FR2459241A1 - Nouveaux pyridylaminotriazoles et composition pharmaceutique les contenant - Google Patents
Nouveaux pyridylaminotriazoles et composition pharmaceutique les contenant Download PDFInfo
- Publication number
- FR2459241A1 FR2459241A1 FR8013401A FR8013401A FR2459241A1 FR 2459241 A1 FR2459241 A1 FR 2459241A1 FR 8013401 A FR8013401 A FR 8013401A FR 8013401 A FR8013401 A FR 8013401A FR 2459241 A1 FR2459241 A1 FR 2459241A1
- Authority
- FR
- France
- Prior art keywords
- amino
- triazole
- mono
- pyridyl
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- -1 4-PYRIDYL Chemical class 0.000 claims abstract description 102
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- PHYOJNNPPUPKEA-UHFFFAOYSA-N 5-pyridin-4-yl-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2C=CN=CC=2)=N1 PHYOJNNPPUPKEA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003699 antiulcer agent Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- IAZIYGZZKVBVTH-UHFFFAOYSA-N 4-(3-amino-1h-1,2,4-triazol-5-yl)-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC(C=2NN=C(N)N=2)=C1 IAZIYGZZKVBVTH-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000000767 anti-ulcer Effects 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- 239000000203 mixture Substances 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
- 239000000047 product Substances 0.000 description 41
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 40
- 239000007787 solid Substances 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- 239000012467 final product Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000126 substance Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- 239000003480 eluent Substances 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000000967 suction filtration Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000003852 triazoles Chemical class 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- 208000008469 Peptic Ulcer Diseases 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- QMKZZQPPJRWDED-UHFFFAOYSA-N 2-aminopyridine-4-carboxylic acid Chemical compound NC1=CC(C(O)=O)=CC=N1 QMKZZQPPJRWDED-UHFFFAOYSA-N 0.000 description 5
- QXCOHSRHFCHCHN-UHFFFAOYSA-N 2-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Cl)=C1 QXCOHSRHFCHCHN-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 5
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 108010079943 Pentagastrin Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- 210000004211 gastric acid Anatomy 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 4
- 229960000444 pentagastrin Drugs 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 3
- MZIIYNBBSHJOLD-UHFFFAOYSA-N 2-chloropyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC(Cl)=C1 MZIIYNBBSHJOLD-UHFFFAOYSA-N 0.000 description 3
- 206010016717 Fistula Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000003890 fistula Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- VXTAZRUAUNHEFO-UHFFFAOYSA-N 2-amino-n-(diaminomethylideneamino)pyridine-4-carboxamide Chemical class NC(=N)NNC(=O)C1=CC=NC(N)=C1 VXTAZRUAUNHEFO-UHFFFAOYSA-N 0.000 description 2
- JWUWTBDKCYJSLE-UHFFFAOYSA-N 2-aminopyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC(N)=C1 JWUWTBDKCYJSLE-UHFFFAOYSA-N 0.000 description 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 2
- OYJDWYWNACFAQB-UHFFFAOYSA-N 4-(1h-1,2,4-triazol-5-yl)pyridine Chemical compound C1=NNC(C=2C=CN=CC=2)=N1 OYJDWYWNACFAQB-UHFFFAOYSA-N 0.000 description 2
- FHCPSUQTPGBNTR-UHFFFAOYSA-N 5-(2,6-dichloropyridin-4-yl)-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2C=C(Cl)N=C(Cl)C=2)=N1 FHCPSUQTPGBNTR-UHFFFAOYSA-N 0.000 description 2
- NIIQWECJBWGDNJ-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2C=C(Cl)N=CC=2)=N1 NIIQWECJBWGDNJ-UHFFFAOYSA-N 0.000 description 2
- CZTQZXZIADLWOZ-UHFFFAOYSA-O 8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1SC2C(NC(=O)CC=3SC=CC=3)C(=O)N2C(C(=O)O)=C1C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-UHFFFAOYSA-O 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- WJAASTDRAAMYNK-UHFFFAOYSA-N benzyl carbamimidothioate;hydron;chloride Chemical compound Cl.NC(=N)SCC1=CC=CC=C1 WJAASTDRAAMYNK-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
- 229960000582 mepyramine Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- 235000011083 sodium citrates Nutrition 0.000 description 2
- 239000008259 solid foam Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- MPWSRGAWRAYBJK-UHFFFAOYSA-N (4-tert-butylphenyl)methanamine Chemical compound CC(C)(C)C1=CC=C(CN)C=C1 MPWSRGAWRAYBJK-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- PEFSXVDJORRUCT-UHFFFAOYSA-N 2-(2,2,2-trifluoroethylamino)pyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC(NCC(F)(F)F)=C1 PEFSXVDJORRUCT-UHFFFAOYSA-N 0.000 description 1
- CJINBGGVTQYDFK-UHFFFAOYSA-N 2-(2,2,2-trifluoroethylamino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NCC(F)(F)F)=C1 CJINBGGVTQYDFK-UHFFFAOYSA-N 0.000 description 1
- XVUXMMXRSXRTAP-UHFFFAOYSA-N 2-(butylamino)pyridine-4-carboxylic acid Chemical compound CCCCNC1=CC(C(O)=O)=CC=N1 XVUXMMXRSXRTAP-UHFFFAOYSA-N 0.000 description 1
- JGGZIHFGEMXEQU-UHFFFAOYSA-N 2-(dimethylamino)pyridine-4-carbohydrazide Chemical compound CN(C)C1=CC(C(=O)NN)=CC=N1 JGGZIHFGEMXEQU-UHFFFAOYSA-N 0.000 description 1
- ONNSLUVHHJGCMH-UHFFFAOYSA-N 2-(dimethylamino)pyridine-4-carboxylic acid Chemical compound CN(C)C1=CC(C(O)=O)=CC=N1 ONNSLUVHHJGCMH-UHFFFAOYSA-N 0.000 description 1
- ITIHDECEGISHMF-UHFFFAOYSA-N 2-(methylamino)pyridine-4-carbohydrazide Chemical compound CNC1=CC(C(=O)NN)=CC=N1 ITIHDECEGISHMF-UHFFFAOYSA-N 0.000 description 1
- RDXOHTUCDYEDPE-UHFFFAOYSA-N 2-(propan-2-ylamino)pyridine-4-carboxylic acid Chemical compound CC(C)NC1=CC(C(O)=O)=CC=N1 RDXOHTUCDYEDPE-UHFFFAOYSA-N 0.000 description 1
- BARJEOMVLKJPRB-UHFFFAOYSA-N 2-amino-6-methylpyridine-4-carboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(N)=N1 BARJEOMVLKJPRB-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- USKGNHNXYLHIIC-UHFFFAOYSA-N 3-(3-amino-1h-1,2,4-triazol-5-yl)pyridin-2-amine;hydrate Chemical compound O.NC1=NNC(C=2C(=NC=CC=2)N)=N1 USKGNHNXYLHIIC-UHFFFAOYSA-N 0.000 description 1
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 1
- GGAJJLWUCNCXCS-UHFFFAOYSA-N 3-[benzyl(methyl)amino]pyridine-4-carboxylic acid Chemical compound C=1N=CC=C(C(O)=O)C=1N(C)CC1=CC=CC=C1 GGAJJLWUCNCXCS-UHFFFAOYSA-N 0.000 description 1
- MYAZXWFEMDJTFE-UHFFFAOYSA-N 3-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1Cl MYAZXWFEMDJTFE-UHFFFAOYSA-N 0.000 description 1
- UZJJIDUWHYUOQW-UHFFFAOYSA-N 4-(3-amino-1h-1,2,4-triazol-5-yl)-6-methylpyridin-2-amine Chemical compound NC1=NC(C)=CC(C=2NN=C(N)N=2)=C1 UZJJIDUWHYUOQW-UHFFFAOYSA-N 0.000 description 1
- LXIFMOWBIITJSB-UHFFFAOYSA-N 4-[3-(dimethylamino)-1h-1,2,4-triazol-5-yl]-n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=NNC(C=2C=C(N=CC=2)N(C)C)=N1 LXIFMOWBIITJSB-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010065713 Gastric Fistula Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 229940124056 Histamine H1 receptor antagonist Drugs 0.000 description 1
- 206010020601 Hyperchlorhydria Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 238000005267 amalgamation Methods 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- VZNRGKFNPCXMFL-UHFFFAOYSA-N methyl 2-(2,2,2-trifluoroethylamino)pyridine-4-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=NC(NCC(F)(F)F)=C1 VZNRGKFNPCXMFL-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/049,737 US4276297A (en) | 1979-06-18 | 1979-06-18 | Pyridylaminotriazole therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2459241A1 true FR2459241A1 (fr) | 1981-01-09 |
| FR2459241B1 FR2459241B1 (enExample) | 1983-06-17 |
Family
ID=21961428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8013401A Granted FR2459241A1 (fr) | 1979-06-18 | 1980-06-17 | Nouveaux pyridylaminotriazoles et composition pharmaceutique les contenant |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4276297A (enExample) |
| JP (1) | JPS565477A (enExample) |
| KR (2) | KR840002173B1 (enExample) |
| AR (2) | AR225766A1 (enExample) |
| AT (2) | AT375655B (enExample) |
| BE (1) | BE883859A (enExample) |
| CA (1) | CA1140133A (enExample) |
| CH (1) | CH644375A5 (enExample) |
| DE (1) | DE3022302C2 (enExample) |
| DK (1) | DK258180A (enExample) |
| ES (2) | ES492522A0 (enExample) |
| FI (1) | FI69842C (enExample) |
| FR (1) | FR2459241A1 (enExample) |
| GB (1) | GB2053910B (enExample) |
| GR (1) | GR68731B (enExample) |
| IE (1) | IE49913B1 (enExample) |
| IL (1) | IL60332A (enExample) |
| IT (1) | IT1140993B (enExample) |
| LU (1) | LU82527A1 (enExample) |
| NL (1) | NL182641C (enExample) |
| PH (1) | PH16875A (enExample) |
| PT (1) | PT71399A (enExample) |
| SE (1) | SE441745B (enExample) |
| YU (2) | YU41717B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR230994A1 (es) * | 1981-08-31 | 1984-08-31 | Pfizer | Procedimiento para preparar compuesto de 3'-substituido-5'-(2-amino-4-piridil)-1',2',4'-triazol |
| JP2518515Y2 (ja) * | 1993-09-22 | 1996-11-27 | 茂郎 槇島 | 水虫用医療包帯 |
| PL415073A1 (pl) * | 2014-12-19 | 2016-06-20 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Podstawione aminotriazole przydatne jako inhibitory kwaśnej chitynazy ssaków |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2107985A1 (enExample) * | 1970-09-25 | 1972-05-12 | Merck & Co Inc | |
| US3663527A (en) * | 1968-03-01 | 1972-05-16 | Ciba Ltd | Quaternary pyridiniumazoleazo dyestuffs |
| US3813400A (en) * | 1971-12-06 | 1974-05-28 | Wyeth John & Brother Ltd | Derivatives of 3-amino-1,2,4-triazoles |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1925654U (de) | 1965-07-23 | 1965-10-21 | Alfons Mann | Zusatzeinrichtung fuer vergaser an benzinmotoren zur steigerung der motorenleistung. |
| GB1264798A (enExample) | 1968-07-10 | 1972-02-23 | ||
| US3647814A (en) * | 1969-07-03 | 1972-03-07 | Rohm & Haas | Method for preparing 4-substituted-1 2 4-triazoles |
| NL7112373A (enExample) * | 1970-09-25 | 1972-03-28 | ||
| US3879404A (en) * | 1972-07-07 | 1975-04-22 | John J Baldwin | Certain 5-(pyridyl)-3(phenyl)-1,2,4-triazoles |
| US3873563A (en) * | 1972-09-29 | 1975-03-25 | Sakai Chemical Industry Co | Method for manufacturing 4-amino-1,2,4-triazoles |
| US3928361A (en) * | 1973-05-21 | 1975-12-23 | Merck & Co Inc | 1-(Sulfamoylphenylalkyl)-3,5-dipyridyl-1,2,4 triazoles |
| US3984558A (en) * | 1973-05-21 | 1976-10-05 | Merck & Co., Inc. | 1,3,5-Trisubstituted-1,2,4-triazole compounds used as bronchodilators |
-
1979
- 1979-06-18 US US06/049,737 patent/US4276297A/en not_active Expired - Lifetime
-
1980
- 1980-06-06 CH CH440280A patent/CH644375A5/fr not_active IP Right Cessation
- 1980-06-06 AR AR281310A patent/AR225766A1/es active
- 1980-06-12 GR GR62187A patent/GR68731B/el unknown
- 1980-06-13 DE DE3022302A patent/DE3022302C2/de not_active Expired
- 1980-06-16 JP JP8126680A patent/JPS565477A/ja active Granted
- 1980-06-16 CA CA000354112A patent/CA1140133A/en not_active Expired
- 1980-06-16 PT PT71399A patent/PT71399A/pt unknown
- 1980-06-16 LU LU82527A patent/LU82527A1/fr unknown
- 1980-06-16 FI FI801929A patent/FI69842C/fi not_active IP Right Cessation
- 1980-06-16 PH PH24137A patent/PH16875A/en unknown
- 1980-06-16 YU YU1587/80A patent/YU41717B/xx unknown
- 1980-06-17 DK DK258180A patent/DK258180A/da not_active Application Discontinuation
- 1980-06-17 BE BE0/201060A patent/BE883859A/fr not_active IP Right Cessation
- 1980-06-17 FR FR8013401A patent/FR2459241A1/fr active Granted
- 1980-06-17 SE SE8004498A patent/SE441745B/sv not_active IP Right Cessation
- 1980-06-17 AT AT0319280A patent/AT375655B/de not_active IP Right Cessation
- 1980-06-17 KR KR1019800002385A patent/KR840002173B1/ko not_active Expired
- 1980-06-17 GB GB8019674A patent/GB2053910B/en not_active Expired
- 1980-06-17 IL IL60332A patent/IL60332A/xx unknown
- 1980-06-17 IE IE1250/80A patent/IE49913B1/en unknown
- 1980-06-17 NL NLAANVRAGE8003496,A patent/NL182641C/xx not_active IP Right Cessation
- 1980-06-17 ES ES492522A patent/ES492522A0/es active Granted
- 1980-06-17 IT IT22825/80A patent/IT1140993B/it active
-
1981
- 1981-01-26 ES ES498821A patent/ES8201155A1/es not_active Expired
- 1981-08-04 AR AR286650A patent/AR227436A1/es active
-
1982
- 1982-11-24 YU YU2633/82A patent/YU41536B/xx unknown
-
1983
- 1983-08-29 AT AT0307583A patent/AT375656B/de not_active IP Right Cessation
-
1984
- 1984-04-30 KR KR1019840002324A patent/KR840002172B1/ko not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3663527A (en) * | 1968-03-01 | 1972-05-16 | Ciba Ltd | Quaternary pyridiniumazoleazo dyestuffs |
| FR2107985A1 (enExample) * | 1970-09-25 | 1972-05-12 | Merck & Co Inc | |
| US3813400A (en) * | 1971-12-06 | 1974-05-28 | Wyeth John & Brother Ltd | Derivatives of 3-amino-1,2,4-triazoles |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100371297B1 (ko) | 치환된티아졸리딘디온유도체 | |
| JPH02292272A (ja) | 抗高血糖症剤として有用な新規ナフタレニルアルキル―３ｈ―１，２，３，５―オキサチアジアゾール２―オキシド類 | |
| LU79761A1 (fr) | Procede de preparation de nouveaux composes de phtalazine et de composition pharmaceutique les contenant | |
| FR2487348A1 (fr) | Nouvelles oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique | |
| BE898278A (fr) | Benzoxazines antipsychotiques. | |
| FR2489823A1 (fr) | Nouvelles n-((4-(3-pyridyle substitue en position 3)-piperazino)alkyl)azaspirodecanediones, leur procede de preparation et medicament les contenant | |
| FR2459241A1 (fr) | Nouveaux pyridylaminotriazoles et composition pharmaceutique les contenant | |
| CH655104A5 (fr) | Derives heterocycliques triazoliques, procedes pour leur preparation et compositions pharmaceutiques les comportant. | |
| MC1143A1 (fr) | Derives de thiouree | |
| CH619950A5 (en) | Process for the preparation of condensed pyrimidines | |
| EP0362006A1 (fr) | Dérivés de quinoléine, leurs procédés de préparation et les médicaments les contenant | |
| US4317914A (en) | Oxazolines | |
| FR2483233A1 (fr) | Compositions cardiotoniques contenant des aminophenylpyridines, nouvelles aminophenylpyridines et leur preparation | |
| CH642953A5 (fr) | Derives acyles de ih-1,2,4-triazole, leur utilisation et procede de synthese desdits derives. | |
| FR2460950A1 (fr) | Nouvelles 4-phenyl-4,5,6,7-tetrahydropyrrolo(2,3-c)pyridines, procede pour leur preparation et medicaments les renfermant | |
| CH594667A5 (en) | Hexahydro-2H-pyrazolo(4,3-C) pyridine derivs | |
| BE882071A (fr) | Composes du guanidinothiazole utiles comme inhibiteurs des secretions d'acide gastrique, leurs procedes de preparation et les compositions medicales contenant de tels composes | |
| BE831758A (fr) | Derives de substitution de 2h-pyrane-2,6 (3h)-dione et leurs utilisations | |
| BE889757A (fr) | Nouvelles oxazolidine -2,4- diones substituees en position 5 douees d'activite hypoglycemique | |
| LU85410A1 (fr) | 1-phenoxy-3-hydroxyindolylalkylamino-3-propanols et leur preparation | |
| MC513A1 (fr) | Nouveaux dérivés de la semicarbazide et leur preparation | |
| CA2038199A1 (fr) | Derives du 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime, leur procede de preparation et leur application comme medicaments | |
| BE847871A (fr) | Nouveaux amides, utiles en tant qu'inhibiteurs de l'ovulation | |
| BE875164A (fr) | N-iminomethylpiperidines substituees | |
| JPH05286951A (ja) | ２−（置換イミノ）チアゾリジン誘導体および製薬上許容されるその塩、それらの製造法、並びにそれらを活性成分として含んでなる製剤組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |