CA2614726A1 - New pyridine analogues - Google Patents
New pyridine analogues Download PDFInfo
- Publication number
- CA2614726A1 CA2614726A1 CA002614726A CA2614726A CA2614726A1 CA 2614726 A1 CA2614726 A1 CA 2614726A1 CA 002614726 A CA002614726 A CA 002614726A CA 2614726 A CA2614726 A CA 2614726A CA 2614726 A1 CA2614726 A1 CA 2614726A1
- Authority
- CA
- Canada
- Prior art keywords
- cyano
- amino
- heterocyclyl
- aryl
- carbonyl
- 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.)
- Abandoned
Links
- 150000003222 pyridines Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 257
- 238000000034 method Methods 0.000 claims abstract description 93
- 230000008569 process Effects 0.000 claims abstract description 46
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003814 drug Substances 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 320
- 125000003118 aryl group Chemical group 0.000 claims description 314
- -1 arylC(O) Chemical group 0.000 claims description 278
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 168
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 163
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 161
- 229910052736 halogen Inorganic materials 0.000 claims description 139
- 239000000460 chlorine Substances 0.000 claims description 137
- 229910052801 chlorine Inorganic materials 0.000 claims description 137
- 229910052731 fluorine Inorganic materials 0.000 claims description 134
- 229910052794 bromium Inorganic materials 0.000 claims description 133
- 229910052740 iodine Inorganic materials 0.000 claims description 128
- 150000002367 halogens Chemical class 0.000 claims description 126
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 115
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 114
- 229910052757 nitrogen Inorganic materials 0.000 claims description 110
- 239000011541 reaction mixture Substances 0.000 claims description 110
- 125000004429 atom Chemical group 0.000 claims description 109
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 98
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 98
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 96
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 88
- 239000001301 oxygen Substances 0.000 claims description 88
- 229910052760 oxygen Inorganic materials 0.000 claims description 88
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 81
- 125000004414 alkyl thio group Chemical group 0.000 claims description 77
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 71
- 229910001868 water Inorganic materials 0.000 claims description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 63
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 57
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 55
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 53
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 48
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 47
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 46
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 45
- 125000004122 cyclic group Chemical group 0.000 claims description 43
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 35
- 125000005110 aryl thio group Chemical group 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 150000007530 organic bases Chemical class 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 239000012442 inert solvent Substances 0.000 claims description 25
- 239000003153 chemical reaction reagent Substances 0.000 claims description 23
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 229960001238 methylnicotinate Drugs 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 19
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000012317 TBTU Substances 0.000 claims description 10
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 150000003868 ammonium compounds Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 102220535958 Dynein axonemal intermediate chain 4_R17S_mutation Human genes 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- LKMOJJVOGNLJLL-UHFFFAOYSA-N tert-butyl 6-[3-(benzylsulfonylcarbamoylamino)azetidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound C1=C(C(=O)OC(C)(C)C)C(C)=NC(N2CC(C2)NC(=O)NS(=O)(=O)CC=2C=CC=CC=2)=C1C#N LKMOJJVOGNLJLL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 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 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 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 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 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 description 2
- LUHXCFFTYVLFQM-UHFFFAOYSA-N cyclopropyl 5-cyano-2-methyl-6-[4-[(4-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)NC(=O)C1CCN(C=2C(=CC(=C(C)N=2)C(=O)OC2CC2)C#N)CC1 LUHXCFFTYVLFQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- RZHRAGRVVVNEIY-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(2-methoxycarbonylphenyl)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(=CC=CC=2)C(=O)OC)CC1 RZHRAGRVVVNEIY-UHFFFAOYSA-N 0.000 claims description 2
- KXINOQPORLBYGK-UHFFFAOYSA-N ethyl 6-[3-[(3-bromophenyl)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(Br)C=CC=2)C1 KXINOQPORLBYGK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 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 description 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N nicotinic acid ethyl ester Natural products CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- VDHCPQNFVJOLDK-UHFFFAOYSA-N propan-2-yl 5-cyano-2-methyl-6-[4-[(4-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-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(C)=CC=2)CC1 VDHCPQNFVJOLDK-UHFFFAOYSA-N 0.000 claims description 2
- WYYZCFJDZXLDES-UHFFFAOYSA-N propan-2-yl 5-cyano-2-methyl-6-[4-[[4-(trifluoromethyl)phenyl]methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-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)C(F)(F)F)CC1 WYYZCFJDZXLDES-UHFFFAOYSA-N 0.000 claims description 2
- 102200078752 rs201827340 Human genes 0.000 claims description 2
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- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 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
- 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
- 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
- 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
- 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
- CBSUFKGUQSMUKL-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(3-fluorophenyl)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=CC=2)CC1 CBSUFKGUQSMUKL-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
- ZOEWYDNFJGUSCM-UHFFFAOYSA-N ethyl 6-[4-amino-4-(benzylsulfonylcarbamoyl)piperidin-1-yl]-5-cyano-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(N)(C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 ZOEWYDNFJGUSCM-UHFFFAOYSA-N 0.000 claims 1
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- CTPGPJGYNRIRCN-UHFFFAOYSA-N propan-2-yl 5-cyano-2-methyl-6-[3-(2-phenylethylsulfonylcarbamoyl)azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CCC=2C=CC=CC=2)C1 CTPGPJGYNRIRCN-UHFFFAOYSA-N 0.000 claims 1
- GCTWCJFKPJBURF-UHFFFAOYSA-N propan-2-yl 5-cyano-2-methyl-6-[4-[(3-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(C)C=CC=2)CC1 GCTWCJFKPJBURF-UHFFFAOYSA-N 0.000 claims 1
- JMGFBFPYEPCOBC-UHFFFAOYSA-N propan-2-yl 5-cyano-2-methyl-6-[4-[2-(2-methylphenyl)ethylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CCC=2C(=CC=CC=2)C)CC1 JMGFBFPYEPCOBC-UHFFFAOYSA-N 0.000 claims 1
- PFLVQDGJTUUYES-UHFFFAOYSA-N propan-2-yl 5-cyano-6-[3-(cyclopentylmethylsulfonylcarbamoyl)azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OC(C)C)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC2CCCC2)C1 PFLVQDGJTUUYES-UHFFFAOYSA-N 0.000 claims 1
- BYFFWHYMGIELAN-UHFFFAOYSA-N propan-2-yl 5-cyano-6-[3-[(2-methoxycarbonylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)C1CN(C=2C(=CC(=C(C)N=2)C(=O)OC(C)C)C#N)C1 BYFFWHYMGIELAN-UHFFFAOYSA-N 0.000 claims 1
- ZUCRQMOGVUZBNG-UHFFFAOYSA-N propan-2-yl 5-cyano-6-[4-[(2-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-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)F)CC1 ZUCRQMOGVUZBNG-UHFFFAOYSA-N 0.000 claims 1
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- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
- YWXSWDQLJWHKMW-UHFFFAOYSA-N ethyl 4-methylpiperidine-4-carboxylate Chemical compound CCOC(=O)C1(C)CCNCC1 YWXSWDQLJWHKMW-UHFFFAOYSA-N 0.000 description 1
- GUKUJHDWNLRSNF-UHFFFAOYSA-N ethyl 5-cyano-2-(difluoromethyl)-6-[3-[(3-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(F)C=CC=2)C1 GUKUJHDWNLRSNF-UHFFFAOYSA-N 0.000 description 1
- ZTQQKXJLPRURAO-UHFFFAOYSA-N ethyl 5-cyano-2-(difluoromethyl)-6-[3-[(4-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)C1 ZTQQKXJLPRURAO-UHFFFAOYSA-N 0.000 description 1
- JVZODDIDPJHVBZ-UHFFFAOYSA-N ethyl 5-cyano-2-(difluoromethyl)-6-[4-[(4-methylcyclohexyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC2CCC(C)CC2)CC1 JVZODDIDPJHVBZ-UHFFFAOYSA-N 0.000 description 1
- YWULDQFLQQFPEP-UHFFFAOYSA-N ethyl 5-cyano-2-(fluoromethyl)-6-[3-[(3-methylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(C)C=CC=2)C1 YWULDQFLQQFPEP-UHFFFAOYSA-N 0.000 description 1
- JKDXEHAGOUJCHY-UHFFFAOYSA-N ethyl 5-cyano-2-(fluoromethyl)-6-[3-[(4-methylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(C)=CC=2)C1 JKDXEHAGOUJCHY-UHFFFAOYSA-N 0.000 description 1
- AMXHRTVTRUOFEM-UHFFFAOYSA-N ethyl 5-cyano-2-(fluoromethyl)-6-[4-[(2-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)F)CC1 AMXHRTVTRUOFEM-UHFFFAOYSA-N 0.000 description 1
- OEVMHGXGLUDGCQ-UHFFFAOYSA-N ethyl 5-cyano-2-(fluoromethyl)-6-[4-[(3-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(F)C=CC=2)CC1 OEVMHGXGLUDGCQ-UHFFFAOYSA-N 0.000 description 1
- MBDYFVRISRMQIO-UHFFFAOYSA-N ethyl 5-cyano-2-(fluoromethyl)-6-[4-[(4-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)CC1 MBDYFVRISRMQIO-UHFFFAOYSA-N 0.000 description 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 description 1
- JNKGXIBCNBZRBO-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-(pyridin-4-ylmethylsulfonylcarbamoyl)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=CN=CC=2)C1 JNKGXIBCNBZRBO-UHFFFAOYSA-N 0.000 description 1
- XITGMFGJIQLRMQ-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(1-oxidopyridin-1-ium-2-yl)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=2[N+](=CC=CC=2)[O-])C1 XITGMFGJIQLRMQ-UHFFFAOYSA-N 0.000 description 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 description 1
- NMRKJMWWTCJMAC-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[3-[(2-methylpropan-2-yl)oxycarbonylamino]azetidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CC(NC(=O)OC(C)(C)C)C1 NMRKJMWWTCJMAC-UHFFFAOYSA-N 0.000 description 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 description 1
- XSAIJRMURHASGT-UHFFFAOYSA-N ethyl 5-cyano-2-methyl-6-[4-[(4-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(C)=CC=2)CC1 XSAIJRMURHASGT-UHFFFAOYSA-N 0.000 description 1
- JEBPPHZTZMFYNX-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(2,4-dichlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(fluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC(Cl)=CC=2)Cl)C1 JEBPPHZTZMFYNX-UHFFFAOYSA-N 0.000 description 1
- ZBXKSBOSSZQTSB-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(2,4-dichlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC(Cl)=CC=2)Cl)C1 ZBXKSBOSSZQTSB-UHFFFAOYSA-N 0.000 description 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 description 1
- TWFDGCKJCVVUMB-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(3-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(F)C=CC=2)C1 TWFDGCKJCVVUMB-UHFFFAOYSA-N 0.000 description 1
- RKRIFAVRMHCSIT-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(3-methylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(C)C=CC=2)C1 RKRIFAVRMHCSIT-UHFFFAOYSA-N 0.000 description 1
- OLRFNERNMJTCFN-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(4-ethylphenyl)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)=CC=2)C1 OLRFNERNMJTCFN-UHFFFAOYSA-N 0.000 description 1
- IVOXUFVCRLLPKV-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(4-fluorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)C1 IVOXUFVCRLLPKV-UHFFFAOYSA-N 0.000 description 1
