CA1252785A - Composes de phenethanolamine - Google Patents

Composes de phenethanolamine

Info

Publication number: CA1252785A
Authority: CA; Canada
Prior art keywords: phenyl; group; hydroxy; amino; methyl
Prior art date: 1984-04-17
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

CA000479396A

Other languages

English (en)

Inventor

Ian F. Skidmore

Lawrence H. C. Lunts

Harry Finch

Alan Naylor

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.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

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.)

1984-04-17

Filing date

1985-04-17

Publication date

1989-04-18

1984-04-17 Priority claimed from GB848409909A external-priority patent/GB8409909D0/en

1984-10-17 Priority claimed from GB848426197A external-priority patent/GB8426197D0/en

1985-04-17 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1989-04-18 Application granted granted Critical

1989-04-18 Publication of CA1252785A publication Critical patent/CA1252785A/fr

Status Expired legal-status Critical Current

Links

ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 238
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 198
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 71
150000003839 salts Chemical class 0.000 claims abstract description 35
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
239000012453 solvate Substances 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000003277 amino group Chemical group 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000004429 atom Chemical group 0.000 claims abstract description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 123
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 claims description 121
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 121
-1 ethyl propyl Chemical group 0.000 claims description 88
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 41
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
238000000034 method Methods 0.000 claims description 31
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 31
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 27
230000008569 process Effects 0.000 claims description 26
125000006239 protecting group Chemical group 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 22
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
230000009467 reduction Effects 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
239000003638 chemical reducing agent Substances 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 claims description 6
YWMLORGQOFONNT-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1 YWMLORGQOFONNT-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
AMZJWTLSPHWCBA-UHFFFAOYSA-N n-[4-[4-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]butyl]phenyl]butane-1-sulfonamide Chemical compound C1=CC(NS(=O)(=O)CCCC)=CC=C1CCCCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 AMZJWTLSPHWCBA-UHFFFAOYSA-N 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
HOPGWDUYWPMYFB-UHFFFAOYSA-N 2,4-bis(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1 HOPGWDUYWPMYFB-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
YXQADNCHCQKDPN-UHFFFAOYSA-N propyl 4-[2-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]ethyl]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1CCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 YXQADNCHCQKDPN-UHFFFAOYSA-N 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
230000002152 alkylating effect Effects 0.000 claims 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 2
XLTXUKXKMOAJMM-UHFFFAOYSA-N methyl 4-[3-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]propyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 XLTXUKXKMOAJMM-UHFFFAOYSA-N 0.000 claims 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
ADRYIDMNPSDXBY-UHFFFAOYSA-N 3-[[6-[4-(4-amino-3,5-dimethylphenyl)butoxy]hexylamino]methyl]-2,4-bis(hydroxymethyl)phenol Chemical compound CC1=C(N)C(C)=CC(CCCCOCCCCCCNCC=2C(=C(O)C=CC=2CO)CO)=C1 ADRYIDMNPSDXBY-UHFFFAOYSA-N 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 7
230000009471 action Effects 0.000 abstract description 5
201000010099 disease Diseases 0.000 abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
150000004677 hydrates Chemical class 0.000 abstract description 3
206010006458 Bronchitis chronic Diseases 0.000 abstract description 2
208000006673 asthma Diseases 0.000 abstract description 2
206010006451 bronchitis Diseases 0.000 abstract description 2
208000007451 chronic bronchitis Diseases 0.000 abstract description 2
230000002441 reversible effect Effects 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 437
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 411
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 272
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
229940086542 triethylamine Drugs 0.000 description 153
238000000746 purification Methods 0.000 description 105
239000000243 solution Substances 0.000 description 104
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 92
239000000203 mixture Substances 0.000 description 89
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 86
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
239000003921 oil Substances 0.000 description 79
235000019198 oils Nutrition 0.000 description 79
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 62
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
229940087646 methanolamine Drugs 0.000 description 50
229910052757 nitrogen Inorganic materials 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 45
239000000284 extract Substances 0.000 description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000002904 solvent Substances 0.000 description 32
239000012267 brine Substances 0.000 description 31
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 30
238000001665 trituration Methods 0.000 description 30
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 29
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
239000004480 active ingredient Substances 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 22
239000003054 catalyst Substances 0.000 description 21
235000017557 sodium bicarbonate Nutrition 0.000 description 20
229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
238000001914 filtration Methods 0.000 description 19
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
229910052799 carbon Inorganic materials 0.000 description 16
SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
238000004458 analytical method Methods 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000000843 powder Substances 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
239000003826 tablet Substances 0.000 description 10
XWRBIXFTHXFQKC-UHFFFAOYSA-N 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone Chemical compound OCC1=CC(C(=O)CBr)=CC=C1O XWRBIXFTHXFQKC-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
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 8
239000000443 aerosol Substances 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 8
239000008101 lactose Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
239000005711 Benzoic acid Substances 0.000 description 7
NRAFYDNRGQMHGF-UHFFFAOYSA-N COC(=C)C.BrCC(=O)C1=CC2=C(OC(OC2)(C)C)C=C1 Chemical compound COC(=C)C.BrCC(=O)C1=CC2=C(OC(OC2)(C)C)C=C1 NRAFYDNRGQMHGF-UHFFFAOYSA-N 0.000 description 7
229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
235000010233 benzoic acid Nutrition 0.000 description 7
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
230000008570 general process Effects 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
229930006000 Sucrose Natural products 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
229910000069 nitrogen hydride Inorganic materials 0.000 description 6
229910003445 palladium oxide Inorganic materials 0.000 description 6
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
239000005720 sucrose Substances 0.000 description 6
229960004793 sucrose Drugs 0.000 description 6
239000001117 sulphuric acid Substances 0.000 description 6
235000011149 sulphuric acid Nutrition 0.000 description 6
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000004338 Dichlorodifluoromethane Substances 0.000 description 5
239000007832 Na2SO4 Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000029936 alkylation Effects 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 5
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
238000007906 compression Methods 0.000 description 5
230000006835 compression Effects 0.000 description 5
235000019404 dichlorodifluoromethane Nutrition 0.000 description 5
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
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PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
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239000000337 buffer salt Substances 0.000 description 1
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
TXUMIRNLNDWCLX-UHFFFAOYSA-N butyl n-[4-[2-[6-(benzylamino)hexoxy]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCC)=CC=C1CCOCCCCCCNCC1=CC=CC=C1 TXUMIRNLNDWCLX-UHFFFAOYSA-N 0.000 description 1
ICHFWAHGELEVDM-UHFFFAOYSA-N butyl n-[4-[2-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCC)=CC=C1CCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 ICHFWAHGELEVDM-UHFFFAOYSA-N 0.000 description 1
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GGOGTAISXVMAGB-UHFFFAOYSA-N ethyl 4-[3-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]propyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1CCCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 GGOGTAISXVMAGB-UHFFFAOYSA-N 0.000 description 1
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230000004927 fusion Effects 0.000 description 1
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239000012362 glacial acetic acid Substances 0.000 description 1
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LBVGDTNHCZMQCD-UHFFFAOYSA-N n-[2-[2-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]ethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1CCOCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 LBVGDTNHCZMQCD-UHFFFAOYSA-N 0.000 description 1
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GVGJUVSDWWEGLV-UHFFFAOYSA-N n-benzyl-2,2,2-trifluoro-n-[6-[2-(4-formamidophenyl)ethoxy]hexyl]acetamide Chemical compound C=1C=CC=CC=1CN(C(=O)C(F)(F)F)CCCCCCOCCC1=CC=C(NC=O)C=C1 GVGJUVSDWWEGLV-UHFFFAOYSA-N 0.000 description 1
ACYNVJJTYLLAGM-UHFFFAOYSA-N n-benzyl-6-[2-(4-piperidin-1-ylphenyl)ethoxy]hexan-1-amine Chemical compound C=1C=CC=CC=1CNCCCCCCOCCC(C=C1)=CC=C1N1CCCCC1 ACYNVJJTYLLAGM-UHFFFAOYSA-N 0.000 description 1
OJEGKABXZDVGRH-UHFFFAOYSA-N n-benzyl-6-[3-(4-piperidin-1-ylphenyl)prop-2-ynoxy]hexan-1-amine Chemical compound C=1C=CC=CC=1CNCCCCCCOCC#CC(C=C1)=CC=C1N1CCCCC1 OJEGKABXZDVGRH-UHFFFAOYSA-N 0.000 description 1
GLZZJTBRGKAUFT-UHFFFAOYSA-N n-benzyl-6-prop-2-ynoxyhexan-1-amine Chemical compound C#CCOCCCCCCNCC1=CC=CC=C1 GLZZJTBRGKAUFT-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
YYLYVEAMQOZFJJ-UHFFFAOYSA-N propyl 4-[2-[6-(benzylamino)hexoxy]ethyl]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1CCOCCCCCCNCC1=CC=CC=C1 YYLYVEAMQOZFJJ-UHFFFAOYSA-N 0.000 description 1
BGTBNAFDFQXIRU-UHFFFAOYSA-N propyl 4-[3-(6-bromohexoxy)propyl]benzoate Chemical compound CCCOC(=O)C1=CC=C(CCCOCCCCCCBr)C=C1 BGTBNAFDFQXIRU-UHFFFAOYSA-N 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
239000002516 radical scavenger Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229960004016 sucrose syrup Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
229940030010 trimethoxybenzene Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000479396A 1984-04-17 1985-04-17 Composes de phenethanolamine Expired CA1252785A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8409909		1984-04-17
GB848409909A GB8409909D0 (en)	1984-04-17	1984-04-17	Chemical compounds
GB8426197		1984-10-17
GB848426197A GB8426197D0 (en)	1984-10-17	1984-10-17	Chemical compounds

Publications (1)

Publication Number	Publication Date
CA1252785A true CA1252785A (fr)	1989-04-18

Family

ID=26287623

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000479396A Expired CA1252785A (fr)	1984-04-17	1985-04-17	Composes de phenethanolamine

Country Status (1)

Country	Link
CA (1)	CA1252785A (fr)

1985
- 1985-04-17 CA CA000479396A patent/CA1252785A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-04-18	MKEX	Expiry

Publication	Publication Date	Title
US4990505A (en)	1991-02-05	Phenethanolamine compounds
CA1335999C (fr)	1995-06-20	Derives de la phenethanolamine
US3341584A (en)	1967-09-12	Anilides
US3712927A (en)	1973-01-23	Alkanolamine derivatives
EP0162576B1 (fr)	1989-07-26	Composés d'éthanolamine
CA1255667A (fr)	1989-06-13	Derives de dichloroaniline
EP0028063A1 (fr)	1981-05-06	Dérivés de phénol, procédés pour leur préparation et composés pharmaceutiques les contenant
EP0178919B1 (fr)	1988-12-21	Dérivés d'aminophénol
AU653398B2 (en)	1994-09-29	Substituted carboxylic acid derivatives
US4908386A (en)	1990-03-13	Ethanolamine derivatives
US4853381A (en)	1989-08-01	Ethanolamine compounds
JPS62187438A (ja)	1987-08-15	エタノ−ルアミン化合物
US3732300A (en)	1973-05-08	Phenylaminoethanol derivatives
USRE38921E1 (en)	2005-12-13	Phenoxyalkylcarboxylic acid derivatives and process for their preparations
EP0028305B1 (fr)	1984-02-01	Composés diaryle et compositions pharmaceutiques les contenant
CA1252785A (fr)	1989-04-18	Composes de phenethanolamine
PL116994B1 (en)	1981-07-31	Process for manufacturing novel derivatives of 1-amino-3-phenoxypropan-2-olpropanola-2
US3478149A (en)	1969-11-11	Therapeutic compositions and methods employing sulfonamidophenethanolamines
US4064257A (en)	1977-12-20	Thiazole cardiovascular agents
Kerwin et al.	1951	Adrenergic Blocking Agents. III. N-(Aryloxyisopropyl)-β-haloethylamines1
IE59466B1 (en)	1994-02-23	Dichloroaniline derivatives
PT93844A (pt)	1990-11-20	Processo para a preparacao de derivados de fenetanolamina
JPS6133147A (ja)	1986-02-17	フエネタノ−ルアミン化合物
US3361790A (en)	1968-01-02	Ether-linked acids and esters of triarylacrylamides
US3060190A (en)	1962-10-23	p-aminophenoxyalkanes