RU2008101924A - Новые аналоги пиридина - Google Patents
Новые аналоги пиридина Download PDFInfo
- Publication number
- RU2008101924A RU2008101924A RU2008101924/04A RU2008101924A RU2008101924A RU 2008101924 A RU2008101924 A RU 2008101924A RU 2008101924/04 A RU2008101924/04 A RU 2008101924/04A RU 2008101924 A RU2008101924 A RU 2008101924A RU 2008101924 A RU2008101924 A RU 2008101924A
- Authority
- RU
- Russia
- Prior art keywords
- heterocyclyl
- aryl
- cyano
- amino
- cycloalkyl
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 124
- 125000003118 aryl group Chemical group 0.000 claims abstract 119
- -1 arylC (O) Chemical group 0.000 claims abstract 76
- 150000001875 compounds Chemical class 0.000 claims abstract 72
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 63
- 229910052794 bromium Inorganic materials 0.000 claims abstract 63
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 63
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 63
- 229910052740 iodine Inorganic materials 0.000 claims abstract 63
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 56
- 125000005843 halogen group Chemical group 0.000 claims abstract 55
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 46
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 41
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 41
- 239000001301 oxygen Substances 0.000 claims abstract 41
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 32
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 31
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 28
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 27
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 24
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract 23
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract 16
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 16
- 125000005110 aryl thio group Chemical group 0.000 claims abstract 16
- 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract 13
- 150000002367 halogens Chemical class 0.000 claims abstract 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 12
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 64
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 43
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 37
- 229960001238 methylnicotinate Drugs 0.000 claims 36
- 235000001968 nicotinic acid Nutrition 0.000 claims 24
- 239000011664 nicotinic acid Substances 0.000 claims 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 19
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 19
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 125000004122 cyclic group Chemical group 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 8
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 7
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- 238000005304 joining Methods 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- ZETANZUWYPHWDA-UHFFFAOYSA-N azetidine;pyrrolidine Chemical compound C1CNC1.C1CCNC1 ZETANZUWYPHWDA-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DSMIBOGQTGQEDW-UHFFFAOYSA-N (4-fluorophenyl)methyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OCC=2C=CC(F)=CC=2)C(C)=NC=1N(CC1)CCC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 DSMIBOGQTGQEDW-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- WLXBIIXQTWAAQL-UHFFFAOYSA-N 2,2,2-trifluoroethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OCC(F)(F)F)C(C)=NC(N2CC(C2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)=C1C#N WLXBIIXQTWAAQL-UHFFFAOYSA-N 0.000 claims 1
- GNRNQOQWCLJMFS-UHFFFAOYSA-N 2,2,2-trifluoroethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OCC(F)(F)F)C(C)=NC(N2CCC(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)=C1C#N GNRNQOQWCLJMFS-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- BZNVZLHHMIUXDP-UHFFFAOYSA-N 2,2-dimethylpropyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OCC(C)(C)C)C(C)=NC(N2CCC(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)=C1C#N BZNVZLHHMIUXDP-UHFFFAOYSA-N 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- ZXVQGNIVTPFDQM-UHFFFAOYSA-N 2-hydroxyethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OCCO)C(C)=NC(N2CC(C2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)=C1C#N ZXVQGNIVTPFDQM-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- VPLBKEKVVMABJJ-UHFFFAOYSA-N 2-methylpropyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC(C)C)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 VPLBKEKVVMABJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- UBTJPCGCHZLWOX-UHFFFAOYSA-N 4-[2-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-ethoxycarbonyl-6-methylpyridin-3-yl]oxybutanoic acid Chemical compound N1=C(C)C(C(=O)OCC)=CC(OCCCC(O)=O)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 UBTJPCGCHZLWOX-UHFFFAOYSA-N 0.000 claims 1
- XNQKOANEUJKIFO-UHFFFAOYSA-N 4-[2-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-ethoxycarbonyl-6-methylpyridin-3-yl]oxybutanoic acid Chemical compound N1=C(C)C(C(=O)OCC)=CC(OCCCC(O)=O)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 XNQKOANEUJKIFO-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000003868 ammonium compounds Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- ZJWIYTDVQVMBDZ-UHFFFAOYSA-N benzyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OCC=2C=CC=CC=2)C(C)=NC=1N(C1)CC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 ZJWIYTDVQVMBDZ-UHFFFAOYSA-N 0.000 claims 1
- PBOQDJVWNSTWCJ-UHFFFAOYSA-N benzyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OCC=2C=CC=CC=2)C(C)=NC=1N(CC1)CCC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 PBOQDJVWNSTWCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- UMTRKVMYQFZJMO-UHFFFAOYSA-N cyclobutyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OC2CCC2)C(C)=NC=1N(C1)CC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 UMTRKVMYQFZJMO-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ULVLKRBRUKKOCE-UHFFFAOYSA-N cyclopentyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OC2CCCC2)C(C)=NC=1N(C1)CC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 ULVLKRBRUKKOCE-UHFFFAOYSA-N 0.000 claims 1
- FJCSFEJMLKZLMT-UHFFFAOYSA-N cyclopropyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OC2CC2)C(C)=NC=1N(C1)CC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 FJCSFEJMLKZLMT-UHFFFAOYSA-N 0.000 claims 1
- KNVDTAVEWDSSEK-UHFFFAOYSA-N cyclopropyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N#CC=1C=C(C(=O)OC2CC2)C(C)=NC=1N(CC1)CCC1C(=O)NS(=O)(=O)CC1=CC=CC=C1 KNVDTAVEWDSSEK-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- HQOVDLZFJOBAPA-UHFFFAOYSA-N ethyl 4-amino-6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-chloropyridine-3-carboxylate Chemical compound ClC1=C(N)C(C(=O)OCC)=CN=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 HQOVDLZFJOBAPA-UHFFFAOYSA-N 0.000 claims 1
- SRRYCJVTVMZIHX-UHFFFAOYSA-N ethyl 5-acetyl-6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C(C)=O)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 SRRYCJVTVMZIHX-UHFFFAOYSA-N 0.000 claims 1
- TXYSLOQUANFYQS-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-(2-phenylethylsulfonylcarbamoyl)azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C=CC=CC=2)C1 TXYSLOQUANFYQS-UHFFFAOYSA-N 0.000 claims 1
- GGTGWEIXAJXKKN-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(2-methylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C)C1 GGTGWEIXAJXKKN-UHFFFAOYSA-N 0.000 claims 1
- JVXCWCNUHNQFJT-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(2-nitrophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)C1 JVXCWCNUHNQFJT-UHFFFAOYSA-N 0.000 claims 1
- AHPLEFBSLFSXQR-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(3-nitrophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(C=CC=2)[N+]([O-])=O)C1 AHPLEFBSLFSXQR-UHFFFAOYSA-N 0.000 claims 1
- QEWJFGLCRRYNHH-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(4-nitrophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(=CC=2)[N+]([O-])=O)C1 QEWJFGLCRRYNHH-UHFFFAOYSA-N 0.000 claims 1
- NTXGBBFZHIKABO-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[[2-(trifluoromethyl)phenyl]methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(F)(F)F)C1 NTXGBBFZHIKABO-UHFFFAOYSA-N 0.000 claims 1
- YEBSUQZFWGNSHC-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[[3-(trifluoromethyl)phenyl]methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(C=CC=2)C(F)(F)F)C1 YEBSUQZFWGNSHC-UHFFFAOYSA-N 0.000 claims 1
- VPLUUYJJYUEQQB-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[[4-(trifluoromethyl)phenyl]methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(=CC=2)C(F)(F)F)C1 VPLUUYJJYUEQQB-UHFFFAOYSA-N 0.000 claims 1
- PDPLLSUKTDXTRW-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[4-(phenylsulfamoylcarbamoyl)piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)NC=2C=CC=CC=2)CC1 PDPLLSUKTDXTRW-UHFFFAOYSA-N 0.000 claims 1
- AXOZUWQJVWCETH-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[4-[[methyl(phenyl)sulfamoyl]carbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)N(C)C=2C=CC=CC=2)CC1 AXOZUWQJVWCETH-UHFFFAOYSA-N 0.000 claims 1
- WGFQRYABVMIEHB-UHFFFAOYSA-N ethyl 5-cyano-6-[3-(cyclohexylmethylsulfonylcarbamoyl)azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC2CCCCC2)C1 WGFQRYABVMIEHB-UHFFFAOYSA-N 0.000 claims 1
- NWTXBNNLXZXHMB-UHFFFAOYSA-N ethyl 5-cyano-6-[3-(cyclopentylmethylsulfonylcarbamoyl)azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC2CCCC2)C1 NWTXBNNLXZXHMB-UHFFFAOYSA-N 0.000 claims 1
- IMJUSMMVQCRREF-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(2-methoxycarbonylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(=O)OC)C1 IMJUSMMVQCRREF-UHFFFAOYSA-N 0.000 claims 1
- GEUWGPOYJULDMW-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(3,5-dichlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(Cl)C=C(Cl)C=2)C1 GEUWGPOYJULDMW-UHFFFAOYSA-N 0.000 claims 1
- APRNRDHUNOUQBH-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(3-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(F)C=CC=2)C1 APRNRDHUNOUQBH-UHFFFAOYSA-N 0.000 claims 1
- GKUTXOAQZPNFCB-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(4-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)C1 GKUTXOAQZPNFCB-UHFFFAOYSA-N 0.000 claims 1
- MHVCUXIPQLILBY-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[2-(2-fluorophenyl)ethylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C(=CC=CC=2)F)C1 MHVCUXIPQLILBY-UHFFFAOYSA-N 0.000 claims 1
- ZQKOJZJZZZIJES-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[2-(3-fluorophenyl)ethylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C=C(F)C=CC=2)C1 ZQKOJZJZZZIJES-UHFFFAOYSA-N 0.000 claims 1
- CRMGZAQUXRSVMC-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[2-(4-fluorophenyl)ethylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C=CC(F)=CC=2)C1 CRMGZAQUXRSVMC-UHFFFAOYSA-N 0.000 claims 1
- REZODNUYNHOHNL-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[2-[(4-fluorophenyl)methylsulfonylamino]-2-oxoethyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(CC(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)C1 REZODNUYNHOHNL-UHFFFAOYSA-N 0.000 claims 1
- HDZJHDQIFRZTQI-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(3-fluoro-4-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(F)C(C)=CC=2)CC1 HDZJHDQIFRZTQI-UHFFFAOYSA-N 0.000 claims 1
- PIIPBUHRYZTOBN-UHFFFAOYSA-N ethyl 6-[3-(1,2-benzoxazol-3-ylmethylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C3=CC=CC=C3ON=2)C1 PIIPBUHRYZTOBN-UHFFFAOYSA-N 0.000 claims 1
- OUVUTJDZUWKAFY-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-(4-methoxy-4-oxobutoxy)-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(OCCCC(=O)OC)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 OUVUTJDZUWKAFY-UHFFFAOYSA-N 0.000 claims 1
- MJJANTQEMALEFE-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-chloro-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(Cl)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 MJJANTQEMALEFE-UHFFFAOYSA-N 0.000 claims 1
- GVCOWNSYYVZKDI-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-ethylpyridine-3-carboxylate Chemical compound N1=C(CC)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 GVCOWNSYYVZKDI-UHFFFAOYSA-N 0.000 claims 1
- AOOWVFPXPVQQGP-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 AOOWVFPXPVQQGP-UHFFFAOYSA-N 0.000 claims 1
- XCSORGQATWEGRC-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-propan-2-ylpyridine-3-carboxylate Chemical compound N1=C(C(C)C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 XCSORGQATWEGRC-UHFFFAOYSA-N 0.000 claims 1
- RBXZVMWNFVOQSK-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-methoxy-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(OC)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 RBXZVMWNFVOQSK-UHFFFAOYSA-N 0.000 claims 1
- WWDNTQYRTZSERA-UHFFFAOYSA-N ethyl 6-[3-(benzylsulfonylcarbamoylamino)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(NC(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 WWDNTQYRTZSERA-UHFFFAOYSA-N 0.000 claims 1
- HTHLMJZCNFPPMO-UHFFFAOYSA-N ethyl 6-[3-[(2-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)Cl)C1 HTHLMJZCNFPPMO-UHFFFAOYSA-N 0.000 claims 1
- OXCAXVZZNQBTKJ-UHFFFAOYSA-N ethyl 6-[3-[(3-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(Cl)C=CC=2)C1 OXCAXVZZNQBTKJ-UHFFFAOYSA-N 0.000 claims 1
- FZGNWTQJSVKAPD-UHFFFAOYSA-N ethyl 6-[3-[(4-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(Cl)=CC=2)C1 FZGNWTQJSVKAPD-UHFFFAOYSA-N 0.000 claims 1
- RCAVJWRLMXMMMY-UHFFFAOYSA-N ethyl 6-[3-[2-(3-chlorophenyl)ethylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C=C(Cl)C=CC=2)C1 RCAVJWRLMXMMMY-UHFFFAOYSA-N 0.000 claims 1
- NMPBGGNVVITFFE-UHFFFAOYSA-N ethyl 6-[3-[2-(benzylsulfonylamino)-2-oxoethyl]azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(CC(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 NMPBGGNVVITFFE-UHFFFAOYSA-N 0.000 claims 1
- MHLSMSJZGMWZDH-UHFFFAOYSA-N ethyl 6-[3-[2-(benzylsulfonylamino)-2-oxoethyl]piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(CC(=O)NS(=O)(=O)CC=2C=CC=CC=2)CCC1 MHLSMSJZGMWZDH-UHFFFAOYSA-N 0.000 claims 1
- PZBGLWIOHXYBOZ-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)(NC(=O)OC(C)(C)C)CC1 PZBGLWIOHXYBOZ-UHFFFAOYSA-N 0.000 claims 1
- LJFYTTRWLIZFAV-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)-4-methylpiperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C)(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 LJFYTTRWLIZFAV-UHFFFAOYSA-N 0.000 claims 1
- PRVVDXMDRTTWIS-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperazin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCN(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 PRVVDXMDRTTWIS-UHFFFAOYSA-N 0.000 claims 1
- QGFBBJWQEKQPQP-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-(4-methoxy-4-oxobutoxy)-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(OCCCC(=O)OC)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 QGFBBJWQEKQPQP-UHFFFAOYSA-N 0.000 claims 1
- HTTBICQNSWIDFU-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-chloro-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(Cl)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 HTTBICQNSWIDFU-UHFFFAOYSA-N 0.000 claims 1
- GSGKAPDDEQEGJK-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-(dimethylamino)pyridine-3-carboxylate Chemical compound N1=C(N(C)C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 GSGKAPDDEQEGJK-UHFFFAOYSA-N 0.000 claims 1
- OBOPZXVABNAFRJ-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-ethylpyridine-3-carboxylate Chemical compound N1=C(CC)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 OBOPZXVABNAFRJ-UHFFFAOYSA-N 0.000 claims 1
- NCKCXIUOOHBJPL-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methyl-1-oxidopyridin-1-ium-3-carboxylate Chemical compound [O-][N+]1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 NCKCXIUOOHBJPL-UHFFFAOYSA-N 0.000 claims 1
- NEMHKCNXXRQYRF-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 NEMHKCNXXRQYRF-UHFFFAOYSA-N 0.000 claims 1
- IXBMBIDEPNYMBM-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-propan-2-ylpyridine-3-carboxylate Chemical compound N1=C(C(C)C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 IXBMBIDEPNYMBM-UHFFFAOYSA-N 0.000 claims 1
- XBDVSNZJEZABEP-UHFFFAOYSA-N ethyl 6-[4-(benzylsulfonylcarbamoylamino)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(NC(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 XBDVSNZJEZABEP-UHFFFAOYSA-N 0.000 claims 1
- KSDUUXIKUZKXAU-UHFFFAOYSA-N ethyl 6-[4-[(3-bromophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(Br)C=CC=2)CC1 KSDUUXIKUZKXAU-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- JSARWDFDTMLIQR-UHFFFAOYSA-N methyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 JSARWDFDTMLIQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- DAQKYANULOKBQC-UHFFFAOYSA-N n-(1,2-benzoxazol-3-ylmethylsulfonyl)-1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]piperidine-4-carboxamide Chemical compound O1C(CC)=CN=C1C1=CC(C#N)=C(N2CCC(CC2)C(=O)NS(=O)(=O)CC=2C3=CC=CC=C3ON=2)N=C1C DAQKYANULOKBQC-UHFFFAOYSA-N 0.000 claims 1
- AEXXLDKPHLKGSZ-UHFFFAOYSA-N n-benzylsulfonyl-1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]azetidine-3-carboxamide Chemical compound O1C(CC)=CN=C1C1=CC(C#N)=C(N2CC(C2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)N=C1C AEXXLDKPHLKGSZ-UHFFFAOYSA-N 0.000 claims 1
- ZJFUNJPZCMPXMF-UHFFFAOYSA-N n-benzylsulfonyl-1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]piperidine-4-carboxamide Chemical compound O1C(CC)=CN=C1C1=CC(C#N)=C(N2CCC(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)N=C1C ZJFUNJPZCMPXMF-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical group CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 claims 1
- AHHWRQDGAKBSPU-UHFFFAOYSA-N propan-2-yl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 AHHWRQDGAKBSPU-UHFFFAOYSA-N 0.000 claims 1
- HLCHHYWSCZAXFP-UHFFFAOYSA-N propan-2-yl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 HLCHHYWSCZAXFP-UHFFFAOYSA-N 0.000 claims 1
- XVLFWTQTUQZDJX-UHFFFAOYSA-N propyl 6-[3-(benzylsulfonylcarbamoyl)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 XVLFWTQTUQZDJX-UHFFFAOYSA-N 0.000 claims 1
- TXDUMJCBSYDACJ-UHFFFAOYSA-N propyl 6-[4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 TXDUMJCBSYDACJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 102220535958 Dynein axonemal intermediate chain 4_R17S_mutation Human genes 0.000 abstract 1
- 102200078752 rs201827340 Human genes 0.000 abstract 1
- 0 Cc(c(C(O)=O)c1C)c(C(C2)=C2C2CC2)c(*(CC2)CCC2(*)C(*)=O)*1I Chemical compound Cc(c(C(O)=O)c1C)c(C(C2)=C2C2CC2)c(*(CC2)CCC2(*)C(*)=O)*1I 0.000 description 1
Classifications
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
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- Communicable Diseases (AREA)
- Obesity (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
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| SE0501663 | 2005-07-13 | ||
| SE0501663-9 | 2005-07-13 | ||
| SE0502354 | 2005-10-24 | ||
| SE0502354-4 | 2005-10-24 |
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| RU2008101924A true RU2008101924A (ru) | 2009-08-20 |
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| JP (1) | JP2009501216A (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10759781B2 (en) | 2015-08-06 | 2020-09-01 | Ube Industries, Ltd. | Substituted guanidine derivatives |
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| WO2008004941A1 (en) * | 2006-07-04 | 2008-01-10 | Astrazeneca Ab | New pyridine analogues |
| US20080027103A1 (en) * | 2006-07-04 | 2008-01-31 | Astrazeneca Ab | Novel Crystalline Forms 1 |
| UY30867A1 (es) * | 2007-01-12 | 2008-09-02 | Astrazeneca Ab | Nuevos analogos de piridina vii 543 |
| UY30866A1 (es) * | 2007-01-12 | 2008-09-02 | Astrazeneca Ab | Nuevos compuestos de piridina, composiciones farmacéuticas conteniéndolos y aplicaciones (519) |
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| US20090018166A1 (en) * | 2007-07-13 | 2009-01-15 | Astrazeneca Ab | New Pyridine Analogues X 161 |
| AR072697A1 (es) * | 2008-07-07 | 2010-09-15 | Astrazeneca Ab | Compuestos de piridina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de trastorno de agregacion plaquetaria |
| WO2010005385A1 (en) * | 2008-07-07 | 2010-01-14 | Astrazeneca Ab | 2-amino-6-alkyl substituted pyridine derivatives useful as p2y12 inhibitors 308 |
| JP2014051434A (ja) * | 2010-12-28 | 2014-03-20 | Dainippon Sumitomo Pharma Co Ltd | 二環性ピリミジン誘導体 |
| EP2750676B1 (en) | 2011-08-30 | 2018-01-10 | University of Utah Research Foundation | Methods and compositions for treating nephrogenic diabetes insipidus |
| CN103483274B (zh) * | 2013-09-25 | 2016-03-09 | 江苏快达农化股份有限公司 | 一种制备苄嘧磺隆的方法 |
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| US6156758A (en) * | 1999-09-08 | 2000-12-05 | Isis Pharmaceuticals, Inc. | Antibacterial quinazoline compounds |
| WO2001057037A1 (en) * | 2000-02-04 | 2001-08-09 | Cor Therapeutics, Inc. | Platelet adp receptor inhibitors |
| US6906063B2 (en) * | 2000-02-04 | 2005-06-14 | Portola Pharmaceuticals, Inc. | Platelet ADP receptor inhibitors |
| US7452870B2 (en) * | 2000-08-21 | 2008-11-18 | Inspire Pharmaceuticals, Inc. | Drug-eluting stents coated with P2Y12 receptor antagonist compound |
| US7018985B1 (en) * | 2000-08-21 | 2006-03-28 | Inspire Pharmaceuticals, Inc. | Composition and method for inhibiting platelet aggregation |
| US7132408B2 (en) * | 2000-08-21 | 2006-11-07 | Inspire Pharmaceuticals, Inc. | Composition and method for inhibiting platelet aggregation |
| FR2820057A1 (fr) * | 2001-01-30 | 2002-08-02 | Ct De Transfert De Technologie | Membrane pour chambre d'encapsulation de cellules produisant au moins une substance biologiquement active et organe bio-artificiel comprenant une telle membrane |
| AR037097A1 (es) * | 2001-10-05 | 2004-10-20 | Novartis Ag | Compuestos acilsulfonamidas, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de un medicamento |
| PT1466912E (pt) * | 2002-01-18 | 2013-06-28 | Astellas Pharma Inc | Derivado de 2-aciloaminotiazol ou seu sal |
| GB0312609D0 (en) * | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| KR20060113699A (ko) * | 2003-10-03 | 2006-11-02 | 포톨라 파마슈티컬스, 인코포레이티드 | 치환된 이소퀴놀리논 |
| US7749981B2 (en) * | 2003-10-21 | 2010-07-06 | Inspire Pharmaceuticals, Inc. | Drug-eluting stents coated with non-nucleotide P2Y12 receptor antagonist compound |
| US7335648B2 (en) * | 2003-10-21 | 2008-02-26 | Inspire Pharmaceuticals, Inc. | Non-nucleotide composition and method for inhibiting platelet aggregation |
| US7504497B2 (en) * | 2003-10-21 | 2009-03-17 | Inspire Pharmaceuticals, Inc. | Orally bioavailable compounds and methods for inhibiting platelet aggregation |
| WO2005056354A2 (en) * | 2003-12-03 | 2005-06-23 | Gedeon Anthony A | Method of resisting contaminant build up and oxidation of vehicle surfaces and other surfaces |
| WO2006012226A2 (en) * | 2004-06-24 | 2006-02-02 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| WO2006073361A1 (en) * | 2005-01-06 | 2006-07-13 | Astrazeneca Ab | Novel pyridine compounds |
| CN101511815A (zh) * | 2006-07-04 | 2009-08-19 | 阿斯利康(瑞典)有限公司 | 新型吡啶类似物 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10759781B2 (en) | 2015-08-06 | 2020-09-01 | Ube Industries, Ltd. | Substituted guanidine derivatives |
| RU2733951C2 (ru) * | 2015-08-06 | 2020-10-08 | Убе Индастриз, Лтд. | Замещенные производные гуанидина |
| RU2733951C9 (ru) * | 2015-08-06 | 2020-12-22 | Убе Индастриз, Лтд. | Замещенные производные гуанидина |
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| TW200726758A (en) | 2007-07-16 |
| ECSP088140A (es) | 2008-02-20 |
| MX2008000470A (es) | 2008-03-11 |
| JP2009501216A (ja) | 2009-01-15 |
| NO20076682L (no) | 2008-03-05 |
| AU2006267148A1 (en) | 2007-01-18 |
| AR054632A1 (es) | 2007-07-04 |
| US20080312208A1 (en) | 2008-12-18 |
| IL188293A0 (en) | 2008-04-13 |
| WO2007008140A1 (en) | 2007-01-18 |
| CA2614726A1 (en) | 2007-01-18 |
| EP1904474A1 (en) | 2008-04-02 |
| UY29667A1 (es) | 2007-02-28 |
| KR20080039405A (ko) | 2008-05-07 |
| EP1904474A4 (en) | 2010-06-16 |
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