SK148896A3 - Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them - Google Patents

Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them Download PDF

Info

Publication number: SK148896A3
Authority: SK; Slovakia
Prior art keywords: group; trifluoromethyl; carbon atoms; substituted; methyl
Prior art date: 1995-11-20

Application number

SK1488-96A

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.)

1995-11-20

Filing date

1996-11-18

Publication date

1997-10-08

1995-11-20 Priority claimed from DE19543194A external-priority patent/DE19543194A1/de

1996-07-01 Priority claimed from DE1996126327 external-priority patent/DE19626327A1/de

1996-11-18 Application filed by Hoechst Ag filed Critical Hoechst Ag

1997-10-08 Publication of SK148896A3 publication Critical patent/SK148896A3/sk

Links

XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims abstract description 25
239000003814 drug Substances 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 8
229940079593 drug Drugs 0.000 title claims description 4
229940039227 diagnostic agent Drugs 0.000 title description 2
239000000032 diagnostic agent Substances 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 50
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 70
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 67
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
229910052801 chlorine Inorganic materials 0.000 claims description 46
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
229910052731 fluorine Inorganic materials 0.000 claims description 43
125000001424 substituent group Chemical group 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
125000001153 fluoro group Chemical group F* 0.000 claims description 32
239000000460 chlorine Substances 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 30
125000001309 chloro group Chemical group Cl* 0.000 claims description 26
-1 benzoic dicarboxylic acids Chemical class 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 15
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
230000000302 ischemic effect Effects 0.000 claims description 8
210000000056 organ Anatomy 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 8
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000004663 cell proliferation Effects 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
206010016654 Fibrosis Diseases 0.000 claims description 4
206010020852 Hypertonia Diseases 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
230000004761 fibrosis Effects 0.000 claims description 4
230000005764 inhibitory process Effects 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
239000011593 sulfur Substances 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
206010020718 hyperplasia Diseases 0.000 claims description 3
238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
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238000001356 surgical procedure Methods 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 2
208000002249 Diabetes Complications Diseases 0.000 claims description 2
206010012655 Diabetic complications Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
230000000879 anti-atherosclerotic effect Effects 0.000 claims description 2
206010003119 arrhythmia Diseases 0.000 claims description 2
201000011510 cancer Diseases 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
230000003176 fibrotic effect Effects 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
230000002062 proliferating effect Effects 0.000 claims description 2
238000003860 storage Methods 0.000 claims description 2
230000006793 arrhythmia Effects 0.000 claims 1
238000003745 diagnosis Methods 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
210000003734 kidney Anatomy 0.000 claims 1
210000004185 liver Anatomy 0.000 claims 1
210000001428 peripheral nervous system Anatomy 0.000 claims 1
238000004321 preservation Methods 0.000 claims 1
101100114470 Arabidopsis thaliana COR28 gene Proteins 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
239000011734 sodium Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 10
239000000203 mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 7
210000003743 erythrocyte Anatomy 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229960004198 guanidine Drugs 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000004941 influx Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
244000166550 Strophanthus gratus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
239000013078 crystal Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000007574 infarction Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
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230000008018 melting Effects 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
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235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-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
YVHYXEKWROLVIT-UHFFFAOYSA-N 5-cyclohexylbenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(=O)O)=CC(C2CCCCC2)=C1 YVHYXEKWROLVIT-UHFFFAOYSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
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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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 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
150000007513 acids Chemical class 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 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
210000004369 blood Anatomy 0.000 description 2
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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
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206010012601 diabetes mellitus Diseases 0.000 description 2
XMWPXWPRLLEJDF-UHFFFAOYSA-N dimethyl 5-[3,5-bis(trifluoromethyl)phenyl]benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 XMWPXWPRLLEJDF-UHFFFAOYSA-N 0.000 description 2
XKXIJIWVCNPXNK-UHFFFAOYSA-N dimethyl 5-cyclohexylbenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C2CCCCC2)=C1 XKXIJIWVCNPXNK-UHFFFAOYSA-N 0.000 description 2
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DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 2
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239000008103 glucose Substances 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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BSPBOZTXYSWGKE-UHFFFAOYSA-N 5-[3,5-bis(trifluoromethyl)phenyl]benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 BSPBOZTXYSWGKE-UHFFFAOYSA-N 0.000 description 1
BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 1
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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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
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002827 triflate group Chemical group 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
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
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238000005303 weighing Methods 0.000 description 1
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- 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
- 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
- A61P9/08—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
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups

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

SK1488-96A 1995-11-20 1996-11-18 Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them SK148896A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19543194A DE19543194A1 (de)	1995-11-20	1995-11-20	Substituierte Benzoldicarbonsäure-diguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE1996126327 DE19626327A1 (de)	1996-07-01	1996-07-01	Substituierte Benzoldicarbonsäure-diguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (1)

Publication Number	Publication Date
SK148896A3 true SK148896A3 (en)	1997-10-08

Family

ID=26020503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1488-96A SK148896A3 (en)	1995-11-20	1996-11-18	Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them

Country Status (18)

Country	Link
US (1)	US5731350A (no)
EP (1)	EP0774457A1 (no)
JP (1)	JPH09169718A (no)
KR (1)	KR980009237A (no)
AR (1)	AR004332A1 (no)
AU (1)	AU7180396A (no)
BR (1)	BR9605613A (no)
CA (1)	CA2190692A1 (no)
CZ (1)	CZ338396A3 (no)
HR (1)	HRP960548A2 (no)
HU (1)	HUP9603195A3 (no)
IL (1)	IL119636A0 (no)
MX (1)	MX9605675A (no)
NO (1)	NO964904L (no)
PL (1)	PL316439A1 (no)
SK (1)	SK148896A3 (no)
TR (1)	TR199600917A2 (no)
TW (1)	TW349945B (no)

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3780027A (en) *	1970-04-29	1973-12-18	Merck & Co Inc	Anthranilic acid derivatives
US5140039A (en) *	1988-01-15	1992-08-18	Abbott Laboratories	Aminomethyl-thiochroman compounds
WO1989006534A1 (en) *	1988-01-15	1989-07-27	Abbott Laboratories	Aminomethyl-chroman and -thiochroman compounds
US5185364A (en) *	1988-01-15	1993-02-09	Abbott Laboratories	Aminomethyl-chroman and -thiochroman compounds
DE3929582A1 (de)	1989-09-06	1991-03-07	Hoechst Ag	Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament
CZ284456B6 (cs) *	1992-02-15	1998-12-16	Hoechst Aktiengesellschaft	Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje
ATE139526T1 (de) *	1992-02-15	1996-07-15	Hoechst Ag	3,5-substituierte benzoylguanidine, mit antiarrythmischer wirkung und inhibierender wirkung auf die proliferationen von zellen
ES2108144T3 (es) *	1992-02-15	1997-12-16	Hoechst Ag	Benzoilguanidinas sustituidas en orto, procedimiento para su preparacion, su utilizacion como medicamento o agente de diagnostico, asi como medicamento que las contiene.
DK0577024T3 (no) *	1992-07-01	1997-02-24	Hoechst Ag
EP0589336B1 (de) *	1992-09-22	1997-01-08	Hoechst Aktiengesellschaft	Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika
ATE198328T1 (de) *	1992-09-28	2001-01-15	Hoechst Ag	Antiarrhythmische und cardioprotektive substituierte 1(2h)-isochinoline, verfahren zu deren herstellung, diese enthaltende arzneimittel und ihre anwendung für die herstellung eines arzneimittels zur behandlung von herzinsuffizienzen
DK0600371T3 (da) *	1992-12-02	1999-09-20	Hoechst Ag	Guanidinalkyl-1,1-bisphosphonsyrederivater, fremgangsmåde til deres fremstilling samt deres anvendelse
TW250479B (no) *	1992-12-15	1995-07-01	Hoechst Ag
TW250477B (no) *	1992-12-15	1995-07-01	Hoechst Ag
ATE151071T1 (de) *	1992-12-16	1997-04-15	Hoechst Ag	3,5-substituierte aminobenzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltendes medikament
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
EP0612723B1 (de) *	1993-02-20	1997-08-27	Hoechst Aktiengesellschaft	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, als Inhibitoren des zellulären Na+/H+-Austauschs oder als Diagnostikum sowie sie enthaltendes Medikament
DE59401361D1 (de) *	1993-02-23	1997-02-06	Hoechst Ag	Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe- Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika
IL109570A0 (en) *	1993-05-17	1994-08-26	Fujisawa Pharmaceutical Co	Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof
DE4318658A1 (de) *	1993-06-04	1994-12-08	Hoechst Ag	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4318756A1 (de) *	1993-06-05	1994-12-08	Hoechst Ag	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4325822A1 (de) *	1993-07-31	1995-02-02	Hoechst Ag	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
EP0639573A1 (de) *	1993-08-03	1995-02-22	Hoechst Aktiengesellschaft	Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament
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
DE4328869A1 (de) *	1993-08-27	1995-03-02	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4344550A1 (de) *	1993-12-24	1995-06-29	Hoechst Ag	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
TW415937B (en) *	1994-01-25	2000-12-21	Hoechst Ag	Phenyl-substituted alkylcarboxylic acid guanidides bearing perfluoroalkyl groups, process for their preparation, their use as a medicament or diagnostic, and medicament containing them
DE4412334A1 (de) *	1994-04-11	1995-10-19	Hoechst Ag	Substituierte N-Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4415873A1 (de) *	1994-05-05	1995-11-09	Hoechst Ag	Substituierte bizyklische Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4417004A1 (de) *	1994-05-13	1995-11-16	Hoechst Ag	Perfluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4422685A1 (de) *	1994-06-29	1996-01-04	Hoechst Ag	Ortho-amino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
IL114670A0 (en) *	1994-08-05	1995-11-27	Fujisawa Pharmaceutical Co	Guanidine derivatives pharmaceutical compositions containing the same and processes for the preparation thereof
DE4432106A1 (de) *	1994-09-09	1996-03-14	Hoechst Ag	Mit Heterocyclen-N-Oxid-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum, sie enthaltendes Medikament sowie Zwischenprodukte zu ihrer Herstellung
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
DE4432101A1 (de) *	1994-09-09	1996-03-14	Hoechst Ag	Aminosäure-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
DE59603311D1 (de) *	1995-01-30	1999-11-18	Hoechst Ag	Basisch-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

1996
- 1996-10-08 PL PL96316439A patent/PL316439A1/xx unknown
- 1996-11-07 US US08/747,004 patent/US5731350A/en not_active Expired - Fee Related
- 1996-11-07 EP EP96117821A patent/EP0774457A1/de not_active Withdrawn
- 1996-11-18 TW TW085114094A patent/TW349945B/zh active
- 1996-11-18 AU AU71803/96A patent/AU7180396A/en not_active Abandoned
- 1996-11-18 AR ARP960105231A patent/AR004332A1/es unknown
- 1996-11-18 IL IL11963696A patent/IL119636A0/xx unknown
- 1996-11-18 SK SK1488-96A patent/SK148896A3/sk unknown
- 1996-11-18 CZ CZ963383A patent/CZ338396A3/cs unknown
- 1996-11-18 TR TR96/00917A patent/TR199600917A2/xx unknown
- 1996-11-19 JP JP8307830A patent/JPH09169718A/ja active Pending
- 1996-11-19 HR HR19626327.1A patent/HRP960548A2/hr not_active Application Discontinuation
- 1996-11-19 CA CA002190692A patent/CA2190692A1/en not_active Abandoned
- 1996-11-19 NO NO964904A patent/NO964904L/no unknown
- 1996-11-19 BR BR9605613A patent/BR9605613A/pt not_active Application Discontinuation
- 1996-11-19 MX MX9605675A patent/MX9605675A/es unknown
- 1996-11-19 HU HU9603195A patent/HUP9603195A3/hu unknown
- 1996-11-20 KR KR1019960055717A patent/KR980009237A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
HRP960548A2 (en)	1998-02-28
EP0774457A1 (de)	1997-05-21
AU7180396A (en)	1997-05-29
NO964904D0 (no)	1996-11-19
NO964904L (no)	1997-05-21
HU9603195D0 (en)	1997-01-28
TR199600917A2 (tr)	1997-06-21
HUP9603195A3 (en)	1997-11-28
CZ338396A3 (cs)	1998-05-13
CA2190692A1 (en)	1997-05-21
PL316439A1 (en)	1997-05-26
AR004332A1 (es)	1998-11-04
HUP9603195A2 (en)	1997-05-28
TW349945B (en)	1999-01-11
IL119636A0 (en)	1997-02-18
MX9605675A (es)	1997-08-30
US5731350A (en)	1998-03-24
JPH09169718A (ja)	1997-06-30
BR9605613A (pt)	1998-08-18
KR980009237A (ko)	1998-04-30

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US5708034A (en)	1998-01-13	Substituted sulfonimidamides, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
HRP960230A2 (en)	1997-12-31	Fluorophenyl substituted alkenyl carboxylic acid guanidines, processes for their preparation, their use as medicinal or diagnostic agent as well as medicaments containing them
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SK122596A3 (en)	1997-05-07	Substituted benzoylguanidines, their preparation method, their application as a medicament or a diagnostic agent and medicaments containing them
RU2182901C2 (ru)	2002-05-27	Замещенные 1-нафтоилгуанидины и лекарственное средство на их основе
AU706231B2 (en)	1999-06-10	Sulfonylamino-substituted benzoylguanidines, a process for their preparation, their use as medicament or diagnostic aid, and medicament containing them
SK148896A3 (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
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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
MXPA96005675A (en)	1997-08-01	Diguanididas of bencenodicarboxilicos substitute acids, procedure for its preparation, its employment as a diagnostic medicine or agent, as well as a medication that the
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