NO128653B - - Google Patents
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- Publication number
- NO128653B NO128653B NO00611/70A NO61170A NO128653B NO 128653 B NO128653 B NO 128653B NO 00611/70 A NO00611/70 A NO 00611/70A NO 61170 A NO61170 A NO 61170A NO 128653 B NO128653 B NO 128653B
- Authority
- NO
- Norway
- Prior art keywords
- radical
- compound
- formula
- propanol
- given above
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 alkylcarbamoyl radical Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 28
- 239000007858 starting material Substances 0.000 claims description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 3
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 229960004592 isopropanol Drugs 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 229960001317 isoprenaline Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- DVYKQANXDBJSGF-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(O)C=C1 DVYKQANXDBJSGF-UHFFFAOYSA-N 0.000 description 5
- 239000002026 chloroform extract Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
- 229940080818 propionamide Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- BVTCJCWLWJMGCG-UHFFFAOYSA-N 2-(3-bromo-4-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C(Br)=C1 BVTCJCWLWJMGCG-UHFFFAOYSA-N 0.000 description 4
- YBPAYPRLUDCSEY-UHFFFAOYSA-N 2-(4-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 230000009249 intrinsic sympathomimetic activity Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- USVBRYYVBBNSIN-UHFFFAOYSA-N 2-[3-bromo-4-(3-chloro-2-hydroxypropoxy)phenyl]acetamide Chemical compound BrC1=C(OCC(CCl)O)C=CC(=C1)CC(N)=O USVBRYYVBBNSIN-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229940124630 bronchodilator Drugs 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 3
- 230000000763 evoking effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- IYTUKSIOQKTZEG-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(Cl)=C1 IYTUKSIOQKTZEG-UHFFFAOYSA-N 0.000 description 2
- HCTDRZMGZRHFJV-UHFFFAOYSA-N 1-chloro-3-phenoxypropan-2-ol Chemical class ClCC(O)COC1=CC=CC=C1 HCTDRZMGZRHFJV-UHFFFAOYSA-N 0.000 description 2
- ORFVLZDPZCEXSD-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C(Cl)=C1 ORFVLZDPZCEXSD-UHFFFAOYSA-N 0.000 description 2
- QYRRSSMPZDPEJB-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C(F)=C1 QYRRSSMPZDPEJB-UHFFFAOYSA-N 0.000 description 2
- YRFBZAHYMOSSGX-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(F)=C1 YRFBZAHYMOSSGX-UHFFFAOYSA-N 0.000 description 2
- LCYBGDHBXIKVEZ-UHFFFAOYSA-N 2-[3-bromo-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1Br LCYBGDHBXIKVEZ-UHFFFAOYSA-N 0.000 description 2
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N N-acetyl-para-amino-phenol Natural products CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000674 adrenergic antagonist Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- YYAJJKZSQWOLIP-HWKANZROSA-N (e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide Chemical compound COC1=CC(\C=C\C(N)=O)=CC=C1O YYAJJKZSQWOLIP-HWKANZROSA-N 0.000 description 1
- FJWXQQCKEVEHBJ-UHFFFAOYSA-N 1-chloro-3-(propan-2-ylamino)propan-2-ol;hydrochloride Chemical compound Cl.CC(C)NCC(O)CCl FJWXQQCKEVEHBJ-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 1
- AGQIFSXGAJQNKC-UHFFFAOYSA-N 2-(2-butan-2-ylphenyl)acetic acid Chemical compound CCC(C)C1=CC=CC=C1CC(O)=O AGQIFSXGAJQNKC-UHFFFAOYSA-N 0.000 description 1
- BFVCOQXPSXVGPS-UHFFFAOYSA-N 2-(3-bromo-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(Br)=C1 BFVCOQXPSXVGPS-UHFFFAOYSA-N 0.000 description 1
- XEDVOAJPHAUIRX-UHFFFAOYSA-N 2-(4-hydroxy-3-methylphenyl)acetamide Chemical compound CC1=CC(CC(N)=O)=CC=C1O XEDVOAJPHAUIRX-UHFFFAOYSA-N 0.000 description 1
- JQJMAHBZVDMIIT-UHFFFAOYSA-N 2-(4-hydroxy-3-methylphenyl)acetic acid Chemical compound CC1=CC(CC(O)=O)=CC=C1O JQJMAHBZVDMIIT-UHFFFAOYSA-N 0.000 description 1
- SKCMKKMMQWEXHB-UHFFFAOYSA-N 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-iodophenyl]acetamide Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1I SKCMKKMMQWEXHB-UHFFFAOYSA-N 0.000 description 1
- CMUJOPQSQDHDAB-UHFFFAOYSA-N 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methoxyphenyl]acetamide Chemical compound COC1=CC(CC(N)=O)=CC=C1OCC(O)CNC(C)C CMUJOPQSQDHDAB-UHFFFAOYSA-N 0.000 description 1
- HRWABHSGGKDLMG-UHFFFAOYSA-N 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methylphenyl]acetamide Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1C HRWABHSGGKDLMG-UHFFFAOYSA-N 0.000 description 1
- NRBLEHWCRWBQJV-UHFFFAOYSA-N 2-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-chlorophenyl]acetamide Chemical compound CC(C)(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1Cl NRBLEHWCRWBQJV-UHFFFAOYSA-N 0.000 description 1
- BQAYEZHYNONGGN-UHFFFAOYSA-N 2-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-fluorophenyl]acetamide Chemical compound CC(C)(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1F BQAYEZHYNONGGN-UHFFFAOYSA-N 0.000 description 1
- IVWPXKTWJKRDAI-UHFFFAOYSA-N 2-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methoxyphenyl]acetamide Chemical compound COC1=CC(CC(N)=O)=CC=C1OCC(O)CNC(C)(C)C IVWPXKTWJKRDAI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- BGHLBXLHZRCXRY-UHFFFAOYSA-N 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzaldehyde Chemical compound CC(C)NCC(O)COC1=CC=C(C=O)C=C1 BGHLBXLHZRCXRY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- SBGCCISFOTZEHN-UHFFFAOYSA-N C(C)(CC)C=1C=C(C=CC1O)CC(=O)O Chemical compound C(C)(CC)C=1C=C(C=CC1O)CC(=O)O SBGCCISFOTZEHN-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- 108010039579 PHI peptide receptor Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- ZCDNRPPFBQDQHR-SSYATKPKSA-N Syrosingopine Chemical compound C1=C(OC)C(OC(=O)OCC)=C(OC)C=C1C(=O)O[C@H]1[C@H](OC)[C@@H](C(=O)OC)[C@H]2C[C@@H]3C(NC=4C5=CC=C(OC)C=4)=C5CCN3C[C@H]2C1 ZCDNRPPFBQDQHR-SSYATKPKSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- METKIMKYRPQLGS-LBPRGKRZSA-N esatenolol Chemical compound CC(C)NC[C@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-LBPRGKRZSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- URBNYOULFVVQQK-UHFFFAOYSA-N ethyl 2-(3-bromo-4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(Br)=C1 URBNYOULFVVQQK-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960001749 practolol Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229950006534 syrosingopine Drugs 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000005090 tracheal smooth muscle Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB944569 | 1969-02-21 | ||
| GB47048/69A GB1285038A (en) | 1969-02-21 | 1969-02-21 | Alkanolamine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128653B true NO128653B (pl) | 1973-12-27 |
Family
ID=26242944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00611/70A NO128653B (pl) | 1969-02-21 | 1970-02-20 |
Country Status (20)
| Country | Link |
|---|---|
| JP (2) | JPS535287B1 (pl) |
| AT (3) | AT303005B (pl) |
| BE (1) | BE746107A (pl) |
| CA (1) | CA945172A (pl) |
| CH (3) | CH547257A (pl) |
| CS (3) | CS153062B2 (pl) |
| DE (1) | DE2007751C2 (pl) |
| DK (1) | DK135278B (pl) |
| ES (1) | ES376788A1 (pl) |
| FI (1) | FI53120C (pl) |
| FR (1) | FR2034561A1 (pl) |
| IE (1) | IE34003B1 (pl) |
| IL (1) | IL33931A (pl) |
| KE (1) | KE2582A (pl) |
| NL (1) | NL162363C (pl) |
| NO (1) | NO128653B (pl) |
| PL (3) | PL77781B1 (pl) |
| SE (1) | SE391517B (pl) |
| SU (3) | SU493062A3 (pl) |
| YU (4) | YU34275B (pl) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1311521A (en) * | 1970-02-13 | 1973-03-28 | Ici Ltd | Alkanolamine derivatives |
| DE2048838A1 (de) * | 1970-10-05 | 1972-04-06 | C H Boehnnger Sohn, 6507 Ingel heim | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
| FR2132570B1 (pl) * | 1971-04-09 | 1974-08-02 | Lipha | |
| GB1387630A (en) * | 1971-05-07 | 1975-03-19 | Ici Ltd | Phenoxyalkanolamine derivatives |
| GB1433595A (en) * | 1972-07-06 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
| DE2623314C2 (de) * | 1976-05-25 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE2818999A1 (de) * | 1978-04-29 | 1979-11-15 | Basf Ag | Aminoderivate von 3-alkyl-5-(2- hydroxystyryl)-isoxazolen |
| DE2943405A1 (de) | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Neue aminoderivate des 5-(2-hydroxystyryl)-isoxazols |
| US4387103A (en) * | 1980-11-28 | 1983-06-07 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| US4593119A (en) * | 1980-11-28 | 1986-06-03 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| JPS57105206U (pl) * | 1980-12-16 | 1982-06-29 | ||
| DE3407695A1 (de) * | 1984-03-02 | 1985-09-12 | Röhm Pharma GmbH, 6108 Weiterstadt | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
| DE3500761A1 (de) * | 1985-01-11 | 1986-09-04 | SOUR "PODRAVKA" OOUR "BELUPO 2", Proizvodnja kozmetičkih preparata i lijekova, Koprivnica | Verfahren zur gewinnung von atenolol und seiner derivate |
| US4971959A (en) * | 1987-04-14 | 1990-11-20 | Warner-Lambert Company | Trisubstituted phenyl analogs having activity for congestive heart failure |
| WO1994013631A1 (en) * | 1992-12-10 | 1994-06-23 | Teikoku Chemical Industries Co., Ltd. | Propionic acid derivative |
| WO1998048787A1 (en) * | 1997-04-30 | 1998-11-05 | Eli Lilly And Company | INTERMEDIATES AND A PROCESS FOR PREPARING BENZO[b]THIOPHENES |
| JP5225574B2 (ja) * | 2006-11-09 | 2013-07-03 | エムキュア ファーマシューティカルズ リミテッド | β遮断薬化合物の改善された調製方法 |
| US8552036B2 (en) | 2009-01-12 | 2013-10-08 | Hetero Research Foundation | Polymorph of atazanavir sulfate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593762A1 (de) * | 1967-02-06 | 1972-06-08 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
-
1970
- 1970-02-09 CA CA074,353A patent/CA945172A/en not_active Expired
- 1970-02-10 IE IE174/70A patent/IE34003B1/xx unknown
- 1970-02-11 PL PL1970138762A patent/PL77781B1/pl unknown
- 1970-02-11 PL PL1970174450A patent/PL87019B1/pl unknown
- 1970-02-11 PL PL1970174445A patent/PL93998B1/pl unknown
- 1970-02-17 BE BE746107D patent/BE746107A/xx not_active IP Right Cessation
- 1970-02-18 AT AT146270A patent/AT303005B/de not_active IP Right Cessation
- 1970-02-18 CH CH232770A patent/CH547257A/xx not_active IP Right Cessation
- 1970-02-18 CH CH1804972A patent/CH561175A5/xx not_active IP Right Cessation
- 1970-02-18 CH CH1804472A patent/CH553747A/xx not_active IP Right Cessation
- 1970-02-18 AT AT762071A patent/AT305249B/de not_active IP Right Cessation
- 1970-02-18 AT AT761571A patent/AT305244B/de not_active IP Right Cessation
- 1970-02-19 FI FI443/70A patent/FI53120C/fi active
- 1970-02-19 DK DK81370AA patent/DK135278B/da unknown
- 1970-02-19 YU YU410/70A patent/YU34275B/xx unknown
- 1970-02-19 IL IL33931A patent/IL33931A/xx unknown
- 1970-02-19 DE DE2007751A patent/DE2007751C2/de not_active Expired
- 1970-02-20 JP JP1473970A patent/JPS535287B1/ja active Pending
- 1970-02-20 CS CS118670A patent/CS153062B2/cs unknown
- 1970-02-20 CS CS561770*A patent/CS153069B2/cs unknown
- 1970-02-20 SU SU1689989A patent/SU493062A3/ru active
- 1970-02-20 FR FR7006241A patent/FR2034561A1/fr active Granted
- 1970-02-20 NO NO00611/70A patent/NO128653B/no unknown
- 1970-02-20 CS CS561270*A patent/CS153064B2/cs unknown
- 1970-02-20 NL NL7002414.A patent/NL162363C/xx not_active IP Right Cessation
- 1970-02-20 SU SU701404586K patent/SU482943A3/ru active
- 1970-02-20 SE SE7002190A patent/SE391517B/xx unknown
- 1970-02-21 ES ES376788A patent/ES376788A1/es not_active Expired
-
1971
- 1971-08-03 SU SU1690969A patent/SU537626A3/ru active
-
1973
- 1973-01-18 JP JP48008227A patent/JPS5037182B1/ja active Pending
-
1975
- 1975-06-29 YU YU1933/75A patent/YU34278B/xx unknown
- 1975-07-29 YU YU1936/75A patent/YU34281B/xx unknown
- 1975-07-29 YU YU1934/75A patent/YU34279B/xx unknown
- 1975-11-24 KE KE2582*UA patent/KE2582A/xx unknown
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