CA1084507A - 1-aryloxy-4-amino-2-butanols - Google Patents

1-aryloxy-4-amino-2-butanols

Info

Publication number: CA1084507A
Authority: CA; Canada
Prior art keywords: butanol; chloro; process according; prepared; dichloro
Prior art date: 1974-10-25
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

Application number

CA312,946A

Other languages

English (en)

Inventor

Carl D. Lunsford

Ying-Ho Chen

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.)

AH Robins Co Inc

Original Assignee

AH Robins Co Inc

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.)

1974-10-25

Filing date

1978-10-10

Publication date

1980-08-26

1975-10-24 Priority claimed from CA238,243A external-priority patent/CA1077474A/fr

1978-10-10 Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc

1978-10-10 Priority to CA312,946A priority Critical patent/CA1084507A/fr

1980-08-26 Application granted granted Critical

1980-08-26 Publication of CA1084507A publication Critical patent/CA1084507A/fr

Status Expired legal-status Critical Current

Links

125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000000460 chlorine Substances 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical group 0.000 claims abstract description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 5
101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 claims abstract description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
229910052740 iodine Inorganic materials 0.000 claims abstract description 3
239000011630 iodine Substances 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 41
230000008569 process Effects 0.000 claims description 36
CKNNDWZSFAPUJS-UHFFFAOYSA-N 1,4-dichlorobutan-2-ol Chemical compound ClCC(O)CCCl CKNNDWZSFAPUJS-UHFFFAOYSA-N 0.000 claims description 27
239000000126 substance Substances 0.000 claims description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims description 4
INIFSXSGXVPPCW-UHFFFAOYSA-N 4-chloro-1-(4-chloro-2-methylphenoxy)butan-2-ol Chemical compound CC1=CC(Cl)=CC=C1OCC(O)CCCl INIFSXSGXVPPCW-UHFFFAOYSA-N 0.000 claims description 4
LSZJJYQYOLWYTK-UHFFFAOYSA-N 4-chloro-1-(4-chlorophenoxy)butan-2-ol Chemical compound ClCCC(O)COC1=CC=C(Cl)C=C1 LSZJJYQYOLWYTK-UHFFFAOYSA-N 0.000 claims description 4
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 claims description 4
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 4
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
JSHIKWCFBDJYEB-UHFFFAOYSA-N 4-chloro-1-(2-methoxyphenoxy)butan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CCCl JSHIKWCFBDJYEB-UHFFFAOYSA-N 0.000 claims description 3
LOGSDDBVWYRABF-UHFFFAOYSA-N 4-chloro-1-(4-methoxyphenoxy)butan-2-ol Chemical compound COC1=CC=C(OCC(O)CCCl)C=C1 LOGSDDBVWYRABF-UHFFFAOYSA-N 0.000 claims description 3
DJXKWNXZCQOZKJ-UHFFFAOYSA-N 4-chloro-1-(5-chloro-2-methylphenoxy)butan-2-ol Chemical compound CC1=CC=C(Cl)C=C1OCC(O)CCCl DJXKWNXZCQOZKJ-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
MJMNSESDGVLRGF-UHFFFAOYSA-N n-[4-(4-chloro-2-hydroxybutoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(O)CCCl)C=C1 MJMNSESDGVLRGF-UHFFFAOYSA-N 0.000 claims description 3
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 2
UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 claims description 2
XTYNIPUFKBBALX-UHFFFAOYSA-N 3-chloro-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1Cl XTYNIPUFKBBALX-UHFFFAOYSA-N 0.000 claims description 2
WCMQUXXIUKJBHK-UHFFFAOYSA-N 4-chloro-1-(3-chloropyridin-2-yl)oxybutan-2-ol Chemical compound ClCCC(O)COC1=NC=CC=C1Cl WCMQUXXIUKJBHK-UHFFFAOYSA-N 0.000 claims description 2
OKVBCEXRAAQUTC-UHFFFAOYSA-N 4-chloro-1-phenoxybutan-2-ol Chemical compound ClCCC(O)COC1=CC=CC=C1 OKVBCEXRAAQUTC-UHFFFAOYSA-N 0.000 claims description 2
RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 claims description 2
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 2
KKFPXGXMSBBNJI-UHFFFAOYSA-N 5-chloro-2-methylphenol Chemical compound CC1=CC=C(Cl)C=C1O KKFPXGXMSBBNJI-UHFFFAOYSA-N 0.000 claims description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
229950011260 betanaphthol Drugs 0.000 claims description 2
229960001867 guaiacol Drugs 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 2
HSYYDOZUCRRCDJ-UHFFFAOYSA-N 4-chloro-1-(2-chlorophenoxy)butan-2-ol Chemical compound ClCCC(O)COC1=CC=CC=C1Cl HSYYDOZUCRRCDJ-UHFFFAOYSA-N 0.000 claims 2
VTWJDLPHOGHGNN-UHFFFAOYSA-N 4-chloro-1-(3,5-dimethylphenoxy)butan-2-ol Chemical compound CC1=CC(C)=CC(OCC(O)CCCl)=C1 VTWJDLPHOGHGNN-UHFFFAOYSA-N 0.000 claims 2
GPOWEBKTSUZCDL-UHFFFAOYSA-N 4-chloro-1-(4-chloro-3-methylphenoxy)butan-2-ol Chemical compound CC1=CC(OCC(O)CCCl)=CC=C1Cl GPOWEBKTSUZCDL-UHFFFAOYSA-N 0.000 claims 2
DZAWKDGFUDCKLY-UHFFFAOYSA-N 4-chloro-1-(4-phenylphenoxy)butan-2-ol Chemical compound C1=CC(OCC(CCCl)O)=CC=C1C1=CC=CC=C1 DZAWKDGFUDCKLY-UHFFFAOYSA-N 0.000 claims 2
TVMPXSWBLSQTSM-UHFFFAOYSA-N 4-chloro-1-[3-(trifluoromethyl)phenoxy]butan-2-ol Chemical compound ClCCC(O)COC1=CC=CC(C(F)(F)F)=C1 TVMPXSWBLSQTSM-UHFFFAOYSA-N 0.000 claims 2
IWNOYNQILKRDHU-UHFFFAOYSA-N 4-chloro-1-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OCC(CCCl)O)=CC=CC2=C1 IWNOYNQILKRDHU-UHFFFAOYSA-N 0.000 claims 2
OGJDQHFIBWUGAA-UHFFFAOYSA-N 4-chloro-1-naphthalen-2-yloxybutan-2-ol Chemical compound C1=CC=CC2=CC(OCC(CCCl)O)=CC=C21 OGJDQHFIBWUGAA-UHFFFAOYSA-N 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
229920005721 BUTONAL® Polymers 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
-1 monosubstituted phenyl Chemical group 0.000 abstract description 19
125000000217 alkyl group Chemical group 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
125000000623 heterocyclic group Chemical group 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
125000003884 phenylalkyl group Chemical group 0.000 abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000203 mixture Substances 0.000 description 25
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229960004592 isopropanol Drugs 0.000 description 9
239000007787 solid Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
229960003010 sodium sulfate Drugs 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
238000003756 stirring Methods 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
238000007792 addition Methods 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000008187 granular material Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000003637 basic solution Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
229940093932 potassium hydroxide Drugs 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
JWTVKBNHWATNEL-UHFFFAOYSA-N 1-chloro-1-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OC(Cl)C(O)CC)=CC=CC2=C1 JWTVKBNHWATNEL-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
APYCNQFSOVJLPN-UHFFFAOYSA-N 1,4-dichlorobutan-1-ol Chemical compound OC(Cl)CCCCl APYCNQFSOVJLPN-UHFFFAOYSA-N 0.000 description 1
WTUXVPKJCQXXDW-UHFFFAOYSA-N 1-[4-(4-chloro-2-hydroxybutoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(OCC(O)CCCl)C=C1 WTUXVPKJCQXXDW-UHFFFAOYSA-N 0.000 description 1
MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-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
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
PODHIIGQVAJGOK-UHFFFAOYSA-N 3h-inden-5-ol Chemical compound OC1=CC=C2C=CCC2=C1 PODHIIGQVAJGOK-UHFFFAOYSA-N 0.000 description 1
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
PVICBBHJLRCQNM-UHFFFAOYSA-N 4-chloro-1-(2-ethoxyphenoxy)butan-2-ol Chemical compound CCOC1=CC=CC=C1OCC(O)CCCl PVICBBHJLRCQNM-UHFFFAOYSA-N 0.000 description 1
RLMQIBYEJGJMLN-UHFFFAOYSA-N 4-chloro-1-(2-phenylphenoxy)butan-2-ol Chemical compound ClCCC(O)COC1=CC=CC=C1C1=CC=CC=C1 RLMQIBYEJGJMLN-UHFFFAOYSA-N 0.000 description 1
HFTQORWYDLVSEM-UHFFFAOYSA-N 4-chloro-1-(3-chlorophenoxy)butan-2-ol Chemical compound ClCCC(O)COC1=CC=CC(Cl)=C1 HFTQORWYDLVSEM-UHFFFAOYSA-N 0.000 description 1
PAIYHFSAECVLGG-UHFFFAOYSA-N 4-chloro-1-(5-chloropyridin-2-yl)oxybutan-2-ol Chemical compound ClCCC(O)COC1=CC=C(Cl)C=N1 PAIYHFSAECVLGG-UHFFFAOYSA-N 0.000 description 1
SZFUWUOHDRMCKD-UHFFFAOYSA-N 5-chloro-1h-pyridin-2-one Chemical compound OC1=CC=C(Cl)C=N1 SZFUWUOHDRMCKD-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000006793 arrhythmia Effects 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
239000002876 beta blocker Substances 0.000 description 1
229940030611 beta-adrenergic blocking agent Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([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
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000005801 respiratory difficulty Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
PRAJLVIUHUDWDZ-UHFFFAOYSA-M sodium;chloroform;hydroxide Chemical compound [OH-].[Na+].ClC(Cl)Cl PRAJLVIUHUDWDZ-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA312,946A 1974-10-25 1978-10-10 1-aryloxy-4-amino-2-butanols Expired CA1084507A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA312,946A CA1084507A (fr)	1974-10-25	1978-10-10	1-aryloxy-4-amino-2-butanols

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US51812274A	1974-10-25	1974-10-25
US518,122		1974-10-25
US61898475A	1975-10-02	1975-10-02
US618,984		1975-10-02
CA238,243A CA1077474A (fr)	1974-10-25	1975-10-24	1-aryloxy-4-amino-2-butanols
CA312,946A CA1084507A (fr)	1974-10-25	1978-10-10	1-aryloxy-4-amino-2-butanols

Publications (1)

Publication Number	Publication Date
CA1084507A true CA1084507A (fr)	1980-08-26

Family

ID=27425868

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA312,946A Expired CA1084507A (fr)	1974-10-25	1978-10-10	1-aryloxy-4-amino-2-butanols

Country Status (1)

Country	Link
CA (1)	CA1084507A (fr)

1978
- 1978-10-10 CA CA312,946A patent/CA1084507A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-08-26	MKEX	Expiry

Publication	Publication Date	Title
EP0210849B1 (fr)	1990-08-29	2-Hydroxy-3-phénoxypropylamines
EP0253327B1 (fr)	1992-05-06	Dérivés de la diphénylpropylamine, leur préparation et leur utilisation pharmaceutique
DE1493955A1 (de)	1971-08-19	Verfahren zur Herstellung substituierter Sulfonanilide
DE3026201A1 (de)	1981-02-26	Aminoaetheroxide, verfahren zu ihrer herstellung sowie ihre therapeutische verwendung
CH506536A (de)	1971-04-30	Verfahren zur Herstellung von aromatischen Äthern
DE2651083C2 (fr)	1988-08-04
EP0008645A1 (fr)	1980-03-19	Alcoxyphénylpyrrolidones, procédé pour leur préparation et médicaments les contenant
US4806555A (en)	1989-02-21	1-aryloxy-4-amino-2-butanols
DE3613573A1 (de)	1986-10-30	Cyclopentylether und ihre herstellung sowie pharmazeutische formulierung
CA1084507A (fr)	1980-08-26	1-aryloxy-4-amino-2-butanols
US4379167A (en)	1983-04-05	1-Aryloxy-4-amino-2-butanols and the pharmaceutical use thereof
EP0243905B1 (fr)	1990-10-10	1(Oméga-[bis-(phényl)alcoxy]-alcoyl)-4-(di-(phényl)-méthyl-pipérazines, leur procédé de préparation et médicaments qui les contiennent
DE19748469A1 (de)	1999-05-06	Sulfonamid-substituierte Benzopyranderivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
EP0011747B1 (fr)	1982-05-19	Dérivés aminopropanols de 6-hydroxy-2,3,4,5-tétrahydro-1H-1-benzazépin-2-ones, procédé pour leur préparation, et compositions pharmaceutiques les contenant
US4463190A (en)	1984-07-31	1-Aryloxy-4-amino-2-butanols
DE2217329A1 (de)	1972-11-02	Benzofuranderivate
DE2514334A1 (de)	1975-10-09	Neue pyridinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazeutischen zusammensetzungen
DE3124673A1 (de)	1983-01-13	Subsituierte 2-amino-pyridinderivate, verfahren zu ihrer herstellung, ihre verwendung in arzneimitteln, sowie deren herstellung
EP0533056A2 (fr)	1993-03-24	Aminopropanes substitués, procédé de leur préparation et leur utilisation comme agents antimycotiques
CH636076A5 (de)	1983-05-13	Benzylalkoholderivate und verfahren zu deren herstellung.
EP0027928A2 (fr)	1981-05-06	Dérivés pipéridiniques d'esters de l'acide 4,5-dialkyle-3-hydroxy-pyrrol-2-carboxylique, leur préparation et compositions pharmaceutiques les contenant
EP0056486A2 (fr)	1982-07-28	Phénylpiperazinyl-propanoles de hétarylphénoles, leur préparation et leurs compositions pharmaceutiques
EP0006458B1 (fr)	1981-10-07	N1-Benzoyl-N2-phényl-1,3-diaminopropane-2-oles et leurs sels, procédé pour les préparer et médicaments les contenant
CA1077474A (fr)	1980-05-13	1-aryloxy-4-amino-2-butanols
EP0297435B1 (fr)	1991-10-16	Dérivés aminopropanols de 3-(3'-hydroxyphényl)-1-propanone, procédé pour leur préparation et mèdicaments contenant ces composés