NO781127L - Nye 2,4,6-trisubstituerte-2,3-dihydro-benzofuranderivater, og fremgangsmaate til deres fremstilling - Google Patents
Nye 2,4,6-trisubstituerte-2,3-dihydro-benzofuranderivater, og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO781127L NO781127L NO781127A NO781127A NO781127L NO 781127 L NO781127 L NO 781127L NO 781127 A NO781127 A NO 781127A NO 781127 A NO781127 A NO 781127A NO 781127 L NO781127 L NO 781127L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- group
- dihydro
- alkoxy
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 65
- -1 2,4,6-trisubstituted-2,3-dihydrobenzofuran Chemical class 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- PTVRPORHQJWFJF-UHFFFAOYSA-N 6-methoxy-n,2-dimethyl-2,3-dihydro-1-benzofuran-4-amine Chemical compound CNC1=CC(OC)=CC2=C1CC(C)O2 PTVRPORHQJWFJF-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 88
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 29
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- JQDQRXJARTYHCG-UHFFFAOYSA-N 6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-amine Chemical compound NC1=CC(OC)=CC2=C1CC(C)O2 JQDQRXJARTYHCG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
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- 230000002829 reductive effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
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- 239000000047 product Substances 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 4
- 208000009386 Experimental Arthritis Diseases 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- DIPDXGIPAWMAJQ-UHFFFAOYSA-N 6-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC(OCC)=CC2=C1CC(C)O2 DIPDXGIPAWMAJQ-UHFFFAOYSA-N 0.000 description 3
- YVUFDCXTAJWMIP-UHFFFAOYSA-N 6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC(OC)=CC2=C1CC(C)O2 YVUFDCXTAJWMIP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001907 coumarones Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- IUZZEKOGLDLEEN-UHFFFAOYSA-N 4-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carboxylic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1CC(C)O2 IUZZEKOGLDLEEN-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical class OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- 206010003246 arthritis Diseases 0.000 description 2
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- 150000001540 azides Chemical class 0.000 description 2
- MWOYLWFXZPHYBG-UHFFFAOYSA-N benzyl n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)carbamate Chemical compound C=1C(OC)=CC=2OC(C)CC=2C=1NC(=O)OCC1=CC=CC=C1 MWOYLWFXZPHYBG-UHFFFAOYSA-N 0.000 description 2
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- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- OZVVMZQTRLNZEU-UHFFFAOYSA-N ethyl n-(4-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)carbamate Chemical compound COC1=CC(NC(=O)OCC)=CC2=C1CC(C)O2 OZVVMZQTRLNZEU-UHFFFAOYSA-N 0.000 description 2
- XVFADRNOAGELQG-UHFFFAOYSA-N ethyl n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)carbamate Chemical compound CCOC(=O)NC1=CC(OC)=CC2=C1CC(C)O2 XVFADRNOAGELQG-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- MOEZEUSSYUDLFZ-UHFFFAOYSA-N [2-methyl-4-(methylamino)-2,3-dihydro-1-benzofuran-6-yl] acetate Chemical compound CNC1=CC(OC(C)=O)=CC2=C1CC(C)O2 MOEZEUSSYUDLFZ-UHFFFAOYSA-N 0.000 description 1
- MDCFUPGKKXLJLH-UHFFFAOYSA-N [2-methyl-4-(methylamino)-2,3-dihydro-1-benzofuran-6-yl] acetate;hydrochloride Chemical compound Cl.CNC1=CC(OC(C)=O)=CC2=C1CC(C)O2 MDCFUPGKKXLJLH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011668 ascorbic acid Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical class OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 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
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- CABNHQVOPZJGOH-UHFFFAOYSA-N ethyl n-(6-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)carbamate Chemical compound CCOC(=O)NC1=CC(OCC)=CC2=C1CC(C)O2 CABNHQVOPZJGOH-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PNPJUFRRNVEKLR-UHFFFAOYSA-N methyl 2-but-2-enyl-3-hydroxy-5-methoxybenzoate Chemical class COC(=O)C1=CC(OC)=CC(O)=C1CC=CC PNPJUFRRNVEKLR-UHFFFAOYSA-N 0.000 description 1
- UCKQNVAODWYVBD-UHFFFAOYSA-N methyl 3-hydroxy-5-methoxy-2-prop-2-enylbenzoate Chemical compound COC(=O)C1=CC(OC)=CC(O)=C1CC=C UCKQNVAODWYVBD-UHFFFAOYSA-N 0.000 description 1
- HPGHTFOVECGGKH-UHFFFAOYSA-N methyl 3-hydroxy-5-methoxy-4-prop-2-enylbenzoate Chemical compound COC(=O)C1=CC(O)=C(CC=C)C(OC)=C1 HPGHTFOVECGGKH-UHFFFAOYSA-N 0.000 description 1
- MNWFENBPJIWZOZ-UHFFFAOYSA-N methyl 3-hydroxy-5-methoxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(OC)=C1 MNWFENBPJIWZOZ-UHFFFAOYSA-N 0.000 description 1
- BHURLNKHEWXKHQ-UHFFFAOYSA-N methyl 3-methoxy-5-prop-2-enoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC(OCC=C)=C1 BHURLNKHEWXKHQ-UHFFFAOYSA-N 0.000 description 1
- LJWBMZXBXNBREL-UHFFFAOYSA-N methyl 4-but-2-enyl-3-hydroxy-5-methoxybenzoate Chemical class COC(=O)C1=CC(O)=C(CC=CC)C(OC)=C1 LJWBMZXBXNBREL-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CLDXYHTTXGAWNQ-UHFFFAOYSA-N n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)-2-oxo-2-phenylethanesulfonamide Chemical compound C=1C(OC)=CC=2OC(C)CC=2C=1NS(=O)(=O)CC(=O)C1=CC=CC=C1 CLDXYHTTXGAWNQ-UHFFFAOYSA-N 0.000 description 1
- OQJAFPPAAKLOQU-UHFFFAOYSA-N n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)-n-methylpropanamide Chemical compound CCC(=O)N(C)C1=CC(OC)=CC2=C1CC(C)O2 OQJAFPPAAKLOQU-UHFFFAOYSA-N 0.000 description 1
- HKYQKAYHBARYQX-UHFFFAOYSA-N n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)acetamide Chemical compound CC(=O)NC1=CC(OC)=CC2=C1CC(C)O2 HKYQKAYHBARYQX-UHFFFAOYSA-N 0.000 description 1
- QHJGZXQZHKVNTR-UHFFFAOYSA-N n-acetyl-n-(6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-yl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC(OC)=CC2=C1CC(C)O2 QHJGZXQZHKVNTR-UHFFFAOYSA-N 0.000 description 1
- MDVUUNBSVLPMSY-UHFFFAOYSA-N n-ethyl-6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-4-amine Chemical compound CCNC1=CC(OC)=CC2=C1CC(C)O2 MDVUUNBSVLPMSY-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14242/77A GB1574959A (en) | 1977-04-05 | 1977-04-05 | Benzofuran derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781127L true NO781127L (no) | 1978-10-06 |
Family
ID=10037611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781127A NO781127L (no) | 1977-04-05 | 1978-03-31 | Nye 2,4,6-trisubstituerte-2,3-dihydro-benzofuranderivater, og fremgangsmaate til deres fremstilling |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS53124257A (nl) |
| AU (1) | AU513200B2 (nl) |
| BE (1) | BE865706A (nl) |
| DE (1) | DE2813895A1 (nl) |
| DK (1) | DK147878A (nl) |
| FI (1) | FI780908A (nl) |
| FR (1) | FR2386539A1 (nl) |
| GB (1) | GB1574959A (nl) |
| IL (1) | IL54244A0 (nl) |
| IT (1) | IT1158677B (nl) |
| LU (1) | LU79368A1 (nl) |
| NL (1) | NL7803610A (nl) |
| NO (1) | NO781127L (nl) |
| SE (1) | SE7803804L (nl) |
| ZA (1) | ZA781345B (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5636189B2 (ja) * | 2006-10-27 | 2014-12-03 | ライフ テクノロジーズ コーポレーション | 蛍光発生性ｐＨ感受性色素およびその使用方法 |
-
1977
- 1977-04-05 GB GB14242/77A patent/GB1574959A/en not_active Expired
-
1978
- 1978-03-06 AU AU33856/78A patent/AU513200B2/en not_active Expired
- 1978-03-07 ZA ZA00781345A patent/ZA781345B/xx unknown
- 1978-03-09 IL IL54244A patent/IL54244A0/xx unknown
- 1978-03-22 FI FI780908A patent/FI780908A/fi not_active Application Discontinuation
- 1978-03-30 IT IT21749/78A patent/IT1158677B/it active
- 1978-03-31 DE DE19782813895 patent/DE2813895A1/de not_active Withdrawn
- 1978-03-31 NO NO781127A patent/NO781127L/no unknown
- 1978-04-03 LU LU79368A patent/LU79368A1/xx unknown
- 1978-04-04 SE SE7803804A patent/SE7803804L/xx unknown
- 1978-04-04 JP JP3889178A patent/JPS53124257A/ja active Pending
- 1978-04-04 DK DK147878A patent/DK147878A/da not_active Application Discontinuation
- 1978-04-05 BE BE186578A patent/BE865706A/xx unknown
- 1978-04-05 NL NL7803610A patent/NL7803610A/nl not_active Application Discontinuation
- 1978-04-05 FR FR7810107A patent/FR2386539A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2386539A1 (fr) | 1978-11-03 |
| IT7821749A0 (it) | 1978-03-30 |
| GB1574959A (en) | 1980-09-10 |
| AU513200B2 (en) | 1980-11-20 |
| NL7803610A (nl) | 1978-10-09 |
| DE2813895A1 (de) | 1978-10-19 |
| JPS53124257A (en) | 1978-10-30 |
| IL54244A0 (en) | 1978-06-15 |
| FI780908A (fi) | 1978-10-06 |
| SE7803804L (sv) | 1978-10-06 |
| LU79368A1 (fr) | 1978-11-27 |
| BE865706A (fr) | 1978-10-05 |
| FR2386539B1 (nl) | 1980-08-14 |
| IT1158677B (it) | 1987-02-25 |
| DK147878A (da) | 1978-10-06 |
| AU3385678A (en) | 1979-09-13 |
| ZA781345B (en) | 1979-02-28 |
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