DE2920250C2 - - Google Patents
Info
- Publication number
- DE2920250C2 DE2920250C2 DE2920250A DE2920250A DE2920250C2 DE 2920250 C2 DE2920250 C2 DE 2920250C2 DE 2920250 A DE2920250 A DE 2920250A DE 2920250 A DE2920250 A DE 2920250A DE 2920250 C2 DE2920250 C2 DE 2920250C2
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- chloro
- chlorophenoxy
- phenoxypyridine
- mixture
- 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
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 1-piperazinyl Chemical group 0.000 claims description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000007792 addition Methods 0.000 claims description 13
- 229910052801 chlorine Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- OUTXMSVYLCVSKL-UHFFFAOYSA-N 1-(3-phenoxypyridin-4-yl)piperazine Chemical compound C1CNCCN1C1=CC=NC=C1OC1=CC=CC=C1 OUTXMSVYLCVSKL-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 150000003927 aminopyridines Chemical class 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 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 description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- VBOCSJZZLQOSLS-UHFFFAOYSA-N 1-(3-phenoxypyridin-2-yl)piperazine Chemical compound C1CNCCN1C1=NC=CC=C1OC1=CC=CC=C1 VBOCSJZZLQOSLS-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 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 1
- 241001222610 Anilios Species 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 239000000203 mixture Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- FYMYERCFXFLAJI-UHFFFAOYSA-N 2-chloro-5-phenoxypyridine Chemical compound C1=NC(Cl)=CC=C1OC1=CC=CC=C1 FYMYERCFXFLAJI-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- OAFJWUWAKXLAMQ-UHFFFAOYSA-N 4-chloro-3-phenoxypyridine Chemical compound ClC1=CC=NC=C1OC1=CC=CC=C1 OAFJWUWAKXLAMQ-UHFFFAOYSA-N 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QEKCEGZYIXGKID-UHFFFAOYSA-N 2-chloro-3-phenoxypyridine Chemical compound ClC1=NC=CC=C1OC1=CC=CC=C1 QEKCEGZYIXGKID-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 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 5
- 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 5
- BGPNFMIRDZLCFE-UHFFFAOYSA-N 4-chloro-3-(2-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC=C1OC1=CN=CC=C1Cl BGPNFMIRDZLCFE-UHFFFAOYSA-N 0.000 description 5
- 208000000044 Amnesia Diseases 0.000 description 5
- 208000031091 Amnestic disease Diseases 0.000 description 5
- 230000006986 amnesia Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 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 description 4
- RAWJVKJJJPYTHC-UHFFFAOYSA-N 3-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CC=CN=C1 RAWJVKJJJPYTHC-UHFFFAOYSA-N 0.000 description 4
- NSEUCGOPJSFPEX-UHFFFAOYSA-N 4-chloro-3-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CN=CC=C1Cl NSEUCGOPJSFPEX-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 3
- 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 description 3
- MHSRUMMGBPDJQW-UHFFFAOYSA-N 2-chloro-3-(2-fluorophenoxy)pyridine Chemical compound FC1=CC=CC=C1OC1=CC=CN=C1Cl MHSRUMMGBPDJQW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 238000002474 experimental method Methods 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
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012549 training Methods 0.000 description 3
- 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 2
- PXZKSGHGYGWDCK-UHFFFAOYSA-N 1-[3-(2-chlorophenoxy)pyridin-4-yl]piperazine Chemical compound ClC1=CC=CC=C1OC1=CN=CC=C1N1CCNCC1 PXZKSGHGYGWDCK-UHFFFAOYSA-N 0.000 description 2
- KGOBLNOMRMVTCI-UHFFFAOYSA-N 1-[3-(2-fluorophenoxy)pyridin-2-yl]piperazine Chemical compound FC1=CC=CC=C1OC1=CC=CN=C1N1CCNCC1 KGOBLNOMRMVTCI-UHFFFAOYSA-N 0.000 description 2
- YKNCPWSLUZSGGL-UHFFFAOYSA-N 1-[3-(2-fluorophenoxy)pyridin-4-yl]piperazine Chemical compound FC1=CC=CC=C1OC1=CN=CC=C1N1CCNCC1 YKNCPWSLUZSGGL-UHFFFAOYSA-N 0.000 description 2
- LCNWEESHRWXGRF-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)pyridin-2-yl]piperazine Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CN=C1N1CCNCC1 LCNWEESHRWXGRF-UHFFFAOYSA-N 0.000 description 2
- JYQXWNYSTSQSHG-UHFFFAOYSA-N 1-[5-(2-fluorophenoxy)pyridin-2-yl]piperazine Chemical compound FC1=CC=CC=C1OC1=CC=C(N2CCNCC2)N=C1 JYQXWNYSTSQSHG-UHFFFAOYSA-N 0.000 description 2
- HJHHSDZEAFFSMG-UHFFFAOYSA-N 1-methyl-4-(3-phenoxypyridin-4-yl)-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CC=NC=C1OC1=CC=CC=C1 HJHHSDZEAFFSMG-UHFFFAOYSA-N 0.000 description 2
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 2
- HTDBRJYWLNSKPN-UHFFFAOYSA-N 2-(3-bromopyridin-2-yl)piperazine Chemical compound BrC1=CC=CN=C1C1NCCNC1 HTDBRJYWLNSKPN-UHFFFAOYSA-N 0.000 description 2
- VXVMCTRRZVLNMC-UHFFFAOYSA-N 2-chloro-3-(2-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC=C1OC1=CC=CN=C1Cl VXVMCTRRZVLNMC-UHFFFAOYSA-N 0.000 description 2
- IADJLUNVQVHFSV-UHFFFAOYSA-N 2-chloro-3-(3-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC(OC=2C(=NC=CC=2)Cl)=C1 IADJLUNVQVHFSV-UHFFFAOYSA-N 0.000 description 2
- SJQIFVVSPIHCTN-UHFFFAOYSA-N 2-chloro-3-(4-chlorophenoxy)pyridine Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CN=C1Cl SJQIFVVSPIHCTN-UHFFFAOYSA-N 0.000 description 2
- DYCFWMFPOMJQLF-UHFFFAOYSA-N 3-(2-chlorophenoxy)-4-nitro-1-oxidopyridin-1-ium Chemical compound [O-][N+](=O)C1=CC=[N+]([O-])C=C1OC1=CC=CC=C1Cl DYCFWMFPOMJQLF-UHFFFAOYSA-N 0.000 description 2
- GRCLRWIIFWIFME-UHFFFAOYSA-N 3-(3-chlorophenoxy)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(OC=2C=C(Cl)C=CC=2)=C1 GRCLRWIIFWIFME-UHFFFAOYSA-N 0.000 description 2
- BENAOXJXCWCSKO-UHFFFAOYSA-N 3-(3-chlorophenoxy)pyridine Chemical compound ClC1=CC=CC(OC=2C=NC=CC=2)=C1 BENAOXJXCWCSKO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VAJUMXLXLHVWEN-UHFFFAOYSA-N 3-chloro-5-phenoxypyridine Chemical compound ClC1=CN=CC(OC=2C=CC=CC=2)=C1 VAJUMXLXLHVWEN-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
- NPXCDHVICZEXFS-UHFFFAOYSA-N 3-methyl-1-(3-phenoxypyridin-4-yl)piperazine Chemical compound C1CNC(C)CN1C1=CC=NC=C1OC1=CC=CC=C1 NPXCDHVICZEXFS-UHFFFAOYSA-N 0.000 description 2
- BKFGDUKDIYFDFK-UHFFFAOYSA-N 4-chloro-3-(4-chlorophenoxy)pyridine Chemical compound C1=CC(Cl)=CC=C1OC1=CN=CC=C1Cl BKFGDUKDIYFDFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
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Classifications
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- 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 (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2920250A1 DE2920250A1 (de) | 1979-11-22 |
| DE2920250C2 true DE2920250C2 (en, 2012) | 1988-05-26 |
Family
ID=25424069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792920250 Granted DE2920250A1 (de) | 1978-05-19 | 1979-05-18 | 3-aryloxysubstituierte aminopyridine |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4179563A (en, 2012) |
| JP (1) | JPS55384A (en, 2012) |
| BE (1) | BE876389A (en, 2012) |
| CA (1) | CA1109468A (en, 2012) |
| DE (1) | DE2920250A1 (en, 2012) |
| FR (1) | FR2426051A1 (en, 2012) |
| GB (1) | GB2021113B (en, 2012) |
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 (en, 2012) * | 1990-09-27 | 1993-02-21 | Hoechst Roussel Pharma | |
| DE69826883T2 (de) | 1997-10-27 | 2005-02-03 | Neurosearch A/S | Heteroaryl diazacycloalkane als cholinergische ligande für nikotin-acetylcholin-rezeptoren |
| WO2000064885A1 (en) * | 1999-04-26 | 2000-11-02 | Neurosearch A/S | Heteroaryl diazacycloalkanes, their preparation and use |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| JP2005516927A (ja) * | 2001-12-13 | 2005-06-09 | アボット・ラボラトリーズ | 癌治療用のキナーゼ阻害剤としての３−（フェニル−アルコキシ）−５−（フェニル）−ピリジン誘導体および関連化合物 |
| US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| AU2006206611A1 (en) * | 2005-01-19 | 2006-07-27 | Bristol-Myers Squibb Company | 2-phenoxy-N- (1, 3 , 4-thiadizol-2-yl) pyridin-3-amine derivatives and related compounds as P2Y1 receptor inhibitors for the treatment of thromboembolic disorders |
| US7714002B2 (en) * | 2005-06-27 | 2010-05-11 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| ATE485269T1 (de) * | 2005-06-27 | 2010-11-15 | Bristol Myers Squibb Co | C-verknüpfte zyklische antagonisten des p2y1- rezeptors mit eignung bei der behandlung thrombotischer leiden |
| DE602006020871D1 (de) | 2005-06-27 | 2011-05-05 | Bristol Myers Squibb Co | Lineare harnstoffmimetika-antagonisten des p2y1-rezeptors zur behandlung von thromboseleiden |
| AU2006261828A1 (en) * | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | N-linked heterocyclic 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 |
| JP7426951B2 (ja) | 2019-01-30 | 2024-02-02 | 住友化学株式会社 | クロロベンゼン化合物の製造方法 |
Family Cites Families (2)
| 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 |
| CA1109468A (en) | 1981-09-22 |
| FR2426051A1 (fr) | 1979-12-14 |
| DE2920250A1 (de) | 1979-11-22 |
| BE876389A (fr) | 1979-09-17 |
| GB2021113A (en) | 1979-11-28 |
| JPS55384A (en) | 1980-01-05 |
| GB2021113B (en) | 1982-07-07 |
| FR2426051B1 (en, 2012) | 1981-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |