NO300322B1 - Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem - Google Patents
Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem Download PDFInfo
- Publication number
- NO300322B1 NO300322B1 NO940563A NO940563A NO300322B1 NO 300322 B1 NO300322 B1 NO 300322B1 NO 940563 A NO940563 A NO 940563A NO 940563 A NO940563 A NO 940563A NO 300322 B1 NO300322 B1 NO 300322B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- hydrochloride
- treatment
- preparation
- drug
- Prior art date
Links
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000003814 drug Substances 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- KBPOPCRJLYDSEV-UHFFFAOYSA-N 3,4-dichloro-n-(diaminomethylidene)benzamide Chemical compound NC(=N)NC(=O)C1=CC=C(Cl)C(Cl)=C1 KBPOPCRJLYDSEV-UHFFFAOYSA-N 0.000 claims abstract description 4
- JBUZPXALMCPEIO-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)benzamide Chemical compound NC(=N)NC(=O)C1=CC=C(Cl)C=C1 JBUZPXALMCPEIO-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZYBAROQWZRYRQL-UHFFFAOYSA-N n-(diaminomethylidene)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC(N)=N)C=C1 ZYBAROQWZRYRQL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 50
- 238000011282 treatment Methods 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 210000000056 organ Anatomy 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- KBXJRLWNGSDRBE-UHFFFAOYSA-N n-(diaminomethylidene)-3-methyl-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.CC1=CC(C(=O)NC(N)=N)=CC(C(F)(F)F)=C1 KBXJRLWNGSDRBE-UHFFFAOYSA-N 0.000 claims description 4
- JUVYVPKKFOLLQF-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-4-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C(=O)NC(N)=N)C=C1Cl JUVYVPKKFOLLQF-UHFFFAOYSA-N 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- VWLMUAWJVCLNGN-UHFFFAOYSA-N n-(diaminomethylidene)-3,5-bis(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VWLMUAWJVCLNGN-UHFFFAOYSA-N 0.000 claims description 3
- QOBADSBVYHQKPE-UHFFFAOYSA-N n-(diaminomethylidene)-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=CC(C(F)(F)F)=C1 QOBADSBVYHQKPE-UHFFFAOYSA-N 0.000 claims description 3
- ACOZGENRJJMWHS-UHFFFAOYSA-N n-(diaminomethylidene)-3-fluoro-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(F)=CC(C(F)(F)F)=C1 ACOZGENRJJMWHS-UHFFFAOYSA-N 0.000 claims description 3
- YOZCQEVDZMXRSQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-(4-fluorophenoxy)-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC=C1OC1=CC=C(F)C=C1 YOZCQEVDZMXRSQ-UHFFFAOYSA-N 0.000 claims description 3
- YGDMWRXNSBBPKD-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(F)C(C(F)(F)F)=C1 YGDMWRXNSBBPKD-UHFFFAOYSA-N 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 230000001960 triggered effect Effects 0.000 claims description 3
- SANZATGMJRPJIS-UHFFFAOYSA-N 3-tert-butyl-n-(diaminomethylidene)-4-hydroxybenzamide;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC(C(=O)NC(N)=N)=CC=C1O SANZATGMJRPJIS-UHFFFAOYSA-N 0.000 claims description 2
- TZJKNWFNYSHXNF-UHFFFAOYSA-N 3-tert-butyl-n-(diaminomethylidene)-4-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C(=O)NC(N)=N)C=C1C(C)(C)C TZJKNWFNYSHXNF-UHFFFAOYSA-N 0.000 claims description 2
- XBGJQUZQFVHJCP-UHFFFAOYSA-N 4-tert-butyl-n-(diaminomethylidene)-3-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC(C(=O)NC(N)=N)=CC=C1C(C)(C)C XBGJQUZQFVHJCP-UHFFFAOYSA-N 0.000 claims description 2
- 206010048962 Brain oedema Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 230000009692 acute damage Effects 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 230000009693 chronic damage Effects 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 230000003176 fibrotic effect Effects 0.000 claims description 2
- 206010020718 hyperplasia Diseases 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 230000036523 atherogenesis Effects 0.000 claims 1
- 210000004211 gastric acid Anatomy 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 16
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000008018 melting Effects 0.000 description 66
- 238000002844 melting Methods 0.000 description 66
- 239000013078 crystal Substances 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- -1 4-(4-fluorophenoxy)-3-trifluoromethylbenzoylguanidine hydrochloride -hydrochloride Chemical compound 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229960004198 guanidine Drugs 0.000 description 8
- 229960000789 guanidine hydrochloride Drugs 0.000 description 8
- VHCWLJYCHDIIEA-UHFFFAOYSA-N methyl 3-iodo-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(I)=CC(C(F)(F)F)=C1 VHCWLJYCHDIIEA-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960002576 amiloride Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 238000006880 cross-coupling reaction Methods 0.000 description 6
- DTVRLJMSCKUEEN-UHFFFAOYSA-N methyl 4-bromo-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 DTVRLJMSCKUEEN-UHFFFAOYSA-N 0.000 description 6
- 230000003288 anthiarrhythmic effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000007429 general method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 3
- AOCGCGVTOFDZEC-UHFFFAOYSA-N 3,5-dibromo-n-(diaminomethylidene)benzamide Chemical compound NC(=N)NC(=O)C1=CC(Br)=CC(Br)=C1 AOCGCGVTOFDZEC-UHFFFAOYSA-N 0.000 description 3
- GPBPFDPENZHCPR-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 GPBPFDPENZHCPR-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
- QDERNBXNXJCIQK-UHFFFAOYSA-N ethylisopropylamiloride Chemical compound CCN(C(C)C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl QDERNBXNXJCIQK-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 description 2
- URUYRXJKKBXBMM-UHFFFAOYSA-N 3,5-dichloro-4-[(4-chlorophenyl)methoxy]benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC(Cl)=C1OCC1=CC=C(Cl)C=C1 URUYRXJKKBXBMM-UHFFFAOYSA-N 0.000 description 2
- AULKDLUOQCUNOK-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(O)C(Cl)=C1 AULKDLUOQCUNOK-UHFFFAOYSA-N 0.000 description 2
- CXKCZFDUOYMOOP-UHFFFAOYSA-N 3,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1 CXKCZFDUOYMOOP-UHFFFAOYSA-N 0.000 description 2
- RXMUPNVSYKGKMY-UHFFFAOYSA-N 3-amino-6-chloro-n-(diaminomethylidene)-5-(dimethylamino)pyrazine-2-carboxamide Chemical compound CN(C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl RXMUPNVSYKGKMY-UHFFFAOYSA-N 0.000 description 2
- GFQAOTOMKKFCTM-UHFFFAOYSA-N 3-chloro-4-cyclopentylbenzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C1CCCC1 GFQAOTOMKKFCTM-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- OLDLDJLFPXMYCA-UHFFFAOYSA-N 3-cyclopentyl-n-(diaminomethylidene)-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC(C2CCCC2)=C1 OLDLDJLFPXMYCA-UHFFFAOYSA-N 0.000 description 2
- XCBLRUDPQIAUNC-UHFFFAOYSA-N 4-cyclopentyl-n-(diaminomethylidene)-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC=C1C1CCCC1 XCBLRUDPQIAUNC-UHFFFAOYSA-N 0.000 description 2
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 208000007530 Essential hypertension Diseases 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 206010061216 Infarction Diseases 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
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- QWQOLXDTTZSJBQ-UHFFFAOYSA-M [Cl-].CC(C)[Zn+] Chemical compound [Cl-].CC(C)[Zn+] QWQOLXDTTZSJBQ-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007574 infarction Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- BLMBANMKGXKYQT-UHFFFAOYSA-N methyl 3-chloro-4-cyclooctyloxybenzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1OC1CCCCCCC1 BLMBANMKGXKYQT-UHFFFAOYSA-N 0.000 description 2
- RVJPCLQVTWOLSN-UHFFFAOYSA-N methyl 3-chloro-4-cyclopentyloxybenzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1OC1CCCC1 RVJPCLQVTWOLSN-UHFFFAOYSA-N 0.000 description 2
- ZSBIMTDWIGWJPW-UHFFFAOYSA-N methyl 3-chloro-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Cl)=C1 ZSBIMTDWIGWJPW-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
- 208000010125 myocardial infarction Diseases 0.000 description 2
- FHYBHOAKKBMTAE-UHFFFAOYSA-N n-(diaminomethylidene)-3-(trifluoromethyl)benzamide Chemical compound NC(=N)NC(=O)C1=CC=CC(C(F)(F)F)=C1 FHYBHOAKKBMTAE-UHFFFAOYSA-N 0.000 description 2
- WOMBBKMJYHBFDV-UHFFFAOYSA-N n-(diaminomethylidene)-3-propan-2-yl-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC(C(=O)NC(N)=N)=CC(C(F)(F)F)=C1 WOMBBKMJYHBFDV-UHFFFAOYSA-N 0.000 description 2
- WVOWAZMLIGVZRT-UHFFFAOYSA-N n-(diaminomethylidene)-4-propan-2-yl-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C(=O)NC(N)=N)C=C1C(F)(F)F WVOWAZMLIGVZRT-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000001991 pathophysiological effect Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000054 salidiuretic effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical compound CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 1
- BANZVKGLDQDFDV-UHFFFAOYSA-N 2-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=CC=C1C(O)=O BANZVKGLDQDFDV-UHFFFAOYSA-N 0.000 description 1
- XBEVRVPHAPZSHI-UHFFFAOYSA-N 3,4,5-trichloro-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 XBEVRVPHAPZSHI-UHFFFAOYSA-N 0.000 description 1
- ICUICNRYLHKQGS-UHFFFAOYSA-N 3,4,5-trichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 ICUICNRYLHKQGS-UHFFFAOYSA-N 0.000 description 1
- HVFQJWGYVXKLTE-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HVFQJWGYVXKLTE-UHFFFAOYSA-N 0.000 description 1
- WPJZSCIBCPMPSY-UHFFFAOYSA-N 3,5-dibromo-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Br)=CC(Br)=C1 WPJZSCIBCPMPSY-UHFFFAOYSA-N 0.000 description 1
- UHPJAMSXXUSCKY-UHFFFAOYSA-N 3,5-dichloro-n-(diaminomethylidene)-4-hydroxybenzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Cl)=C(O)C(Cl)=C1 UHPJAMSXXUSCKY-UHFFFAOYSA-N 0.000 description 1
- PPRHKDZDNDJNKV-UHFFFAOYSA-N 3,5-dichloro-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PPRHKDZDNDJNKV-UHFFFAOYSA-N 0.000 description 1
- GONAVIHGXFBTOZ-UHFFFAOYSA-N 3,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC(F)=C1 GONAVIHGXFBTOZ-UHFFFAOYSA-N 0.000 description 1
- UMVOQQDNEYOJOK-UHFFFAOYSA-N 3,5-dimethylbenzoic acid Chemical compound CC1=CC(C)=CC(C(O)=O)=C1 UMVOQQDNEYOJOK-UHFFFAOYSA-N 0.000 description 1
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 1
- VIYKGIPTQKHFDX-UHFFFAOYSA-N 3,5-ditert-butyl-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC(C(=O)NC(N)=N)=CC(C(C)(C)C)=C1 VIYKGIPTQKHFDX-UHFFFAOYSA-N 0.000 description 1
- NCTSLPBQVXUAHR-UHFFFAOYSA-N 3,5-ditert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1 NCTSLPBQVXUAHR-UHFFFAOYSA-N 0.000 description 1
- UYWSNSKCKWIILY-UHFFFAOYSA-N 3-(1,1,2,2,2-pentafluoroethyl)-4-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1C(F)(F)C(F)(F)F UYWSNSKCKWIILY-UHFFFAOYSA-N 0.000 description 1
- OKPFIWIMBJNFSE-UHFFFAOYSA-N 3-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OC(F)(F)F)=C1 OKPFIWIMBJNFSE-UHFFFAOYSA-N 0.000 description 1
- WBTHOSZMTIPJLR-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)benzoic acid Chemical compound NC1=CC(C(O)=O)=CC(C(F)(F)F)=C1 WBTHOSZMTIPJLR-UHFFFAOYSA-N 0.000 description 1
- MOWIZRDXSGSJOC-UHFFFAOYSA-N 3-azido-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(N=[N+]=[N-])=CC(C(F)(F)F)=C1 MOWIZRDXSGSJOC-UHFFFAOYSA-N 0.000 description 1
- HBLBUVCCIFDJCJ-UHFFFAOYSA-N 3-azido-n-(diaminomethylidene)-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(N=[N+]=[N-])=CC(C(F)(F)F)=C1 HBLBUVCCIFDJCJ-UHFFFAOYSA-N 0.000 description 1
- ONELILMJNOWXSA-UHFFFAOYSA-N 3-bromo-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Br)=C1 ONELILMJNOWXSA-UHFFFAOYSA-N 0.000 description 1
- ZFJOMUKPDWNRFI-UHFFFAOYSA-N 3-bromo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1Br ZFJOMUKPDWNRFI-UHFFFAOYSA-N 0.000 description 1
- YEKZVBXRYCBWPG-UHFFFAOYSA-N 3-bromo-5-chloro-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Cl)=CC(Br)=C1 YEKZVBXRYCBWPG-UHFFFAOYSA-N 0.000 description 1
- PBRRUJWXRUGGAW-UHFFFAOYSA-N 3-bromo-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Br)=C1 PBRRUJWXRUGGAW-UHFFFAOYSA-N 0.000 description 1
- NWOMVQDBDBUANF-UHFFFAOYSA-N 3-bromo-5-methylbenzoic acid Chemical compound CC1=CC(Br)=CC(C(O)=O)=C1 NWOMVQDBDBUANF-UHFFFAOYSA-N 0.000 description 1
- FIWNPPHYBSHJFQ-UHFFFAOYSA-N 3-bromo-n-(diaminomethylidene)-4-fluorobenzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(F)C(Br)=C1 FIWNPPHYBSHJFQ-UHFFFAOYSA-N 0.000 description 1
- QMJRDCWXZQVLBV-UHFFFAOYSA-N 3-bromo-n-(diaminomethylidene)-4-methylbenzamide;hydrochloride Chemical compound Cl.CC1=CC=C(C(=O)NC(N)=N)C=C1Br QMJRDCWXZQVLBV-UHFFFAOYSA-N 0.000 description 1
- HMELLIFKGCZNBA-UHFFFAOYSA-N 3-bromo-n-(diaminomethylidene)-5-methylbenzamide;hydrochloride Chemical compound Cl.CC1=CC(Br)=CC(C(=O)NC(N)=N)=C1 HMELLIFKGCZNBA-UHFFFAOYSA-N 0.000 description 1
- PKTSBFXIHLYGEY-UHFFFAOYSA-N 3-chloro-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Cl)=C1 PKTSBFXIHLYGEY-UHFFFAOYSA-N 0.000 description 1
- GQIHORWCUSMSQF-UHFFFAOYSA-N 3-chloro-4-hexylbenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C=C1Cl GQIHORWCUSMSQF-UHFFFAOYSA-N 0.000 description 1
- QQTIONOTZKDOIE-UHFFFAOYSA-N 3-chloro-4-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1Cl QQTIONOTZKDOIE-UHFFFAOYSA-N 0.000 description 1
- IDLOGBMWOUINGG-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 IDLOGBMWOUINGG-UHFFFAOYSA-N 0.000 description 1
- BZJZWLRIXXUFLS-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-4-fluorobenzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(F)C(Cl)=C1 BZJZWLRIXXUFLS-UHFFFAOYSA-N 0.000 description 1
- YLMVYXYBKVDNSC-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-4-hexylbenzamide;hydrochloride Chemical compound Cl.CCCCCCC1=CC=C(C(=O)NC(N)=N)C=C1Cl YLMVYXYBKVDNSC-UHFFFAOYSA-N 0.000 description 1
- SQKUZCUJEGQIBG-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 SQKUZCUJEGQIBG-UHFFFAOYSA-N 0.000 description 1
- WFEZXFYLTICICT-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=CC(Cl)=C1 WFEZXFYLTICICT-UHFFFAOYSA-N 0.000 description 1
- OTZHDJMZVQTSBJ-UHFFFAOYSA-N 3-cyano-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C#N OTZHDJMZVQTSBJ-UHFFFAOYSA-N 0.000 description 1
- IZQGNGSUCGZCJZ-UHFFFAOYSA-N 3-cyano-n-(diaminomethylidene)-4-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC=C(C(=O)NC(N)=N)C=C1C#N IZQGNGSUCGZCJZ-UHFFFAOYSA-N 0.000 description 1
- NSGKIIGVPBTOBF-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(F)=CC(C(F)(F)F)=C1 NSGKIIGVPBTOBF-UHFFFAOYSA-N 0.000 description 1
- WKBZOFRUGGDTEU-UHFFFAOYSA-N 3-iodo-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(I)=CC(C(F)(F)F)=C1 WKBZOFRUGGDTEU-UHFFFAOYSA-N 0.000 description 1
- FQXQBFUUVCDIRK-UHFFFAOYSA-N 3-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1 FQXQBFUUVCDIRK-UHFFFAOYSA-N 0.000 description 1
- RATSANVPHHXDCT-UHFFFAOYSA-N 4-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)F)C=C1 RATSANVPHHXDCT-UHFFFAOYSA-N 0.000 description 1
- KSXUIQQDHHFSRN-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC=C1Br KSXUIQQDHHFSRN-UHFFFAOYSA-N 0.000 description 1
- KWVXDZLVCISXIB-UHFFFAOYSA-N 4-bromo-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1Br KWVXDZLVCISXIB-UHFFFAOYSA-N 0.000 description 1
- AUDJWDXIZDXCOK-UHFFFAOYSA-N 4-bromo-n-(diaminomethylidene)-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 AUDJWDXIZDXCOK-UHFFFAOYSA-N 0.000 description 1
- YLNOCRRATRDDTN-UHFFFAOYSA-N 4-bromo-n-(diaminomethylidene)-3-methylbenzamide;hydrochloride Chemical compound Cl.CC1=CC(C(=O)NC(N)=N)=CC=C1Br YLNOCRRATRDDTN-UHFFFAOYSA-N 0.000 description 1
- ZHHGJCFPDAJYTF-UHFFFAOYSA-N 4-chloro-3,5-dimethylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC(C)=C1Cl ZHHGJCFPDAJYTF-UHFFFAOYSA-N 0.000 description 1
- DABMFJIOFMWPRM-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)-3,5-dimethylbenzamide;hydrochloride Chemical compound Cl.CC1=CC(C(=O)NC(N)=N)=CC(C)=C1Cl DABMFJIOFMWPRM-UHFFFAOYSA-N 0.000 description 1
- AGSWKRDFRMOCAA-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)-3-methylbenzamide;hydrochloride Chemical compound Cl.CC1=CC(C(=O)NC(N)=N)=CC=C1Cl AGSWKRDFRMOCAA-UHFFFAOYSA-N 0.000 description 1
- QCIWHVKGVVQHIY-UHFFFAOYSA-N 4-cyclohexylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1CCCCC1 QCIWHVKGVVQHIY-UHFFFAOYSA-N 0.000 description 1
- WZBPZYCJUADXRS-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(F)C(C(F)(F)F)=C1 WZBPZYCJUADXRS-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PQDZTSSEWJIYOO-UHFFFAOYSA-N 4-methoxy-3-propan-2-ylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C(C)C PQDZTSSEWJIYOO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-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
- 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 206010022714 Intestinal ulcer Diseases 0.000 description 1
- 206010023421 Kidney fibrosis Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000052126 Sodium-Hydrogen Exchangers Human genes 0.000 description 1
- 108091006672 Sodium–hydrogen antiporter Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- YPIAGTACDKOXKS-UHFFFAOYSA-M [Cl-].[Zn+]C1CCCC1 Chemical compound [Cl-].[Zn+]C1CCCC1 YPIAGTACDKOXKS-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 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
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- KFKLBMQLKLKHLU-UHFFFAOYSA-N bromocyclooctane Chemical compound BrC1CCCCCCC1 KFKLBMQLKLKHLU-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 1
- 229960004064 bumetanide Drugs 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-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
- 239000002371 cardiac agent Substances 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000001269 cardiogenic effect Effects 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- BYIHXUHOYZDNTR-UHFFFAOYSA-M chlorozinc(1+);cyclopropane Chemical compound [Cl-].[Zn+2].C1C[CH-]1 BYIHXUHOYZDNTR-UHFFFAOYSA-M 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PCEBAZIVZVIQEO-UHFFFAOYSA-N iodocyclopentane Chemical compound IC1CCCC1 PCEBAZIVZVIQEO-UHFFFAOYSA-N 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000002171 loop diuretic 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
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- YIDCFRMKQAXTLK-UHFFFAOYSA-N methyl 3-cyclopentyl-5-(trifluoromethyl)benzoate Chemical compound FC(F)(F)C1=CC(C(=O)OC)=CC(C2CCCC2)=C1 YIDCFRMKQAXTLK-UHFFFAOYSA-N 0.000 description 1
- VLIDVNRBTMTVGL-UHFFFAOYSA-N methyl 3-phenyl-5-(trifluoromethyl)benzoate Chemical compound FC(F)(F)C1=CC(C(=O)OC)=CC(C=2C=CC=CC=2)=C1 VLIDVNRBTMTVGL-UHFFFAOYSA-N 0.000 description 1
- NPQFYKBYUUBDDR-UHFFFAOYSA-N methyl 3-propan-2-yl-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(C(C)C)=CC(C(F)(F)F)=C1 NPQFYKBYUUBDDR-UHFFFAOYSA-N 0.000 description 1
- RNESLRWEWHPCSY-UHFFFAOYSA-N methyl 4-cyclopentyl-3-(trifluoromethyl)benzoate Chemical compound FC(F)(F)C1=CC(C(=O)OC)=CC=C1C1CCCC1 RNESLRWEWHPCSY-UHFFFAOYSA-N 0.000 description 1
- APRKUJRKJJCBLZ-UHFFFAOYSA-N methyl 4-propan-2-yl-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(C)C)C(C(F)(F)F)=C1 APRKUJRKJJCBLZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- CVJRRXQACIPBGQ-UHFFFAOYSA-N n-(diaminomethylidene)-3,4-dimethylbenzamide;hydrochloride Chemical compound Cl.CC1=CC=C(C(=O)NC(N)=N)C=C1C CVJRRXQACIPBGQ-UHFFFAOYSA-N 0.000 description 1
- NIIYOMPVMNIOBJ-UHFFFAOYSA-N n-(diaminomethylidene)-3,5-difluorobenzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC(F)=CC(F)=C1 NIIYOMPVMNIOBJ-UHFFFAOYSA-N 0.000 description 1
- ULNZAXXOWGKDMS-UHFFFAOYSA-N n-(diaminomethylidene)-3,5-dimethylbenzamide;hydrochloride Chemical compound Cl.CC1=CC(C)=CC(C(=O)NC(N)=N)=C1 ULNZAXXOWGKDMS-UHFFFAOYSA-N 0.000 description 1
- YLBXBQJNKYVLAQ-UHFFFAOYSA-N n-(diaminomethylidene)-3-(1,1,2,2,2-pentafluoroethyl)-4-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C(=O)NC(N)=N)C=C1C(F)(F)C(F)(F)F YLBXBQJNKYVLAQ-UHFFFAOYSA-N 0.000 description 1
- HNCXLHXJOYBVPG-UHFFFAOYSA-N n-(diaminomethylidene)-3-(trifluoromethoxy)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=CC(OC(F)(F)F)=C1 HNCXLHXJOYBVPG-UHFFFAOYSA-N 0.000 description 1
- UGROQDZAFRMZOA-UHFFFAOYSA-N n-(diaminomethylidene)-3-phenyl-5-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC(C=2C=CC=CC=2)=C1 UGROQDZAFRMZOA-UHFFFAOYSA-N 0.000 description 1
- IQZZILWSRQEHRX-UHFFFAOYSA-N n-(diaminomethylidene)-4-(trifluoromethoxy)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 IQZZILWSRQEHRX-UHFFFAOYSA-N 0.000 description 1
- ITGMECDENUJWOB-UHFFFAOYSA-N n-(diaminomethylidene)-4-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=CC=C(C(F)(F)F)C=C1 ITGMECDENUJWOB-UHFFFAOYSA-N 0.000 description 1
- NAHHGRRMALBOGF-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-3-(2-methylpropyl)benzamide;hydrochloride Chemical compound Cl.CC(C)CC1=CC(C(=O)NC(N)=N)=CC=C1F NAHHGRRMALBOGF-UHFFFAOYSA-N 0.000 description 1
- BJZFTZQJLTVMEI-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-3-(trifluoromethyl)benzamide Chemical compound NC(=N)NC(=O)C1=CC=C(F)C(C(F)(F)F)=C1 BJZFTZQJLTVMEI-UHFFFAOYSA-N 0.000 description 1
- GHKDCCBGEBSXHR-UHFFFAOYSA-N n-(diaminomethylidene)-4-methoxy-3-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.COC1=CC=C(C(=O)NC(N)=N)C=C1C(C)C GHKDCCBGEBSXHR-UHFFFAOYSA-N 0.000 description 1
- VOZCCZCDOVRWMO-UHFFFAOYSA-N n-(diaminomethylidene)-4-phenoxy-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC=C1OC1=CC=CC=C1 VOZCCZCDOVRWMO-UHFFFAOYSA-N 0.000 description 1
- AREVHXBBEVHUTQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-propan-2-ylbenzamide;hydrochloride Chemical compound Cl.CC(C)C1=CC=C(C(=O)NC(N)=N)C=C1 AREVHXBBEVHUTQ-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 201000004240 prostatic hypertrophy Diseases 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NMLXKNNXODLJIN-UHFFFAOYSA-M zinc;carbanide;chloride Chemical compound [CH3-].[Zn+]Cl NMLXKNNXODLJIN-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4305250 | 1993-02-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO940563D0 NO940563D0 (no) | 1994-02-18 |
| NO940563L NO940563L (sv) | 1994-08-22 |
| NO300322B1 true NO300322B1 (no) | 1997-05-12 |
Family
ID=6480943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO940563A NO300322B1 (no) | 1993-02-20 | 1994-02-18 | Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5866610A (sv) |
| EP (1) | EP0612723B1 (sv) |
| JP (2) | JP3554352B2 (sv) |
| AT (1) | ATE157351T1 (sv) |
| AU (1) | AU668265B2 (sv) |
| CA (1) | CA2115967A1 (sv) |
| DE (1) | DE59403818D1 (sv) |
| DK (1) | DK0612723T3 (sv) |
| ES (1) | ES2107698T3 (sv) |
| FI (1) | FI114467B (sv) |
| GR (1) | GR3024855T3 (sv) |
| HU (1) | HU218915B (sv) |
| IL (1) | IL108697A (sv) |
| NO (1) | NO300322B1 (sv) |
| NZ (1) | NZ250919A (sv) |
| TW (1) | TW420659B (sv) |
| ZA (1) | ZA941119B (sv) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL109570A0 (en) * | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| DE4318756A1 (de) * | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4421495A1 (de) * | 1994-06-20 | 1995-12-21 | Merck Patent Gmbh | Heterocyclyloxy-benzoylguanidine |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| IL114670A0 (en) * | 1994-08-05 | 1995-11-27 | Fujisawa Pharmaceutical Co | Guanidine derivatives pharmaceutical compositions containing the same and processes for the preparation thereof |
| DE4430213A1 (de) * | 1994-08-28 | 1996-02-29 | Merck Patent Gmbh | Arylbenzoylguanidine |
| DE4432105A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Fluoro-alkyl/alkenyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4441880A1 (de) * | 1994-11-24 | 1996-05-30 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19518073A1 (de) * | 1995-05-17 | 1996-11-21 | Hoechst Ag | Substituierte Benzyloxycarbonylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19518796A1 (de) * | 1995-05-22 | 1996-11-28 | Hoechst Ag | Fluorphenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US6025154A (en) | 1995-06-06 | 2000-02-15 | Human Genome Sciences, Inc. | Polynucleotides encoding human G-protein chemokine receptor HDGNR10 |
| US6743594B1 (en) | 1995-06-06 | 2004-06-01 | Human Genome Sciences, Inc. | Methods of screening using human G-protein chemokine receptor HDGNR10 (CCR5) |
| DE19526381A1 (de) * | 1995-07-19 | 1997-01-23 | Hoechst Ag | 4-Fluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| EP0765867A1 (de) * | 1995-09-27 | 1997-04-02 | Hoechst Aktiengesellschaft | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Antiarrhytmika oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19540995A1 (de) * | 1995-11-03 | 1997-05-07 | Hoechst Ag | Substituierte Sulfonimidamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19542306A1 (de) * | 1995-11-14 | 1997-05-15 | Hoechst Ag | Sulfonylamino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| PL316439A1 (en) * | 1995-11-20 | 1997-05-26 | Hoechst Ag | Novel substituted derivatives of benzoyloguanidine, method of obtaining them, their application in production of pharmaceutic and diagnostic agents and pharmaceutic agent as such |
| DE19546736A1 (de) * | 1995-12-14 | 1997-06-19 | Hoechst Ag | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate |
| WO1997027183A1 (en) * | 1996-01-26 | 1997-07-31 | Fujisawa Pharmaceutical Co., Ltd. | Guanidine derivatives |
| DE19606509A1 (de) * | 1996-02-22 | 1997-08-28 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19608161A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19622222A1 (de) * | 1996-06-03 | 1997-12-04 | Hoechst Ag | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikament zur Normalisierung der Serumlipide |
| DE19622370A1 (de) * | 1996-06-04 | 1997-12-11 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US6677473B1 (en) | 1999-11-19 | 2004-01-13 | Corvas International Inc | Plasminogen activator inhibitor antagonists |
| US6638977B1 (en) | 1999-11-19 | 2003-10-28 | Corvas International, Inc. | Plasminogen activator inhibitor antagonists |
| US7175988B2 (en) | 2001-02-09 | 2007-02-13 | Human Genome Sciences, Inc. | Human G-protein Chemokine Receptor (CCR5) HDGNR10 |
| US6677479B2 (en) | 2001-11-13 | 2004-01-13 | Clariant Finance Lbvi Limited | Substituted fluoroaromatics, process for preparing them and their use |
| US7393934B2 (en) | 2001-12-21 | 2008-07-01 | Human Genome Sciences, Inc. | Human G-protein chemokine receptor (CCR5) HDGNR10 |
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US7375138B2 (en) * | 2002-05-18 | 2008-05-20 | Sanofi-Aventis Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, processes for their preparation, their use as medicaments or diagnostic aids, and medicaments comprising them |
| FR2840302B1 (fr) | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| US6878748B2 (en) | 2002-06-13 | 2005-04-12 | Aventis Pharma Deutschland Gmbh | Fluorinated cycloalkyl-derivatized benzoylguanidines, process for their preparation, their uses as medicament, and medicament containing them |
| FR2850282B1 (fr) | 2003-01-27 | 2007-04-06 | Jerome Asius | Implant injectable a base de ceramique pour le comblement de rides, depressions cutanees et cicatrices, et sa preparation |
| US7745442B2 (en) | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
| US20090253714A1 (en) * | 2003-08-20 | 2009-10-08 | Johnson Michael R | Methods of reducing risk of infection from pathogens |
| CA2559809A1 (en) | 2004-03-12 | 2005-11-10 | Human Genome Sciences, Inc. | Antibodies against human g-protein chemokine receptor (ccr5) hdgnr10 |
| US20070021439A1 (en) * | 2005-07-25 | 2007-01-25 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens with soluble amide and ester pyrazinoylguanidine sodium channel blockers |
| KR101683318B1 (ko) | 2008-12-31 | 2016-12-07 | 알데릭스, 인코포레이티드 | 체액 저류 또는 염 과부하와 연관된 장애 및 위장관 장애의 치료 시에 ｎｈｅ-매개된 역수송을 억제하는 화합물 및 방법 |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
| CN103796689B (zh) | 2011-07-28 | 2017-05-31 | 哈博医疗科技有限公司 | 交联的人或动物组织产品及其制造方法和使用方法 |
| KR102138390B1 (ko) | 2012-08-21 | 2020-07-27 | 알데릭스, 인코포레이티드 | 체액 저류 또는 염 과부하와 연관된 장애 및 위장관 장애의 치료에서 ｎｈｅ-매개된 역수송 저해를 위한 화합물 및 방법 |
| JP6392241B2 (ja) | 2012-12-17 | 2018-09-19 | パリオン・サイエンシィズ・インコーポレーテッド | ３，５−ジアミノ−６−クロロ−ｎ−（ｎ−（４−フェニルブチル）カルバムイミドイル）ピラジン−２−カルボキサミド化合物 |
| DK2931713T3 (en) | 2012-12-17 | 2017-01-30 | Parion Sciences Inc | CHLORPYRAZINE CARBOXAMIDE DERIVATIVES USED FOR THE TREATMENT OF DISEASES BENEFITED BY INDEPENDENT MOSPHEREWIN |
| CA2909169A1 (en) | 2013-04-12 | 2014-10-16 | Ardelyx, Inc. | Nhe3-binding compounds and methods for inhibiting phosphate transport |
| US9102633B2 (en) | 2013-12-13 | 2015-08-11 | Parion Sciences, Inc. | Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds |
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
| KR20240090875A (ko) | 2017-01-09 | 2024-06-21 | 알데릭스, 인코포레이티드 | 위장관 장애를 치료하는 데 유용한 화합물 |
| EP3565811A1 (en) | 2017-01-09 | 2019-11-13 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
| UA126584C2 (uk) | 2017-08-04 | 2022-11-02 | Арделікс, Інк. | Похідні гліцирретинової кислоти для лікування гіперкаліємії |
| CA3129233A1 (en) | 2019-02-07 | 2020-08-13 | Ardelyx, Inc. | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
| EP4142647A1 (en) | 2020-05-01 | 2023-03-08 | Harbor Medtech, Inc. | Port-accessible multidirectional reinforced minimally invasive collagen device for soft tissue repair |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3780027A (en) * | 1970-04-29 | 1973-12-18 | Merck & Co Inc | Anthranilic acid derivatives |
| PH12016A (en) * | 1972-09-22 | 1978-10-06 | Rorer Inc William H | Amidinoureas |
| US4251545A (en) * | 1979-09-19 | 1981-02-17 | Gaf Corporation | Fungicidal process using 1-(alkoxyaroyl)guanidines |
| US4544670A (en) * | 1982-08-24 | 1985-10-01 | William H. Rorer, Inc. | Method of treating coccidiosis with acyl guanidines |
| DE3502629A1 (de) * | 1985-01-26 | 1986-07-31 | Hoechst Ag, 6230 Frankfurt | Phenoxybenzoesaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz |
| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| CZ284456B6 (cs) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje |
| DE59302959D1 (de) * | 1992-02-15 | 1996-07-25 | Hoechst Ag | 3,5-Substituierte Benzoylguanidine, mit antiarrythmischer Wirkung und inhibierender Wirkung auf die Proliferationen von Zellen |
| DE59306029D1 (de) * | 1992-12-16 | 1997-05-07 | Hoechst Ag | 3,5-Substituierte Aminobenzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4318756A1 (de) * | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1994
- 1994-02-16 EP EP94102322A patent/EP0612723B1/de not_active Expired - Lifetime
- 1994-02-16 DE DE59403818T patent/DE59403818D1/de not_active Expired - Lifetime
- 1994-02-16 DK DK94102322.8T patent/DK0612723T3/da active
- 1994-02-16 AT AT94102322T patent/ATE157351T1/de not_active IP Right Cessation
- 1994-02-16 ES ES94102322T patent/ES2107698T3/es not_active Expired - Lifetime
- 1994-02-17 FI FI940756A patent/FI114467B/sv active IP Right Grant
- 1994-02-17 IL IL10869794A patent/IL108697A/xx not_active IP Right Cessation
- 1994-02-18 HU HU9400466A patent/HU218915B/hu unknown
- 1994-02-18 AU AU55229/94A patent/AU668265B2/en not_active Ceased
- 1994-02-18 ZA ZA941119A patent/ZA941119B/xx unknown
- 1994-02-18 NO NO940563A patent/NO300322B1/no unknown
- 1994-02-18 JP JP02076294A patent/JP3554352B2/ja not_active Expired - Fee Related
- 1994-02-18 NZ NZ250919A patent/NZ250919A/en unknown
- 1994-02-18 CA CA002115967A patent/CA2115967A1/en not_active Abandoned
- 1994-04-01 TW TW083102858A patent/TW420659B/zh active
-
1996
- 1996-07-18 US US08/683,141 patent/US5866610A/en not_active Expired - Lifetime
-
1997
- 1997-09-24 GR GR970402499T patent/GR3024855T3/el unknown
-
2004
- 2004-03-24 JP JP2004087016A patent/JP3806431B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL108697A0 (en) | 1994-05-30 |
| FI940756A0 (sv) | 1994-02-17 |
| ZA941119B (en) | 1994-08-30 |
| US5866610A (en) | 1999-02-02 |
| EP0612723A1 (de) | 1994-08-31 |
| EP0612723B1 (de) | 1997-08-27 |
| AU668265B2 (en) | 1996-04-26 |
| DE59403818D1 (de) | 1997-10-02 |
| NO940563L (sv) | 1994-08-22 |
| HU9400466D0 (en) | 1994-05-30 |
| ES2107698T3 (es) | 1997-12-01 |
| HU218915B (hu) | 2000-12-28 |
| JP3554352B2 (ja) | 2004-08-18 |
| HUT70535A (en) | 1995-10-30 |
| JP2004189755A (ja) | 2004-07-08 |
| CA2115967A1 (en) | 1994-08-21 |
| FI940756A (sv) | 1994-08-21 |
| IL108697A (en) | 2000-07-16 |
| AU5522994A (en) | 1994-08-25 |
| NZ250919A (en) | 1996-01-26 |
| GR3024855T3 (en) | 1998-01-30 |
| DK0612723T3 (da) | 1998-03-30 |
| ATE157351T1 (de) | 1997-09-15 |
| NO940563D0 (no) | 1994-02-18 |
| FI114467B (sv) | 2004-10-29 |
| JP3806431B2 (ja) | 2006-08-09 |
| TW420659B (en) | 2001-02-01 |
| JPH06256291A (ja) | 1994-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO300322B1 (no) | Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem | |
| NO179946B (no) | Benzoylguanidiner og deres anvendelse som medikamenter | |
| EP0556673B1 (de) | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament | |
| US5364868A (en) | Amino-substituted benzoylguanidines, process for their preparation, their use as a medicament and medicament containing them | |
| NO179549B (no) | 3,5-substituerte benzoylguanidiner og deres anvendelse som medikament eller diagnostikum | |
| US5849775A (en) | Substituted benzoylguanidines process for their preparation, their use as a medicament or diagnostic, and pharmaceutical containing them | |
| KR100376194B1 (ko) | 퍼플로우로알킬치환된벤조일구아니딘,이의제조방법및이를함유하는약제학적조성물 | |
| NO179673B (no) | 3,4,5-substituerte benzoylguanidiner og anvendelse av forbindelsene for fremstilling av legemidler | |
| DE4344550A1 (de) | Substituierte 1-Oxo-1,2-dihydro-isochinolinoyl- und 1,1-Dioxo-2H-1,2-benzothiazinoylguanidine, Verfahrenzu ihrer Herstellung, ihre Verwendung als Medikamentt oder Diagnostikum sowie sie enthaltendes Medikamen | |
| NO300590B1 (no) | Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikamenter såvel som medikamenter som inneholder dem | |
| NO300416B1 (no) | 3,5-substituerte aminobenzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum | |
| NO300679B1 (no) | Substituerte benzoylguanidiner, deres anvendelse for fremstilling av medikament eller diagnostikum samt medikament inneholdende forbindelsen | |
| US5670544A (en) | Substituted benzoylguanidines process for their preparation their use as a medicament or diagnostic and medicament containing them | |
| CA2186580A1 (en) | Substituted benzoylguanidines, a process for their preparation, their use as medicament or diagnostic agent, and medicament comprising them | |
| RU2165412C2 (ru) | Бензоилгуанидины, способ их получения, способ ингибирования, фармацевтический состав и способ его получения | |
| RU2159762C2 (ru) | Замещенные бензоилгуанидины, способ их получения, способ ингибирования и фармацевтический препарат | |
| NO315424B1 (no) | Substituerte tiofenalkenylkarboksylsyreguanidider, fremgangsmåter for deresfremstilling, deres anvendelse for fremstilling av medikamenteller diagnostikum samt medikament inneholdende forbindelsene | |
| EP0794172B1 (de) | Ortho-substituierte Benzoylguanidine | |
| NO309033B1 (no) | Orto-substituerte benzoylguanidiner, fremgangsmÕte for fremstilling derav, anvendelse i medikament eller diagnostikk, samt medikament derav | |
| KR20020073175A (ko) | 치환된 벤조일구아니딘, 이의 제조방법, 의약 또는진단제로서의 이의 용도 및 이를 함유하는 의약 |