NO834778L - Fremgangsmaate for fremstilling av pyridinderivater for anvendelse som histamin h1-antagonister - Google Patents
Fremgangsmaate for fremstilling av pyridinderivater for anvendelse som histamin h1-antagonisterInfo
- Publication number
- NO834778L NO834778L NO834778A NO834778A NO834778L NO 834778 L NO834778 L NO 834778L NO 834778 A NO834778 A NO 834778A NO 834778 A NO834778 A NO 834778A NO 834778 L NO834778 L NO 834778L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- amino
- pyridine
- pyridyl
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 43
- 239000000938 histamine H1 antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 55
- -1 nitroamino Chemical group 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 217
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 156
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 82
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 55
- 229910001868 water Inorganic materials 0.000 description 55
- 235000019441 ethanol Nutrition 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- 239000000203 mixture Substances 0.000 description 45
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 34
- 239000003153 chemical reaction reagent Substances 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000001953 recrystallisation Methods 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000006308 propyl amino group Chemical group 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- CDHKCMVEGUQUCN-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide Chemical compound COC1=NS(=O)N=C1OC CDHKCMVEGUQUCN-UHFFFAOYSA-N 0.000 description 18
- 238000000605 extraction Methods 0.000 description 17
- 229960001340 histamine Drugs 0.000 description 17
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- RTNAJFYRBGURSJ-UHFFFAOYSA-N n'-benzyl-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CC=C1 RTNAJFYRBGURSJ-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000000725 suspension Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- 239000012259 ether extract Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- XBGXIBMSNZCBFN-UHFFFAOYSA-N n'-[(4-fluorophenyl)methyl]-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=C(F)C=C1 XBGXIBMSNZCBFN-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- CNDAFPBECHAXDU-UHFFFAOYSA-N n'-pyridin-2-ylpropane-1,3-diamine Chemical compound NCCCNC1=CC=CC=N1 CNDAFPBECHAXDU-UHFFFAOYSA-N 0.000 description 10
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- NCGUHISSCDXVCC-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(thiophen-2-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CS1 NCGUHISSCDXVCC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 5
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical compound CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 5
- ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide Chemical compound COC1=NS(=O)(=O)N=C1OC ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- JVXQGCCEIUJGPI-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(pyridin-2-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CC=N1 JVXQGCCEIUJGPI-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 206010012434 Dermatitis allergic Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- JVVSYNUUVZAGHV-UHFFFAOYSA-N n'-[(4-chlorophenyl)methyl]-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=C(Cl)C=C1 JVVSYNUUVZAGHV-UHFFFAOYSA-N 0.000 description 3
- GXVWAPSUGRGEOE-UHFFFAOYSA-N n'-[(4-methoxyphenyl)methyl]-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C1=CC(OC)=CC=C1CN(CCCN)C1=CC=CC=N1 GXVWAPSUGRGEOE-UHFFFAOYSA-N 0.000 description 3
- OWPDARIZDGKRHW-UHFFFAOYSA-N n'-benzyl-n'-pyridin-2-ylbutane-1,4-diamine Chemical compound C=1C=CC=NC=1N(CCCCN)CC1=CC=CC=C1 OWPDARIZDGKRHW-UHFFFAOYSA-N 0.000 description 3
- YMIXDVMMBSPTAU-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(thiophen-3-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC=1C=CSC=1 YMIXDVMMBSPTAU-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
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- 206010039083 rhinitis Diseases 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229960001268 isoetarine Drugs 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BRNXNANMZAKXJV-UHFFFAOYSA-N n'-(furan-2-ylmethyl)-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CO1 BRNXNANMZAKXJV-UHFFFAOYSA-N 0.000 description 1
- UQWRIYBBAXXGQG-UHFFFAOYSA-N n'-[(2-chlorophenyl)methyl]-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CC=C1Cl UQWRIYBBAXXGQG-UHFFFAOYSA-N 0.000 description 1
- QHDCPVFIYNZDJD-UHFFFAOYSA-N n'-[(2-fluorophenyl)methyl]-n'-pyridin-2-ylpropane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CC=C1F QHDCPVFIYNZDJD-UHFFFAOYSA-N 0.000 description 1
- YSBSGLBKFBEQMD-UHFFFAOYSA-N n'-[(4-chlorophenyl)methyl]-n'-pyridin-2-ylbutane-1,4-diamine Chemical compound C=1C=CC=NC=1N(CCCCN)CC1=CC=C(Cl)C=C1 YSBSGLBKFBEQMD-UHFFFAOYSA-N 0.000 description 1
- XBELIORNZFSPPE-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(1,3-thiazol-2-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=NC=CS1 XBELIORNZFSPPE-UHFFFAOYSA-N 0.000 description 1
- PFOBAUOPMDPHSE-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(pyridin-3-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=CN=C1 PFOBAUOPMDPHSE-UHFFFAOYSA-N 0.000 description 1
- LSEVGHVAVUPBDX-UHFFFAOYSA-N n'-pyridin-2-yl-n'-(pyridin-4-ylmethyl)propane-1,3-diamine Chemical compound C=1C=CC=NC=1N(CCCN)CC1=CC=NC=C1 LSEVGHVAVUPBDX-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000278 theophylline Drugs 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
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8236637 | 1982-12-23 | ||
| GB838322349A GB8322349D0 (en) | 1983-08-19 | 1983-08-19 | Pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834778L true NO834778L (no) | 1984-06-25 |
Family
ID=26284767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834778A NO834778L (no) | 1982-12-23 | 1983-12-22 | Fremgangsmaate for fremstilling av pyridinderivater for anvendelse som histamin h1-antagonister |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US4532246A (fi) |
| EP (1) | EP0112704B1 (fi) |
| AU (1) | AU2274783A (fi) |
| DE (1) | DE3374007D1 (fi) |
| DK (1) | DK592183A (fi) |
| ES (1) | ES528309A0 (fi) |
| FI (1) | FI834735A (fi) |
| GR (1) | GR79740B (fi) |
| IL (1) | IL70497A0 (fi) |
| JO (1) | JO1279B1 (fi) |
| NO (1) | NO834778L (fi) |
| NZ (1) | NZ206636A (fi) |
| PT (1) | PT77855B (fi) |
| ZW (1) | ZW27383A1 (fi) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| DE3374313D1 (de) * | 1982-12-23 | 1987-12-10 | Smith Kline French Lab | Aminopyrimidinone derivatives as histamine h1-antagonists |
| CA1275097A (en) * | 1984-10-02 | 1990-10-09 | Fujio Nohara | Pyridyloxy derivatives |
| US4728648A (en) * | 1985-02-09 | 1988-03-01 | Smith Kline & French Laboratories Limited | Histamine antagonist triadiazole derivatives, compositions, and method of use therefor |
| GB8509277D0 (en) * | 1985-04-11 | 1985-05-15 | Smith Kline French Lab | Pyridine derivatives |
| GB8509276D0 (en) * | 1985-04-11 | 1985-05-15 | Smith Kline French Lab | Pyridine derivatives |
| CA1286297C (en) * | 1985-06-13 | 1991-07-16 | George S. Sach | Pyridine derivatives |
| GB8610867D0 (en) * | 1986-05-02 | 1986-06-11 | Smith Kline French Lab | 3-hydroxypyridines |
| US5872139A (en) * | 1996-06-17 | 1999-02-16 | American Home Products Corporation | Heterocyclymethylamino derivatives of cyclobutene-3,4-diones |
| JP4533534B2 (ja) | 1998-06-19 | 2010-09-01 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | グリコーゲンシンターゼキナーゼ３のインヒビター |
| US7045519B2 (en) | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| MXPA05003867A (es) * | 2002-10-09 | 2005-11-23 | Schering Corp | Tiadiazoldioxidos y tiadiazoloxidos como ligandos de receptor cxc-y cc-quimiocina. |
| EP1694659B8 (en) * | 2003-12-19 | 2008-10-08 | Schering Corporation | Thiadiazoles as cxc- and cc- chemokine receptor ligands |
| MXPA06007205A (es) * | 2003-12-22 | 2006-08-31 | Schering Corp | Dioxidos de isotiazol como ligandos del receptor cxc y cc-quimiocina. |
| WO2007002764A2 (en) * | 2005-06-29 | 2007-01-04 | Schering Corporation | Di-substituted oxadiazoles as cxc-chemokine receptor ligands |
| US7897606B2 (en) * | 2005-06-29 | 2011-03-01 | Schering Corporation | 5,6-di-substituted oxadiazolopyrazines and thiadiazolopyrazines as CXC-chemokine receptor ligands |
| MX2011013134A (es) * | 2009-06-09 | 2012-03-16 | Topotarget As | Derivados de piridinil como inhibidores de la enzima nicotinamida fosforribosiltransferasa. |
| CN111349014A (zh) * | 2020-03-30 | 2020-06-30 | 绵阳达高特新材料有限公司 | 一种方酸甲胺甲酯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535328A (en) * | 1967-09-01 | 1970-10-20 | Exxon Research Engineering Co | Certain substituted aminothioethoxy pyridines |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| GB1563090A (en) * | 1975-07-31 | 1980-03-19 | Smith Kline French Lab | Cyclobutene-diones |
| US4120973A (en) * | 1975-07-31 | 1978-10-17 | Smithkline & French Laboratories Limited | Imidazolyl alkylaminocyclobutenediones |
| US4255428A (en) * | 1979-03-24 | 1981-03-10 | Smith Kline & French Laboratories Limited | 5-(Hydroxypyridylalkyl)-4-pyrimidones |
| DE3175201D1 (en) * | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
| US4394508A (en) * | 1980-06-07 | 1983-07-19 | Bristol-Myers Company | Chemical compounds |
-
1983
- 1983-12-19 DE DE8383307708T patent/DE3374007D1/de not_active Expired
- 1983-12-19 PT PT77855A patent/PT77855B/pt unknown
- 1983-12-19 JO JO19831279A patent/JO1279B1/en active
- 1983-12-19 EP EP83307708A patent/EP0112704B1/en not_active Expired
- 1983-12-20 NZ NZ206636A patent/NZ206636A/xx unknown
- 1983-12-20 IL IL70497A patent/IL70497A0/xx unknown
- 1983-12-20 US US06/563,496 patent/US4532246A/en not_active Expired - Fee Related
- 1983-12-20 ZW ZW273/83A patent/ZW27383A1/xx unknown
- 1983-12-21 AU AU22747/83A patent/AU2274783A/en not_active Abandoned
- 1983-12-22 FI FI834735A patent/FI834735A/fi not_active Application Discontinuation
- 1983-12-22 NO NO834778A patent/NO834778L/no unknown
- 1983-12-22 ES ES528309A patent/ES528309A0/es active Granted
- 1983-12-22 DK DK592183A patent/DK592183A/da not_active Application Discontinuation
- 1983-12-22 GR GR73335A patent/GR79740B/el unknown
-
1985
- 1985-05-17 US US06/735,036 patent/US4607106A/en not_active Expired - Fee Related
-
1986
- 1986-06-19 US US06/876,049 patent/US4659725A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0112704A3 (en) | 1985-08-28 |
| ES8506629A1 (es) | 1985-08-01 |
| ZW27383A1 (en) | 1985-07-24 |
| EP0112704A2 (en) | 1984-07-04 |
| ES528309A0 (es) | 1985-08-01 |
| FI834735A (fi) | 1984-06-24 |
| DE3374007D1 (en) | 1987-11-12 |
| US4659725A (en) | 1987-04-21 |
| DK592183D0 (da) | 1983-12-22 |
| DK592183A (da) | 1984-06-24 |
| EP0112704B1 (en) | 1987-10-07 |
| IL70497A0 (en) | 1984-03-30 |
| GR79740B (fi) | 1984-10-31 |
| AU2274783A (en) | 1984-06-28 |
| US4532246A (en) | 1985-07-30 |
| JO1279B1 (en) | 1985-04-20 |
| PT77855B (en) | 1986-04-16 |
| PT77855A (en) | 1984-01-01 |
| FI834735A0 (fi) | 1983-12-22 |
| US4607106A (en) | 1986-08-19 |
| NZ206636A (en) | 1985-07-31 |
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