DK141117B - Analogifremgangsmåde til fremstilling af phenylethanolaminderivater eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af phenylethanolaminderivater eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK141117B DK141117B DK245574A DK245574A DK141117B DK 141117 B DK141117 B DK 141117B DK 245574 A DK245574 A DK 245574A DK 245574 A DK245574 A DK 245574A DK 141117 B DK141117 B DK 141117B
- Authority
- DK
- Denmark
- Prior art keywords
- hydroxy
- ethyl
- benzamide
- amino
- methyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 12
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title claims description 4
- -1 methanesulfonamido groups Chemical group 0.000 claims description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 35
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 34
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- 239000003245 coal Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- 229910052697 platinum Inorganic materials 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910052763 palladium Inorganic materials 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 6
- 229960000581 salicylamide Drugs 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229940071248 anisate Drugs 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- HXXNTEDKEYTYPD-UHFFFAOYSA-N 2-ethoxyethyl 4-methylbenzenesulfonate Chemical compound CCOCCOS(=O)(=O)C1=CC=C(C)C=C1 HXXNTEDKEYTYPD-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
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 240000009023 Myrrhis odorata Species 0.000 description 3
- 235000007265 Myrrhis odorata Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 235000012550 Pimpinella anisum Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003445 palladium oxide Inorganic materials 0.000 description 3
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229960003712 propranolol Drugs 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- VODORXMIWXIFPI-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-[4-(oxan-2-yloxy)butoxy]benzamide Chemical compound NC(=O)C1=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=C1OCCCCOC1CCCCO1 VODORXMIWXIFPI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XVPHPYUMJJWHNT-UHFFFAOYSA-N methyl 2-(2-ethoxyethoxy)-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzoate Chemical compound C(C)OCCOC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCC1=CC=CC=C1)C)O XVPHPYUMJJWHNT-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- IUUWHXKQKONFCC-UHFFFAOYSA-M sodium (2-hydroxybenzoyl)azanide Chemical compound [Na+].C(C=1C(O)=CC=CC=1)(=O)[NH-] IUUWHXKQKONFCC-UHFFFAOYSA-M 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- WECUIGDEWBNQJJ-SECBINFHSA-N (2r)-4-phenylbutan-2-amine Chemical compound C[C@@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-SECBINFHSA-N 0.000 description 1
- WECUIGDEWBNQJJ-VIFPVBQESA-N (2s)-4-phenylbutan-2-amine Chemical compound C[C@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-VIFPVBQESA-N 0.000 description 1
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- IOYHGBZPUZBUTJ-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1OCCBr IOYHGBZPUZBUTJ-UHFFFAOYSA-N 0.000 description 1
- GWIJIQSINPWYNU-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-ethoxybenzene Chemical compound CCOC1=CC=C(OCCBr)C=C1 GWIJIQSINPWYNU-UHFFFAOYSA-N 0.000 description 1
- RZVDMCGNBFASBU-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-phenylmethoxybenzene Chemical compound C1=CC(OCCBr)=CC=C1OCC1=CC=CC=C1 RZVDMCGNBFASBU-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- LMHCYRULPLGEEZ-UHFFFAOYSA-N 1-iodoheptane Chemical compound CCCCCCCI LMHCYRULPLGEEZ-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- 125000004895 1-methylbutylamino group Chemical group CC(CCC)N* 0.000 description 1
- QWAVNXZAQASOML-UHFFFAOYSA-N 1-phenoxypropan-2-one Chemical compound CC(=O)COC1=CC=CC=C1 QWAVNXZAQASOML-UHFFFAOYSA-N 0.000 description 1
- GLVAUXMKXKUEEA-UHFFFAOYSA-N 1-phenylpentan-3-one Chemical compound CCC(=O)CCC1=CC=CC=C1 GLVAUXMKXKUEEA-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- DKHPZPDGBSIALF-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]-n-methylbenzamide Chemical compound C1=C(C(=O)NC)C(OCCOCC)=CC=C1C(O)CNC(C)CCC1=CC=CC=C1 DKHPZPDGBSIALF-UHFFFAOYSA-N 0.000 description 1
- YAVBIOCLDBGJJD-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-5-[1-hydroxy-2-[(2-methyl-3-phenylpropyl)amino]ethyl]benzamide Chemical compound C1=C(C(N)=O)C(OCCOCC)=CC=C1C(O)CNCC(C)CC1=CC=CC=C1 YAVBIOCLDBGJJD-UHFFFAOYSA-N 0.000 description 1
- JSGFOAORXXURMJ-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl 4-methylbenzenesulfonate Chemical compound CCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 JSGFOAORXXURMJ-UHFFFAOYSA-N 0.000 description 1
- SZZINZURZKQZLG-UHFFFAOYSA-N 2-(4-chlorobutoxy)oxane Chemical compound ClCCCCOC1CCCCO1 SZZINZURZKQZLG-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- LLLXGCKPGCZALY-UHFFFAOYSA-N 2-butoxyethyl 4-methylbenzenesulfonate Chemical compound CCCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 LLLXGCKPGCZALY-UHFFFAOYSA-N 0.000 description 1
- DNLPQXRWAKCKPX-UHFFFAOYSA-N 2-carbamoyl-4-[2-(dibenzylazaniumyl)acetyl]phenolate Chemical compound C1=C(O)C(C(=O)N)=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 DNLPQXRWAKCKPX-UHFFFAOYSA-N 0.000 description 1
- MULOYHAWVKRCKQ-UHFFFAOYSA-N 2-ethoxypropyl 4-methylbenzenesulfonate Chemical compound CCOC(C)COS(=O)(=O)C1=CC=C(C)C=C1 MULOYHAWVKRCKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- PRJWYFPDHWJLEV-UHFFFAOYSA-N 2-methyl-4-phenylbutan-2-amine Chemical compound CC(C)(N)CCC1=CC=CC=C1 PRJWYFPDHWJLEV-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- HPEVJTNZYIMANV-UHFFFAOYSA-N 2-methylbutyl 4-methylbenzenesulfonate Chemical compound CCC(C)COS(=O)(=O)C1=CC=C(C)C=C1 HPEVJTNZYIMANV-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- FWLOEZJLQRIKJQ-UHFFFAOYSA-N 2-propan-2-yloxyethyl 4-methylbenzenesulfonate Chemical compound CC(C)OCCOS(=O)(=O)C1=CC=C(C)C=C1 FWLOEZJLQRIKJQ-UHFFFAOYSA-N 0.000 description 1
- CUEIJYXBPFSYAT-UHFFFAOYSA-N 2-propoxyethyl 4-methylbenzenesulfonate Chemical compound CCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 CUEIJYXBPFSYAT-UHFFFAOYSA-N 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- YICXBQCYAZSIEC-UHFFFAOYSA-N 3-methoxy-4-methylbenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1C YICXBQCYAZSIEC-UHFFFAOYSA-N 0.000 description 1
- HWZUQAKHJDKBOE-UHFFFAOYSA-N 3-methoxypropyl 4-methylbenzenesulfonate Chemical compound COCCCOS(=O)(=O)C1=CC=C(C)C=C1 HWZUQAKHJDKBOE-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PCZZZZSXMTUGGG-UHFFFAOYSA-N 3-methylbutyl 4-methylbenzenesulfonate Chemical compound CC(C)CCOS(=O)(=O)C1=CC=C(C)C=C1 PCZZZZSXMTUGGG-UHFFFAOYSA-N 0.000 description 1
- NWCYECXHIYEBJE-UHFFFAOYSA-N 3-oxobutyl acetate Chemical compound CC(=O)CCOC(C)=O NWCYECXHIYEBJE-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- DRWOJIIXBYNGGW-UHFFFAOYSA-N 4-methoxybutan-2-one Chemical compound COCCC(C)=O DRWOJIIXBYNGGW-UHFFFAOYSA-N 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- QOYATPIJAQFSNR-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-(2-hydroxyethoxy)benzamide Chemical compound C1=C(OCCO)C(C(=O)N)=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 QOYATPIJAQFSNR-UHFFFAOYSA-N 0.000 description 1
- LWIQXMPGWMLXJJ-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-(2-phenoxyethoxy)benzamide Chemical compound NC(=O)C1=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=C1OCCOC1=CC=CC=C1 LWIQXMPGWMLXJJ-UHFFFAOYSA-N 0.000 description 1
- KWFPVZSJJFJLAZ-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-(3-hydroxypropoxy)benzamide Chemical compound C1=C(OCCCO)C(C(=O)N)=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 KWFPVZSJJFJLAZ-UHFFFAOYSA-N 0.000 description 1
- MDPVZPLRJWSXJE-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-[2-(2-ethoxyethoxy)ethoxy]benzamide Chemical compound C1=C(C(N)=O)C(OCCOCCOCC)=CC=C1C(=O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MDPVZPLRJWSXJE-UHFFFAOYSA-N 0.000 description 1
- UVJVWUJRSMVLGO-UHFFFAOYSA-N 5-[2-(dibenzylamino)acetyl]-2-pentoxybenzamide Chemical compound C1=C(C(N)=O)C(OCCCCC)=CC=C1C(=O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 UVJVWUJRSMVLGO-UHFFFAOYSA-N 0.000 description 1
- FGORLZYFXFSYAS-UHFFFAOYSA-N 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-hydroxybenzamide;hydrochloride Chemical compound Cl.CC(C)(C)NCC(O)C1=CC=C(O)C(C(O)=N)=C1 FGORLZYFXFSYAS-UHFFFAOYSA-N 0.000 description 1
- DGMYRPFYNFQCHM-UHFFFAOYSA-N 5-phenylpentan-2-one Chemical compound CC(=O)CCCC1=CC=CC=C1 DGMYRPFYNFQCHM-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- OIOMSWFYYOILFQ-UHFFFAOYSA-N Cl.COCCCC1=C(C(=O)N)C=CC=C1 Chemical compound Cl.COCCCC1=C(C(=O)N)C=CC=C1 OIOMSWFYYOILFQ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- 208000019693 Lung disease Diseases 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- NCQOUEUIEVCLCE-UHFFFAOYSA-N [2-acetyloxy-5-[2-[benzyl(tert-butyl)amino]acetyl]phenyl]methyl acetate Chemical compound C1=C(OC(C)=O)C(COC(=O)C)=CC(C(=O)CN(CC=2C=CC=CC=2)C(C)(C)C)=C1 NCQOUEUIEVCLCE-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VIBXPDOAJVVLJK-UHFFFAOYSA-N benzamide;dihydrate;hydrochloride Chemical compound O.O.Cl.NC(=O)C1=CC=CC=C1 VIBXPDOAJVVLJK-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 102000016967 beta-1 Adrenergic Receptors Human genes 0.000 description 1
- 108010014494 beta-1 Adrenergic Receptors Proteins 0.000 description 1
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 210000002318 cardia Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004199 lung function Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- TWEHMQBFPOUFTM-UHFFFAOYSA-N n-[4-(3-oxobutyl)phenyl]methanesulfonamide Chemical compound CC(=O)CCC1=CC=C(NS(C)(=O)=O)C=C1 TWEHMQBFPOUFTM-UHFFFAOYSA-N 0.000 description 1
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000007017 scission Effects 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
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2155373 | 1973-05-07 | ||
| GB2200473 | 1973-05-07 | ||
| GB2200473 | 1973-05-07 | ||
| GB2155373A GB1468673A (en) | 1973-05-07 | 1973-05-07 | Substituted benzamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141117B true DK141117B (da) | 1980-01-21 |
| DK141117C DK141117C (enrdf_load_stackoverflow) | 1980-07-07 |
Family
ID=26255396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK245574A DK141117B (da) | 1973-05-07 | 1974-05-06 | Analogifremgangsmåde til fremstilling af phenylethanolaminderivater eller syreadditionssalte deraf. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5069038A (enrdf_load_stackoverflow) |
| CH (2) | CH611267A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2421805A1 (enrdf_load_stackoverflow) |
| DK (1) | DK141117B (enrdf_load_stackoverflow) |
| FR (1) | FR2228487B1 (enrdf_load_stackoverflow) |
| IE (1) | IE39247B1 (enrdf_load_stackoverflow) |
| LU (1) | LU70005A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7406137A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163053A (en) * | 1977-12-27 | 1979-07-31 | Schering Corporation | Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides |
| CA1142954A (en) * | 1978-07-03 | 1983-03-15 | Jack Mills | Phenethanolamines, compositions containing the same, and method for effecting weight control |
-
1974
- 1974-05-02 IE IE93474A patent/IE39247B1/xx unknown
- 1974-05-06 DK DK245574A patent/DK141117B/da unknown
- 1974-05-06 DE DE19742421805 patent/DE2421805A1/de not_active Withdrawn
- 1974-05-06 FR FR7415549A patent/FR2228487B1/fr not_active Expired
- 1974-05-06 LU LU70005A patent/LU70005A1/xx unknown
- 1974-05-07 NL NL7406137A patent/NL7406137A/xx not_active Application Discontinuation
- 1974-05-07 JP JP5066174A patent/JPS5069038A/ja active Pending
- 1974-05-07 CH CH630574A patent/CH611267A5/xx not_active IP Right Cessation
- 1974-05-07 CH CH1524677A patent/CH611268A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU6867574A (en) | 1975-11-13 |
| CH611267A5 (en) | 1979-05-31 |
| IE39247L (en) | 1974-11-07 |
| FR2228487A1 (enrdf_load_stackoverflow) | 1974-12-06 |
| CH611268A5 (en) | 1979-05-31 |
| DE2421805A1 (de) | 1974-11-28 |
| DK141117C (enrdf_load_stackoverflow) | 1980-07-07 |
| NL7406137A (enrdf_load_stackoverflow) | 1974-11-11 |
| LU70005A1 (enrdf_load_stackoverflow) | 1975-08-20 |
| JPS5069038A (enrdf_load_stackoverflow) | 1975-06-09 |
| IE39247B1 (en) | 1978-08-30 |
| FR2228487B1 (enrdf_load_stackoverflow) | 1977-07-01 |
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