CN1052305A - 新吡啶衍生物、含它们的药物组合物及其制备方法 - Google Patents
新吡啶衍生物、含它们的药物组合物及其制备方法 Download PDFInfo
- Publication number
- CN1052305A CN1052305A CN90109755A CN90109755A CN1052305A CN 1052305 A CN1052305 A CN 1052305A CN 90109755 A CN90109755 A CN 90109755A CN 90109755 A CN90109755 A CN 90109755A CN 1052305 A CN1052305 A CN 1052305A
- Authority
- CN
- China
- Prior art keywords
- pyridine
- formula
- cyanoimino
- benzyl
- definition
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 42
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 4
- 150000001721 carbon Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- 230000036407 pain Effects 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- -1 1-(3-methoxy-benzyl) pyridine Chemical compound 0.000 claims description 10
- RRYOJSJRGRFJDN-UHFFFAOYSA-N (1-benzylpyridin-2-ylidene)cyanamide Chemical compound N#CN=C1C=CC=CN1CC1=CC=CC=C1 RRYOJSJRGRFJDN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- FBUHFQUZAYMTOM-UHFFFAOYSA-N pyridin-2-ylcyanamide Chemical compound N#CNC1=CC=CC=N1 FBUHFQUZAYMTOM-UHFFFAOYSA-N 0.000 claims description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- NNFOHTKXYYCOCC-UHFFFAOYSA-N n-(1-benzylpyridin-2-ylidene)nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=CC=C1 NNFOHTKXYYCOCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims 5
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000000890 drug combination Substances 0.000 claims 1
- 210000004211 gastric acid Anatomy 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 abstract description 7
- 230000027119 gastric acid secretion Effects 0.000 abstract description 4
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 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 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- HPUGHEMIKXEBDN-UHFFFAOYSA-N [1-[(2-chlorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound ClC1=CC=CC=C1CN1C(=NC#N)C=CC=C1 HPUGHEMIKXEBDN-UHFFFAOYSA-N 0.000 description 2
- PBGXNMTZWKHAOL-UHFFFAOYSA-N [1-[(2-fluorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound FC1=CC=CC=C1CN1C(=NC#N)C=CC=C1 PBGXNMTZWKHAOL-UHFFFAOYSA-N 0.000 description 2
- BZLUZSYJLKFGBT-UHFFFAOYSA-N [1-[(2-methylphenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound CC1=CC=CC=C1CN1C(=NC#N)C=CC=C1 BZLUZSYJLKFGBT-UHFFFAOYSA-N 0.000 description 2
- PFYFXVBPTAJTHU-UHFFFAOYSA-N [1-[(3-chlorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound ClC1=CC=CC(CN2C(C=CC=C2)=NC#N)=C1 PFYFXVBPTAJTHU-UHFFFAOYSA-N 0.000 description 2
- MJVADCSFEVDYNE-UHFFFAOYSA-N [1-[(4-fluorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound C1=CC(F)=CC=C1CN1C(=NC#N)C=CC=C1 MJVADCSFEVDYNE-UHFFFAOYSA-N 0.000 description 2
- PGHSRKBOKCRQFM-UHFFFAOYSA-N [1-[[3-(trifluoromethyl)phenyl]methyl]pyridin-2-ylidene]cyanamide Chemical compound FC(F)(F)C1=CC=CC(CN2C(C=CC=C2)=NC#N)=C1 PGHSRKBOKCRQFM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VLZLEPNAKIFDQJ-UHFFFAOYSA-N n-pyridin-2-ylnitramide Chemical group [O-][N+](=O)NC1=CC=CC=N1 VLZLEPNAKIFDQJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FOQPPWJJDPHABU-UHFFFAOYSA-N 1-(1-methylpyridin-2-ylidene)guanidine Chemical class CN1C=CC=CC1=NC(N)=N FOQPPWJJDPHABU-UHFFFAOYSA-N 0.000 description 1
- RYUQBUAHZATWTO-UHFFFAOYSA-N 1-benzylpyridin-2-imine;hydrobromide Chemical compound [Br-].NC1=CC=CC=[N+]1CC1=CC=CC=C1 RYUQBUAHZATWTO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- HJSRHJLZFYUICE-UHFFFAOYSA-N [1-[(2,6-dichlorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound ClC1=CC=CC(Cl)=C1CN1C(=NC#N)C=CC=C1 HJSRHJLZFYUICE-UHFFFAOYSA-N 0.000 description 1
- DSDLQOPBRRTYLG-UHFFFAOYSA-N [1-[(2-nitrophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound [O-][N+](=O)C1=CC=CC=C1CN1C(=NC#N)C=CC=C1 DSDLQOPBRRTYLG-UHFFFAOYSA-N 0.000 description 1
- OBDZTCKZACYFOH-UHFFFAOYSA-N [1-[(3-methoxyphenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound COC1=CC=CC(CN2C(C=CC=C2)=NC#N)=C1 OBDZTCKZACYFOH-UHFFFAOYSA-N 0.000 description 1
- MFLKSTHFTKOCRL-UHFFFAOYSA-N [1-[(4-bromophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound C1=CC(Br)=CC=C1CN1C(=NC#N)C=CC=C1 MFLKSTHFTKOCRL-UHFFFAOYSA-N 0.000 description 1
- XJCDFOUSUSEHOK-UHFFFAOYSA-N [1-[(4-chlorophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound C1=CC(Cl)=CC=C1CN1C(=NC#N)C=CC=C1 XJCDFOUSUSEHOK-UHFFFAOYSA-N 0.000 description 1
- QEGCBSSPDBXDGN-UHFFFAOYSA-N [1-[(4-methylphenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound C1=CC(C)=CC=C1CN1C(=NC#N)C=CC=C1 QEGCBSSPDBXDGN-UHFFFAOYSA-N 0.000 description 1
- WOTUEQJKSVKBFC-UHFFFAOYSA-N [1-[(4-nitrophenyl)methyl]pyridin-2-ylidene]cyanamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C(=NC#N)C=CC=C1 WOTUEQJKSVKBFC-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- XCPMZMUTHQUPSF-UHFFFAOYSA-N benzyl(pyridin-2-yl)cyanamide Chemical compound C=1C=CC=NC=1N(C#N)CC1=CC=CC=C1 XCPMZMUTHQUPSF-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013110 gastrectomy Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- POUAXWUJTSPQNY-UHFFFAOYSA-N n-[1-[(2-chlorophenyl)methyl]pyridin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=CC=C1Cl POUAXWUJTSPQNY-UHFFFAOYSA-N 0.000 description 1
- QXDYWXVCPGOVMJ-UHFFFAOYSA-N n-[1-[(2-fluorophenyl)methyl]pyridin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=CC=C1F QXDYWXVCPGOVMJ-UHFFFAOYSA-N 0.000 description 1
- IQKUYPVPZCMDBQ-UHFFFAOYSA-N n-[1-[(4-bromophenyl)methyl]pyridin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=C(Br)C=C1 IQKUYPVPZCMDBQ-UHFFFAOYSA-N 0.000 description 1
- DMCGOPULNHEEPR-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]pyridin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=C(Cl)C=C1 DMCGOPULNHEEPR-UHFFFAOYSA-N 0.000 description 1
- DMGURWZEMWMLSD-UHFFFAOYSA-N n-[1-[(4-nitrophenyl)methyl]pyridin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1C=CC=CN1CC1=CC=C([N+]([O-])=O)C=C1 DMGURWZEMWMLSD-UHFFFAOYSA-N 0.000 description 1
- REABEKPMOZXDLI-UHFFFAOYSA-N n-benzyl-n-pyridin-2-ylnitramide;hydrochloride Chemical compound Cl.C=1C=CC=NC=1N([N+](=O)[O-])CC1=CC=CC=C1 REABEKPMOZXDLI-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D213/72—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU5807/89 | 1989-11-07 | ||
| HU895807A HU207047B (en) | 1989-11-07 | 1989-11-07 | Process for producing new pyridine derivatives and pharmaceutical copositions comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1052305A true CN1052305A (zh) | 1991-06-19 |
Family
ID=10970765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN90109755A Pending CN1052305A (zh) | 1989-11-07 | 1990-11-07 | 新吡啶衍生物、含它们的药物组合物及其制备方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5155123A (enExample) |
| EP (1) | EP0427526B1 (enExample) |
| JP (1) | JPH03169862A (enExample) |
| KR (1) | KR910009663A (enExample) |
| CN (1) | CN1052305A (enExample) |
| AR (1) | AR248394A1 (enExample) |
| AT (1) | ATE109137T1 (enExample) |
| AU (1) | AU631261B2 (enExample) |
| CA (1) | CA2029222A1 (enExample) |
| DE (1) | DE69011046T2 (enExample) |
| DK (1) | DK0427526T3 (enExample) |
| ES (1) | ES2057441T3 (enExample) |
| FI (1) | FI905493A7 (enExample) |
| HU (1) | HU207047B (enExample) |
| IL (1) | IL96252A (enExample) |
| IN (1) | IN171700B (enExample) |
| NO (1) | NO177263C (enExample) |
| NZ (1) | NZ235984A (enExample) |
| PH (1) | PH27440A (enExample) |
| ZA (1) | ZA908889B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103781764A (zh) * | 2011-08-26 | 2014-05-07 | 明治制果药业株式会社 | 有害生物防除剂的制造法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1035115B1 (en) | 1999-02-24 | 2004-09-29 | F. Hoffmann-La Roche Ag | 4-Phenylpyridine derivatives and their use as NK-1 receptor antagonists |
| US7288658B2 (en) | 2003-07-15 | 2007-10-30 | Hoffmann-La Roche Inc. | Process for preparation of pyridine derivatives |
| ATE453384T1 (de) | 2005-09-23 | 2010-01-15 | Hoffmann La Roche | Neue dosierformulierung |
| AU2011297160B2 (en) * | 2010-08-31 | 2014-11-20 | Mitsui Chemicals Crop & Life Solutions, Inc. | Noxious organism control agent |
| PY1960131A (es) | 2018-08-07 | 2020-11-20 | Syngenta Crop Protection Ag | Compuestos heteroatomáticos bicíclicos activos como pesticidas |
| AR117291A1 (es) | 2018-12-14 | 2021-07-28 | Syngenta Crop Protection Ag | Compuestos heterocíclicos de cianamida con actividad pesticida |
| WO2020169526A1 (en) | 2019-02-18 | 2020-08-27 | Syngenta Crop Protection Ag | Pesticidally-active cyanamide heterocyclic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1201119A (en) * | 1978-09-18 | 1986-02-25 | Mcneilab, Inc. | Diaza-cyclic derivatives of guanidine |
| HU188852B (en) * | 1983-03-16 | 1986-05-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer |
| JPH07121909B2 (ja) * | 1986-09-10 | 1995-12-25 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物及び殺虫剤 |
-
1989
- 1989-11-07 HU HU895807A patent/HU207047B/hu unknown
-
1990
- 1990-10-31 US US07/607,153 patent/US5155123A/en not_active Expired - Fee Related
- 1990-11-02 CA CA002029222A patent/CA2029222A1/en not_active Abandoned
- 1990-11-06 ZA ZA908889A patent/ZA908889B/xx unknown
- 1990-11-06 PH PH41502A patent/PH27440A/en unknown
- 1990-11-06 FI FI905493A patent/FI905493A7/fi not_active Application Discontinuation
- 1990-11-06 IN IN930/CAL/90A patent/IN171700B/en unknown
- 1990-11-06 KR KR1019900017881A patent/KR910009663A/ko not_active Withdrawn
- 1990-11-06 IL IL9625290A patent/IL96252A/en not_active IP Right Cessation
- 1990-11-06 JP JP2299084A patent/JPH03169862A/ja active Pending
- 1990-11-06 NO NO904822A patent/NO177263C/no unknown
- 1990-11-06 NZ NZ235984A patent/NZ235984A/en unknown
- 1990-11-06 AR AR90318303A patent/AR248394A1/es active
- 1990-11-06 AU AU65823/90A patent/AU631261B2/en not_active Ceased
- 1990-11-07 EP EP90312167A patent/EP0427526B1/en not_active Expired - Lifetime
- 1990-11-07 CN CN90109755A patent/CN1052305A/zh active Pending
- 1990-11-07 AT AT90312167T patent/ATE109137T1/de not_active IP Right Cessation
- 1990-11-07 ES ES90312167T patent/ES2057441T3/es not_active Expired - Lifetime
- 1990-11-07 DK DK90312167.1T patent/DK0427526T3/da active
- 1990-11-07 DE DE69011046T patent/DE69011046T2/de not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103781764A (zh) * | 2011-08-26 | 2014-05-07 | 明治制果药业株式会社 | 有害生物防除剂的制造法 |
| CN103781764B (zh) * | 2011-08-26 | 2016-07-20 | 明治制果药业株式会社 | 有害生物防除剂的制造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU631261B2 (en) | 1992-11-19 |
| HU895807D0 (en) | 1990-01-28 |
| EP0427526A1 (en) | 1991-05-15 |
| NO904822L (no) | 1991-05-08 |
| IL96252A0 (en) | 1991-08-16 |
| AR248394A1 (es) | 1995-08-18 |
| NO177263C (no) | 1995-08-16 |
| EP0427526B1 (en) | 1994-07-27 |
| NO177263B (no) | 1995-05-08 |
| DK0427526T3 (da) | 1994-08-29 |
| FI905493A7 (fi) | 1991-05-08 |
| NO904822D0 (no) | 1990-11-06 |
| DE69011046T2 (de) | 1994-11-24 |
| FI905493A0 (fi) | 1990-11-06 |
| ZA908889B (en) | 1991-10-30 |
| ES2057441T3 (es) | 1994-10-16 |
| JPH03169862A (ja) | 1991-07-23 |
| HUT55758A (en) | 1991-06-28 |
| DE69011046D1 (de) | 1994-09-01 |
| CA2029222A1 (en) | 1991-05-08 |
| HU207047B (en) | 1993-03-01 |
| KR910009663A (ko) | 1991-06-28 |
| AU6582390A (en) | 1991-05-23 |
| US5155123A (en) | 1992-10-13 |
| IN171700B (enExample) | 1992-12-12 |
| ATE109137T1 (de) | 1994-08-15 |
| PH27440A (en) | 1993-07-02 |
| IL96252A (en) | 1994-12-29 |
| NZ235984A (en) | 1992-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1105111C (zh) | 吡嗪化合物 | |
| CZ197498A3 (cs) | Fenyl- a aminofenyl-alkylsulfonamidové a močovinové deriváty | |
| CZ300706B6 (cs) | Derivát indolalkanové kyseliny a lécivo pro prevenci nebo zmírnení chronických komplikací vznikajících z diabetes mellitus | |
| CZ398191A3 (en) | Novel 4-amino alkyl-2(3h)-indolones and pharmaceutical compositions containing them | |
| JP2010024243A (ja) | 緑内障および近視を処置するためのベンゾ［ｇ］キノリン誘導体 | |
| MX2008003202A (es) | Derivados de carbazol. | |
| JP3204456B2 (ja) | ２，７―置換オクタヒドロ―ピロロ［１，２―ａ］ピラジン誘導体 | |
| US4554287A (en) | Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones | |
| JP2865255B2 (ja) | １，２，３，４，１０，１４ｂ‐ヘキサヒドロジベンゾ〔ｃ，ｆ〕ピラジノ〔１，２‐ａ〕アゼピノ誘導体及び１０‐アザ，１０‐オキサ及び１０‐チア類似体 | |
| US3600390A (en) | Novel 5-phenyl imidazolidino(5,1-a)5h-quinazolines and process therefor | |
| EP0427526B1 (en) | Pyridine derivatives, processes for their preparation and pharmaceutical compositions thereof | |
| DE69215482T2 (de) | 2,2'-Alkylendiindolderivate, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung als Ulcustherapeutikum | |
| MC1223A1 (fr) | Nouveaux derives de 2-imino-imidazolidine,leur preparation et leur application en tant que medicaments | |
| CN86107151A (zh) | 多巴胺-β-羟化酶抑制剂 | |
| JPS6257606B2 (enExample) | ||
| CN1014992B (zh) | 喹唑啉二酮和吡啶并嘧啶二酮的制备方法 | |
| AU660969B2 (en) | NMDA antagonists | |
| GB2369118A (en) | Bombesin receptor antagonists | |
| FR2563519A1 (fr) | Derives d'iminothiazolidine, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| CA1185603A (en) | Heterocyclic amidoxime derivatives | |
| LU86136A1 (fr) | Nouveaux derives de la phenethylaminoalcoyle-6 furo-(3,4-c)-pyridine,leur preparation et compositions therapeutiques a base de ceux-ci | |
| US3983130A (en) | Anthelmintic isothiocyanobenzoxazoles | |
| JPS6157582A (ja) | 新規なベンゾジアゼピン類 | |
| EP0355098A1 (en) | Novel sulfonamides, a process for their preparation and pharmaceutical compositions containing these new sulfonamides | |
| CN1048034A (zh) | 新颖的环状邻氨基苯甲酸乙酸衍生物及其制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination |