NO760003L - - Google Patents
Info
- Publication number
- NO760003L NO760003L NO760003A NO760003A NO760003L NO 760003 L NO760003 L NO 760003L NO 760003 A NO760003 A NO 760003A NO 760003 A NO760003 A NO 760003A NO 760003 L NO760003 L NO 760003L
- Authority
- NO
- Norway
- Prior art keywords
- benzoic acid
- ethyl
- chloro
- methoxy
- melting point
- Prior art date
Links
- 239000005711 Benzoic acid Substances 0.000 claims description 64
- -1 amino compound Chemical class 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 239000008280 blood Substances 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 158
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- 238000002844 melting Methods 0.000 description 99
- 230000008018 melting Effects 0.000 description 98
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000155 melt Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000001559 benzoic acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FZOOOJPISNODNI-UHFFFAOYSA-N 5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(N)=O FZOOOJPISNODNI-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DLOUWTXKCYSYGH-UHFFFAOYSA-N 4-(2-acetamidoethyl)-3-hydroxybenzoic acid Chemical compound CC(=O)NCCC1=CC=C(C(O)=O)C=C1O DLOUWTXKCYSYGH-UHFFFAOYSA-N 0.000 description 2
- GFUFUJMSZWBPNH-UHFFFAOYSA-N 4-(2-acetamidoethyl)benzoic acid Chemical compound CC(=O)NCCC1=CC=C(C(O)=O)C=C1 GFUFUJMSZWBPNH-UHFFFAOYSA-N 0.000 description 2
- BANRONBXBRYLQF-UHFFFAOYSA-N 4-(2-aminoethyl)-2-methoxybenzoic acid Chemical compound COC1=CC(CCN)=CC=C1C(O)=O BANRONBXBRYLQF-UHFFFAOYSA-N 0.000 description 2
- UJKAJVDHXHAOBG-UHFFFAOYSA-N 4-(2-aminoethyl)-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.COC1=CC(CCN)=CC=C1C(O)=O UJKAJVDHXHAOBG-UHFFFAOYSA-N 0.000 description 2
- MRBFWTDIRYEDBQ-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid Chemical compound NCCC1=CC=C(C(O)=O)C=C1 MRBFWTDIRYEDBQ-UHFFFAOYSA-N 0.000 description 2
- WCLAVUGBGKPHOR-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid;sodium Chemical compound [Na].NCCC1=CC=C(C(O)=O)C=C1 WCLAVUGBGKPHOR-UHFFFAOYSA-N 0.000 description 2
- CJFMXPAXDDBNPI-UHFFFAOYSA-N 4-[2-[(3-chlorobenzoyl)amino]ethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCNC(=O)C1=CC=CC(Cl)=C1 CJFMXPAXDDBNPI-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- YFLWCZIVJVCWNQ-UHFFFAOYSA-N ethyl 4-(2-aminoethyl)benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=C(CCN)C=C1 YFLWCZIVJVCWNQ-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SVYOXGBINYWSDQ-UHFFFAOYSA-N 1,4-dioxane;ethanol Chemical compound CCO.C1COCCO1 SVYOXGBINYWSDQ-UHFFFAOYSA-N 0.000 description 1
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- UHCPCZKBZOSOLC-UHFFFAOYSA-N 1-ethyl-3,1-benzoxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)N(CC)C2=C1 UHCPCZKBZOSOLC-UHFFFAOYSA-N 0.000 description 1
