SK12797A3 - Substituted diarylcarboxylic acid diguanidines, preparation method thereof, their use as a drug or a diagnostic agent, as well as drug containing the same - Google Patents

Substituted diarylcarboxylic acid diguanidines, preparation method thereof, their use as a drug or a diagnostic agent, as well as drug containing the same Download PDF

Info

Publication number: SK12797A3
Authority: SK; Slovakia
Prior art keywords: group; hydrogen; independently; another; alkyl
Prior art date: 1996-01-31

Application number

SK127-97A

Other languages

English (en)

Slovak (sk)

Inventor

Heinz-Werner Kleemann

Joachim Brendel

Jan-Robert Schwark

Andreas Weichert

Hans J Lang

Udo Albus

Wolfgang Scholz

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.)

1996-01-31

Filing date

1997-01-29

Publication date

1998-02-04

1997-01-29 Application filed by Hoechst Ag filed Critical Hoechst Ag

1998-02-04 Publication of SK12797A3 publication Critical patent/SK12797A3/sk

Links

239000002253 acid Substances 0.000 title claims description 25
239000003814 drug Substances 0.000 title description 14
238000002360 preparation method Methods 0.000 title description 11
229940079593 drug Drugs 0.000 title description 6
229940039227 diagnostic agent Drugs 0.000 title 1
239000000032 diagnostic agent Substances 0.000 title 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 84
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 83
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 75
229910052801 chlorine Inorganic materials 0.000 claims abstract description 72
229910052731 fluorine Inorganic materials 0.000 claims abstract description 69
125000000217 alkyl group Chemical group 0.000 claims abstract description 59
-1 Diaryl dicarboxylic acid Chemical compound 0.000 claims abstract description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 19
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
229910052740 iodine Inorganic materials 0.000 claims abstract description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 14
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 12
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims description 73
125000004432 carbon atom Chemical group C* 0.000 claims description 64
125000001153 fluoro group Chemical group F* 0.000 claims description 52
125000001424 substituent group Chemical group 0.000 claims description 46
125000001309 chloro group Chemical group Cl* 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 35
239000000460 chlorine Substances 0.000 claims description 25
239000011737 fluorine Substances 0.000 claims description 24
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical group [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 abstract description 11
229910052757 nitrogen Inorganic materials 0.000 abstract description 4
125000001589 carboacyl group Chemical group 0.000 abstract description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
101100114470 Arabidopsis thaliana COR28 gene Proteins 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 38
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000011734 sodium Substances 0.000 description 15
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
238000011282 treatment Methods 0.000 description 12
239000000243 solution Substances 0.000 description 11
238000001819 mass spectrum Methods 0.000 description 10
238000000034 method Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 9
150000002825 nitriles Chemical group 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
210000003743 erythrocyte Anatomy 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
125000000714 pyrimidinyl group Chemical group 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000004663 cell proliferation Effects 0.000 description 4
238000000451 chemical ionisation Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000006378 damage Effects 0.000 description 4
238000003795 desorption Methods 0.000 description 4
238000010265 fast atom bombardment Methods 0.000 description 4
230000000302 ischemic effect Effects 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000008569 process Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
206010061216 Infarction Diseases 0.000 description 3
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
244000166550 Strophanthus gratus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 3
229960002576 amiloride Drugs 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000000132 electrospray ionisation Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000007574 infarction Effects 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
208000028867 ischemia Diseases 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 3
229960003343 ouabain Drugs 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 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
206010002383 Angina Pectoris Diseases 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
208000007530 Essential hypertension Diseases 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
206010020880 Hypertrophy 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
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 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
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
229910000024 caesium carbonate Inorganic materials 0.000 description 2
230000003293 cardioprotective effect Effects 0.000 description 2
UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000003480 eluent Substances 0.000 description 2
DFTXGSKTFDBVQM-UHFFFAOYSA-N ethyl 4-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 DFTXGSKTFDBVQM-UHFFFAOYSA-N 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000001727 glucose Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
