JPH0412275B2 - - Google Patents
Info
- Publication number
- JPH0412275B2 JPH0412275B2 JP6791083A JP6791083A JPH0412275B2 JP H0412275 B2 JPH0412275 B2 JP H0412275B2 JP 6791083 A JP6791083 A JP 6791083A JP 6791083 A JP6791083 A JP 6791083A JP H0412275 B2 JPH0412275 B2 JP H0412275B2
- Authority
- JP
- Japan
- Prior art keywords
- indole
- furo
- phenyl
- pharmaceutically acceptable
- methoxy
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 86
- -1 amine cation Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical group 0.000 claims description 9
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 4
- NKGUHSIMKXPTGH-UHFFFAOYSA-N 4h-furo[3,2-b]indole-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)O)O2 NKGUHSIMKXPTGH-UHFFFAOYSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical class OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- YUEDRIPQRRVFJV-UHFFFAOYSA-N 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C1=2C(OCC)=C(C(O)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 YUEDRIPQRRVFJV-UHFFFAOYSA-N 0.000 claims description 2
- VFWAJXMRCXLCOW-UHFFFAOYSA-N 3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C1=2C(OCC)=C(C(O)=O)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 VFWAJXMRCXLCOW-UHFFFAOYSA-N 0.000 claims description 2
- UIUZYXSRFZINPJ-UHFFFAOYSA-N 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C1=2C(OC)=C(C(O)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 UIUZYXSRFZINPJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- XQVAUXSFORHCLN-UHFFFAOYSA-N 4h-furo[3,2-b]indole-2-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)N)O2 XQVAUXSFORHCLN-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 238000002844 melting Methods 0.000 description 52
- 230000008018 melting Effects 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000000034 method Methods 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000012043 crude product Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 17
- 239000002253 acid Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 150000003536 tetrazoles Chemical class 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 6
- 239000000427 antigen Substances 0.000 description 6
- 102000036639 antigens Human genes 0.000 description 6
- 108091007433 antigens Proteins 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- NQPIEWBAWBFGOB-UHFFFAOYSA-N methyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=C1 NQPIEWBAWBFGOB-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- UZGBWUYYTOHRQR-UHFFFAOYSA-N 2-[n-(carboxymethyl)anilino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1N(CC(O)=O)C1=CC=CC=C1 UZGBWUYYTOHRQR-UHFFFAOYSA-N 0.000 description 2
- YDQILENBFVCDPN-UHFFFAOYSA-N 2-[n-(cyanomethyl)anilino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1N(CC#N)C1=CC=CC=C1 YDQILENBFVCDPN-UHFFFAOYSA-N 0.000 description 2
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 2
- JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 2
- YCXRJOZNRPGVCN-UHFFFAOYSA-N 3,7-dimethoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(=O)NC3=NNN=N3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 YCXRJOZNRPGVCN-UHFFFAOYSA-N 0.000 description 2
- FQUMPJZPUCNMHI-UHFFFAOYSA-N 3-ethoxy-7-methoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OCC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 FQUMPJZPUCNMHI-UHFFFAOYSA-N 0.000 description 2
- DUUYWVFGLXQTMD-UHFFFAOYSA-N 3-methoxy-4-methyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound O1C=2C3=CC=CC=C3N(C)C=2C(OC)=C1C1=NN=NN1 DUUYWVFGLXQTMD-UHFFFAOYSA-N 0.000 description 2
- WZCCJHJBIGMHLJ-UHFFFAOYSA-N 3-methoxy-4-methyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound O1C=2C3=CC=CC=C3N(C)C=2C(OC)=C1C(=O)NC1=NN=NN1 WZCCJHJBIGMHLJ-UHFFFAOYSA-N 0.000 description 2
- FWOGNFJKYGQZOW-UHFFFAOYSA-N 3-methoxy-4-methylfuro[3,2-b]indole-2-carbonitrile Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C#N)=C2OC FWOGNFJKYGQZOW-UHFFFAOYSA-N 0.000 description 2
- KAPSRMBETRZKSK-UHFFFAOYSA-N 3-methoxy-4-methylfuro[3,2-b]indole-2-carboxamide Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C(N)=O)=C2OC KAPSRMBETRZKSK-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- FRAOAVMBDZUBCZ-UHFFFAOYSA-N 6-methoxy-1-phenyl-2h-3,1-benzoxazin-4-one Chemical compound C1OC(=O)C2=CC(OC)=CC=C2N1C1=CC=CC=C1 FRAOAVMBDZUBCZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 108010058846 Ovalbumin Proteins 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
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001483 arginine derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- NPEIRKVWYZPQHS-UHFFFAOYSA-N ethyl 3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C(=O)OCC)=C2OC NPEIRKVWYZPQHS-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-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
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- SQGMODLFBXUZFC-UHFFFAOYSA-N methyl 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OCC)=C(C(=O)OC)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 SQGMODLFBXUZFC-UHFFFAOYSA-N 0.000 description 2
- ODWPOBLOANXRFF-UHFFFAOYSA-N methyl 3-hydroxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(O)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 ODWPOBLOANXRFF-UHFFFAOYSA-N 0.000 description 2
