JPS63502585A - アリルオキシプロパノ−ルアミン類及びアリルエタノ−ルアミン類の合成法 - Google Patents

アリルオキシプロパノ−ルアミン類及びアリルエタノ−ルアミン類の合成法

Info

Publication number: JPS63502585A
Authority: JP; Japan
Prior art keywords: allyl; alkyl; metal; manufacturing; phenyl
Prior art date: 1985-12-04
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.): Pending

Application number

JP62500136A

Other languages

English (en)

Japanese (ja)

Inventor

パテイル，ガーンシィアム

メイ，クオング　エイチ．エックス

マティアー，ウイリアム　エル

Original Assignee

ザ　デュポン　メルク　ファーマシュウティカル　カンパニー

Priority date (The priority date 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 date listed.)

1985-12-04

Filing date

1986-11-14

Publication date

1988-09-29

1986-11-14 Application filed by ザ　デュポン　メルク　ファーマシュウティカル　カンパニー filed Critical ザ　デュポン　メルク　ファーマシュウティカル　カンパニー

1988-09-29 Publication of JPS63502585A publication Critical patent/JPS63502585A/ja

Status Pending legal-status Critical Current

Links

238000001308 synthesis method Methods 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
238000004519 manufacturing process Methods 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
-1 alkoxyallyl Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
150000003944 halohydrins Chemical class 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
239000004593 Epoxy Substances 0.000 claims description 4
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 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 3
150000003973 alkyl amines Chemical group 0.000 claims description 3
150000002009 diols Chemical class 0.000 claims description 3
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 3
PAKCOSURAUIXFG-UHFFFAOYSA-N 3-prop-2-enoxypropane-1,2-diol Chemical compound OCC(O)COCC=C PAKCOSURAUIXFG-UHFFFAOYSA-N 0.000 claims description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
241000577218 Phenes Species 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000005124 aminocycloalkyl group Chemical group 0.000 claims description 2
239000000908 ammonium hydroxide Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
239000002585 base Substances 0.000 claims 5
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
229910000000 metal hydroxide Inorganic materials 0.000 claims 2
150000004692 metal hydroxides Chemical class 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
JTWOSPUWOVJQHH-UHFFFAOYSA-N 3-prop-2-enoxypropan-1-ol Chemical compound OCCCOCC=C JTWOSPUWOVJQHH-UHFFFAOYSA-N 0.000 claims 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
150000002924 oxiranes Chemical class 0.000 claims 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000010410 layer Substances 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
239000002876 beta blocker Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
229940097320 beta blocking agent Drugs 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
229940125388 beta agonist Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 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
239000011541 reaction mixture Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 description 1
WUCHYGSGPTWIRP-UHFFFAOYSA-N 1-aminopent-4-en-2-ol Chemical compound NCC(O)CC=C WUCHYGSGPTWIRP-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
241001489212 Tuber Species 0.000 description 1
241000609666 Tuber aestivum Species 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000000464 adrenergic agent Substances 0.000 description 1
239000000808 adrenergic beta-agonist Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000003328 mesylation reaction Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
HPVMXAKKZWDYLT-UHFFFAOYSA-N n'-aminoacetohydrazide Chemical compound CC(=O)NNN HPVMXAKKZWDYLT-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Indole Compounds (AREA)
Epoxy Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP62500136A 1985-12-04 1986-11-14 アリルオキシプロパノ−ルアミン類及びアリルエタノ−ルアミン類の合成法 Pending JPS63502585A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80440685A	1985-12-04	1985-12-04
US804,406		1985-12-04

Publications (1)

Publication Number	Publication Date
JPS63502585A true JPS63502585A (ja)	1988-09-29

Family

ID=25188898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62500136A Pending JPS63502585A (ja)	1985-12-04	1986-11-14	アリルオキシプロパノ−ルアミン類及びアリルエタノ−ルアミン類の合成法

Country Status (6)

Country	Link
EP (1)	EP0248879A4 (fr)
JP (1)	JPS63502585A (fr)
AU (2)	AU604005B2 (fr)
CA (1)	CA1282787C (fr)
WO (1)	WO1987003583A1 (fr)
ZA (1)	ZA868713B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4990668A (en) *	1985-12-04	1991-02-05	E. I. Du Pont De Nemours And Company	Optically active aryloxypropanolamines and arylethanolamines
SE8801518D0 (sv) *	1988-04-22	1988-04-22	Astra Pharma Prod	A novel process
US4992535A (en) *	1988-10-26	1991-02-12	G. D. Searle & Co.	Methods of making novel R and S diastereomers of N6 -[(2-hydroxypropyl)aryl]adenosines
US5030624A (en) *	1988-10-26	1991-07-09	G. D. Searle & Co.	R-diastereomer of an N6 -[(2-hydroxypropyl)aryl]adenosine and its medicinal uses
US5032584A (en) *	1988-10-26	1991-07-16	G. D. Searle & Co.	S-diastereomer of an n6 -((2-hydroxypropyl)aryl)adenosine and its medicinal uses
DE3844410A1 (de) *	1988-12-30	1990-07-19	Lindner Wolfgang	Inversion der alkohol-konfiguration in alpha-aminoalkoholen ueber intramolekulare substitution der sulfonsaeureester
US5629345A (en) *	1993-07-23	1997-05-13	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
US5965620A (en) *	1993-07-23	1999-10-12	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
AR011626A1 (es) *	1997-02-07	2000-08-30	Shell Int Research	Un procedimiento para la elaboracion de compuestos epoxidos, resinas epoxidas obtenidas mediante dicho procedimiento y un procedimiento para laelaboracion de compuestos intermedios para la elaboracion de compuestos epoxidos
BR112013018598A2 (pt) *	2011-01-27	2016-10-18	Baxter Healthcare Sa	composição farmacêutica, método para tratar uma doença cardíaca, uso de (s)-metil-3-[4-(2-hidroxi-3-[4-(2-hidroxi-3-isopropilamino) propoxi] fenilpropionato, e, método para controlar frequência cardíaca
JP2014505074A (ja) *	2011-01-27	2014-02-27	バクスター・インターナショナル・インコーポレイテッド	血圧低下を最小化しおよび／または制御しながら頻脈を治療しおよび／または心拍数を制御する方法
CN102408285B (zh) *	2011-09-15	2013-11-20	东北师范大学	一种甲苯衍生物的苄基碳氢直接胺化方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4202978A (en) *	1978-02-08	1980-05-13	Hoffmann-La Roche Inc.	(S)-1-[2-(4-(2-Hydroxy-s-(1-alkylaminopropoxy)phenylalkyl]-4-phenylpiperazines
US4990668A (en) *	1985-12-04	1991-02-05	E. I. Du Pont De Nemours And Company	Optically active aryloxypropanolamines and arylethanolamines

1986
- 1986-11-14 EP EP19870900373 patent/EP0248879A4/fr not_active Withdrawn
- 1986-11-14 CA CA000522978A patent/CA1282787C/fr not_active Expired - Lifetime
- 1986-11-14 AU AU67749/87A patent/AU604005B2/en not_active Ceased
- 1986-11-14 WO PCT/US1986/002406 patent/WO1987003583A1/fr not_active Ceased
- 1986-11-14 JP JP62500136A patent/JPS63502585A/ja active Pending
- 1986-11-17 ZA ZA868713A patent/ZA868713B/xx unknown
1990
- 1990-06-18 AU AU57562/90A patent/AU631433B2/en not_active Ceased

Also Published As

Publication number	Publication date
AU631433B2 (en)	1992-11-26
EP0248879A4 (fr)	1990-02-26
CA1282787C (fr)	1991-04-09
AU5756290A (en)	1990-10-11
AU6774987A (en)	1987-06-30
ZA868713B (en)	1987-06-24
EP0248879A1 (fr)	1987-12-16
AU604005B2 (en)	1990-12-06
WO1987003583A1 (fr)	1987-06-18

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