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 PDF

Info

Publication number: NO300322B1
Authority: NO; Norway
Prior art keywords: compound; hydrochloride; treatment; preparation; drug
Prior art date: 1993-02-20

Application number

NO940563A

Other languages

English (en)

Norwegian (no)

Other versions

NO940563L (sv

NO940563D0 (no

Inventor

Hans-Jochen Lang

Andreas Weichert

Heinz-Werner Kleemann

Jan-Robert Schwark

Wolfgang Scholz

Udo Albus

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-02-20

Filing date

1994-02-18

Publication date

1997-05-12

1994-02-18 Application filed by Hoechst Ag filed Critical Hoechst Ag

1994-02-18 Publication of NO940563D0 publication Critical patent/NO940563D0/no

1994-08-22 Publication of NO940563L publication Critical patent/NO940563L/no

1997-05-12 Publication of NO300322B1 publication Critical patent/NO300322B1/no

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
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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)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Gastroenterology & Hepatology (AREA)
Obesity (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)
Quinoline Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Saccharide Compounds (AREA)

NO940563A 1993-02-20 1994-02-18 Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem NO300322B1 (no)

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)

* Cited by examiner, † Cited by third party
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
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
DE4421495A1 (de) *	1994-06-20	1995-12-21	Merck Patent Gmbh	Heterocyclyloxy-benzoylguanidine
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
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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 ES ES94102322T patent/ES2107698T3/es not_active Expired - Lifetime
- 1994-02-16 AT AT94102322T patent/ATE157351T1/de not_active IP Right Cessation
- 1994-02-16 DK DK94102322.8T patent/DK0612723T3/da active
- 1994-02-17 IL IL10869794A patent/IL108697A/xx not_active IP Right Cessation
- 1994-02-17 FI FI940756A patent/FI114467B/sv active IP Right Grant
- 1994-02-18 CA CA002115967A patent/CA2115967A1/en not_active Abandoned
- 1994-02-18 AU AU55229/94A patent/AU668265B2/en not_active Ceased
- 1994-02-18 HU HU9400466A patent/HU218915B/hu unknown
- 1994-02-18 NO NO940563A patent/NO300322B1/no unknown
- 1994-02-18 NZ NZ250919A patent/NZ250919A/en unknown
- 1994-02-18 JP JP02076294A patent/JP3554352B2/ja not_active Expired - Fee Related
- 1994-02-18 ZA ZA941119A patent/ZA941119B/xx unknown
- 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
FI114467B (sv)	2004-10-29
EP0612723B1 (de)	1997-08-27
DE59403818D1 (de)	1997-10-02
TW420659B (en)	2001-02-01
AU5522994A (en)	1994-08-25
JPH06256291A (ja)	1994-09-13
GR3024855T3 (en)	1998-01-30
DK0612723T3 (da)	1998-03-30
ZA941119B (en)	1994-08-30
JP3806431B2 (ja)	2006-08-09
JP3554352B2 (ja)	2004-08-18
FI940756A0 (sv)	1994-02-17
CA2115967A1 (en)	1994-08-21
HUT70535A (en)	1995-10-30
ATE157351T1 (de)	1997-09-15
NO940563L (sv)	1994-08-22
US5866610A (en)	1999-02-02
HU218915B (hu)	2000-12-28
JP2004189755A (ja)	2004-07-08
HU9400466D0 (en)	1994-05-30
AU668265B2 (en)	1996-04-26
NO940563D0 (no)	1994-02-18
EP0612723A1 (de)	1994-08-31
IL108697A (en)	2000-07-16
NZ250919A (en)	1996-01-26
FI940756A (sv)	1994-08-21
IL108697A0 (en)	1994-05-30
ES2107698T3 (es)	1997-12-01

Publication	Publication Date	Title
NO300322B1 (no)	1997-05-12	Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum, samt medikamenter inneholdende dem
NO179946B (no)	1996-10-07	Benzoylguanidiner og deres anvendelse som medikamenter
EP0556673B1 (de)	1997-09-17	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
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NO179549B (no)	1996-07-22	3,5-substituerte benzoylguanidiner og deres anvendelse som medikament eller diagnostikum
US5849775A (en)	1998-12-15	Substituted benzoylguanidines process for their preparation, their use as a medicament or diagnostic, and pharmaceutical containing them
EP0686627B1 (de)	1998-08-19	Perfluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
NO179673B (no)	1996-08-19	3,4,5-substituerte benzoylguanidiner og anvendelse av forbindelsene for fremstilling av legemidler
DE4344550A1 (de)	1995-06-29	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)	1997-06-23	Substituerte benzoylguanidiner, deres anvendelse til fremstilling av medikamenter såvel som medikamenter som inneholder dem
NO300416B1 (no)	1997-05-26	3,5-substituerte aminobenzoylguanidiner, deres anvendelse til fremstilling av medikament eller diagnostikum
NO300679B1 (no)	1997-07-07	Substituerte benzoylguanidiner, deres anvendelse for fremstilling av medikament eller diagnostikum samt medikament inneholdende forbindelsen
US5670544A (en)	1997-09-23	Substituted benzoylguanidines process for their preparation their use as a medicament or diagnostic and medicament containing them
CA2186580A1 (en)	1997-03-28	Substituted benzoylguanidines, a process for their preparation, their use as medicament or diagnostic agent, and medicament comprising them
RU2165412C2 (ru)	2001-04-20	Бензоилгуанидины, способ их получения, способ ингибирования, фармацевтический состав и способ его получения
RU2159762C2 (ru)	2000-11-27	Замещенные бензоилгуанидины, способ их получения, способ ингибирования и фармацевтический препарат
NO315424B1 (no)	2003-09-01	Substituerte tiofenalkenylkarboksylsyreguanidider, fremgangsmåter for deresfremstilling, deres anvendelse for fremstilling av medikamenteller diagnostikum samt medikament inneholdende forbindelsene
EP0794172B1 (de)	2001-10-24	Ortho-substituierte Benzoylguanidine
NO309033B1 (no)	2000-12-04	Orto-substituerte benzoylguanidiner, fremgangsmÕte for fremstilling derav, anvendelse i medikament eller diagnostikk, samt medikament derav
KR20020073175A (ko)	2002-09-19	치환된 벤조일구아니딘, 이의 제조방법, 의약 또는진단제로서의 이의 용도 및 이를 함유하는 의약