- AGXBHBJDSLZGAP-UHFFFAOYSA-N 2-(cyanomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC#N AGXBHBJDSLZGAP-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- DDNLKGZAXUDTMJ-UHFFFAOYSA-N 2-ethoxy-4-methylbenzoic acid Chemical compound CCOC1=CC(C)=CC=C1C(O)=O DDNLKGZAXUDTMJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- MKCOMHDKPCQWNS-UHFFFAOYSA-N 4-(2-acetamidoethyl)-3-aminobenzoic acid Chemical compound C(C)(=O)NCCC1=C(C=C(C(=O)O)C=C1)N MKCOMHDKPCQWNS-UHFFFAOYSA-N 0.000 description 1
- ZXADJYYPNWHMPH-UHFFFAOYSA-N 4-(2-acetamidoethyl)-3-chlorobenzoic acid Chemical compound CC(=O)NCCC1=CC=C(C(O)=O)C=C1Cl ZXADJYYPNWHMPH-UHFFFAOYSA-N 0.000 description 1
- SNVGSWBDLCYVHK-UHFFFAOYSA-N 4-(2-acetamidoethyl)-3-nitrobenzoic acid Chemical compound CC(=O)NCCC1=CC=C(C(O)=O)C=C1[N+]([O-])=O SNVGSWBDLCYVHK-UHFFFAOYSA-N 0.000 description 1
- VCCPPGGFPNSMJP-UHFFFAOYSA-N 4-(2-aminoethyl)-2-ethoxybenzoic acid;sodium Chemical compound [Na].CCOC1=CC(CCN)=CC=C1C(O)=O VCCPPGGFPNSMJP-UHFFFAOYSA-N 0.000 description 1
- ROEDYWLFNWMELV-UHFFFAOYSA-N 4-(2-aminoethyl)-5-bromo-2-methoxybenzoic acid Chemical class COC1=CC(CCN)=C(Br)C=C1C(O)=O ROEDYWLFNWMELV-UHFFFAOYSA-N 0.000 description 1
- RJGUALMBFBSSFS-UHFFFAOYSA-N 4-(2-aminoethyl)-5-chloro-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.COC1=CC(CCN)=C(Cl)C=C1C(O)=O RJGUALMBFBSSFS-UHFFFAOYSA-N 0.000 description 1
- GRQLJCQMQXXDTR-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid;hydrochloride Chemical compound Cl.NCCC1=CC=C(C(O)=O)C=C1 GRQLJCQMQXXDTR-UHFFFAOYSA-N 0.000 description 1
- YLTQEXSEXHPOMC-UHFFFAOYSA-N 4-(bromomethyl)-2-ethoxybenzoic acid Chemical compound CCOC1=CC(CBr)=CC=C1C(O)=O YLTQEXSEXHPOMC-UHFFFAOYSA-N 0.000 description 1
- SHWHMQDCKXTDDM-UHFFFAOYSA-N 4-(cyanomethyl)-2-methoxybenzoic acid Chemical compound COC1=CC(CC#N)=CC=C1C(O)=O SHWHMQDCKXTDDM-UHFFFAOYSA-N 0.000 description 1
- BWEZLVXHJJZXID-UHFFFAOYSA-N 4-[(5-chloro-2-ethoxybenzoyl)amino]-2-methoxybenzoic acid Chemical compound CCOC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C(OC)=C1 BWEZLVXHJJZXID-UHFFFAOYSA-N 0.000 description 1
- YESIEIKPZZXRJT-UHFFFAOYSA-N 4-[(5-chloro-2-ethoxybenzoyl)amino]-2-methylbenzoic acid Chemical compound CCOC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C(C)=C1 YESIEIKPZZXRJT-UHFFFAOYSA-N 0.000 description 1
- LMZYIJJUXADXEP-UHFFFAOYSA-N 4-[(5-chloro-2-ethoxybenzoyl)amino]-3-methylbenzoic acid Chemical compound CCOC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1C LMZYIJJUXADXEP-UHFFFAOYSA-N 0.000 description 1
- SWIWTZJJMKATMM-UHFFFAOYSA-N 4-[(5-chloro-2-methoxybenzoyl)amino]-2-ethoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC(NC(=O)C=2C(=CC=C(Cl)C=2)OC)=C1 SWIWTZJJMKATMM-UHFFFAOYSA-N 0.000 description 1
- YVLUDKRJZJVKRZ-UHFFFAOYSA-N 4-[(5-chloro-2-methoxybenzoyl)amino]-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC(NC(=O)C=2C(=CC=C(Cl)C=2)OC)=C1 YVLUDKRJZJVKRZ-UHFFFAOYSA-N 0.000 description 1
- RAFQPVZBCDVMBY-UHFFFAOYSA-N 4-[(5-chloro-2-methoxybenzoyl)amino]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(C(O)=O)C=C1 RAFQPVZBCDVMBY-UHFFFAOYSA-N 0.000 description 1
- KZMZCRDSZVJWSP-UHFFFAOYSA-N 4-[(6-chloro-3,4-dihydro-2h-chromene-8-carbonyl)amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC(=O)C=2C=3OCCCC=3C=C(Cl)C=2)=C1 KZMZCRDSZVJWSP-UHFFFAOYSA-N 0.000 description 1
- NQARTHXHYICPMA-UHFFFAOYSA-N 4-[2-[[2-(ethylamino)benzoyl]amino]ethyl]benzoic acid Chemical compound CCNC1=CC=CC=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 NQARTHXHYICPMA-UHFFFAOYSA-N 0.000 description 1
- AMCHOXWHBYTEPU-UHFFFAOYSA-N 4-[[(5-bromo-2-methoxybenzoyl)amino]methyl]benzoic acid Chemical compound COC1=CC=C(Br)C=C1C(=O)NCC1=CC=C(C(O)=O)C=C1 AMCHOXWHBYTEPU-UHFFFAOYSA-N 0.000 description 1
- CULZEHIRIGTMKD-UHFFFAOYSA-N 4-[[(5-chloro-2-methoxybenzoyl)amino]methyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(C(O)=O)C=C1 CULZEHIRIGTMKD-UHFFFAOYSA-N 0.000 description 1
- VWKSRDFIGWFBMV-UHFFFAOYSA-N 4-methyl-2-nitrobenzamide Chemical compound CC1=CC=C(C(N)=O)C([N+]([O-])=O)=C1 VWKSRDFIGWFBMV-UHFFFAOYSA-N 0.000 description 1
- NGWLWEKYLVWRNX-UHFFFAOYSA-N 4-methyl-2-nitrobenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C([N+]([O-])=O)=C1 NGWLWEKYLVWRNX-UHFFFAOYSA-N 0.000 description 1
- SJLXURQPRRMPIV-UHFFFAOYSA-N 5-bromo-2-methoxypyridine-3-carboxylic acid Chemical compound COC1=NC=C(Br)C=C1C(O)=O SJLXURQPRRMPIV-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- BXINAIGLJUMHPW-UHFFFAOYSA-N 5-chloro-2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(Cl)C=C1C(Cl)=O BXINAIGLJUMHPW-UHFFFAOYSA-N 0.000 description 1
- MTPTUMXFGUUUSZ-UHFFFAOYSA-N 5-chloro-2-methoxy-n-(2-phenylethyl)benzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=CC=C1 MTPTUMXFGUUUSZ-UHFFFAOYSA-N 0.000 description 1
- OQHKMSIQDOYXLE-UHFFFAOYSA-N 5-chloro-2-phenoxybenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC=C1OC1=CC=CC=C1 OQHKMSIQDOYXLE-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 229920001615 Tragacanth Polymers 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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 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
- 239000002552 dosage form Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- RBLUWLZGAZETKS-UHFFFAOYSA-N ethyl 4-(2-aminoethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CCN)C=C1 RBLUWLZGAZETKS-UHFFFAOYSA-N 0.000 description 1
- GIPAOTPHSZRHQX-UHFFFAOYSA-N ethyl 4-[(5-chloro-2-methoxybenzoyl)amino]-2-ethoxybenzoate Chemical compound C1=C(OCC)C(C(=O)OCC)=CC=C1NC(=O)C1=CC(Cl)=CC=C1OC GIPAOTPHSZRHQX-UHFFFAOYSA-N 0.000 description 1
- PAUZMIPXCIIDRZ-UHFFFAOYSA-N ethyl 4-amino-2-ethoxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1OCC PAUZMIPXCIIDRZ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- IEJRSHQPFLVOGU-UHFFFAOYSA-N methyl 4-(2-acetamidoethyl)-3-methoxybenzoate Chemical compound COC(=O)C1=CC=C(CCNC(C)=O)C(OC)=C1 IEJRSHQPFLVOGU-UHFFFAOYSA-N 0.000 description 1
- HYBVWCPWTPZFQE-UHFFFAOYSA-N methyl 4-(2-aminoethyl)benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(CCN)C=C1 HYBVWCPWTPZFQE-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2500157A DE2500157C2 (de) | 1975-01-03 | 1975-01-03 | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO760003L true NO760003L (fr) | 1976-07-06 |
Family
ID=5935941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO760003A NO760003L (fr) | 1975-01-03 | 1976-01-02 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4221815A (fr) |
| JP (1) | JPS51131846A (fr) |
| AT (1) | AT347922B (fr) |
| AU (1) | AU501010B2 (fr) |
| BE (1) | BE837311A (fr) |
| CA (1) | CA1064933A (fr) |
| CH (1) | CH619209A5 (fr) |
| DE (1) | DE2500157C2 (fr) |
| DK (1) | DK276A (fr) |
| EG (1) | EG12067A (fr) |
| ES (1) | ES443910A1 (fr) |
| FI (1) | FI753721A (fr) |
| FR (1) | FR2296407A1 (fr) |
| GB (1) | GB1538482A (fr) |
| HU (1) | HU174325B (fr) |
| IE (1) | IE42391B1 (fr) |
| IL (1) | IL48749A (fr) |
| IT (1) | IT1052091B (fr) |
| LU (1) | LU74129A1 (fr) |
| NL (1) | NL7515129A (fr) |
| NO (1) | NO760003L (fr) |
| PT (1) | PT64670B (fr) |
| SE (1) | SE7600012L (fr) |
| ZA (1) | ZA767B (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517229A1 (de) * | 1975-04-18 | 1976-10-28 | Boehringer Mannheim Gmbh | Phenylalkylcarbonsaeure-derivate und verfahren zu ihrer herstellung |
| DE2532420A1 (de) * | 1975-07-19 | 1977-02-03 | Boehringer Mannheim Gmbh | Phenylessigsaeure-derivate und verfahren zu ihrer herstellung |
| DE2639935A1 (de) * | 1976-09-04 | 1978-03-09 | Hoechst Ag | Benzoesaeuren und verfahren zu ihrer herstellung |
| DE2706977A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
| LU79008A1 (de) * | 1978-02-03 | 1979-09-06 | Byk Gulden Lomberg Chem Fab | W-(n-alkyl-n-benzoyl-amino)-phenylalkansaeuren,ihre verwendung und herstellung sowie sie enthaltende arzneimittel |
| DE3063878D1 (en) * | 1979-07-13 | 1983-07-28 | Thomae Gmbh Dr K | Derivatives of carboxylic acids, their preparation and medicaments containing them |
| DE3070865D1 (en) * | 1979-11-15 | 1985-08-14 | Beecham Group Plc | Secondary ethanol amines, their preparation and their use in pharmaceutical compositions |
| DE3100535A1 (de) * | 1981-01-10 | 1982-08-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue carbonsaeure-derivate, ihre herstellung und ihre verwendung als arzneimittel" |
| DE3211934A1 (de) * | 1982-03-31 | 1983-10-13 | Hoechst Ag, 6230 Frankfurt | Salicylsaeurederivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| PT77219B (fr) * | 1982-08-24 | 1986-02-04 | May & Baker Ltd | Procede de preparation des derives de la benzamide |
| LU86258A1 (fr) * | 1986-01-21 | 1987-09-03 | Rech Dermatologiques C I R D S | Composes benzamido aromatique,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| GB8708833D0 (en) * | 1987-04-13 | 1987-05-20 | Lilly S A E | Organic compounds |
| GB8823042D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| GB8823041D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| GB8823040D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| EP0478787B1 (fr) * | 1990-03-20 | 1994-12-21 | Shionogi & Co., Ltd. | Procede nouveau pour fabriquer un derive d'acide benzoique |
| CA2057324A1 (fr) * | 1990-12-18 | 1992-06-19 | Lora Louise Fitch | Agents hypoglycemiques de type benzamide et sulfonamide |
| US6916489B2 (en) | 1992-06-15 | 2005-07-12 | Emisphere Technologies, Inc. | Active agent transport systems |
| US20010003001A1 (en) | 1993-04-22 | 2001-06-07 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6001347A (en) | 1995-03-31 | 1999-12-14 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| IL126318A (en) | 1996-03-29 | 2004-09-27 | Emisphere Tech Inc | Compounds and compositions for delivering active agents and some novel carrier compounds |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6194458B1 (en) * | 1998-10-30 | 2001-02-27 | Merck & Co., Inc. | Benzamide potassium channel inhibitors |
| CA2369591C (fr) | 1999-04-05 | 2011-06-14 | Emisphere Technologies, Inc. | Sels disodiques, monohydrate, et solvates d'ethanol |
| US6693208B2 (en) | 1999-12-16 | 2004-02-17 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| CN1209336C (zh) * | 2000-04-28 | 2005-07-06 | 日本农药株式会社 | 生产2－卤代苯甲酸的方法 |
| EP1346982B1 (fr) * | 2000-12-28 | 2011-09-14 | Daiichi Pharmaceutical Co., Ltd. | Inhibiteurs de vla-4 |
| CA2770493A1 (fr) | 2003-07-24 | 2005-02-03 | Daiichi Pharmaceutical Co., Ltd. | Compose acide cyclohexanecarboxylique |
| KR100747401B1 (ko) | 2003-09-03 | 2007-08-08 | 화이자 인코포레이티드 | 프로스타글란딘 ｅ2 길항제로서의 페닐 또는 피리딜 아미드 화합물 |
| JP2005209106A (ja) * | 2004-01-26 | 2005-08-04 | Nec Corp | 携帯通信端末、受信メール管理方法、プログラムおよび記録媒体 |
| EA200601830A1 (ru) * | 2004-05-04 | 2007-04-27 | Пфайзер Инк. | Ортозамещённые арильные или гетероарильные амидные соединения |
| EP1960350B1 (fr) * | 2005-11-22 | 2015-08-19 | Bayer Intellectual Property GmbH | Nouveaux derives de n-(1-methyl-2phenylethyl)benzamide |
| CA2648729A1 (fr) * | 2006-04-24 | 2007-11-01 | Merck Frosst Canada Ltd. | Derives d'indolamide comme antagonistes du recepteur ep4 |
| US9714238B2 (en) | 2010-07-02 | 2017-07-25 | Allergan, Inc. | Therapeutic agents for ocular hypertension |
| WO2012003145A2 (fr) | 2010-07-02 | 2012-01-05 | Allergan, Inc. | Agents thérapeutiques pour l'hypertension oculaire |
| AR091429A1 (es) | 2012-06-29 | 2015-02-04 | Lilly Co Eli | Compuestos de fenoxietil piperidina |
| TWI636046B (zh) | 2013-05-17 | 2018-09-21 | 美國禮來大藥廠 | 苯氧基乙基二氫－１ｈ－異喹啉化合物 |
| CA2928593A1 (fr) | 2013-12-17 | 2015-06-25 | Eli Lilly And Company | Derives d'amine cyclique de phenoxyethyle et leur activite en tant que modulateurs du recepteur ep4 |
| US11001564B2 (en) * | 2016-09-13 | 2021-05-11 | Arbutus Biopharma Corporation | Substituted chromane-8-carboxamide compounds and analogues thereof, and methods using same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100226A (en) * | 1959-10-16 | 1963-08-06 | Amchem Prod | 2,5 dichloro-3 acylaminobenzoic acids |
| US3536753A (en) * | 1969-05-27 | 1970-10-27 | Geigy Chem Corp | O-(substituted benzamido)phenylacetic acids |
| US3636094A (en) * | 1969-07-25 | 1972-01-18 | Searle & Co | Norbornanecarboxylic acid amides of anthranilic acid |
| FR2088225A1 (en) * | 1970-05-29 | 1972-01-07 | Ugine Kuhlmann | Substd salicylanilides - having antiuric props |
