CA1282787C - Synthese de derives d'amino(arloxy)propanols et d'amino(aryl)ethanols - Google Patents

Synthese de derives d'amino(arloxy)propanols et d'amino(aryl)ethanols

Info

Publication number: CA1282787C
Authority: CA; Canada
Prior art keywords: aryl; alkyl; phenyl; metal; propoxy
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.): Expired - Lifetime

Application number

CA000522978A

Other languages

English (en)

Inventor

Ghanshyam Patil

Khuong H.X. Mai

William L. Matier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Squibb Pharma Co

Original Assignee

EI Du Pont de Nemours and Co

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

1991-04-09

1986-11-14 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1991-04-09 Application granted granted Critical

1991-04-09 Publication of CA1282787C publication Critical patent/CA1282787C/fr

2008-04-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000015572 biosynthetic process Effects 0.000 title description 2
238000003786 synthesis reaction Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000003118 aryl group Chemical group 0.000 claims abstract description 23
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
125000004171 alkoxy aryl group Chemical group 0.000 claims abstract description 4
125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract 2
125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
-1 aryl 1,2- ethanediol Chemical compound 0.000 claims description 8
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 7
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000003944 halohydrins Chemical class 0.000 claims 5
239000004593 Epoxy Substances 0.000 claims 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 claims 2
150000004703 alkoxides Chemical class 0.000 claims 2
150000003973 alkyl amines Chemical group 0.000 claims 2
229910052987 metal hydride Inorganic materials 0.000 claims 2
150000004681 metal hydrides Chemical class 0.000 claims 2
229910000000 metal hydroxide Inorganic materials 0.000 claims 2
150000004692 metal hydroxides Chemical class 0.000 claims 2
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 2
229910052708 sodium Inorganic materials 0.000 claims 2
239000011734 sodium Substances 0.000 claims 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
125000005124 aminocycloalkyl group Chemical group 0.000 claims 1
239000000908 ammonium hydroxide Substances 0.000 claims 1
229910052791 calcium Inorganic materials 0.000 claims 1
239000000920 calcium hydroxide Substances 0.000 claims 1
150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
150000002924 oxiranes Chemical class 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
239000002876 beta blocker Substances 0.000 abstract description 5
229940097320 beta blocking agent Drugs 0.000 abstract description 5
230000000747 cardiac effect Effects 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
AQHHHDLHHXJYJD-AWEZNQCLSA-N (2s)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC=C2C(OC[C@@H](O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-AWEZNQCLSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 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
239000003480 eluent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
MMOPHTBJNNBLFU-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-piperidin-1-ylpropan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCN1CCCCC1 MMOPHTBJNNBLFU-UHFFFAOYSA-N 0.000 description 1
UUOJIACWOAYWEZ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1 UUOJIACWOAYWEZ-UHFFFAOYSA-N 0.000 description 1
QGONODUKOFNSOY-UHFFFAOYSA-N 1-(tert-butylamino)-3-[2-(6-hydrazinylpyridazin-3-yl)phenoxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1C1=CC=C(NN)N=N1 QGONODUKOFNSOY-UHFFFAOYSA-N 0.000 description 1
FBMYKMYQHCBIGU-UHFFFAOYSA-N 2-[2-hydroxy-3-[[1-(1h-indol-3-yl)-2-methylpropan-2-yl]amino]propoxy]benzonitrile Chemical compound C=1NC2=CC=CC=C2C=1CC(C)(C)NCC(O)COC1=CC=CC=C1C#N FBMYKMYQHCBIGU-UHFFFAOYSA-N 0.000 description 1
VURUWFSVRBGGPO-UHFFFAOYSA-N 4-(cyclohexylamino)-1-naphthalen-1-yloxybutan-2-ol Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(O)CCNC1CCCCC1 VURUWFSVRBGGPO-UHFFFAOYSA-N 0.000 description 1
RTLJQOLVPIGICL-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(methylsulfonylmethyl)phenol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CS(C)(=O)=O)=C1 RTLJQOLVPIGICL-UHFFFAOYSA-N 0.000 description 1
SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 description 1
IXJJPGSXJXQFGI-UHFFFAOYSA-N 5-[3-[2-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropoxy]-8-(2-oxopropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=C(OCC(C)=O)C2=C1CCC(=O)N2 IXJJPGSXJXQFGI-UHFFFAOYSA-N 0.000 description 1
BAPQHWDWPMIUKD-UHFFFAOYSA-N 6-[2-[[3-(4-butoxyphenoxy)-2-hydroxypropyl]amino]ethylamino]-1,3-dimethylpyrimidine-2,4-dione Chemical compound C1=CC(OCCCC)=CC=C1OCC(O)CNCCNC1=CC(=O)N(C)C(=O)N1C BAPQHWDWPMIUKD-UHFFFAOYSA-N 0.000 description 1
GEVXLKYQQIKELK-UHFFFAOYSA-N 6-[3-(tert-butylamino)-2-hydroxypropoxy]-1,8,9,10,11,12-hexahydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-dien-3-ol Chemical compound C1CC2CCC1C1=C2C(O)=CC=C1OCC(O)CNC(C)(C)C GEVXLKYQQIKELK-UHFFFAOYSA-N 0.000 description 1
NACJSVRGPPMZRS-BWUCMLAFSA-N CC(C)NCC(O)COc1ccccc1[C@H]1C[C@@H]2CC[C@H]1C2 Chemical compound CC(C)NCC(O)COc1ccccc1[C@H]1C[C@@H]2CC[C@H]1C2 NACJSVRGPPMZRS-BWUCMLAFSA-N 0.000 description 1
JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
ADUKCCWBEDSMEB-NSHDSACASA-N Prenalterol Chemical compound CC(C)NC[C@H](O)COC1=CC=C(O)C=C1 ADUKCCWBEDSMEB-NSHDSACASA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
HTWFXPCUFWKXOP-UHFFFAOYSA-N Tertatalol Chemical compound C1CCSC2=C1C=CC=C2OCC(O)CNC(C)(C)C HTWFXPCUFWKXOP-UHFFFAOYSA-N 0.000 description 1
DXPOSRCHIDYWHW-UHFFFAOYSA-N Xamoterol Chemical compound C=1C=C(O)C=CC=1OCC(O)CNCCNC(=O)N1CCOCC1 DXPOSRCHIDYWHW-UHFFFAOYSA-N 0.000 description 1
229960002122 acebutolol Drugs 0.000 description 1
GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
NFXPPCYKSAAUMQ-UHFFFAOYSA-N afurolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC2=C1C(=O)OC2 NFXPPCYKSAAUMQ-UHFFFAOYSA-N 0.000 description 1
229950006115 afurolol Drugs 0.000 description 1
125000004450 alkenylene group Chemical group 0.000 description 1
229960002213 alprenolol Drugs 0.000 description 1
PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
XBRNQRFNEAHCPR-UHFFFAOYSA-N ancarolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1NC(=O)C1=CC=CO1 XBRNQRFNEAHCPR-UHFFFAOYSA-N 0.000 description 1
229950006766 ancarolol Drugs 0.000 description 1
BHIAIPWSVYSKJS-UHFFFAOYSA-N arotinolol Chemical compound S1C(SCC(O)CNC(C)(C)C)=NC(C=2SC(=CC=2)C(N)=O)=C1 BHIAIPWSVYSKJS-UHFFFAOYSA-N 0.000 description 1
229950010731 arotinolol Drugs 0.000 description 1
125000002102 aryl alkyloxo group Chemical group 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
229960004374 befunolol Drugs 0.000 description 1
ZPQPDBIHYCBNIG-UHFFFAOYSA-N befunolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1OC(C(C)=O)=C2 ZPQPDBIHYCBNIG-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229960004324 betaxolol Drugs 0.000 description 1
NWIUTZDMDHAVTP-UHFFFAOYSA-N betaxolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-UHFFFAOYSA-N 0.000 description 1
229960003588 bevantolol Drugs 0.000 description 1
HXLAFSUPPDYFEO-UHFFFAOYSA-N bevantolol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC(C)=C1 HXLAFSUPPDYFEO-UHFFFAOYSA-N 0.000 description 1
229950000729 bometolol Drugs 0.000 description 1
229960001035 bopindolol Drugs 0.000 description 1
229950002803 bornaprolol Drugs 0.000 description 1
229950005341 bucindolol Drugs 0.000 description 1
CIJVBYRUFLGDHY-UHFFFAOYSA-N bucumolol Chemical compound O1C(=O)C=CC2=C1C(OCC(O)CNC(C)(C)C)=CC=C2C CIJVBYRUFLGDHY-UHFFFAOYSA-N 0.000 description 1
