CA1255666A - Composes de phenethanolamine - Google Patents

Composes de phenethanolamine

Info

Publication number: CA1255666A
Authority: CA; Canada
Prior art keywords: group; phenyl; hydroxy; general formula; compounds
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

CA000479394A

Other languages

English (en)

Inventor

Ian F. Skidmore

Lawrence H.C. Lunts

Harry Finch

Alan Naylor

Ian B. Campbell

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

1989-06-13

1984-04-17 Priority claimed from GB848409910A external-priority patent/GB8409910D0/en

1984-10-17 Priority claimed from GB848426206A external-priority patent/GB8426206D0/en

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

1989-06-13 Application granted granted Critical

1989-06-13 Publication of CA1255666A publication Critical patent/CA1255666A/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 3
150000001875 compounds Chemical class 0.000 claims abstract description 127
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 48
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 34
239000012453 solvate Substances 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
125000001424 substituent group Chemical group 0.000 claims abstract description 9
125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims abstract description 8
125000004419 alkynylene group Chemical group 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims abstract description 5
125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
125000003277 amino group Chemical group 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
125000004429 atom Chemical group 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 2
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract 2
-1 hydroxy, methoxy, ethoxy, amino, methylamino, ethylamino, dimethylamino, diethylamino, morpholino, piperidino, piperazino, N-methylpiperazino Chemical group 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000006239 protecting group Chemical group 0.000 claims description 27
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 23
238000000034 method Methods 0.000 claims description 22
230000008569 process Effects 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
230000009467 reduction Effects 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 11
239000003638 chemical reducing agent Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
150000001502 aryl halides Chemical class 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 9
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
230000002152 alkylating effect Effects 0.000 claims 2
PRBSNDAXVAPHDS-SREVYHEPSA-N n-[4-[(z)-3-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]prop-1-enyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1\C=C/COCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 PRBSNDAXVAPHDS-SREVYHEPSA-N 0.000 claims 2
PDLIJYOTAFRSKY-UHFFFAOYSA-N N-[4-[3-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]prop-1-ynyl]phenyl]acetamide Chemical compound C(C)(=O)NC1=CC=C(C=C1)C#CCOCCCCCCNCC(C1=CC(=C(C=C1)O)CO)O PDLIJYOTAFRSKY-UHFFFAOYSA-N 0.000 claims 1
YWMLORGQOFONNT-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1 YWMLORGQOFONNT-UHFFFAOYSA-N 0.000 claims 1
230000000875 corresponding effect Effects 0.000 claims 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
HZXFHYZAQYJPEM-SREVYHEPSA-N n-[4-[(z)-3-[6-[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]hexoxy]prop-1-enyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1\C=C/COCCCCCCNCC(O)C1=CC=C(O)C(CO)=C1 HZXFHYZAQYJPEM-SREVYHEPSA-N 0.000 claims 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 6
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
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 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 44
239000000243 solution Substances 0.000 description 40
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
239000004480 active ingredient Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000843 powder Substances 0.000 description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000000746 purification Methods 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 10
239000002585 base Substances 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
239000000725 suspension Substances 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 9
230000008570 general process Effects 0.000 description 9
239000003826 tablet Substances 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000000377 silicon dioxide Substances 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 7
239000000443 aerosol Substances 0.000 description 7
150000004678 hydrides Chemical class 0.000 description 7
239000008101 lactose Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
239000004338 Dichlorodifluoromethane Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
229930006000 Sucrose Natural products 0.000 description 5
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 5
235000019404 dichlorodifluoromethane Nutrition 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
229960004793 sucrose Drugs 0.000 description 5
238000001665 trituration Methods 0.000 description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000005642 Oleic acid Substances 0.000 description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000006071 cream Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
150000002466 imines Chemical class 0.000 description 4
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
229910052987 metal hydride Inorganic materials 0.000 description 4
150000004681 metal hydrides Chemical class 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
230000002335 preservative effect Effects 0.000 description 4
239000008213 purified water Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
XPBQQAHIVODAIC-UHFFFAOYSA-N 4-bromobutylbenzene Chemical compound BrCCCCC1=CC=CC=C1 XPBQQAHIVODAIC-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000000872 buffer Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
238000007906 compression Methods 0.000 description 3
230000006835 compression Effects 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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238000011321 prophylaxis Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 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
239000012258 stirred mixture Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229960004016 sucrose syrup 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
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 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
239000003981 vehicle Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000479394A 1984-04-17 1985-04-17 Composes de phenethanolamine Expired CA1255666A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8409910		1984-04-17
GB848409910A GB8409910D0 (en)	1984-04-17	1984-04-17	Chemical compounds
GB848426206A GB8426206D0 (en)	1984-10-17	1984-10-17	Chemical compounds
GB8426206		1984-10-17

Publications (1)

Publication Number	Publication Date
CA1255666A true CA1255666A (fr)	1989-06-13

Family

ID=26287624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000479394A Expired CA1255666A (fr)	1984-04-17	1985-04-17	Composes de phenethanolamine

Country Status (1)

Country	Link
CA (1)	CA1255666A (fr)

1985
- 1985-04-17 CA CA000479394A patent/CA1255666A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-06-13	MKEX	Expiry

Publication	Publication Date	Title
CA1336004C (fr)	1995-06-20	Derives phenethanolamine
EP0162576A1 (fr)	1985-11-27	Composés d'éthanolamine
US4963564A (en)	1990-10-16	Phenethanolamine derivatives
IE870350L (en)	1987-08-12	Dichloroaniline derivatives
CA1255667A (fr)	1989-06-13	Derives de dichloroaniline
US4990505A (en)	1991-02-05	Phenethanolamine compounds
US4853382A (en)	1989-08-01	Aminophenol derivatives
US4908386A (en)	1990-03-13	Ethanolamine derivatives
EP0220878A2 (fr)	1987-05-06	Composés d'éthanolamine
US4853381A (en)	1989-08-01	Ethanolamine compounds
GB2162842A (en)	1986-02-12	Aminophenol compounds
EP0028305B1 (fr)	1984-02-01	Composés diaryle et compositions pharmaceutiques les contenant
CA1296335C (fr)	1992-02-25	Derives dichloroaniline
GB2160863A (en)	1986-01-02	Ethanolamine compounds
PT93844A (pt)	1990-11-20	Processo para a preparacao de derivados de fenetanolamina
CA1253864A (fr)	1989-05-09	Derives d'aminophenol
EP0278728A2 (fr)	1988-08-17	Dérivés de 1-(4-amino-3,5-dichlorophényl)-2-(amino substitué)éthanol et leur utilisation pour le traitement des maladies respiratoires
EP0278727A2 (fr)	1988-08-17	Dérivés de 1-(4-amino-3-chloro-5-trifluorométhylphényl)-2-(amino substitué)éthanol et leur utilisation pour le traitement des maladies respiratoires
IE58865B1 (en)	1993-11-17	Aminophenol derivatives
JPS6133147A (ja)	1986-02-17	フエネタノ−ルアミン化合物
NZ227365A (en)	1990-10-26	Aromatic amino ethers and pharmaceutical compositions
JPS62129259A (ja)	1987-06-11	エタノ−ルアミン誘導体
EP0219350A2 (fr)	1987-04-22	Composés d'éthanolamine
JPS60248650A (ja)	1985-12-09	エタノ−ルアミン化合物