NO127350B - - Google Patents
Download PDFInfo
- Publication number
- NO127350B NO127350B NO03754/71*[A NO375471A NO127350B NO 127350 B NO127350 B NO 127350B NO 375471 A NO375471 A NO 375471A NO 127350 B NO127350 B NO 127350B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- solution
- acid
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000004992 fission Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 4
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- KBYGABSMKUYDEM-UHFFFAOYSA-N 2,3-dihydroimidazo[1,2-b]isoindol-5-one Chemical compound C12=CC=CC=C2C(=O)N2C1=NCC2 KBYGABSMKUYDEM-UHFFFAOYSA-N 0.000 description 3
- DKUKKXXCBPICGC-UHFFFAOYSA-N [2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C=2NCCN=2)C=1C(=O)C1=CC=CC=C1 DKUKKXXCBPICGC-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003368 psychostimulant agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- 208000020401 Depressive disease Diseases 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 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
- 239000011976 maleic acid Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YHWQUWUHLPRUID-UHFFFAOYSA-N (2-chlorophenyl)-[2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1C1=NCCN1 YHWQUWUHLPRUID-UHFFFAOYSA-N 0.000 description 1
- PNIZNQBBRNKJNE-UHFFFAOYSA-N (4-chlorophenyl)-[2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1C1=NCCN1 PNIZNQBBRNKJNE-UHFFFAOYSA-N 0.000 description 1
- MCZXMWARUTZVDK-UHFFFAOYSA-N 1,2,3,9b-tetrahydroimidazo[1,2-b]isoindol-5-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(=O)N2C1NCC2 MCZXMWARUTZVDK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- KKOKHHOCVNERRO-UHFFFAOYSA-N 2h-isoindol-5-ol Chemical compound C1=C(O)C=CC2=CNC=C21 KKOKHHOCVNERRO-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
- AYCFVKGYERYDRT-UHFFFAOYSA-N 5-phenyl-2,3-dihydroimidazo[1,2-b]isoindol-5-ol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=CC=C1 AYCFVKGYERYDRT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010065369 Burnout syndrome Diseases 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- OKLWLPRHLAFEOO-UHFFFAOYSA-N [2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C1=NCCN1 OKLWLPRHLAFEOO-UHFFFAOYSA-N 0.000 description 1
- SEKMRBQYRDZNSZ-UHFFFAOYSA-N [2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]-phenylmethanone;hydrochloride Chemical compound Cl.C=1C=CC=C(C=2NCCN=2)C=1C(=O)C1=CC=CC=C1 SEKMRBQYRDZNSZ-UHFFFAOYSA-N 0.000 description 1
- VOLQKIUWZXBTNB-UHFFFAOYSA-N [5-chloro-2-(4,5-dihydro-1h-imidazol-2-yl)phenyl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1C1=NCCN1 VOLQKIUWZXBTNB-UHFFFAOYSA-N 0.000 description 1
- WSWOKFODOPIESP-UHFFFAOYSA-M [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 Chemical compound [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 WSWOKFODOPIESP-UHFFFAOYSA-M 0.000 description 1
- SNIYGPDAYLBEMK-UHFFFAOYSA-M [I-].[Mg+]C1=CC=CC=C1 Chemical compound [I-].[Mg+]C1=CC=CC=C1 SNIYGPDAYLBEMK-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 201000003929 dermatomycosis Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SOWOYMBNJVLWGP-UHFFFAOYSA-N isoindol-5-one Chemical compound O=C1C=CC2=CN=CC2=C1 SOWOYMBNJVLWGP-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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- -1 propy1 Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 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
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000725 suspension Substances 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62696567A | 1967-03-30 | 1967-03-30 | |
| US639315A US3888846A (en) | 1967-03-30 | 1967-05-18 | Process for 2(2-(1,3-diazacycloalk-2-enyl))benzophenone derivatives and 1,3-diazacycloalkenyl(2,1-a)isoindole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127350B true NO127350B (enrdf_load_stackoverflow) | 1973-06-12 |
Family
ID=27090306
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1212/68A NO124111B (enrdf_load_stackoverflow) | 1967-03-30 | 1968-03-29 | |
| NO03752/71*[A NO127238B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 | |
| NO03755/71*[A NO127351B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 | |
| NO03753/71*[A NO127239B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 | |
| NO03754/71*[A NO127350B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1212/68A NO124111B (enrdf_load_stackoverflow) | 1967-03-30 | 1968-03-29 | |