206010020718 hyperplasia Diseases 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
ROTQXZRSKZFJSX-UHFFFAOYSA-N methyl 4-(ethoxycarbonylsulfamoyl)benzoate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C(=O)OC)C=C1 ROTQXZRSKZFJSX-UHFFFAOYSA-N 0.000 description 2
208000010125 myocardial infarction Diseases 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
230000035778 pathophysiological process Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
239000003826 tablet Substances 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
VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 1
AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
XGWQJFUMZRUDFV-UHFFFAOYSA-N 3-[(4-carboxyphenyl)sulfonylcarbamoylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC(C(O)=O)=C1 XGWQJFUMZRUDFV-UHFFFAOYSA-N 0.000 description 1
NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
OMSFWMDOSUTBHT-UHFFFAOYSA-N 4-(ethoxycarbonylsulfamoyl)benzoic acid Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 OMSFWMDOSUTBHT-UHFFFAOYSA-N 0.000 description 1
102000003669 Antiporters Human genes 0.000 description 1
108090000084 Antiporters Proteins 0.000 description 1
206010048962 Brain oedema Diseases 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
229920002261 Corn starch Polymers 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
208000002249 Diabetes Complications Diseases 0.000 description 1
206010012655 Diabetic complications Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
244000165918 Eucalyptus papuana Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
206010019668 Hepatic fibrosis Diseases 0.000 description 1
206010021137 Hypovolaemia Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
206010023421 Kidney fibrosis Diseases 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
241000283977 Oryctolagus Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
HOROOAXLDFZVDR-UHFFFAOYSA-J [F-].[F-].[F-].[F-].C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C Chemical compound [F-].[F-].[F-].[F-].C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C HOROOAXLDFZVDR-UHFFFAOYSA-J 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 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
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000879 anti-atherosclerotic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
150000001638 boron Chemical class 0.000 description 1
208000006752 brain edema Diseases 0.000 description 1
239000010974 bronze Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000001269 cardiogenic effect Effects 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000006880 cross-coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
BIHHBTVQFPVSTE-UHFFFAOYSA-N ethyl 2-bromobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1Br BIHHBTVQFPVSTE-UHFFFAOYSA-N 0.000 description 1
UMPRJGKLMUDRHL-UHFFFAOYSA-N ethyl 4-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1 UMPRJGKLMUDRHL-UHFFFAOYSA-N 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
230000003176 fibrotic effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
238000005048 flame photometry Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000005534 hematocrit Methods 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000002727 hyperosmolar Effects 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000002513 implantation Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000004941 influx Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
210000004072 lung Anatomy 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
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
XLOVNJUCAFIANM-UHFFFAOYSA-N methyl 4-sulfamoylbenzoate Chemical compound COC(=O)C1=CC=C(S(N)(=O)=O)C=C1 XLOVNJUCAFIANM-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
210000000663 muscle cell Anatomy 0.000 description 1
HUOHKEMRKNDEBV-UHFFFAOYSA-N n-(diaminomethylidene)-3-[[4-(diaminomethylidenecarbamoyl)phenyl]sulfonylcarbamoylamino]benzamide Chemical compound C1=CC(C(=O)N=C(N)N)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC(C(=O)N=C(N)N)=C1 HUOHKEMRKNDEBV-UHFFFAOYSA-N 0.000 description 1
AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 description 1
WCZHVEONHLZGNW-UHFFFAOYSA-N n-carbamimidoyl-n-phenylbenzamide Chemical class C=1C=CC=CC=1N(C(=N)N)C(=O)C1=CC=CC=C1 WCZHVEONHLZGNW-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 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
230000001575 pathological effect Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
208000037921 secondary disease Diseases 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000000891 standard diet Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- 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
- 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
- A61P9/06—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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

SK127-97A 1996-01-31 1997-01-29 Substituted diarylcarboxylic acid diguanidines, preparation method thereof, their use as a drug or a diagnostic agent, as well as drug containing the same SK12797A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19603425A DE19603425A1 (de)	1996-01-31	1996-01-31	Substituierte Diaryldicarbonsäure-diguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (1)

Publication Number	Publication Date
SK12797A3 true SK12797A3 (en)	1998-02-04

Family

ID=7784136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK127-97A SK12797A3 (en)	1996-01-31	1997-01-29	Substituted diarylcarboxylic acid diguanidines, preparation method thereof, their use as a drug or a diagnostic agent, as well as drug containing the same