229950002568 bucumolol Drugs 0.000 description 1
AKLNLVOZXMQGSI-UHFFFAOYSA-N bufetolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1OCC1OCCC1 AKLNLVOZXMQGSI-UHFFFAOYSA-N 0.000 description 1
229950009385 bufetolol Drugs 0.000 description 1
VCVQSRCYSKKPBA-UHFFFAOYSA-N bunitrolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1C#N VCVQSRCYSKKPBA-UHFFFAOYSA-N 0.000 description 1
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HQIRNZOQPUAHHV-UHFFFAOYSA-N bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 description 1
229950011621 butocrolol Drugs 0.000 description 1
NMBNQRJDEPOXCP-UHFFFAOYSA-N butofilolol Chemical compound CCCC(=O)C1=CC(F)=CC=C1OCC(O)CNC(C)(C)C NMBNQRJDEPOXCP-UHFFFAOYSA-N 0.000 description 1
229950009191 butofilolol Drugs 0.000 description 1
BQXQGZPYHWWCEB-UHFFFAOYSA-N carazolol Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2OCC(O)CNC(C)C BQXQGZPYHWWCEB-UHFFFAOYSA-N 0.000 description 1
229960004634 carazolol Drugs 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
229960001222 carteolol Drugs 0.000 description 1
LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 1
229960004195 carvedilol Drugs 0.000 description 1
NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
229960002320 celiprolol Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960004893 cloranolol Drugs 0.000 description 1
XYCMOTOFHFTUIU-UHFFFAOYSA-N cloranolol Chemical compound CC(C)(C)NCC(O)COC1=CC(Cl)=CC=C1Cl XYCMOTOFHFTUIU-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
AWOGXJOBNAWQSF-UHFFFAOYSA-N diacetolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1C(C)=O AWOGXJOBNAWQSF-UHFFFAOYSA-N 0.000 description 1
229950003563 diacetolol Drugs 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
ABXHHEZNIJUQFM-UHFFFAOYSA-N exaprolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C1CCCCC1 ABXHHEZNIJUQFM-UHFFFAOYSA-N 0.000 description 1
229950003436 exaprolol Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229960000831 levobunolol Drugs 0.000 description 1
IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 description 1
229960002237 metoprolol Drugs 0.000 description 1
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229960004255 nadolol Drugs 0.000 description 1
VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
229950009741 nafetolol Drugs 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229960004570 oxprenolol Drugs 0.000 description 1
BMAJJBHGPUHERB-LICLKQGHSA-N pacrinolol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=C(C(\C)=C\C#N)C=C1 BMAJJBHGPUHERB-LICLKQGHSA-N 0.000 description 1
229950007902 pacrinolol Drugs 0.000 description 1
PKWZWSXSCKVUJB-UHFFFAOYSA-N pafenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CCNC(=O)NC(C)C)C=C1 PKWZWSXSCKVUJB-UHFFFAOYSA-N 0.000 description 1
229950003300 pafenolol Drugs 0.000 description 1
UGENBJKPPGFFAT-UHFFFAOYSA-N pamatolol Chemical compound COC(=O)NCCC1=CC=C(OCC(O)CNC(C)C)C=C1 UGENBJKPPGFFAT-UHFFFAOYSA-N 0.000 description 1
229950007530 pamatolol Drugs 0.000 description 1
229960002035 penbutolol Drugs 0.000 description 1
KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
229950005644 pirepolol Drugs 0.000 description 1
229960004358 prenalterol Drugs 0.000 description 1
229950002322 prizidilol Drugs 0.000 description 1
229950003404 spirendolol Drugs 0.000 description 1
229950007862 sulfonterol Drugs 0.000 description 1
229960003352 tertatolol Drugs 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
CSUNLSYSEQIDMO-UHFFFAOYSA-N tiprenolol Chemical compound CSC1=CC=CC=C1OCC(O)CNC(C)C CSUNLSYSEQIDMO-UHFFFAOYSA-N 0.000 description 1
229950004988 tiprenolol Drugs 0.000 description 1
229950003004 tolamolol Drugs 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229960004928 xamoterol Drugs 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

Landscapes

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)

CA000522978A 1985-12-04 1986-11-14 Synthese de derives d'amino(arloxy)propanols et d'amino(aryl)ethanols Expired - Lifetime CA1282787C (fr)

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
CA1282787C true CA1282787C (fr)	1991-04-09

Family

ID=25188898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000522978A Expired - Lifetime CA1282787C (fr)	1985-12-04	1986-11-14	Synthese de derives d'amino(arloxy)propanols et d'amino(aryl)ethanols

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
JPS63502585A (ja)	1988-09-29
AU631433B2 (en)	1992-11-26
EP0248879A4 (fr)	1990-02-26
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

Legal Events

Date	Code	Title	Description
1993-10-11	MKLA	Lapsed

Publication	Publication Date	Title
CA1282787C (fr)	1991-04-09	Synthese de derives d'amino(arloxy)propanols et d'amino(aryl)ethanols
US4221807A (en)	1980-09-09	Alkanolamine derivatives
CA1313669C (fr)	1993-02-16	Synthese d'aryloxypropanolamines et d'arylethanolamines optiquement actives
Wei et al.	1998	anti-Prelog microbial reduction of aryl α-halomethyl or α-hydroxymethyl ketones with Geotrichum sp. 38
EP1238973A1 (fr)	2002-09-11	Nouveaux composes tricycliques substitues
US4115409A (en)	1978-09-19	Alkanolamine derivatives
EP0156331B1 (fr)	1989-05-31	Dérivés de benzofuranne, procédé pour leur préparation et agents antihypertensifs les contenant
US4141987A (en)	1979-02-27	1-Aryloxy-3-thenamidoalkylamino-2-propanol derivatives
CA1080720A (fr)	1980-07-01	Derives d'aminopropoxyindole
EP0057572B1 (fr)	1985-07-31	Dérivés d'alcanolamines
EP0331078A2 (fr)	1989-09-06	Procédé de préparation de dérivés optiquement actifs de l'acide 4-oxo-benzopyranne-2-carboxylique et leurs intermédiaires
CA1183148A (fr)	1985-02-26	COMPOSES .beta.BLOQUANT A ACTION RAPIDE CONTENANT UN ESTER ET PROCEDE DE PREPARATION
EP0664799B1 (fr)	1999-07-14	Derives d'amide
CN1137085C (zh)	2004-02-04	制备5,6-二羟基-2-氨基-1,2,3,4-四氢化萘的方法
US4086357A (en)	1978-04-25	Amide derivatives
EP0750608A1 (fr)	1997-01-02	Produit pharmaceutique comportant un salicylate d'un agent beta-bloquant esterifiable
US4071686A (en)	1978-01-31	Novel benzylidene amino-oxyalkyl carboxylic acids and carboxylic acid derivatives
CN1039245A (zh)	1990-01-31	一种新颖噻吩衍生物和其制备方法
KR940003298B1 (ko)	1994-04-20	인덴류 화합물의 제조방법
US4200652A (en)	1980-04-29	Alkanolamine derivatives
CA1183849A (fr)	1985-03-12	¬alkyl- et alcenyl-3 piperidyl-4)-2 ethyl\|-3 indoles et leur utilisation comme medicaments
KR101249868B1 (ko)	2013-04-03	아토르바스타틴의 제조를 위한 키랄 중간체의 제조방법
CA2017897A1 (fr)	1990-12-02	Derives de biphenyle, procede de preparation et composes intermediaires utilises a cette fin
CA1080721A (fr)	1980-07-01	Derive de l'aminopropoxy-indole
CN1188762A (zh)	1998-07-29	氧杂茚衍生物及其制备的方法