HRP970612A2 - Process for substituted pyridines - Google Patents

Process for substituted pyridines Download PDF

Info

Publication number: HRP970612A2
Authority: HR; Croatia
Prior art keywords: alkyl; compound; formula; independently; halo
Prior art date: 1996-11-14

Application number

HR60/030,880A

Other languages

English (en)

Croatian (hr)

Inventor

Stephan Wayne Wright

Original Assignee

Stephan Wayne Wright

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-11-14

Filing date

1997-11-13

Publication date

1998-08-31

1997-11-13 Application filed by Stephan Wayne Wright filed Critical Stephan Wayne Wright

1998-08-31 Publication of HRP970612A2 publication Critical patent/HRP970612A2/hr

Links

238000000034 method Methods 0.000 title claims description 70
230000008569 process Effects 0.000 title claims description 43
150000003222 pyridines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 257
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 203
125000005843 halogen group Chemical group 0.000 claims description 118
-1 nitro, amino Chemical group 0.000 claims description 112
229910052739 hydrogen Inorganic materials 0.000 claims description 110
239000001257 hydrogen Substances 0.000 claims description 91
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 75
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 59
229910052760 oxygen Inorganic materials 0.000 claims description 56
238000006243 chemical reaction Methods 0.000 claims description 53
229910052757 nitrogen Inorganic materials 0.000 claims description 53
229910052717 sulfur Chemical group 0.000 claims description 53
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 52
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 50
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 47
239000001301 oxygen Substances 0.000 claims description 47
125000004093 cyano group Chemical group *C#N 0.000 claims description 45
125000000623 heterocyclic group Chemical group 0.000 claims description 45
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 44
239000011593 sulfur Chemical group 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 42
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 38
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 36
125000001424 substituent group Chemical group 0.000 claims description 32
125000001153 fluoro group Chemical group F* 0.000 claims description 30
125000001309 chloro group Chemical group Cl* 0.000 claims description 28
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 27
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 23
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 15
239000003446 ligand Substances 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
125000006242 amine protecting group Chemical group 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000011260 aqueous acid Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 10
230000000269 nucleophilic effect Effects 0.000 claims description 10
230000003287 optical effect Effects 0.000 claims description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
229910052762 osmium Inorganic materials 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 7
239000007800 oxidant agent Substances 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000002907 osmium Chemical class 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 5
YUCBLVFHJWOYDN-HVLQGHBFSA-N 1,4-bis[(s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]phthalazine Chemical compound C1=C(OC)C=C2C([C@H](OC=3C4=CC=CC=C4C(O[C@H]([C@@H]4N5CC[C@H]([C@H](C5)CC)C4)C=4C5=CC(OC)=CC=C5N=CC=4)=NN=3)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 YUCBLVFHJWOYDN-HVLQGHBFSA-N 0.000 claims description 4
YUCBLVFHJWOYDN-PPIALRKJSA-N 4-[(r)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-1-[(r)-[(2r,4r,5s)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]phthalazine Chemical compound C1=C(OC)C=C2C([C@@H](OC=3C4=CC=CC=C4C(O[C@@H]([C@@H]4N5CC[C@@H]([C@@H](C5)CC)C4)C=4C5=CC(OC)=CC=C5N=CC=4)=NN=3)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 YUCBLVFHJWOYDN-PPIALRKJSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
239000012320 chlorinating reagent Substances 0.000 claims description 4
125000002346 iodo group Chemical group I* 0.000 claims description 4
DUTJLVHVDAXHDN-UHFFFAOYSA-N n-[5-(1,2-dihydroxyethyl)pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=C(C(O)CO)C=N1 DUTJLVHVDAXHDN-UHFFFAOYSA-N 0.000 claims description 4
MNRSVDHPRAZFQV-NRFANRHFSA-N tert-butyl n-[(2r)-2-(6-acetamidopyridin-3-yl)-2-hydroxyethyl]-n-[2-[4-[2-(methylamino)-2-oxoethyl]phenoxy]ethyl]carbamate Chemical compound C1=CC(CC(=O)NC)=CC=C1OCCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=C(NC(C)=O)N=C1 MNRSVDHPRAZFQV-NRFANRHFSA-N 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 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 description 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
239000000243 solution Substances 0.000 description 73
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000002585 base Substances 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 14
239000000725 suspension Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000000758 substrate Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
239000013078 crystal Substances 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000002253 acid Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000012267 brine Substances 0.000 description 8
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000011282 treatment Methods 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
LJOQGZACKSYWCH-UHFFFAOYSA-N dihydro quinine Natural products C1=C(OC)C=C2C(C(O)C3CC4CCN3CC4CC)=CC=NC2=C1 LJOQGZACKSYWCH-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
LJOQGZACKSYWCH-WZBLMQSHSA-N hydroquinine Chemical compound C1=C(OC)C=C2C([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-WZBLMQSHSA-N 0.000 description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
108020003175 receptors Proteins 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000000048 adrenergic agonist Substances 0.000 description 5
229940126157 adrenergic receptor agonist Drugs 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
102000004877 Insulin Human genes 0.000 description 4
108090001061 Insulin Proteins 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
101000924984 Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720) 3-dehydroquinate dehydratase Proteins 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
DGODWNOPHMXOTR-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium;dihydrate Chemical compound O.O.[K+].[K+].[O-][Os]([O-])(=O)=O DGODWNOPHMXOTR-UHFFFAOYSA-N 0.000 description 4
201000010099 disease Diseases 0.000 description 4
239000000284 extract Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
229960004251 hydroquinine Drugs 0.000 description 4
229940125396 insulin Drugs 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
235000010265 sodium sulphite Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
XGDZEDRBLVIUMX-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1 XGDZEDRBLVIUMX-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000011268 mixed slurry Substances 0.000 description 1
230000004899 motility Effects 0.000 description 1
ZFIULJUUXQPOQO-UHFFFAOYSA-N n-(3-ethenylpyridin-2-yl)acetamide Chemical compound CC(=O)NC1=NC=CC=C1C=C ZFIULJUUXQPOQO-UHFFFAOYSA-N 0.000 description 1
TWQWUMXFNVQDGQ-UHFFFAOYSA-N n-[5-(2-oxo-1,3-dioxolan-4-yl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1OC(=O)OC1 TWQWUMXFNVQDGQ-UHFFFAOYSA-N 0.000 description 1
MOALRZFUXFUIFP-VIFPVBQESA-N n-[5-[(1r)-1,2-dihydroxyethyl]pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=C([C@@H](O)CO)C=N1 MOALRZFUXFUIFP-VIFPVBQESA-N 0.000 description 1
DUTJLVHVDAXHDN-QMMMGPOBSA-N n-[5-[(1r)-1,2-dihydroxyethyl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=C([C@@H](O)CO)C=N1 DUTJLVHVDAXHDN-QMMMGPOBSA-N 0.000 description 1
WAXONIBXUBSLKF-QMMMGPOBSA-N n-[5-[(1r)-2-chloro-1-hydroxyethyl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=C([C@@H](O)CCl)C=N1 WAXONIBXUBSLKF-QMMMGPOBSA-N 0.000 description 1
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001151 other effect Effects 0.000 description 1
125000000914 phenoxymethylpenicillanyl group Chemical group CC1(S[C@H]2N([C@H]1C(=O)*)C([C@H]2NC(COC2=CC=CC=C2)=O)=O)C 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000000291 postprandial effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
230000002265 prevention Effects 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000012501 relaxation of skeletal muscle Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000007873 sieving Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
UAIHPMFLFVHDIN-UHFFFAOYSA-K trichloroosmium Chemical compound Cl[Os](Cl)Cl UAIHPMFLFVHDIN-UHFFFAOYSA-K 0.000 description 1
DCXPBOFGQPCWJY-UHFFFAOYSA-N trisodium;iron(3+);hexacyanide Chemical compound [Na+].[Na+].[Na+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCXPBOFGQPCWJY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Obesity (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

HR60/030,880A 1996-11-14 1997-11-13 Process for substituted pyridines HRP970612A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3088096P	1996-11-14	1996-11-14

Publications (1)

Publication Number	Publication Date
HRP970612A2 true HRP970612A2 (en)	1998-08-31

Family

ID=21856496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR60/030,880A HRP970612A2 (en)	1996-11-14	1997-11-13	Process for substituted pyridines

Country Status (32)

Country	Link
US (1)	US6291489B1 (fr)
EP (1)	EP0938476B1 (fr)
JP (1)	JP3510635B2 (fr)
KR (1)	KR20000053314A (fr)
CN (1)	CN1237160A (fr)
AP (1)	AP805A (fr)
AR (1)	AR010584A1 (fr)
AT (1)	ATE319687T1 (fr)
AU (1)	AU4634697A (fr)
BG (1)	BG103393A (fr)
BR (1)	BR9712951A (fr)
CA (1)	CA2270386C (fr)
CO (1)	CO4930261A1 (fr)
DE (1)	DE69735433D1 (fr)
EA (1)	EA199900375A1 (fr)
GT (1)	GT199700118A (fr)
HR (1)	HRP970612A2 (fr)
ID (1)	ID18898A (fr)
IL (1)	IL129688A0 (fr)
IS (1)	IS5029A (fr)
MA (1)	MA24401A1 (fr)
MY (1)	MY132507A (fr)
NO (1)	NO992296D0 (fr)
OA (1)	OA11044A (fr)
PA (1)	PA8441401A1 (fr)
PE (1)	PE10299A1 (fr)
TN (1)	TNSN97172A1 (fr)
TR (1)	TR199901063T2 (fr)
UY (1)	UY24774A1 (fr)
WO (1)	WO1998021184A1 (fr)
YU (1)	YU22099A (fr)
ZA (1)	ZA9710186B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ID26299A (id) *	1998-04-08	2000-12-14	Novartis Ag	Herbisida baru
US6090942A (en) *	1998-10-15	2000-07-18	Pfizer Inc.	Process and intermediates for a β3 -adrenergic receptor agonist
CA2362070A1 (fr) *	1999-02-16	2000-08-24	Masaru Mitsuda	Derives d'acetylpyridine substituee et procede de preparation d'intermediaires pour agoniste du recepteur adrenergique .beta.3 optiquement actif, faisant appel a ces derives
US6455734B1 (en) *	2000-08-09	2002-09-24	Magnesium Diagnostics, Inc.	Antagonists of the magnesium binding defect as therapeutic agents and methods for treatment of abnormal physiological states
DE60015036T2 (de) *	1999-07-23	2006-03-02	Pfizer Products Inc., Groton	Zwischenprodukte und ein Verfahren zur Herstellung von beta3-Adrenergischer Rezeptor-Agoniste
US20040265991A1 (en) *	2001-10-17	2004-12-30	Naoaki Taoka	Process for preparation of (s)-alpha-halomethylpyridine-methanol derivatives
WO2003072573A1 (fr) *	2002-02-27	2003-09-04	Pfizer Products Inc.	Formes cristallines de (r)-2-(2-(4-oxazol-4-yl-phenoxy)-ethylamino)-1-pyridin-3-yl-ethanol
US6864268B2 (en)	2002-02-27	2005-03-08	Pfizer Inc.	β3 adrenergic receptor agonists
EP1478625A1 (fr)	2002-02-27	2004-11-24	Pfizer Products Inc.	Procedes et intermediaires utiles dans la preparation d'agonistes du recepteur beta-3-adrenergique
EP1424079A1 (fr) *	2002-11-27	2004-06-02	Boehringer Ingelheim International GmbH	Combinaison d'un agoniste du beta-3-récepteur et d'un inhibiteur de recaptage de sérotonine et/ou norépinéphrine
ATE406363T1 (de)	2003-05-09	2008-09-15	Hoffmann La Roche	Methylindole und methylpyrrolopyridine als alpha- 1-adrenerge agonisten
GB2431927B (en)	2005-11-04	2010-03-17	Amira Pharmaceuticals Inc	5-Lipoxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en)	2005-11-04	2013-03-19	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en)	2005-11-04	2011-07-12	Amira Pharmaceuticals, Inc.	5-lipdxygenase-activating protein (FLAP) inhibitors
JP5791500B2 (ja)	2008-05-23	2015-10-07	パンミラファーマシューティカルズ，エルエルシー．	５−リポキシゲナーゼ活性化タンパク質阻害剤
US8546431B2 (en)	2008-10-01	2013-10-01	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4358455A (en)	1980-12-23	1982-11-09	Merck & Co., Inc.	Aralkylamindethanol heterocyclic compounds
US5019578A (en)	1987-11-27	1991-05-28	Merck & Co., Inc.	β-adrenergic agonists
ATE154935T1 (de)	1993-06-14	1997-07-15	Pfizer	Zweite amine als antidiabetische mittel und für die behandlung von fettleibigkeit
IL113410A (en)	1994-04-26	1999-11-30	Merck & Co Inc	Substituted sulfonamides having an asymmetric center and pharmaceutical compositions containing them
WO1996035670A1 (fr) *	1995-05-10	1996-11-14	Pfizer Inc.	AGONISTES DU RECEPTEUR β-ADRENERGIQUE
JPH11504649A (ja) *	1995-05-10	1999-04-27	ファイザー・インコーポレーテッド	β−アドレナリン作働性アゴニスト

1997
- 1997-11-03 WO PCT/IB1997/001367 patent/WO1998021184A1/fr not_active Ceased
- 1997-11-03 US US09/297,694 patent/US6291489B1/en not_active Expired - Fee Related
- 1997-11-03 AT AT97945047T patent/ATE319687T1/de not_active IP Right Cessation
- 1997-11-03 EA EA199900375A patent/EA199900375A1/ru unknown
- 1997-11-03 BR BR9712951-8A patent/BR9712951A/pt not_active Application Discontinuation
- 1997-11-03 IL IL12968897A patent/IL129688A0/xx unknown
- 1997-11-03 TR TR1999/01063T patent/TR199901063T2/xx unknown
- 1997-11-03 CA CA002270386A patent/CA2270386C/fr not_active Expired - Fee Related
- 1997-11-03 YU YU22099A patent/YU22099A/sh unknown
- 1997-11-03 KR KR1019990704312A patent/KR20000053314A/ko not_active Abandoned
- 1997-11-03 EP EP97945047A patent/EP0938476B1/fr not_active Expired - Lifetime
- 1997-11-03 CN CN97199663A patent/CN1237160A/zh active Pending
- 1997-11-03 DE DE69735433T patent/DE69735433D1/de not_active Expired - Lifetime
- 1997-11-03 JP JP52233298A patent/JP3510635B2/ja not_active Expired - Fee Related
- 1997-11-03 AU AU46346/97A patent/AU4634697A/en not_active Abandoned
- 1997-11-11 GT GT199700118A patent/GT199700118A/es unknown
- 1997-11-11 PE PE1997001004A patent/PE10299A1/es not_active Application Discontinuation
- 1997-11-11 MA MA24864A patent/MA24401A1/fr unknown
- 1997-11-12 PA PA19978441401A patent/PA8441401A1/es unknown
- 1997-11-12 UY UY24774A patent/UY24774A1/es unknown
- 1997-11-12 AR ARP970105279A patent/AR010584A1/es not_active Application Discontinuation
- 1997-11-12 ZA ZA9710186A patent/ZA9710186B/xx unknown
- 1997-11-12 TN TNTNSN97172A patent/TNSN97172A1/fr unknown
- 1997-11-12 MY MYPI97005396A patent/MY132507A/en unknown
- 1997-11-13 HR HR60/030,880A patent/HRP970612A2/hr not_active Application Discontinuation
- 1997-11-13 AP APAP/P/1997/001147A patent/AP805A/en active
- 1997-11-13 ID IDP973662A patent/ID18898A/id unknown
- 1997-11-13 CO CO97066763A patent/CO4930261A1/es unknown
1999
- 1999-04-16 IS IS5029A patent/IS5029A/is unknown
- 1999-05-07 OA OA9900096A patent/OA11044A/en unknown
- 1999-05-11 BG BG103393A patent/BG103393A/xx unknown
- 1999-05-12 NO NO992296A patent/NO992296D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO1998021184A1 (fr)	1998-05-22
OA11044A (en)	2002-02-20
ATE319687T1 (de)	2006-03-15
PE10299A1 (es)	1999-02-10
AP805A (en)	2000-01-28
ID18898A (id)	1998-05-20
AU4634697A (en)	1998-06-03
EP0938476A1 (fr)	1999-09-01
EA199900375A1 (ru)	1999-12-29
EP0938476B1 (fr)	2006-03-08
BR9712951A (pt)	1999-12-07
GT199700118A (es)	1999-05-05
AR010584A1 (es)	2000-06-28
US6291489B1 (en)	2001-09-18
CO4930261A1 (es)	2000-06-27
IL129688A0 (en)	2000-02-29
UY24774A1 (es)	1998-05-05
TR199901063T2 (xx)	1999-08-23
CN1237160A (zh)	1999-12-01
CA2270386C (fr)	2004-08-03
DE69735433D1 (de)	2006-05-04
JP3510635B2 (ja)	2004-03-29
AP9701147A0 (en)	1998-01-31
TNSN97172A1 (fr)	2005-03-15
MY132507A (en)	2007-10-31
ZA9710186B (en)	1999-05-12
NO992296L (no)	1999-05-12
BG103393A (en)	2000-07-31
IS5029A (is)	1999-04-16
KR20000053314A (ko)	2000-08-25
MA24401A1 (fr)	1998-07-01
CA2270386A1 (fr)	1998-05-22
JP2000504347A (ja)	2000-04-11
NO992296D0 (no)	1999-05-12
YU22099A (sh)	2001-09-28
PA8441401A1 (es)	2000-05-24

Legal Events

Date	Code	Title	Description
1997-11-13	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1998-08-31	A1OB	Publication of a patent application
2000-11-13	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20001113 Year of fee payment: 4
2007-01-19	ODBI	Application refused

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