Country Status (19)

Country	Link
EP (1)	EP0787717A1 (cs)
JP (1)	JPH09221465A (cs)
KR (1)	KR970059165A (cs)
AR (1)	AR005596A1 (cs)
AU (1)	AU1239097A (cs)
BR (1)	BR9700817A (cs)
CA (1)	CA2196388A1 (cs)
CZ (1)	CZ27197A3 (cs)
DE (1)	DE19603425A1 (cs)
HR (1)	HRP970057A2 (cs)
HU (1)	HUP9700277A3 (cs)
IL (1)	IL120093A0 (cs)
NO (1)	NO970406L (cs)
NZ (1)	NZ314145A (cs)
PL (1)	PL317844A1 (cs)
SK (1)	SK12797A3 (cs)
TR (1)	TR199700059A2 (cs)
TW (1)	TW430642B (cs)
ZA (1)	ZA97770B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10024319A1 (de) *	2000-05-17	2001-11-22	Merck Patent Gmbh	Bisacylguanidine
AR065785A1 (es) *	2007-03-19	2009-07-01	Xenon Pharmaceuticals Inc	Compuestos biarilo y biheteroarilo de utilidad en el tratamiento de trastornos de hierro

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3929582A1 (de) *	1989-09-06	1991-03-07	Hoechst Ag	Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament
DK0556674T3 (da)	1992-02-15	1996-10-14	Hoechst Ag	3,5-Substituerede benzoylguanidiner med antiarytmisk virkning og inhiberende virkning på celleproliferation
US5278933A (en)	1992-06-30	1994-01-11	Hunsinger Terrance D	Fiber optic splice organizer and associated method
EP0604852A1 (de) *	1992-12-28	1994-07-06	Hoechst Aktiengesellschaft	2,4-Substituierte 5-(N-substituierte-Sulfamoyl)-Benzoylguanidine, als Antiarrythmika, Inhibitoren der Proliferationen von Zellen, und Inhibitoren des Natrium-Protonen-Antiporters
IL109570A0 (en) *	1993-05-17	1994-08-26	Fujisawa Pharmaceutical Co	Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof
DE4327244A1 (de) *	1993-08-13	1995-02-16	Hoechst Ag	Harnstoffsubstituierte Benzoylguandine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

1996
- 1996-01-31 DE DE19603425A patent/DE19603425A1/de not_active Withdrawn
1997
- 1997-01-08 PL PL97317844A patent/PL317844A1/xx unknown
- 1997-01-20 EP EP97100776A patent/EP0787717A1/de not_active Withdrawn
- 1997-01-29 IL IL12009397A patent/IL120093A0/xx unknown
- 1997-01-29 HU HU9700277A patent/HUP9700277A3/hu unknown
- 1997-01-29 NZ NZ314145A patent/NZ314145A/en unknown
- 1997-01-29 AR ARP970100360A patent/AR005596A1/es unknown
- 1997-01-29 CZ CZ97271A patent/CZ27197A3/cs unknown
- 1997-01-29 SK SK127-97A patent/SK12797A3/sk unknown
- 1997-01-29 AU AU12390/97A patent/AU1239097A/en not_active Abandoned
- 1997-01-29 TW TW086100957A patent/TW430642B/zh active
- 1997-01-29 TR TR97/00059A patent/TR199700059A2/xx unknown
- 1997-01-30 CA CA002196388A patent/CA2196388A1/en not_active Abandoned
- 1997-01-30 BR BR9700817A patent/BR9700817A/pt not_active Application Discontinuation
- 1997-01-30 JP JP9016046A patent/JPH09221465A/ja active Pending
- 1997-01-30 NO NO970406A patent/NO970406L/no unknown
- 1997-01-30 ZA ZA97770A patent/ZA97770B/xx unknown
- 1997-01-30 HR HR19603425.6A patent/HRP970057A2/hr not_active Application Discontinuation
- 1997-01-31 KR KR1019970003012A patent/KR970059165A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
EP0787717A1 (de)	1997-08-06
NO970406D0 (no)	1997-01-30
AU1239097A (en)	1997-08-07
DE19603425A1 (de)	1997-08-07
NO970406L (no)	1997-08-01
HUP9700277A3 (en)	1998-04-28
HRP970057A2 (en)	1998-04-30
ZA97770B (en)	1997-07-31
AR005596A1 (es)	1999-06-23
PL317844A1 (en)	1997-08-04
HUP9700277A2 (en)	1997-10-28
CZ27197A3 (cs)	1998-05-13
TR199700059A2 (tr)	1997-08-21
HU9700277D0 (en)	1997-03-28
CA2196388A1 (en)	1997-08-01
JPH09221465A (ja)	1997-08-26
IL120093A0 (en)	1997-04-15
NZ314145A (en)	1997-11-24
TW430642B (en)	2001-04-21
KR970059165A (ko)	1997-08-12
BR9700817A (pt)	1998-07-07

Publication	Publication Date	Title
FI106856B (fi)	2001-04-30	Menetelmä terapeuttisesti aktiivisten heterosyklisellä ryhmällä substituoitujen bentsoyyliguanidiinijohdannaisten valmistamiseksi
KR100368513B1 (ko)	2003-03-19	퍼플루오로알킬그룹을갖는페닐-치환된알케닐카보구아니디드,이의제조방법및이를함유하는약제학적조성물
JPH06345643A (ja)	1994-12-20	置換ベンゾイルグアニジン、その製造方法、医薬または診断薬としてのその使用およびそれらを含有する医薬
RU2188191C2 (ru)	2002-08-27	Замещенные бензилоксикарбонилгуанидины, способ их получения и средство, ингибирующее na+/h+-обмен
HUT72089A (en)	1996-03-28	Substituted bicyclic heteroaryl-guanidine derivatives, pharmaceutical and diagnostical compositions containing them
SK282018B6 (sk)	2001-10-08	Substituované guanididy kyseliny škoricovej, spôsob ich výroby, ich použitie ako liečiva alebo diagnostika, ako aj liečivo, ktoré ich obsahuje
SK13196A3 (en)	1996-09-04	Alkalicly substituted benzoylguanidines, manufacturing process thereof, their use as drug or diagnostic agent and drugs containing these compositions
SK84195A3 (en)	1996-10-02	Orto-aminosubstituted benzoylguanidines, method of their manufacture, their use as medicament or diagnostic agent and a medicament containing them
RU2160727C2 (ru)	2000-12-20	Бензоилгуанидины, способ их получения, промежуточное соединение для их получения, способ ингибирования и лекарственное средство
SK122596A3 (en)	1997-05-07	Substituted benzoylguanidines, their preparation method, their application as a medicament or a diagnostic agent and medicaments containing them
JPH07224022A (ja)	1995-08-22	パーフルオロアルキル基を有するフェニル置換アルキルカルボグアニジドおよびその調製方法
US5665739A (en)	1997-09-09	Substituted benzoylguanidines, process and their preparation, their use as pharmaceutical or diagnostic, and pharmaceutical containing them
RU2182901C2 (ru)	2002-05-27	Замещенные 1-нафтоилгуанидины и лекарственное средство на их основе
SK12797A3 (en)	1998-02-04	Substituted diarylcarboxylic acid diguanidines, preparation method thereof, their use as a drug or a diagnostic agent, as well as drug containing the same
US5856344A (en)	1999-01-05	Sulfonylamino-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic aid, and medicament containing them
SK282351B6 (sk)	2002-01-07	Orto-substituované benzoylguanidíny, spôsob ich výroby, ich použitie ako liečiva alebo diagnostického prostriedku a liečivo, ktoré ich obsahuje
SK148796A3 (en)	1997-10-08	Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them
SK281753B6 (sk)	2001-07-10	Orto-substituované benzoylguanidíny, spôsob ich výroby, ich použitie ako liečiva alebo diagnostika, ako aj liečivo, ktoré ich obsahuje
JPH107644A (ja)	1998-01-13	オルト−置換されたベンゾイルグアニジン、それらの製造方法、医薬または診断薬としてのそれらの使用およびそれらを含有する医薬
US5731350A (en)	1998-03-24	Substituted benzenedicarboxylic acid diguanides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them
SK27597A3 (en)	1997-11-05	Ortho-substituted benzoylguanidines, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing the same