES398802A1/es not_active Expired
- 1972-01-12 ES ES398803A patent/ES398803A1/es not_active Expired
Also Published As
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