DE1793048A1 - Verfahren zur Herstellung von neuen heterocyclischen Aminocarbonsaeuren - Google Patents
Verfahren zur Herstellung von neuen heterocyclischen AminocarbonsaeurenInfo
- Publication number
- DE1793048A1 DE1793048A1 DE19681793048 DE1793048A DE1793048A1 DE 1793048 A1 DE1793048 A1 DE 1793048A1 DE 19681793048 DE19681793048 DE 19681793048 DE 1793048 A DE1793048 A DE 1793048A DE 1793048 A1 DE1793048 A1 DE 1793048A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- meaning given
- methyl
- compound
- butyryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 heterocyclic aminocarboxylic acids Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010030113 Oedema Diseases 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- FQLJJWZKTKXFCL-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(CN(C)C)CC)=CC2=C1OC(C(O)=O)=C2 FQLJJWZKTKXFCL-UHFFFAOYSA-N 0.000 claims 1
- CAIRECFOICRPMQ-UHFFFAOYSA-N 6-methyl-5-[2-(morpholin-4-ylmethyl)butanoyl]-1-benzofuran-2-carboxylic acid Chemical compound O1CCN(CC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC CAIRECFOICRPMQ-UHFFFAOYSA-N 0.000 claims 1
- UQTCWYYSPDJIHG-UHFFFAOYSA-N 6-methyl-5-[2-(piperidin-1-ylmethyl)butanoyl]-1-benzofuran-2-carboxylic acid Chemical compound N1(CCCCC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC UQTCWYYSPDJIHG-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ISHJFUWRRWBXGC-UHFFFAOYSA-N 5-butanoyl-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(CCC)=O ISHJFUWRRWBXGC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- IKMJGHPYOYVETB-UHFFFAOYSA-N 1,4-dioxane;ethyl acetate Chemical compound CCOC(C)=O.C1COCCO1 IKMJGHPYOYVETB-UHFFFAOYSA-N 0.000 description 1
- DXJACICATILYIZ-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2OC(C(=O)O)=CC2=C1 DXJACICATILYIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- FGDDXPCJZXDRKD-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-1-benzofuran-2-carboxylic acid hydrochloride Chemical compound Cl.CN(C)CC(C(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1)CC FGDDXPCJZXDRKD-UHFFFAOYSA-N 0.000 description 1
- ZNCWIQRZAFXNOO-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-6-methyl-1-benzofuran-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C)C(C(=O)C(CN(C)C)CC)=CC2=C1OC(C(O)=O)=C2 ZNCWIQRZAFXNOO-UHFFFAOYSA-N 0.000 description 1
- UBCPUILNPLSVBH-UHFFFAOYSA-N 5-[3-(dimethylamino)propanoyl]-6-methyl-1-benzofuran-2-carboxylic acid hydrochloride Chemical compound Cl.CN(CCC(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)C UBCPUILNPLSVBH-UHFFFAOYSA-N 0.000 description 1
- HILLAFZODPUECD-UHFFFAOYSA-N 5-butanoyl-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1 HILLAFZODPUECD-UHFFFAOYSA-N 0.000 description 1
- STGSJLZWQHRTGE-UHFFFAOYSA-N 6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1 STGSJLZWQHRTGE-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- XQIKSPLJHYKGKT-UHFFFAOYSA-N Cl.N1(CCCCC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC Chemical compound Cl.N1(CCCCC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC XQIKSPLJHYKGKT-UHFFFAOYSA-N 0.000 description 1
- FVKZEDRMMPQLFB-UHFFFAOYSA-N Cl.O1CCN(CC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC Chemical compound Cl.O1CCN(CC1)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)CC FVKZEDRMMPQLFB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-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
- 241001466453 Laminaria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 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
- 238000010992 reflux Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 238000005303 weighing 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
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1076567A CH484093A (de) | 1967-07-28 | 1967-07-28 | Verfahren zur Herstellung von neuen heterocyclischen Aminocarbonsäuren |
| CH1363867 | 1967-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793048A1 true DE1793048A1 (de) | 1972-04-20 |
Family
ID=25707251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681793048 Granted DE1793048A1 (de) | 1967-07-28 | 1968-07-26 | Verfahren zur Herstellung von neuen heterocyclischen Aminocarbonsaeuren |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3723619A (en, 2012) |
| AT (1) | AT275509B (en, 2012) |
| BE (1) | BE718656A (en, 2012) |
| CH (1) | CH484093A (en, 2012) |
| DE (1) | DE1793048A1 (en, 2012) |
| DK (1) | DK121086B (en, 2012) |
| ES (1) | ES356581A1 (en, 2012) |
| FR (2) | FR1585130A (en, 2012) |
| GB (1) | GB1227967A (en, 2012) |
| IE (1) | IE32221B1 (en, 2012) |
| IL (1) | IL30444A (en, 2012) |
| NL (1) | NL6810305A (en, 2012) |
| NO (1) | NO122657B (en, 2012) |
| SE (1) | SE364271B (en, 2012) |
| YU (2) | YU178168A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663347A (en) * | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
| US4933351A (en) * | 1983-10-31 | 1990-06-12 | Merck Frosst Canada, Inc. | Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis |
| US4822803A (en) * | 1983-10-31 | 1989-04-18 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis |
| US4654365A (en) * | 1985-09-26 | 1987-03-31 | Merck & Co., Inc. | 2,3-dihydro-5-(3-oxo-2-cyclohexen-1-yl)-2-benzofurancarboxylic acids, and their salts useful in the treatment of brain injury |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1152871A (en) * | 1966-04-29 | 1969-05-21 | Roche Products Ltd | Benzofuran Derivatives and the manufacture thereof |
-
1963
- 1963-07-25 YU YU01781/68A patent/YU178168A/xx unknown
-
1967
- 1967-07-28 CH CH1076567A patent/CH484093A/de not_active IP Right Cessation
-
1968
- 1968-07-19 NL NL6810305A patent/NL6810305A/xx unknown
- 1968-07-19 SE SE09916/68A patent/SE364271B/xx unknown
- 1968-07-19 NO NO2866/68A patent/NO122657B/no unknown
- 1968-07-19 DK DK350968AA patent/DK121086B/da unknown
- 1968-07-25 YU YU1781/68A patent/YU32295B/xx unknown
- 1968-07-26 IE IE902/68A patent/IE32221B1/xx unknown
- 1968-07-26 AT AT730068A patent/AT275509B/de active
- 1968-07-26 BE BE718656D patent/BE718656A/xx unknown
- 1968-07-26 DE DE19681793048 patent/DE1793048A1/de active Granted
- 1968-07-26 GB GB1227967D patent/GB1227967A/en not_active Expired
- 1968-07-26 IL IL30444A patent/IL30444A/en unknown
- 1968-07-26 FR FR1585130D patent/FR1585130A/fr not_active Expired
- 1968-07-27 ES ES356581A patent/ES356581A1/es not_active Expired
- 1968-10-25 FR FR171419A patent/FR7990M/fr not_active Expired
-
1970
- 1970-11-18 US US00090818A patent/US3723619A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK121086B (da) | 1971-09-06 |
| YU32295B (en) | 1974-08-31 |
| AT275509B (de) | 1969-10-27 |
| FR7990M (en, 2012) | 1970-06-08 |
| GB1227967A (en, 2012) | 1971-04-15 |
| NL6810305A (en, 2012) | 1969-01-30 |
| YU178168A (en) | 1974-02-28 |
| ES356581A1 (es) | 1970-04-01 |
| SE364271B (en, 2012) | 1974-02-18 |
| IE32221B1 (en) | 1973-05-16 |
| NO122657B (en, 2012) | 1971-07-26 |
| IE32221L (en) | 1969-01-28 |
| CH484093A (de) | 1970-01-15 |
| BE718656A (en, 2012) | 1969-01-27 |
| FR1585130A (en, 2012) | 1970-01-09 |
| IL30444A0 (en) | 1968-09-26 |
| US3723619A (en) | 1973-03-27 |
| IL30444A (en) | 1972-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |