SU659089A3 - Способ получени производных 2-окси-3-аминопропана или их -окисей или солей - Google Patents
Способ получени производных 2-окси-3-аминопропана или их -окисей или солейInfo
- Publication number
- SU659089A3 SU659089A3 SU741995950A SU1995950A SU659089A3 SU 659089 A3 SU659089 A3 SU 659089A3 SU 741995950 A SU741995950 A SU 741995950A SU 1995950 A SU1995950 A SU 1995950A SU 659089 A3 SU659089 A3 SU 659089A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- isopropyl
- carbon atoms
- alkyl
- hours
- ether
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 title description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 125000000217 alkyl group Chemical group 0.000 description 71
- 125000004432 carbon atom Chemical group C* 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- 125000003545 alkoxy group Chemical group 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- -1 hydroxy, phenyl Chemical group 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 125000002947 alkylene group Chemical group 0.000 description 25
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 23
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 229910000104 sodium hydride Inorganic materials 0.000 description 21
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 239000012312 sodium hydride Substances 0.000 description 20
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000005236 alkanoylamino group Chemical group 0.000 description 12
- 125000003302 alkenyloxy group Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- HNOAXSVPMXZKBT-UHFFFAOYSA-N (2-phenyl-3-propan-2-yl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)N1CC(CO)OC1C1=CC=CC=C1 HNOAXSVPMXZKBT-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000004849 alkoxymethyl group Chemical group 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000534944 Thia Species 0.000 description 5
- 125000005237 alkyleneamino group Chemical group 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- DZICZUFDHZVEOW-UHFFFAOYSA-N 1-methoxy-2H-pyrimidine Chemical compound O(C)N1CN=CC=C1 DZICZUFDHZVEOW-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- YLZYSVYZMDJYOT-UHFFFAOYSA-N 2-methoxypyrimidine Chemical compound COC1=NC=CC=N1 YLZYSVYZMDJYOT-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- ZCWJDKLOOUVUBD-UHFFFAOYSA-N n-hexylpyridine-2-carboxamide Chemical compound CCCCCCNC(=O)C1=CC=CC=N1 ZCWJDKLOOUVUBD-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000002917 oxazolidines Chemical group 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JNUZADQZHYFJGW-JOCHJYFZSA-N (2R)-N-[3-[5-fluoro-2-(2-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]-1H-indol-7-yl]-3-methoxy-2-(4-methylpiperazin-1-yl)propanamide Chemical compound FC=1C(=NC(=NC=1)NC1=C(C(=CC=C1)S(=O)(=O)C)F)C1=CNC2=C(C=CC=C12)NC([C@@H](COC)N1CCN(CC1)C)=O JNUZADQZHYFJGW-JOCHJYFZSA-N 0.000 description 1
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- WGNPQKFEZAUVBF-UHFFFAOYSA-N 1-(3-chloropyridin-2-yl)oxy-3-(propan-2-ylamino)propan-2-ol;hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=NC=CC=C1Cl WGNPQKFEZAUVBF-UHFFFAOYSA-N 0.000 description 1
- AOZADRZLLPNIMX-UHFFFAOYSA-N 1-(3-nitropyridin-2-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=NC=CC=C1[N+]([O-])=O AOZADRZLLPNIMX-UHFFFAOYSA-N 0.000 description 1
- UWWXYDGOUMUTMF-UHFFFAOYSA-N 1-(5-methoxypyridin-2-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CNC(C)C)N=C1 UWWXYDGOUMUTMF-UHFFFAOYSA-N 0.000 description 1
- BLDRAVRJOYFYKJ-UHFFFAOYSA-N 1-(6-methylpyridin-2-yl)oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=N1 BLDRAVRJOYFYKJ-UHFFFAOYSA-N 0.000 description 1
- AXFKMGILMZQYFH-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(3-propylpyridin-2-yl)oxypropan-2-ol Chemical compound CCCC1=CC=CN=C1OCC(O)CNC(C)C AXFKMGILMZQYFH-UHFFFAOYSA-N 0.000 description 1
- CQYRZWFRGWWADN-UHFFFAOYSA-N 1-(tert-butylamino)-3-(3-chloropyrazin-2-yl)oxypropan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=NC=CN=C1Cl CQYRZWFRGWWADN-UHFFFAOYSA-N 0.000 description 1
- MCKZXOLGMUVKQH-UHFFFAOYSA-N 1-[3-chloro-5-(hydroxymethyl)pyridin-2-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=NC=C(CO)C=C1Cl MCKZXOLGMUVKQH-UHFFFAOYSA-N 0.000 description 1
- IMCQXCPTQKOHCY-UHFFFAOYSA-N 2,3-dichloro-5-methylpyrazine Chemical compound CC1=CN=C(Cl)C(Cl)=N1 IMCQXCPTQKOHCY-UHFFFAOYSA-N 0.000 description 1
- DSJPCYWXUGROQW-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)ethanamine Chemical compound NCCC1=CC=C(Cl)N=C1 DSJPCYWXUGROQW-UHFFFAOYSA-N 0.000 description 1
- PZSISEFPCYMBDL-UHFFFAOYSA-N 2-bromo-3-methylpyridine Chemical compound CC1=CC=CN=C1Br PZSISEFPCYMBDL-UHFFFAOYSA-N 0.000 description 1
- KRIILKQTJUOQCJ-UHFFFAOYSA-N 2-bromo-4-phenylpyridine Chemical compound C1=NC(Br)=CC(C=2C=CC=CC=2)=C1 KRIILKQTJUOQCJ-UHFFFAOYSA-N 0.000 description 1
- RKVUCIFREKHYTL-UHFFFAOYSA-N 2-chloro-3-methylpyridine Chemical compound CC1=CC=CN=C1Cl RKVUCIFREKHYTL-UHFFFAOYSA-N 0.000 description 1
- MZVSTDHRRYQFGI-UHFFFAOYSA-N 2-chloro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1 MZVSTDHRRYQFGI-UHFFFAOYSA-N 0.000 description 1
- VVXXREZPSINGBU-UHFFFAOYSA-N 2-chloro-5-(methylsulfanylmethyl)pyrimidine Chemical compound CSCC1=CN=C(Cl)N=C1 VVXXREZPSINGBU-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- VAVGOGHLNAJECD-UHFFFAOYSA-N 2-chloro-6-methoxypyridine Chemical compound COC1=CC=CC(Cl)=N1 VAVGOGHLNAJECD-UHFFFAOYSA-N 0.000 description 1
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- DVGNYVVFWIWKON-UHFFFAOYSA-N 2-methoxy-3-methylpyridine Chemical compound COC1=NC=CC=C1C DVGNYVVFWIWKON-UHFFFAOYSA-N 0.000 description 1
- HGRXBKDKSYDWLD-UHFFFAOYSA-N 2-methoxy-4-methylpyridine Chemical compound COC1=CC(C)=CC=N1 HGRXBKDKSYDWLD-UHFFFAOYSA-N 0.000 description 1
- JQBGXZBRNVIYRH-UHFFFAOYSA-N 2-methoxy-4-phenylpyridine Chemical compound C1=NC(OC)=CC(C=2C=CC=CC=2)=C1 JQBGXZBRNVIYRH-UHFFFAOYSA-N 0.000 description 1
- GKHXZGJHTBCABG-UHFFFAOYSA-N 2h-pyridin-1-ium-1-ylidenemethanone Chemical compound O=C=[N+]1CC=CC=C1 GKHXZGJHTBCABG-UHFFFAOYSA-N 0.000 description 1
- KPDCZLPRTABGFY-UHFFFAOYSA-N 3-ethoxy-2-methoxypyridine Chemical compound CCOC1=CC=CN=C1OC KPDCZLPRTABGFY-UHFFFAOYSA-N 0.000 description 1
- OWQYAKLAVISYKC-UHFFFAOYSA-N 4-(3-chloro-6-methylpyrazin-2-yl)morpholine Chemical compound CC1=CN=C(Cl)C(N2CCOCC2)=N1 OWQYAKLAVISYKC-UHFFFAOYSA-N 0.000 description 1
- OEKVRRZDWAIQHT-UHFFFAOYSA-N 4-(6-methylpyrazin-2-yl)morpholine Chemical compound CC1=CN=CC(N2CCOCC2)=N1 OEKVRRZDWAIQHT-UHFFFAOYSA-N 0.000 description 1
- DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 1
- SOQYMYKRQSYPSG-UHFFFAOYSA-N 5-chloro-6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=C(OCC(O)CNC(C)C)C(Cl)=C1 SOQYMYKRQSYPSG-UHFFFAOYSA-N 0.000 description 1
- HFLSGQBZLCWOQX-UHFFFAOYSA-N 6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(OCC(O)CNC(C)C)N=C1 HFLSGQBZLCWOQX-UHFFFAOYSA-N 0.000 description 1
- ABCZGIVCAPFYNI-UHFFFAOYSA-N 6-chloro-1-methyl-2H-pyridine-3-carboxylic acid Chemical compound CN1CC(C(O)=O)=CC=C1Cl ABCZGIVCAPFYNI-UHFFFAOYSA-N 0.000 description 1
- KEWWNDNFWZNNLD-UHFFFAOYSA-N 6-methoxy-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(OC)N=C1 KEWWNDNFWZNNLD-UHFFFAOYSA-N 0.000 description 1
- DFPYAQAFVHRSAG-UHFFFAOYSA-N 6-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=C(C#N)C=N1 DFPYAQAFVHRSAG-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- YIFMKKPCWZBKLZ-UHFFFAOYSA-N CC(CCC1=CC=CC=C1)N2CC(OC2C3=CC=CC=C3)C4=C(N=CC=C4)OC Chemical compound CC(CCC1=CC=CC=C1)N2CC(OC2C3=CC=CC=C3)C4=C(N=CC=C4)OC YIFMKKPCWZBKLZ-UHFFFAOYSA-N 0.000 description 1
- BMEBBXWZJZCZRE-UHFFFAOYSA-N CCC(CC1=CC=CC=C1)N2CC(OC2C3=CC=CC=C3)C4=C(N=CC=C4)OC Chemical compound CCC(CC1=CC=CC=C1)N2CC(OC2C3=CC=CC=C3)C4=C(N=CC=C4)OC BMEBBXWZJZCZRE-UHFFFAOYSA-N 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 101150082479 GAL gene Proteins 0.000 description 1
- QRBVCAWHUSTDOT-UHFFFAOYSA-N Methyridine Chemical compound COCCC1=CC=CC=N1 QRBVCAWHUSTDOT-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100276209 Rhizobium meliloti (strain 1021) cya1 gene Proteins 0.000 description 1
- 241001481789 Rupicapra Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- HYYWMBIWYPMBGO-UHFFFAOYSA-N ethyl 4-chloro-2-(dimethylamino)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(N(C)C)N=C1Cl HYYWMBIWYPMBGO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- SIGPWCVHTYIKME-UHFFFAOYSA-N hexamethanol Chemical compound OC.OC.OC.OC.OC.OC SIGPWCVHTYIKME-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- HXXAUIXTYRHFNO-UHFFFAOYSA-N n-methylpyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC=N1 HXXAUIXTYRHFNO-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244473A CH584209A5 (en) | 1973-02-20 | 1973-02-20 | 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU659089A3 true SU659089A3 (ru) | 1979-04-25 |
Family
ID=4233957
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU741995950A SU659089A3 (ru) | 1973-02-20 | 1974-02-18 | Способ получени производных 2-окси-3-аминопропана или их -окисей или солей |
| SU7502137664A SU577978A3 (ru) | 1973-02-20 | 1975-05-27 | Способ получени производных 1пиразинил-окси-2-окси-3-аминопропана или их солей |
| SU752141281A SU593657A3 (ru) | 1973-02-20 | 1975-06-06 | Способ получени производных 1-пиридилокси-2-окси-3-аминопропана или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502137664A SU577978A3 (ru) | 1973-02-20 | 1975-05-27 | Способ получени производных 1пиразинил-окси-2-окси-3-аминопропана или их солей |
| SU752141281A SU593657A3 (ru) | 1973-02-20 | 1975-06-06 | Способ получени производных 1-пиридилокси-2-окси-3-аминопропана или их солей |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5823666A (enExample) |
| CH (1) | CH584209A5 (enExample) |
| FI (1) | FI60391C (enExample) |
| HU (1) | HU173821B (enExample) |
| MC (1) | MC1013A1 (enExample) |
| NO (1) | NO139682C (enExample) |
| PL (7) | PL100172B1 (enExample) |
| SU (3) | SU659089A3 (enExample) |
| ZA (1) | ZA741070B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4517188A (en) * | 1983-05-09 | 1985-05-14 | Mead Johnson & Company | 1-Pyrimidinyloxy-3-hetaryl-alkylamino-2-propanols |
| DE4421495A1 (de) * | 1994-06-20 | 1995-12-21 | Merck Patent Gmbh | Heterocyclyloxy-benzoylguanidine |
| DE4426346A1 (de) * | 1994-07-25 | 1996-02-01 | Basf Ag | Herbizide Pyrazinderivate |
-
1973
- 1973-02-20 CH CH244473A patent/CH584209A5/de not_active IP Right Cessation
-
1974
- 1974-01-23 FI FI193/74A patent/FI60391C/fi active
- 1974-02-13 NO NO740486A patent/NO139682C/no unknown
- 1974-02-18 SU SU741995950A patent/SU659089A3/ru active
- 1974-02-19 PL PL1974184285A patent/PL100172B1/pl unknown
- 1974-02-19 PL PL1974184284A patent/PL100314B1/pl unknown
- 1974-02-19 PL PL1974189132A patent/PL98967B1/pl unknown
- 1974-02-19 PL PL1974184283A patent/PL100171B1/pl unknown
- 1974-02-19 PL PL1974203732A patent/PL101376B1/pl unknown
- 1974-02-19 PL PL1974189131A patent/PL98964B1/pl unknown
- 1974-02-19 HU HU74CI1447A patent/HU173821B/hu unknown
- 1974-02-19 MC MC1097A patent/MC1013A1/fr unknown
- 1974-02-19 PL PL1974168938A patent/PL94250B1/pl unknown
- 1974-02-19 ZA ZA00741070A patent/ZA741070B/xx unknown
-
1975
- 1975-05-27 SU SU7502137664A patent/SU577978A3/ru active
- 1975-06-06 SU SU752141281A patent/SU593657A3/ru active
-
1982
- 1982-07-30 JP JP57132301A patent/JPS5823666A/ja active Pending
- 1982-07-30 JP JP57132300A patent/JPS603391B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU173821B (hu) | 1979-08-28 |
| SU593657A3 (ru) | 1978-02-15 |
| PL101376B1 (pl) | 1978-12-30 |
| PL100172B1 (pl) | 1978-09-30 |
| FI60391C (fi) | 1982-01-11 |
| PL100171B1 (pl) | 1978-09-30 |
| NO139682C (no) | 1979-04-25 |
| NO139682B (no) | 1979-01-15 |
| JPS603391B2 (ja) | 1985-01-28 |
| PL100314B1 (pl) | 1978-09-30 |
| SU577978A3 (ru) | 1977-10-25 |
| JPS5823675A (ja) | 1983-02-12 |
| ZA741070B (en) | 1975-01-29 |
| MC1013A1 (fr) | 1974-10-18 |
| PL98964B1 (pl) | 1978-06-30 |
| JPS5823666A (ja) | 1983-02-12 |
| CH584209A5 (en) | 1977-01-31 |
| NO740486L (no) | 1974-08-21 |
| PL98967B1 (pl) | 1978-06-30 |
| FI60391B (fi) | 1981-09-30 |
| PL94250B1 (enExample) | 1977-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5646082B2 (ja) | Ｈｄｌコレステロール上昇剤としてのオキシム化合物 | |
| EP0220518B1 (en) | Preparation of substituted and disubstituted pyridine-2,3-dicarboxylate esters | |
| US4432979A (en) | Pyridone compounds | |
| CS203970B2 (en) | Method of producing novel heterocyclyl-oxy-hydroxy-amino-propanes | |
| US2543972A (en) | 1,4-disubstituted piperazines | |
| NO120426B (enExample) | ||
| JPS63139182A (ja) | チアゾリジンジオン誘導体の製造法 | |
| JP2005507367A (ja) | １，４−二置換ベンゾ縮合化合物 | |
| CZ2004714A3 (cs) | Sloučeniny a jejich použití ke snížení aktivity lipázy citlivé vůči hormonu | |
| WO2007043835A1 (en) | Fab i inhibitor and process for preparing same | |
| US4218457A (en) | 2-Substituted 5-hydroxy-1H-imidazole-4-carboxamide derivatives and use | |
| KR820002136B1 (ko) | 2-아미노 피리미돈 화합물의 제조방법 | |
| SU659089A3 (ru) | Способ получени производных 2-окси-3-аминопропана или их -окисей или солей | |
| US2723270A (en) | Thiosemicarbazones of pyridylaldehydes and pyridylketones | |
| EP0077534B1 (en) | Benzamide derivatives, a process for preparing the same, and pharmaceutical compositions containing the same | |
| US4469871A (en) | Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones | |
| JP5762548B2 (ja) | Ｎ−ピリジン−３−イル又はｎ−ピラジン−２−イルカルボキサミド類 | |
| US3290320A (en) | Benzoyl pyridine oximino ethers and methods for their manufacture | |
| Becher et al. | Pyridinethiones. IX preparation of ricinidine, thioricinidine and other 2 (1H)‐pyridones and‐thiones related to nicotinic acid | |
| NO165248B (no) | Kammervegg for anvendelse i en konverter for behandling av stoepejernsmelter. | |
| JPS6325584B2 (enExample) | ||
| US3966741A (en) | Process for the preparation of substituted or unsubstituted 4-pyridylthioacetic acid | |
| US4517192A (en) | 6-Alkyl-5-[4-(alkylsulfinyl or alkylsulfonyl)phenyl]-2(1H)-pyridinones and their use as cardiatonics | |
| US3271402A (en) | Carbon-z-thiobarbituric acids | |
| AT338787B (de) | Verfahren zur herstellung von neuen heterocyclischen verbindungen |