- PHFUJJYLQGKDEJ-UHFFFAOYSA-N methyl 5-methoxy-3-(2-methoxy-2-oxoethoxy)-1-phenylindole-2-carboxylate Chemical compound C12=CC=C(OC)C=C2C(OCC(=O)OC)=C(C(=O)OC)N1C1=CC=CC=C1 PHFUJJYLQGKDEJ-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OLFPNWJCEUTPNJ-VWMHFEHESA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;3,7-dimethoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N.C1=2C(OC)=C(C(=O)NC3=NNN=N3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 OLFPNWJCEUTPNJ-VWMHFEHESA-N 0.000 description 1
- JNJNRHBPVSHRQY-UHFFFAOYSA-N 2-anilino-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC=CC=C1 JNJNRHBPVSHRQY-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- DCEMUONUJXUSHM-UHFFFAOYSA-N 3,7-dimethoxy-4-phenyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound C1=2C(OC)=C(C=3NN=NN=3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 DCEMUONUJXUSHM-UHFFFAOYSA-N 0.000 description 1
- LTNCFABAGCHHCV-UHFFFAOYSA-N 3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C1=2C(OC)=C(C(O)=O)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 LTNCFABAGCHHCV-UHFFFAOYSA-N 0.000 description 1
- JOINTFUOXCQRLQ-UHFFFAOYSA-N 3-ethoxy-4-phenyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound C1=2C(OCC)=C(C=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 JOINTFUOXCQRLQ-UHFFFAOYSA-N 0.000 description 1
- NDGDVSWGNSXCMK-UHFFFAOYSA-N 3-ethoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OCC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 NDGDVSWGNSXCMK-UHFFFAOYSA-N 0.000 description 1
- JDJJPIVMJFSLJS-UHFFFAOYSA-N 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OCC)=C(C(N)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 JDJJPIVMJFSLJS-UHFFFAOYSA-N 0.000 description 1
- PWSDIAIDLOFYPB-UHFFFAOYSA-N 3-methoxy-4-phenyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound C1=2C(OC)=C(C=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 PWSDIAIDLOFYPB-UHFFFAOYSA-N 0.000 description 1
- UOCRBEBVQFQIKZ-UHFFFAOYSA-N 3-methoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 UOCRBEBVQFQIKZ-UHFFFAOYSA-N 0.000 description 1
- BKFIBMISQJZFFP-UHFFFAOYSA-N 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(N)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 BKFIBMISQJZFFP-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- MLOQSKIDJAEDOJ-UHFFFAOYSA-N 4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C12=CC=CC=C2C=2OC(C(=O)O)=CC=2N1C1=CC=CC=C1 MLOQSKIDJAEDOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 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 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241001465754 Metazoa Species 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 description 1
- QBYZWKQETPWEPB-UHFFFAOYSA-N ethyl 3-(2-ethoxy-2-oxoethoxy)-1-methylindole-2-carboxylate Chemical compound C1=CC=C2C(OCC(=O)OCC)=C(C(=O)OCC)N(C)C2=C1 QBYZWKQETPWEPB-UHFFFAOYSA-N 0.000 description 1
- WCYURHXDMXGKQD-UHFFFAOYSA-N ethyl 3-hydroxy-1-methylindole-2-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)OCC)=C(O)C2=C1 WCYURHXDMXGKQD-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- PPYPKYLOIVTCHE-UHFFFAOYSA-N methyl 3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OC)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 PPYPKYLOIVTCHE-UHFFFAOYSA-N 0.000 description 1
- SKQDAKUPRAMWKY-UHFFFAOYSA-N methyl 3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OCC)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 SKQDAKUPRAMWKY-UHFFFAOYSA-N 0.000 description 1
- ZUITVCHBXUDBHR-UHFFFAOYSA-N methyl 3-hydroxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(O)=C(C(=O)OC)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 ZUITVCHBXUDBHR-UHFFFAOYSA-N 0.000 description 1
- CQVGHRNBLPXJBR-UHFFFAOYSA-N methyl 3-hydroxy-5-methoxy-1-phenylindole-2-carboxylate Chemical compound COC(=O)C1=C(O)C2=CC(OC)=CC=C2N1C1=CC=CC=C1 CQVGHRNBLPXJBR-UHFFFAOYSA-N 0.000 description 1
- LBJWKXZFFSDGRE-UHFFFAOYSA-N methyl 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OC)=C(C(=O)OC)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 LBJWKXZFFSDGRE-UHFFFAOYSA-N 0.000 description 1
- JUACTQRSNRGGON-UHFFFAOYSA-N methyl 4h-furo[3,2-b]indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)OC)O2 JUACTQRSNRGGON-UHFFFAOYSA-N 0.000 description 1
- XRYUQPQOMXOEGO-UHFFFAOYSA-N methyl 5-methoxy-2-(n-(2-methoxy-2-oxoethyl)anilino)benzoate Chemical compound C=1C=C(OC)C=C(C(=O)OC)C=1N(CC(=O)OC)C1=CC=CC=C1 XRYUQPQOMXOEGO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36944882A | 1982-04-19 | 1982-04-19 | |
| US369448 | 1982-04-19 | ||
| US456121 | 1983-01-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58189183A JPS58189183A (ja) | 1983-11-04 |
| JPH0412275B2 true JPH0412275B2 (OSRAM) | 1992-03-04 |
Family
ID=23455525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6791083A Granted JPS58189183A (ja) | 1982-04-19 | 1983-04-19 | 抗アレルギ−性４Ｈ−フロ〔３．２−ｂ〕インド−ル化合物 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58189183A (OSRAM) |
| ZA (1) | ZA832371B (OSRAM) |
-
1983
- 1983-03-31 ZA ZA832371A patent/ZA832371B/xx unknown
- 1983-04-19 JP JP6791083A patent/JPS58189183A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58189183A (ja) | 1983-11-04 |
| ZA832371B (en) | 1984-05-30 |
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