| US3855285A (en) * | 1971-06-21 | 1974-12-17 | Pfizer | Acylmethylthio-trifluoromethyl-benzoic acids |
| DE2230383C3 (de) * | 1971-10-01 | 1981-12-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Phenoxyalkylcarbonsäurederivate und Verfahren zur Herstellung derselben |
| DE2320387A1 (de) * | 1973-04-21 | 1974-10-31 | Boehringer Mannheim Gmbh | Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben |
-
1975
- 1975-01-03 DE DE2500157A patent/DE2500157C2/de not_active Expired
- 1975-12-27 ES ES443910A patent/ES443910A1/es not_active Expired
- 1975-12-28 IL IL48749A patent/IL48749A/xx unknown
- 1975-12-29 NL NL7515129A patent/NL7515129A/xx not_active Application Discontinuation
- 1975-12-29 EG EG75768A patent/EG12067A/xx active
- 1975-12-30 CH CH1689175A patent/CH619209A5/de not_active IP Right Cessation
- 1975-12-31 IT IT30935/75A patent/IT1052091B/it active
- 1975-12-31 CA CA242,877A patent/CA1064933A/fr not_active Expired
- 1975-12-31 AU AU87964/75A patent/AU501010B2/en not_active Expired
- 1975-12-31 FI FI753721A patent/FI753721A/fi not_active Application Discontinuation
- 1975-12-31 FR FR7540257A patent/FR2296407A1/fr active Granted
-
1976
- 1976-01-02 NO NO760003A patent/NO760003L/no unknown
- 1976-01-02 IE IE2/76A patent/IE42391B1/en unknown
- 1976-01-02 US US05/646,378 patent/US4221815A/en not_active Expired - Lifetime
- 1976-01-02 LU LU74129A patent/LU74129A1/xx unknown
- 1976-01-02 SE SE7600012A patent/SE7600012L/xx not_active Application Discontinuation
- 1976-01-02 PT PT64670A patent/PT64670B/fr unknown
- 1976-01-02 ZA ZA00760007A patent/ZA767B/xx unknown
- 1976-01-02 DK DK276*BA patent/DK276A/da unknown
- 1976-01-02 AT AT1876A patent/AT347922B/de not_active IP Right Cessation
- 1976-01-02 HU HU76HO1869A patent/HU174325B/hu unknown
- 1976-01-05 GB GB145/76A patent/GB1538482A/en not_active Expired
- 1976-01-05 BE BE163313A patent/BE837311A/fr not_active IP Right Cessation
- 1976-01-05 JP JP51000731A patent/JPS51131846A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE7600012L (sv) | 1976-07-05 |
| IE42391B1 (en) | 1980-07-30 |
| CH619209A5 (fr) | 1980-09-15 |
| DE2500157A1 (de) | 1976-07-22 |
| IE42391L (en) | 1976-07-03 |
| NL7515129A (nl) | 1976-07-06 |
| AU501010B2 (en) | 1979-06-07 |
| DK276A (da) | 1976-07-04 |
| FR2296407A1 (fr) | 1976-07-30 |
| JPS51131846A (en) | 1976-11-16 |
| IT1052091B (it) | 1981-06-20 |
| ATA1876A (de) | 1978-06-15 |
| US4221815A (en) | 1980-09-09 |
| LU74129A1 (fr) | 1976-11-11 |
| PT64670A (fr) | 1976-05-01 |
| CA1064933A (fr) | 1979-10-23 |
| PT64670B (fr) | 1977-08-08 |
| IL48749A (en) | 1979-09-30 |
| ES443910A1 (es) | 1977-04-16 |
| DE2500157C2 (de) | 1983-09-15 |
| HU174325B (hu) | 1979-12-28 |
| AT347922B (de) | 1979-01-25 |
| GB1538482A (en) | 1979-01-17 |
| FI753721A (fr) | 1976-07-04 |
| IL48749A0 (en) | 1976-02-29 |
| BE837311A (fr) | 1976-07-05 |
| ZA767B (en) | 1976-12-29 |
| FR2296407B1 (fr) | 1979-06-29 |
| AU8796475A (en) | 1977-07-07 |
| EG12067A (en) | 1978-12-31 |
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