| NO03752/71*[A NO127238B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 | |
| NO03755/71*[A NO127351B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 | |
| NO03753/71*[A NO127239B (enrdf_load_stackoverflow) | 1967-03-30 | 1971-10-12 |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS4843360B1 (enrdf_load_stackoverflow) |
| ES (1) | ES352173A1 (enrdf_load_stackoverflow) |
| IE (1) | IE31999B1 (enrdf_load_stackoverflow) |
| IL (1) | IL29651A (enrdf_load_stackoverflow) |
| MY (1) | MY7300459A (enrdf_load_stackoverflow) |
| NO (5) | NO124111B (enrdf_load_stackoverflow) |
| SE (1) | SE346318B (enrdf_load_stackoverflow) |
| YU (1) | YU33929B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50125392U (enrdf_load_stackoverflow) * | 1974-03-30 | 1975-10-14 |
-
1968
- 1968-03-18 IL IL29651A patent/IL29651A/en unknown
- 1968-03-27 SE SE4081/68A patent/SE346318B/xx unknown
- 1968-03-29 YU YU717/68A patent/YU33929B/xx unknown
- 1968-03-29 IE IE366/68A patent/IE31999B1/xx unknown
- 1968-03-29 NO NO1212/68A patent/NO124111B/no unknown
-
1969
- 1969-05-19 ES ES352173A patent/ES352173A1/es not_active Expired
-
1970
- 1970-08-03 JP JP45067352A patent/JPS4843360B1/ja active Pending
-
1971
- 1971-10-12 NO NO03752/71*[A patent/NO127238B/no unknown
- 1971-10-12 NO NO03755/71*[A patent/NO127351B/no unknown
- 1971-10-12 NO NO03753/71*[A patent/NO127239B/no unknown
- 1971-10-12 NO NO03754/71*[A patent/NO127350B/no unknown
-
1973
- 1973-02-09 JP JP48016353A patent/JPS5017479B1/ja active Pending
- 1973-12-30 MY MY459/73A patent/MY7300459A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO124111B (enrdf_load_stackoverflow) | 1972-03-06 |
| NO127351B (enrdf_load_stackoverflow) | 1973-06-12 |
| YU71768A (en) | 1978-02-28 |
| NO127238B (enrdf_load_stackoverflow) | 1973-05-28 |
| SE346318B (enrdf_load_stackoverflow) | 1972-07-03 |
| IL29651A (en) | 1972-07-26 |
| IE31999L (en) | 1968-09-30 |
| JPS5017479B1 (enrdf_load_stackoverflow) | 1975-06-20 |
| NO127239B (enrdf_load_stackoverflow) | 1973-05-28 |
| JPS4843360B1 (enrdf_load_stackoverflow) | 1973-12-18 |
| YU33929B (en) | 1978-09-08 |
| MY7300459A (en) | 1973-12-31 |
| ES352173A1 (es) | 1969-10-01 |
| IE31999B1 (en) | 1973-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4430343A (en) | Benzimidazole derivatives, process for the preparation thereof and pharmaceutical composition containing the same | |
| DE60003949T2 (de) | 5-aryl-1h-1,2,4 triazolverbindungen als cyclooxygenase -2 inhibitoren und dieseenthaltende pharmazeutische zusammensetzungen | |
| EP0221376B1 (de) | N-substituierte Diphenylpiperidine | |
| DE4036645A1 (de) | Substituierte azole, verfahren zu deren herstellung, deren enthaltende mittel und deren verwendung | |
| PL101099B1 (pl) | Sposob wytwarzania nowych trojchloroacetamidyn | |
| DE2239648A1 (de) | Polycyclische verbindungen | |
| NO152064B (no) | Utvidet stiveranordning for en selvreisende vinge | |
| CH636099A5 (de) | Verfahren zur herstellung von piperidinopropanolderivaten. | |
| US4086353A (en) | Certain azolinylamino (azolidinylimino) indazoles | |
| US4515944A (en) | 1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates | |
| AT400845B (de) | Neue thienothiazinderivate, ein verfahren zu ihrer herstellung und ihre verwendung | |
| US4950677A (en) | Benzimidazole derivative compounds and method of making | |
| NO127350B (enrdf_load_stackoverflow) | ||
| NO123530B (enrdf_load_stackoverflow) | ||
| DE2412520A1 (de) | Tricyclische verbindungen | |
| NO813107L (no) | Fremgangsmaate for fremstilling av imidazoler med antidepressiv aktivitet. | |
| CH644125A5 (de) | Benzo-as-triazin-derivate und verfahren zur herstellung derselben. | |
| DE60007748T2 (de) | Benzimidazolderivate und sie enthaltende medikamente | |
| CH461489A (de) | Verfahren zur Herstellung von neuen Oxazolderivaten | |
| US3429885A (en) | Pyridylethyl and piperidylethyl pyrroles | |
| DE69612413T2 (de) | 1-(Hetero)Arylvinyl-5H-2,3-benzodiazepinderivative verwendbar zur Behandlung von Erkrankungen des Zentralnervensystems, sowie Benzopyrylium Intermediate zu ihrer Herstellung | |
| US3812135A (en) | Pyrroloindole and pyridoindole derivatives | |
| DE2340217A1 (de) | 3-benzoylthiophene, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| US3517020A (en) | Certain 1-(3'-nicotinoyl)-2-loweralkylthio-benzimidazoles | |
| DE2302383A1 (de) | Pyrido- eckige klammer auf 4,3-c eckige klammer zu -pyridazinderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |