FI70008C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-enyletanolaminderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-enyletanolaminderivat Download PDFInfo
- Publication number
- FI70008C FI70008C FI782498A FI782498A FI70008C FI 70008 C FI70008 C FI 70008C FI 782498 A FI782498 A FI 782498A FI 782498 A FI782498 A FI 782498A FI 70008 C FI70008 C FI 70008C
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- Finland
- Prior art keywords
- formula
- solution
- nhq
- ether
- cr2r3
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- 238000000034 method Methods 0.000 title claims description 21
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 phenylacetyl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 239000007858 starting material Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- SAFBWLLTIPIZTP-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-2-oxoacetaldehyde;hydrate Chemical compound O.NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl SAFBWLLTIPIZTP-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 3
- JLPKZJDZXIKSCP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=C(N)C(Cl)=C1 JLPKZJDZXIKSCP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 150000003947 ethylamines Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WEMKUJXGNHGSFH-UHFFFAOYSA-N n-[2-(benzylamino)ethyl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1CNCCNC(=O)CC1=CC=CC=C1 WEMKUJXGNHGSFH-UHFFFAOYSA-N 0.000 description 3
- QYJQYQYOORTDHY-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-2-phenylacetamide Chemical compound C=1C(Cl)=C(N)C(Cl)=CC=1C(O)CNC(C)(C)CNC(=O)CC1=CC=CC=C1 QYJQYQYOORTDHY-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VKQCLPIEZOYNKL-UHFFFAOYSA-N 1-(2-amino-2-methylpropyl)-3-phenylurea Chemical compound CC(C)(N)CNC(=O)NC1=CC=CC=C1 VKQCLPIEZOYNKL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- UISUEFRISDPFLA-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-2-phenoxyacetamide Chemical compound CC(C)(N)CNC(=O)COC1=CC=CC=C1 UISUEFRISDPFLA-UHFFFAOYSA-N 0.000 description 2
- DUVVKZQEZWPDOD-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-2-phenylacetamide Chemical compound CC(C)(N)CNC(=O)CC1=CC=CC=C1 DUVVKZQEZWPDOD-UHFFFAOYSA-N 0.000 description 2
- JNWNPLJATOLWGI-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCC(C)(C)N JNWNPLJATOLWGI-UHFFFAOYSA-N 0.000 description 2
- ZIMOHSZCIYGHAR-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenylacetamide Chemical compound NCCNC(=O)CC1=CC=CC=C1 ZIMOHSZCIYGHAR-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 1
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- YZMBUAASUAYJFC-UHFFFAOYSA-N 1-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-3-phenylurea;hydrochloride Chemical compound Cl.C=1C(Cl)=C(N)C(Cl)=CC=1C(O)CNC(C)(C)CNC(=O)NC1=CC=CC=C1 YZMBUAASUAYJFC-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 240000001307 Myosotis scorpioides Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001117 clenbuterol Drugs 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
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- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
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- 210000004072 lung Anatomy 0.000 description 1
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
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- QECOTRRNHXIEFK-UHFFFAOYSA-N n-(2,6-dichloro-4-oxaldehydoylphenyl)-2,2-dimethylpropanamide;hydrate Chemical compound O.CC(C)(C)C(=O)NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl QECOTRRNHXIEFK-UHFFFAOYSA-N 0.000 description 1
- KATFZJUODZHMPV-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-2-phenylacetamide;hydrochloride Chemical compound Cl.CC(C)(N)CNC(=O)CC1=CC=CC=C1 KATFZJUODZHMPV-UHFFFAOYSA-N 0.000 description 1
- SKGYVELDSNNACR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-phenylacetamide Chemical compound CN(C)CCNC(=O)CC1=CC=CC=C1 SKGYVELDSNNACR-UHFFFAOYSA-N 0.000 description 1
- RAMMUYTVRDCLOH-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-benzylamino]ethyl]-2-phenylacetamide Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CN(CC=1C=CC=CC=1)CCNC(=O)CC1=CC=CC=C1 RAMMUYTVRDCLOH-UHFFFAOYSA-N 0.000 description 1
- MRAFUPNSGVHNBT-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-2-phenoxyacetamide Chemical compound C=1C(Cl)=C(N)C(Cl)=CC=1C(O)CNC(C)(C)CNC(=O)COC1=CC=CC=C1 MRAFUPNSGVHNBT-UHFFFAOYSA-N 0.000 description 1
- LCRZFQKQEMLEGU-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-2-methylpropyl]-2-phenylacetamide;dihydrochloride Chemical compound Cl.Cl.C=1C(Cl)=C(N)C(Cl)=CC=1C(O)CNC(C)(C)CNC(=O)CC1=CC=CC=C1 LCRZFQKQEMLEGU-UHFFFAOYSA-N 0.000 description 1
- MBJYIWKHRGKCIG-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-2-methylpropyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 MBJYIWKHRGKCIG-UHFFFAOYSA-N 0.000 description 1
- UBNQWULXRDQHQA-UHFFFAOYSA-N n-[2-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]ethyl]-2-phenylacetamide Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CNCCNC(=O)CC1=CC=CC=C1 UBNQWULXRDQHQA-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3434677 | 1977-08-16 | ||
| GB3434677 | 1977-08-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782498A7 FI782498A7 (fi) | 1979-02-17 |
| FI70008B FI70008B (fi) | 1986-01-31 |
| FI70008C true FI70008C (fi) | 1986-09-12 |
Family
ID=10364512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782498A FI70008C (fi) | 1977-08-16 | 1978-08-16 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-enyletanolaminderivat |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4355045A (it) |
| EP (1) | EP0000809B1 (it) |
| JP (1) | JPS5448727A (it) |
| AR (1) | AR221704A1 (it) |
| AT (1) | AT359481B (it) |
| AU (1) | AU521456B2 (it) |
| BE (1) | BE869639A (it) |
| CA (1) | CA1108183A (it) |
| CS (1) | CS207661B2 (it) |
| DE (2) | DE2861733D1 (it) |
| DK (1) | DK362178A (it) |
| ES (1) | ES472591A1 (it) |
| FI (1) | FI70008C (it) |
| FR (1) | FR2400505A1 (it) |
| GR (1) | GR66025B (it) |
| HU (1) | HU177107B (it) |
| IE (1) | IE47283B1 (it) |
| IL (1) | IL55284A (it) |
| IT (1) | IT1098051B (it) |
| NL (1) | NL7808440A (it) |
| NO (1) | NO145656C (it) |
| NZ (1) | NZ188040A (it) |
| PL (2) | PL114031B1 (it) |
| PT (1) | PT68422A (it) |
| SU (1) | SU820658A3 (it) |
| ZA (1) | ZA784335B (it) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE54220B1 (en) * | 1981-12-23 | 1989-07-19 | Ici Plc | Phenol esters |
| US5530029A (en) * | 1987-09-15 | 1996-06-25 | The Rowett Research Institute | Therapeutic applications of clenbuterol |
| US5541188A (en) * | 1987-09-15 | 1996-07-30 | The Rowett Research Institute | Therapeutic applications of beta-adrenergic agonists |
| FR2626878B1 (fr) * | 1988-02-10 | 1990-06-08 | Lafon Labor | Derives de 1-(aminophenyl)-2-dimethylaminopropanone, procede de preparation et utilisation en therapeutique |
| US6421336B1 (en) * | 1999-02-23 | 2002-07-16 | Tantivy Communications, Inc. | Variable rate orthogonally coded reverse link structure |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618005A1 (de) * | 1966-09-22 | 1971-09-09 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Amino-dihalogen-phenyl-aethylaminen |
| US3975443A (en) * | 1972-06-06 | 1976-08-17 | Allen & Hanburys Limited | 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine |
| GB1460593A (en) * | 1973-06-22 | 1977-01-06 | Ici Ltd | Ethanolamine derivatives |
| GB1468156A (en) * | 1973-07-19 | 1977-03-23 | Ici Ltd | Phenylethylamine derivatives |
-
1978
- 1978-07-14 EP EP78300153A patent/EP0000809B1/en not_active Expired
- 1978-07-14 DE DE7878300153T patent/DE2861733D1/de not_active Expired
- 1978-07-27 IE IE1519/78A patent/IE47283B1/en unknown
- 1978-07-31 CA CA308,489A patent/CA1108183A/en not_active Expired
- 1978-07-31 ZA ZA00784335A patent/ZA784335B/xx unknown
- 1978-08-01 AU AU38505/78A patent/AU521456B2/en not_active Expired
- 1978-08-02 NZ NZ188040A patent/NZ188040A/xx unknown
- 1978-08-03 US US05/930,859 patent/US4355045A/en not_active Expired - Lifetime
- 1978-08-04 IL IL55284A patent/IL55284A/xx unknown
- 1978-08-09 BE BE78189800A patent/BE869639A/xx unknown
- 1978-08-10 IT IT26671/78A patent/IT1098051B/it active
- 1978-08-11 FR FR7823790A patent/FR2400505A1/fr active Granted
- 1978-08-11 GR GR56982A patent/GR66025B/el unknown
- 1978-08-11 CS CS785271A patent/CS207661B2/cs unknown
- 1978-08-14 DE DE19782835537 patent/DE2835537A1/de not_active Withdrawn
- 1978-08-14 HU HU78IE844A patent/HU177107B/hu unknown
- 1978-08-14 PL PL1978215005A patent/PL114031B1/pl unknown
- 1978-08-14 PT PT68422A patent/PT68422A/pt unknown
- 1978-08-14 PL PL1978209049A patent/PL113842B1/pl unknown
- 1978-08-15 SU SU782650053A patent/SU820658A3/ru active
- 1978-08-15 NO NO782767A patent/NO145656C/no unknown
- 1978-08-15 NL NL7808440A patent/NL7808440A/xx not_active Application Discontinuation
- 1978-08-15 AR AR273324A patent/AR221704A1/es active
- 1978-08-16 ES ES472591A patent/ES472591A1/es not_active Expired
- 1978-08-16 AT AT595378A patent/AT359481B/de not_active IP Right Cessation
- 1978-08-16 FI FI782498A patent/FI70008C/fi not_active IP Right Cessation
- 1978-08-16 DK DK362178A patent/DK362178A/da not_active Application Discontinuation
- 1978-08-16 JP JP9993478A patent/JPS5448727A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: IMPERIAL CHEMICAL INDUSTRIES LIMITED |