- HGHPWWSOBOPMPY-UHFFFAOYSA-N ethyl 5-cyano-6-[3-[(4-methylphenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(C)=CC=2)C1 HGHPWWSOBOPMPY-UHFFFAOYSA-N 0.000 description 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 description 1
- XYJPLPXCGUNDGC-UHFFFAOYSA-N ethyl 5-cyano-6-[4-(cyclopentylmethylsulfonylcarbamoyl)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)CC2CCCC2)CC1 XYJPLPXCGUNDGC-UHFFFAOYSA-N 0.000 description 1
- PKZUYAOLJCGVGE-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(2-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)F)CC1 PKZUYAOLJCGVGE-UHFFFAOYSA-N 0.000 description 1
- XNKVSBVPFBVLLF-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(3,4-difluorophenyl)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(F)=CC=2)CC1 XNKVSBVPFBVLLF-UHFFFAOYSA-N 0.000 description 1
- VRXDSTXQMKIGSN-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(3-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(F)C=CC=2)CC1 VRXDSTXQMKIGSN-UHFFFAOYSA-N 0.000 description 1
- OOJYYOXDEDQMPL-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(3-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(C)C=CC=2)CC1 OOJYYOXDEDQMPL-UHFFFAOYSA-N 0.000 description 1
- ZKRINNSKLLABDY-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(4-fluorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(F)=CC=2)CC1 ZKRINNSKLLABDY-UHFFFAOYSA-N 0.000 description 1
- DBAOAOZGDFXAPN-UHFFFAOYSA-N ethyl 5-cyano-6-[4-[(4-methylphenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(C)=CC=2)CC1 DBAOAOZGDFXAPN-UHFFFAOYSA-N 0.000 description 1
- KQHJOVOQCLUIBG-UHFFFAOYSA-N ethyl 5-cyano-6-oxo-2-propan-2-yl-1h-pyridine-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C#N)C(=O)NC=1C(C)C KQHJOVOQCLUIBG-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- MMGYQZFQELUPKV-UHFFFAOYSA-N ethyl 6-[3-[(2-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)Cl)C1 MMGYQZFQELUPKV-UHFFFAOYSA-N 0.000 description 1
- PECXZSSVLFSZDJ-UHFFFAOYSA-N ethyl 6-[3-[(3-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=C(Cl)C=CC=2)C1 PECXZSSVLFSZDJ-UHFFFAOYSA-N 0.000 description 1
- DMHHLQDNINBLAE-UHFFFAOYSA-N ethyl 6-[3-[(4-chlorophenyl)methylsulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)CC=2C=CC(Cl)=CC=2)C1 DMHHLQDNINBLAE-UHFFFAOYSA-N 0.000 description 1
- WNXPTUQAFZRDBV-UHFFFAOYSA-N ethyl 6-[3-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]azetidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(C(=O)NS(=O)(=O)C=2SC(Cl)=CC=2)C1 WNXPTUQAFZRDBV-UHFFFAOYSA-N 0.000 description 1
- IKUFXVUEOKBWRQ-UHFFFAOYSA-N ethyl 6-[3-[2-(benzylsulfonylamino)-2-oxoethyl]azetidin-1-yl]-5-cyano-2-(difluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(CC(=O)NS(=O)(=O)CC=2C=CC=CC=2)C1 IKUFXVUEOKBWRQ-UHFFFAOYSA-N 0.000 description 1
- ABZPNJLQUVSKKT-UHFFFAOYSA-N ethyl 6-[3-[2-[(5-chlorothiophen-2-yl)sulfonylamino]-2-oxoethyl]pyrrolidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CC(CC(=O)NS(=O)(=O)C=2SC(Cl)=CC=2)CC1 ABZPNJLQUVSKKT-UHFFFAOYSA-N 0.000 description 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 description 1
- NQRLLCMUTSZWKR-UHFFFAOYSA-N ethyl 6-[4-[(2-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(difluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)Cl)CC1 NQRLLCMUTSZWKR-UHFFFAOYSA-N 0.000 description 1
- DUDDAAYGALWKPO-UHFFFAOYSA-N ethyl 6-[4-[(2-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(fluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(CF)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)Cl)CC1 DUDDAAYGALWKPO-UHFFFAOYSA-N 0.000 description 1
- XWTQVMBAGJEEBX-UHFFFAOYSA-N ethyl 6-[4-[(2-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C(=CC=CC=2)Cl)CC1 XWTQVMBAGJEEBX-UHFFFAOYSA-N 0.000 description 1
- VUUJUDOAADAJRW-UHFFFAOYSA-N ethyl 6-[4-[(3-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=C(Cl)C=CC=2)CC1 VUUJUDOAADAJRW-UHFFFAOYSA-N 0.000 description 1
- FHYFEVMYBZKMSM-UHFFFAOYSA-N ethyl 6-[4-[(4-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(difluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(Cl)=CC=2)CC1 FHYFEVMYBZKMSM-UHFFFAOYSA-N 0.000 description 1
- JDRAQWPAOXKLKC-UHFFFAOYSA-N ethyl 6-[4-[(4-chlorophenyl)methylsulfonylcarbamoyl]piperidin-1-yl]-5-cyano-2-(trifluoromethyl)pyridine-3-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OCC)=CC(C#N)=C1N1CCC(C(=O)NS(=O)(=O)CC=2C=CC(Cl)=CC=2)CC1 JDRAQWPAOXKLKC-UHFFFAOYSA-N 0.000 description 1
- VZHPMTPVCUAQQR-UHFFFAOYSA-N ethyl 6-chloro-5-cyano-2-propan-2-ylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(C#N)=C(Cl)N=C1C(C)C VZHPMTPVCUAQQR-UHFFFAOYSA-N 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940064982 ethylnicotinate Drugs 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002618 extracorporeal membrane oxygenation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008713 feedback mechanism Effects 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D213/84—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)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0501663 | 2005-07-13 | ||
| SE0501663-9 | 2005-07-13 | ||
| SE0502354 | 2005-10-24 | ||
| SE0502354-4 | 2005-10-24 | ||
| PCT/SE2006/000832 WO2007008140A1 (en) | 2005-07-13 | 2006-07-04 | New pyridine analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2614726A1 true CA2614726A1 (en) | 2007-01-18 |
Family
ID=37637403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002614726A Abandoned CA2614726A1 (en) | 2005-07-13 | 2006-07-04 | New pyridine analogues |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080312208A1 (enExample) |
| EP (1) | EP1904474A4 (enExample) |
| JP (1) | JP2009501216A (enExample) |
| KR (1) | KR20080039405A (enExample) |
| AR (1) | AR054632A1 (enExample) |
| AU (1) | AU2006267148A1 (enExample) |
| CA (1) | CA2614726A1 (enExample) |
| EC (1) | ECSP088140A (enExample) |
| IL (1) | IL188293A0 (enExample) |
| MX (1) | MX2008000470A (enExample) |
| NO (1) | NO20076682L (enExample) |
| RU (1) | RU2008101924A (enExample) |
| TW (1) | TW200726758A (enExample) |
| UY (1) | UY29667A1 (enExample) |
| WO (1) | WO2007008140A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| UY30868A1 (es) * | 2007-01-12 | 2008-09-02 | Astrazeneca Ab | Nuevos compuestos de piridina, composiciones farmacéuticas conteniéndolas y aplicaciones. |
| 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 |
| EP3333163A4 (en) | 2015-08-06 | 2019-01-09 | UBE Industries, Ltd. | SUBSTITUTED GUANIDINE DERIVATIVE |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2007270083A1 (en) * | 2006-07-04 | 2008-01-10 | Astrazeneca Ab | New pyridine analogues |
| WO2008004941A1 (en) * | 2006-07-04 | 2008-01-10 | Astrazeneca Ab | New pyridine analogues |
-
2006
- 2006-07-04 US US11/995,326 patent/US20080312208A1/en not_active Abandoned
- 2006-07-04 EP EP06758023A patent/EP1904474A4/en not_active Withdrawn
- 2006-07-04 AU AU2006267148A patent/AU2006267148A1/en not_active Abandoned
- 2006-07-04 WO PCT/SE2006/000832 patent/WO2007008140A1/en not_active Ceased
- 2006-07-04 JP JP2008521353A patent/JP2009501216A/ja active Pending
- 2006-07-04 KR KR1020087002914A patent/KR20080039405A/ko not_active Withdrawn
- 2006-07-04 CA CA002614726A patent/CA2614726A1/en not_active Abandoned
- 2006-07-04 MX MX2008000470A patent/MX2008000470A/es not_active Application Discontinuation
- 2006-07-04 RU RU2008101924/04A patent/RU2008101924A/ru not_active Application Discontinuation
- 2006-07-12 UY UY29667A patent/UY29667A1/es not_active Application Discontinuation
- 2006-07-12 AR ARP060102992A patent/AR054632A1/es not_active Application Discontinuation
- 2006-07-13 TW TW095125590A patent/TW200726758A/zh unknown
-
2007
- 2007-12-20 IL IL188293A patent/IL188293A0/en unknown
- 2007-12-28 NO NO20076682A patent/NO20076682L/no not_active Application Discontinuation
-
2008
- 2008-01-25 EC EC2008008140A patent/ECSP088140A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| EP1904474A1 (en) | 2008-04-02 |
| UY29667A1 (es) | 2007-02-28 |
| RU2008101924A (ru) | 2009-08-20 |
| KR20080039405A (ko) | 2008-05-07 |
| EP1904474A4 (en) | 2010-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |