CA1109468A - 3-aryloxy-substituted-aminopyridines and methods for their production - Google Patents
3-aryloxy-substituted-aminopyridines and methods for their productionInfo
- Publication number
- CA1109468A CA1109468A CA327,810A CA327810A CA1109468A CA 1109468 A CA1109468 A CA 1109468A CA 327810 A CA327810 A CA 327810A CA 1109468 A CA1109468 A CA 1109468A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- acid addition
- formula
- chloro
- phenoxy
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- -1 3-bromo-substituted-aminopyridine Chemical class 0.000 claims abstract description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 47
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 31
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910052801 chlorine Chemical group 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- QEKCEGZYIXGKID-UHFFFAOYSA-N 2-chloro-3-phenoxypyridine Chemical compound ClC1=NC=CC=C1OC1=CC=CC=C1 QEKCEGZYIXGKID-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- OAFJWUWAKXLAMQ-UHFFFAOYSA-N 4-chloro-3-phenoxypyridine Chemical compound ClC1=CC=NC=C1OC1=CC=CC=C1 OAFJWUWAKXLAMQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- QQDIKVZFOKBWGG-UHFFFAOYSA-N 4-chloro-3-(3-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC(OC=2C(=CC=NC=2)Cl)=C1 QQDIKVZFOKBWGG-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- WYKWCLVPFKWFTK-UHFFFAOYSA-N 1-(1-oxido-5-phenoxypyridin-1-ium-3-yl)piperazine Chemical compound C=1C(N2CCNCC2)=C[N+]([O-])=CC=1OC1=CC=CC=C1 WYKWCLVPFKWFTK-UHFFFAOYSA-N 0.000 claims description 2
- ZRESGPGOHDLDHO-UHFFFAOYSA-N 1-(3-phenoxypyridin-4-yl)piperazine;dihydrochloride Chemical compound Cl.Cl.C1CNCCN1C1=CC=NC=C1OC1=CC=CC=C1 ZRESGPGOHDLDHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 5
- VBOCSJZZLQOSLS-UHFFFAOYSA-N 1-(3-phenoxypyridin-2-yl)piperazine Chemical compound C1CNCCN1C1=NC=CC=C1OC1=CC=CC=C1 VBOCSJZZLQOSLS-UHFFFAOYSA-N 0.000 claims 2
- OUTXMSVYLCVSKL-UHFFFAOYSA-N 1-(3-phenoxypyridin-4-yl)piperazine Chemical compound C1CNCCN1C1=CC=NC=C1OC1=CC=CC=C1 OUTXMSVYLCVSKL-UHFFFAOYSA-N 0.000 claims 2
- VZQWFIMLBIBELZ-UHFFFAOYSA-N 1-(5-phenoxypyridin-2-yl)piperazine Chemical compound C1CNCCN1C(N=C1)=CC=C1OC1=CC=CC=C1 VZQWFIMLBIBELZ-UHFFFAOYSA-N 0.000 claims 2
- AOHJVZRVQOGHCE-UHFFFAOYSA-N 3-phenoxy-n-phenylpyridin-2-amine Chemical compound N=1C=CC=C(OC=2C=CC=CC=2)C=1NC1=CC=CC=C1 AOHJVZRVQOGHCE-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- CLLVLNOITPDZJL-UHFFFAOYSA-N 1-(5-phenoxypyridin-3-yl)piperazine Chemical compound C1CNCCN1C1=CN=CC(OC=2C=CC=CC=2)=C1 CLLVLNOITPDZJL-UHFFFAOYSA-N 0.000 claims 1
- HTDBRJYWLNSKPN-UHFFFAOYSA-N 2-(3-bromopyridin-2-yl)piperazine Chemical compound BrC1=CC=CN=C1C1NCCNC1 HTDBRJYWLNSKPN-UHFFFAOYSA-N 0.000 claims 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 4
- 239000012190 activator Substances 0.000 abstract description 3
- 230000019771 cognition Effects 0.000 abstract description 3
- 239000002831 pharmacologic agent Substances 0.000 abstract description 2
- 238000006392 deoxygenation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 68
- 239000000203 mixture Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 8
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 229940083608 sodium hydroxide Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000035939 shock Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 208000000044 Amnesia Diseases 0.000 description 5
- 208000031091 Amnestic disease Diseases 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 230000006986 amnesia Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FYMYERCFXFLAJI-UHFFFAOYSA-N 2-chloro-5-phenoxypyridine Chemical compound C1=NC(Cl)=CC=C1OC1=CC=CC=C1 FYMYERCFXFLAJI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 3
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 2
- UBRHUPQXDLTSPM-UHFFFAOYSA-N 2-chloro-5-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CC=C(Cl)N=C1 UBRHUPQXDLTSPM-UHFFFAOYSA-N 0.000 description 2
- FEKAXCSBZQRANH-UHFFFAOYSA-N 2-chloro-5-(4-chlorophenoxy)pyridine Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(Cl)N=C1 FEKAXCSBZQRANH-UHFFFAOYSA-N 0.000 description 2
- VEZNYKAAWIWXKS-UHFFFAOYSA-N 3-(2-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC=C1OC1=CC=CN=C1 VEZNYKAAWIWXKS-UHFFFAOYSA-N 0.000 description 2
- QHWIGULJOZAPAQ-UHFFFAOYSA-N 3-fluoro-4-nitro-1-oxidopyridin-1-ium Chemical compound [O-][N+](=O)C1=CC=[N+]([O-])C=C1F QHWIGULJOZAPAQ-UHFFFAOYSA-N 0.000 description 2
- JYZUKJACRQUZEM-UHFFFAOYSA-N 3-phenoxy-n-phenylpyridin-4-amine Chemical compound C=1C=NC=C(OC=2C=CC=CC=2)C=1NC1=CC=CC=C1 JYZUKJACRQUZEM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000003927 aminopyridines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000644 isotonic solution Substances 0.000 description 2
- 238000011005 laboratory method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- ISPQHPJHCAZKQQ-UHFFFAOYSA-N 1-(5-phenoxypyridin-3-yl)piperazine;hydrochloride Chemical compound Cl.C1CNCCN1C1=CN=CC(OC=2C=CC=CC=2)=C1 ISPQHPJHCAZKQQ-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
- YKNCPWSLUZSGGL-UHFFFAOYSA-N 1-[3-(2-fluorophenoxy)pyridin-4-yl]piperazine Chemical group FC1=CC=CC=C1OC1=CN=CC=C1N1CCNCC1 YKNCPWSLUZSGGL-UHFFFAOYSA-N 0.000 description 1
- JYQXWNYSTSQSHG-UHFFFAOYSA-N 1-[5-(2-fluorophenoxy)pyridin-2-yl]piperazine Chemical group FC1=CC=CC=C1OC1=CC=C(N2CCNCC2)N=C1 JYQXWNYSTSQSHG-UHFFFAOYSA-N 0.000 description 1
- CQCJWARBGJHIHV-UHFFFAOYSA-N 1-oxido-3-phenoxypyridin-1-ium Chemical compound [O-][N+]1=CC=CC(OC=2C=CC=CC=2)=C1 CQCJWARBGJHIHV-UHFFFAOYSA-N 0.000 description 1
- WDCQCMFALZKBAJ-UHFFFAOYSA-N 2-chloro-2-(2-chlorophenoxy)-1H-pyridine Chemical compound ClC1(NC=CC=C1)OC1=C(C=CC=C1)Cl WDCQCMFALZKBAJ-UHFFFAOYSA-N 0.000 description 1
- VXVMCTRRZVLNMC-UHFFFAOYSA-N 2-chloro-3-(2-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC=C1OC1=CC=CN=C1Cl VXVMCTRRZVLNMC-UHFFFAOYSA-N 0.000 description 1
- MHSRUMMGBPDJQW-UHFFFAOYSA-N 2-chloro-3-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CC=CN=C1Cl MHSRUMMGBPDJQW-UHFFFAOYSA-N 0.000 description 1
- FANQVXHNUUERHL-UHFFFAOYSA-N 2-chloro-5-(2-chlorophenoxy)pyridine Chemical compound C1=NC(Cl)=CC=C1OC1=CC=CC=C1Cl FANQVXHNUUERHL-UHFFFAOYSA-N 0.000 description 1
- XQRWHBHPGRISIO-UHFFFAOYSA-N 2-chloro-5-(3-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC(OC=2C=NC(Cl)=CC=2)=C1 XQRWHBHPGRISIO-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WWWJDCQANDPHSB-UHFFFAOYSA-N 3-(2-chlorophenoxy)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1 WWWJDCQANDPHSB-UHFFFAOYSA-N 0.000 description 1
- NDIGRNJFASLSQR-UHFFFAOYSA-N 3-(2-fluorophenoxy)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(OC=2C(=CC=CC=2)F)=C1 NDIGRNJFASLSQR-UHFFFAOYSA-N 0.000 description 1
- RAWJVKJJJPYTHC-UHFFFAOYSA-N 3-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CC=CN=C1 RAWJVKJJJPYTHC-UHFFFAOYSA-N 0.000 description 1
- GAXYPVMANWPADW-UHFFFAOYSA-N 3-(4-chlorophenoxy)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 GAXYPVMANWPADW-UHFFFAOYSA-N 0.000 description 1
- WBBOYAFEUKQDFW-UHFFFAOYSA-N 3-bromo-1-oxido-5-phenoxypyridin-1-ium Chemical compound [O-][N+]1=CC(Br)=CC(OC=2C=CC=CC=2)=C1 WBBOYAFEUKQDFW-UHFFFAOYSA-N 0.000 description 1
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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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/907,422 US4179563A (en) | 1978-05-19 | 1978-05-19 | 3-Aryloxy-substituted-aminopyridines and methods for their production |
| US907,422 | 1978-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109468A true CA1109468A (en) | 1981-09-22 |
Family
ID=25424069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA327,810A Expired CA1109468A (en) | 1978-05-19 | 1979-05-17 | 3-aryloxy-substituted-aminopyridines and methods for their production |
Country Status (7)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4386094A (en) * | 1980-08-18 | 1983-05-31 | Warner-Lambert Company | 4-Lower alkyl-3-phenoxypyridine-1-oxide and a method for its production |
| TW200462B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-09-27 | 1993-02-21 | Hoechst Roussel Pharma | |
| HU226859B1 (en) * | 1997-10-27 | 2009-12-28 | Neurosearch As | Phenyl- or heteroaryl-homopiperazines, their use and medicaments containing them |
| WO2000064885A1 (en) * | 1999-04-26 | 2000-11-02 | Neurosearch A/S | Heteroaryl diazacycloalkanes, their preparation and use |
| CA2470214A1 (en) * | 2001-12-13 | 2003-06-26 | Abbott Laboratories | 3-(phenyl-alkoxy)-5-(phenyl)-pyridine derivatives and related compounds as kinase inhibitors for the treatment of cancer |
| US20030187026A1 (en) * | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| ATE499370T1 (de) * | 2005-01-19 | 2011-03-15 | Bristol Myers Squibb Co | 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3- aminderivate und verwandte verbindungen als p2y1- rezeptor-hemmer zur behandlung thromboembolischer erkrankungen |
| MX2007016501A (es) * | 2005-06-27 | 2008-03-06 | Squibb Bristol Myers Co | Antagonistas heterociclicos n-enlazados del receptor de p2y1, utiles en el tratamiento de condiciones tromboticas. |
| ATE502924T1 (de) | 2005-06-27 | 2011-04-15 | Bristol Myers Squibb Co | Lineare harnstoffmimetika-antagonisten des p2y1- rezeptors zur behandlung von thromboseleiden |
| US7700620B2 (en) * | 2005-06-27 | 2010-04-20 | Bristol-Myers Squibb Company | C-linked cyclic antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| WO2007002634A1 (en) * | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
| US7960569B2 (en) * | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| GB0719559D0 (en) * | 2007-10-05 | 2007-11-14 | Senexis Ltd | Compounds |
| JP5769348B2 (ja) * | 2010-03-22 | 2015-08-26 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | １−（２−フェノキシメチルヘテロアリール）ピペリジン化合物および１−（２−フェノキシメチルヘテロアリール）ピペラジン化合物 |
| CN113286783B (zh) | 2019-01-30 | 2024-11-22 | 住友化学株式会社 | 氯苯化合物的制造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2285883A1 (fr) * | 1974-09-30 | 1976-04-23 | Cerm Cent Europ Rech Mauvernay | Nouveaux composes chimiques a activite bronchospasmolytique et antitussive, et procede pour leur obtention |
| US4078063A (en) * | 1976-09-24 | 1978-03-07 | Merck & Co., Inc. | Piperazinylpyridines |
-
1978
- 1978-05-19 US US05/907,422 patent/US4179563A/en not_active Expired - Lifetime
-
1979
- 1979-05-17 CA CA327,810A patent/CA1109468A/en not_active Expired
- 1979-05-17 FR FR7912592A patent/FR2426051A1/fr active Granted
- 1979-05-18 DE DE19792920250 patent/DE2920250A1/de active Granted
- 1979-05-18 BE BE0/195269A patent/BE876389A/xx not_active IP Right Cessation
- 1979-05-18 JP JP6138179A patent/JPS55384A/ja active Pending
- 1979-05-21 GB GB7917597A patent/GB2021113B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4179563A (en) | 1979-12-18 |
| FR2426051A1 (fr) | 1979-12-14 |
| JPS55384A (en) | 1980-01-05 |
| GB2021113A (en) | 1979-11-28 |
| DE2920250A1 (de) | 1979-11-22 |
| DE2920250C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-05-26 |
| BE876389A (fr) | 1979-09-17 |
| GB2021113B (en) | 1982-07-07 |
| FR2426051B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-06 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |