CA1085398A - Oxygenated n-aryl-diazacyclic compounds - Google Patents
Oxygenated n-aryl-diazacyclic compoundsInfo
- Publication number
- CA1085398A CA1085398A CA270,045A CA270045A CA1085398A CA 1085398 A CA1085398 A CA 1085398A CA 270045 A CA270045 A CA 270045A CA 1085398 A CA1085398 A CA 1085398A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- phenyl
- propyl
- hydroxy
- 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 title claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- WIDFNOIYHYOUQG-UHFFFAOYSA-N 1-phenyl-3-piperidin-4-ylimidazolidin-2-one Chemical compound O=C1N(C2CCNCC2)CCN1C1=CC=CC=C1 WIDFNOIYHYOUQG-UHFFFAOYSA-N 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- OSQALEDZUJAUFD-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-piperidin-4-ylimidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CCNCC2)CC1 OSQALEDZUJAUFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 claims description 3
- AEXSVWXMXFHLCQ-UHFFFAOYSA-N 1-[4-(2-anilinoethylamino)piperidin-1-yl]-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(NCCNC=2C=CC=CC=2)CC1 AEXSVWXMXFHLCQ-UHFFFAOYSA-N 0.000 claims description 2
- FYEKJXSXDASODO-UHFFFAOYSA-N 2-chloro-3-(oxiran-2-ylmethoxy)pyrazine Chemical compound ClC1=NC=CN=C1OCC1OC1 FYEKJXSXDASODO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- OFFSTJBYUMSCEB-UHFFFAOYSA-N 1-[1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperidin-4-yl]-3-(4-methoxyphenyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CCN(CC(O)COC=3C(=CC=CC=3)OC)CC2)CC1 OFFSTJBYUMSCEB-UHFFFAOYSA-N 0.000 claims 1
- XHAJMPJJYDDPHG-UHFFFAOYSA-N 1-[1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperidin-4-yl]-3-phenylimidazolidin-2-one Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(N2C(N(CC2)C=2C=CC=CC=2)=O)CC1 XHAJMPJJYDDPHG-UHFFFAOYSA-N 0.000 claims 1
- BQEXGIJHWRMSAH-UHFFFAOYSA-N 1-[1-[2-hydroxy-3-(3-methoxypyrazin-2-yl)oxypropyl]piperidin-4-yl]-3-phenylimidazolidin-2-one Chemical compound COC1=NC=CN=C1OCC(O)CN1CCC(N2C(N(CC2)C=2C=CC=CC=2)=O)CC1 BQEXGIJHWRMSAH-UHFFFAOYSA-N 0.000 claims 1
- OCPMZUQPHAZZNW-UHFFFAOYSA-N 1-[1-[3-(3-chloropyrazin-2-yl)oxy-2-hydroxypropyl]piperidin-4-yl]-3-phenylimidazolidin-2-one Chemical compound C1CC(N2C(N(CC2)C=2C=CC=CC=2)=O)CCN1CC(O)COC1=NC=CN=C1Cl OCPMZUQPHAZZNW-UHFFFAOYSA-N 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 22
- 239000007858 starting material Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 235000011167 hydrochloric acid Nutrition 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 229960000443 hydrochloric acid Drugs 0.000 description 15
- 229960004592 isopropanol Drugs 0.000 description 15
- -1 n-bu~yl Chemical group 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- VGRGYZHTRQHSRL-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-phenylimidazolidin-2-one Chemical compound O=C1N(C2CCN(CC=3C=CC=CC=3)CC2)CCN1C1=CC=CC=C1 VGRGYZHTRQHSRL-UHFFFAOYSA-N 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- VRJHQPZVIGNGMX-UHFFFAOYSA-N piperidine-4-one Natural products O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- DYQPAVDDRLNLKW-UHFFFAOYSA-N 1-(4-chlorophenyl)ethane-1,2-diamine Chemical compound NCC(N)C1=CC=C(Cl)C=C1 DYQPAVDDRLNLKW-UHFFFAOYSA-N 0.000 description 2
- BBTWNLMGIZFHPV-UHFFFAOYSA-N 1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperidin-4-one Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(=O)CC1 BBTWNLMGIZFHPV-UHFFFAOYSA-N 0.000 description 2
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YLLORXQFHZAMRT-UHFFFAOYSA-N 1-(4-methoxyphenyl)ethane-1,2-diamine Chemical compound COC1=CC=C(C(N)CN)C=C1 YLLORXQFHZAMRT-UHFFFAOYSA-N 0.000 description 1
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- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 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
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH70276 | 1976-01-21 | ||
| CH702/76 | 1976-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085398A true CA1085398A (en) | 1980-09-09 |
Family
ID=4193177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,045A Expired CA1085398A (en) | 1976-01-21 | 1977-01-19 | Oxygenated n-aryl-diazacyclic compounds |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4144344A (OSRAM) |
| JP (1) | JPS52105182A (OSRAM) |
| AT (1) | AT355570B (OSRAM) |
| AU (1) | AU512020B2 (OSRAM) |
| BE (1) | BE850556A (OSRAM) |
| CA (1) | CA1085398A (OSRAM) |
| DD (1) | DD129650A5 (OSRAM) |
| DE (1) | DE2701794A1 (OSRAM) |
| DK (1) | DK21777A (OSRAM) |
| ES (2) | ES455151A1 (OSRAM) |
| FI (1) | FI770190A7 (OSRAM) |
| FR (1) | FR2338940A1 (OSRAM) |
| GB (1) | GB1565902A (OSRAM) |
| GR (1) | GR62393B (OSRAM) |
| IE (1) | IE44276B1 (OSRAM) |
| IL (1) | IL51301A0 (OSRAM) |
| NL (1) | NL7700530A (OSRAM) |
| NO (1) | NO770176L (OSRAM) |
| NZ (1) | NZ183134A (OSRAM) |
| PL (1) | PL195461A1 (OSRAM) |
| PT (1) | PT66086B (OSRAM) |
| SE (1) | SE7700577L (OSRAM) |
| ZA (1) | ZA77336B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217350A (en) * | 1976-01-21 | 1980-08-12 | Ciba-Geigy Corporation | Oxygenated N-aryl-diazacyclic compounds |
| EP0000485A1 (de) * | 1977-07-08 | 1979-02-07 | Ciba-Geigy Ag | Piperidino-propanole, ihre Herstellung und pharmazeutische Präparate die diese enthalten |
| US4264599A (en) * | 1977-07-08 | 1981-04-28 | Ciba-Geigy Corporation | Piperidino-propanols |
| US4314943A (en) * | 1977-07-13 | 1982-02-09 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| LU77856A1 (de) * | 1977-07-27 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von neuen piperidin-derivaten |
| US4304912A (en) * | 1978-07-20 | 1981-12-08 | Ciba-Geigy Corporation | Piperidine derivatives |
| US4495352A (en) * | 1979-02-13 | 1985-01-22 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| DE2905876A1 (de) * | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4342761A (en) * | 1979-11-01 | 1982-08-03 | John Wyeth & Brother Limited | Piperidine derivatives |
| DE3066434D1 (en) * | 1979-11-21 | 1984-03-08 | Kyowa Hakko Kogyo Kk | Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them |
| US4344945A (en) * | 1980-03-10 | 1982-08-17 | Kyowa Hakko Kogyo Co., Ltd. | Piperidine derivatives |
| DE3324903A1 (de) * | 1983-07-09 | 1985-01-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung substituierter ethylenharnstoffe sowie neue n-vinylethylenharnstoffe |
| US4816585A (en) * | 1987-03-05 | 1989-03-28 | Olin Corporation | Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers |
| US4904714A (en) * | 1987-10-02 | 1990-02-27 | Olin Corporation | Synthetic resin composition and its method of use |
| FR2803298A1 (fr) * | 1999-12-30 | 2001-07-06 | Adir | Nouvelles urees lineaires ou cycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| SG176105A1 (en) * | 2009-06-26 | 2011-12-29 | Novartis Ag | 1, 3-disubstituted imidazolidin-2-one derivatives as inhibitors of cyp 17 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459757A (en) * | 1965-10-22 | 1969-08-05 | American Cyanamid Co | Imidazolidines |
| US3956335A (en) * | 1972-08-24 | 1976-05-11 | Ciba-Geigy Corporation | 1-Substituted-4-(2-oxo-1-imidazolidinyl) piperidines |
-
1977
- 1977-01-18 DE DE19772701794 patent/DE2701794A1/de active Pending
- 1977-01-19 CA CA270,045A patent/CA1085398A/en not_active Expired
- 1977-01-19 PT PT66086A patent/PT66086B/pt unknown
- 1977-01-19 ES ES455151A patent/ES455151A1/es not_active Expired
- 1977-01-19 NL NL7700530A patent/NL7700530A/xx not_active Application Discontinuation
- 1977-01-19 FR FR7701421A patent/FR2338940A1/fr active Granted
- 1977-01-19 DD DD7700197003A patent/DD129650A5/xx unknown
- 1977-01-20 IE IE108/77A patent/IE44276B1/en unknown
- 1977-01-20 AU AU21491/77A patent/AU512020B2/en not_active Expired
- 1977-01-20 DK DK21777A patent/DK21777A/da not_active Application Discontinuation
- 1977-01-20 SE SE7700577A patent/SE7700577L/xx unknown
- 1977-01-20 GB GB2312/77A patent/GB1565902A/en not_active Expired
- 1977-01-20 BE BE174221A patent/BE850556A/xx unknown
- 1977-01-20 ZA ZA770336A patent/ZA77336B/xx unknown
- 1977-01-20 FI FI770190A patent/FI770190A7/fi not_active Application Discontinuation
- 1977-01-20 IL IL51301A patent/IL51301A0/xx unknown
- 1977-01-20 NO NO770176A patent/NO770176L/no unknown
- 1977-01-20 AT AT33377A patent/AT355570B/de not_active IP Right Cessation
- 1977-01-20 GR GR52610A patent/GR62393B/el unknown
- 1977-01-20 NZ NZ183134A patent/NZ183134A/xx unknown
- 1977-01-21 JP JP504377A patent/JPS52105182A/ja active Pending
- 1977-01-21 PL PL19546177A patent/PL195461A1/xx unknown
- 1977-01-21 US US05/761,510 patent/US4144344A/en not_active Expired - Lifetime
-
1978
- 1978-02-01 ES ES466532A patent/ES466532A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NZ183134A (en) | 1979-08-31 |
| JPS52105182A (en) | 1977-09-03 |
| ATA33377A (de) | 1979-08-15 |
| SE7700577L (sv) | 1977-07-22 |
| AU2149177A (en) | 1978-07-27 |
| FR2338940B1 (OSRAM) | 1980-03-14 |
| PL195461A1 (pl) | 1978-12-18 |
| NL7700530A (nl) | 1977-07-25 |
| BE850556A (fr) | 1977-07-20 |
| IE44276B1 (en) | 1981-09-23 |
| AU512020B2 (en) | 1980-09-18 |
| ES455151A1 (es) | 1978-04-16 |
| AT355570B (de) | 1980-03-10 |
| GB1565902A (en) | 1980-04-23 |
| GR62393B (en) | 1979-04-10 |
| US4144344A (en) | 1979-03-13 |
| FR2338940A1 (fr) | 1977-08-19 |
| DE2701794A1 (de) | 1977-07-28 |
| ES466532A1 (es) | 1978-10-01 |
| PT66086A (en) | 1977-02-01 |
| NO770176L (no) | 1977-07-22 |
| PT66086B (en) | 1978-06-26 |
| IE44276L (en) | 1977-07-21 |
| DD129650A5 (de) | 1978-02-01 |
| ZA77336B (en) | 1977-11-30 |
| DK21777A (da) | 1977-07-22 |
| FI770190A7 (OSRAM) | 1977-07-22 |
| IL51301A0 (en) | 1977-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |