DD300542A5 - Chemische verbindungen - Google Patents
Chemische verbindungen Download PDFInfo
- Publication number
- DD300542A5 DD300542A5 DD340389A DD34038990A DD300542A5 DD 300542 A5 DD300542 A5 DD 300542A5 DD 340389 A DD340389 A DD 340389A DD 34038990 A DD34038990 A DD 34038990A DD 300542 A5 DD300542 A5 DD 300542A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- formula
- hydroxy
- ethoxy
- phenoxypropylamino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 134
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 238000001727 in vivo Methods 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- -1 2- (2-hydroxy-3-phenoxypropylamino) ethoxy Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- PAZMQVNUXLLYGP-UHFFFAOYSA-N 1-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]butan-2-one Chemical compound C1=CC(CC(=O)CC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 PAZMQVNUXLLYGP-UHFFFAOYSA-N 0.000 claims description 2
- QQZWMYLQJIARKI-UHFFFAOYSA-N 1-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]nonan-2-one Chemical compound C1=CC(CC(=O)CCCCCCC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 QQZWMYLQJIARKI-UHFFFAOYSA-N 0.000 claims description 2
- RPHUDXMFTGVLHF-UHFFFAOYSA-N 1-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OCCNCC(O)COC1=CC=CC=C1 RPHUDXMFTGVLHF-UHFFFAOYSA-N 0.000 claims description 2
- JQVZXNGTVYGJAX-INIZCTEOSA-N 2-[4-[2-[[(2s)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenyl]acetic acid Chemical compound C([C@H](O)COC=1C=CC=CC=1)NCCOC1=CC=C(CC(O)=O)C=C1 JQVZXNGTVYGJAX-INIZCTEOSA-N 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 2
- VLVMTDAKXAWJJT-UHFFFAOYSA-N 1-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]heptan-2-one Chemical compound C1=CC(CC(=O)CCCCC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 VLVMTDAKXAWJJT-UHFFFAOYSA-N 0.000 claims 1
- RUPYQQOTMFBRLQ-UHFFFAOYSA-N 1-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]octan-2-one Chemical compound C1=CC(CC(=O)CCCCCC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 RUPYQQOTMFBRLQ-UHFFFAOYSA-N 0.000 claims 1
- RPHUDXMFTGVLHF-SFHVURJKSA-N 1-[4-[2-[[(2s)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OCCNC[C@H](O)COC1=CC=CC=C1 RPHUDXMFTGVLHF-SFHVURJKSA-N 0.000 claims 1
- JQVZXNGTVYGJAX-UHFFFAOYSA-N 2-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenyl]acetic acid Chemical compound C=1C=CC=CC=1OCC(O)CNCCOC1=CC=C(CC(O)=O)C=C1 JQVZXNGTVYGJAX-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 11
- 208000008589 Obesity Diseases 0.000 abstract description 8
- 235000020824 obesity Nutrition 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000004452 microanalysis Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000000476 thermogenic effect Effects 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 210000003486 adipose tissue brown Anatomy 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002024 ethyl acetate extract Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- JLRRSNMDGHJYTD-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pentan-2-one Chemical class CCCC(=O)CC1=CC=C(O)C=C1 JLRRSNMDGHJYTD-UHFFFAOYSA-N 0.000 description 4
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 4
- 102000015779 HDL Lipoproteins Human genes 0.000 description 4
- 108010010234 HDL Lipoproteins Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 229960001317 isoprenaline Drugs 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- AJDBFQIAUFCBRO-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-methylbutan-2-one Chemical class CC(C)C(=O)CC1=CC=C(O)C=C1 AJDBFQIAUFCBRO-UHFFFAOYSA-N 0.000 description 3
- PARHMNZPOUVEIQ-UHFFFAOYSA-N 1-(4-hydroxyphenyl)butan-2-one Chemical compound CCC(=O)CC1=CC=C(O)C=C1 PARHMNZPOUVEIQ-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 230000035924 thermogenesis Effects 0.000 description 3
- FGGFJGCTPLMHDU-VIFPVBQESA-N (5s)-5-(phenoxymethyl)-1,3-oxazolidin-2-one Chemical compound O1C(=O)NC[C@H]1COC1=CC=CC=C1 FGGFJGCTPLMHDU-VIFPVBQESA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VWYROVQSKFYRSG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-4-methylpentan-2-one Chemical class CC(C)CC(=O)CC1=CC=C(O)C=C1 VWYROVQSKFYRSG-UHFFFAOYSA-N 0.000 description 2
- NYNJRYFHRRAPNH-UHFFFAOYSA-N 1-(4-hydroxyphenyl)heptan-2-one Chemical class CCCCCC(=O)CC1=CC=C(O)C=C1 NYNJRYFHRRAPNH-UHFFFAOYSA-N 0.000 description 2
- PCHHLTVOULTBMO-UHFFFAOYSA-N 1-(4-hydroxyphenyl)hexan-2-one Chemical class CCCCC(=O)CC1=CC=C(O)C=C1 PCHHLTVOULTBMO-UHFFFAOYSA-N 0.000 description 2
- UTONSWLECICCPR-UHFFFAOYSA-N 1-(4-hydroxyphenyl)nonan-2-one Chemical class CCCCCCCC(=O)CC1=CC=C(O)C=C1 UTONSWLECICCPR-UHFFFAOYSA-N 0.000 description 2
- KPGZXYRRKXSCQK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-methylbutan-2-one Chemical compound COC1=CC=C(CC(=O)C(C)C)C=C1 KPGZXYRRKXSCQK-UHFFFAOYSA-N 0.000 description 2
- GCSQSSSVLZYNCC-UHFFFAOYSA-N 1-[2-[4-[(2-ethyl-1,3-dioxolan-2-yl)methyl]phenoxy]ethylamino]-3-phenoxypropan-2-ol Chemical compound C=1C=C(OCCNCC(O)COC=2C=CC=CC=2)C=CC=1CC1(CC)OCCO1 GCSQSSSVLZYNCC-UHFFFAOYSA-N 0.000 description 2
- AAWHWDIATRBIQY-FQEVSTJZSA-N 1-[4-[2-[[(2s)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenyl]pentan-2-one Chemical compound C1=CC(CC(=O)CCC)=CC=C1OCCNC[C@H](O)COC1=CC=CC=C1 AAWHWDIATRBIQY-FQEVSTJZSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- GXWROUVNWKTVCU-UHFFFAOYSA-N 3-[2-[4-(2-oxobutyl)phenoxy]ethyl]-5-(phenoxymethyl)-1,3-oxazolidin-2-one Chemical compound C1=CC(CC(=O)CC)=CC=C1OCCN1C(=O)OC(COC=2C=CC=CC=2)C1 GXWROUVNWKTVCU-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- QCCDLTOVEPVEJK-UHFFFAOYSA-N benzyl methyl ketone Natural products CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000003085 diluting agent 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
- 238000010828 elution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000037323 metabolic rate Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 210000003470 mitochondria Anatomy 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
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- 150000003140 primary amides Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 230000000892 thymomimetic effect Effects 0.000 description 1
- 230000008280 toxic mechanism Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (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)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898910374A GB8910374D0 (en) | 1989-05-05 | 1989-05-05 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD300542A5 true DD300542A5 (de) | 1992-06-17 |
Family
ID=10656286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD340389A DD300542A5 (de) | 1989-05-05 | 1990-05-04 | Chemische verbindungen |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0426804B1 (hu) |
| JP (1) | JPH03506037A (hu) |
| KR (1) | KR920701123A (hu) |
| CN (1) | CN1047857A (hu) |
| AT (1) | ATE100439T1 (hu) |
| AU (1) | AU622027B2 (hu) |
| BG (1) | BG93509A (hu) |
| CA (1) | CA2015705A1 (hu) |
| DD (1) | DD300542A5 (hu) |
| DE (1) | DE69006178T2 (hu) |
| DK (1) | DK0426804T3 (hu) |
| ES (1) | ES2062526T3 (hu) |
| FI (1) | FI910059A7 (hu) |
| GB (2) | GB8910374D0 (hu) |
| GR (1) | GR1001610B (hu) |
| HU (1) | HUT58277A (hu) |
| IE (1) | IE63533B1 (hu) |
| MW (1) | MW4190A1 (hu) |
| NO (1) | NO910033L (hu) |
| NZ (1) | NZ233425A (hu) |
| PL (1) | PL285062A1 (hu) |
| PT (1) | PT93954A (hu) |
| WO (1) | WO1990013535A1 (hu) |
| ZA (1) | ZA903111B (hu) |
| ZW (1) | ZW6790A1 (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9111426D0 (en) * | 1991-05-28 | 1991-07-17 | Ici Plc | Chemical compounds |
| US5502078A (en) * | 1991-05-28 | 1996-03-26 | Zeneca Limited | Chemical compounds |
| GB9111425D0 (en) * | 1991-05-28 | 1991-07-17 | Ici Plc | Chemical compounds |
| NO179246C (no) * | 1991-11-20 | 1996-09-04 | Sankyo Co | Aromatiske amino-alkoholderivater og mellomprodukter til fremstilling derav |
| GB9207964D0 (en) * | 1992-04-10 | 1992-05-27 | Ici Plc | Chemical compounds |
| US5563171A (en) * | 1993-11-05 | 1996-10-08 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3-adrenergic agonists |
| US5578638A (en) * | 1993-11-05 | 1996-11-26 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3 -adrenergic agonists |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US463323A (en) * | 1891-11-17 | Temporary binder | ||
| GB1245148A (en) * | 1968-11-18 | 1971-09-08 | Pfizer Ltd | Propanolamine derivatives |
| US4263323A (en) * | 1976-10-07 | 1981-04-21 | Aktiebolaget Hassle | β-Receptor blocking compounds and treatment of cardiovascular disorders therewith |
| DE3271132D1 (en) * | 1981-07-11 | 1986-06-19 | Beecham Group Plc | Secondary phenylethanol amines, processes for their preparation and their pharmaceutical application |
| GB8519154D0 (en) * | 1985-07-30 | 1985-09-04 | Ici Plc | Aromatic ethers |
-
1989
- 1989-05-05 GB GB898910374A patent/GB8910374D0/en active Pending
-
1990
- 1990-04-20 GB GB909008867A patent/GB9008867D0/en active Pending
- 1990-04-23 IE IE143890A patent/IE63533B1/en not_active IP Right Cessation
- 1990-04-24 NZ NZ233425A patent/NZ233425A/en unknown
- 1990-04-24 ZA ZA903111A patent/ZA903111B/xx unknown
- 1990-04-26 MW MW41/90A patent/MW4190A1/xx unknown
- 1990-04-30 WO PCT/GB1990/000668 patent/WO1990013535A1/en not_active Ceased
- 1990-04-30 CA CA002015705A patent/CA2015705A1/en not_active Abandoned
- 1990-04-30 DK DK90907243.1T patent/DK0426804T3/da active
- 1990-04-30 HU HU903384A patent/HUT58277A/hu unknown
- 1990-04-30 ZW ZW67/90A patent/ZW6790A1/xx unknown
- 1990-04-30 AT AT90907243T patent/ATE100439T1/de not_active IP Right Cessation
- 1990-04-30 ES ES90907243T patent/ES2062526T3/es not_active Expired - Lifetime
- 1990-04-30 AU AU55403/90A patent/AU622027B2/en not_active Ceased
- 1990-04-30 FI FI910059A patent/FI910059A7/fi not_active Application Discontinuation
- 1990-04-30 KR KR1019910700017A patent/KR920701123A/ko not_active Withdrawn
- 1990-04-30 EP EP90907243A patent/EP0426804B1/en not_active Expired - Lifetime
- 1990-04-30 JP JP2506670A patent/JPH03506037A/ja active Pending
- 1990-04-30 DE DE90907243T patent/DE69006178T2/de not_active Expired - Fee Related
- 1990-05-04 DD DD340389A patent/DD300542A5/de unknown
- 1990-05-04 PT PT93954A patent/PT93954A/pt not_active Application Discontinuation
- 1990-05-04 PL PL28506290A patent/PL285062A1/xx unknown
- 1990-05-04 GR GR900100332A patent/GR1001610B/el unknown
- 1990-05-05 CN CN90102708A patent/CN1047857A/zh active Pending
- 1990-12-21 BG BG093509A patent/BG93509A/bg unknown
-
1991
- 1991-01-04 NO NO91910033A patent/NO910033L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI910059A0 (fi) | 1991-01-04 |
| GR1001610B (el) | 1994-07-29 |
| DK0426804T3 (da) | 1994-05-30 |
| IE901438L (en) | 1990-11-05 |
| ATE100439T1 (de) | 1994-02-15 |
| AU5540390A (en) | 1990-11-29 |
| WO1990013535A1 (en) | 1990-11-15 |
| FI910059A7 (fi) | 1991-01-04 |
| ZA903111B (en) | 1991-12-24 |
| MW4190A1 (en) | 1991-03-13 |
| NO910033D0 (no) | 1991-01-04 |
| DE69006178T2 (de) | 1994-05-05 |
| NZ233425A (en) | 1992-07-28 |
| AU622027B2 (en) | 1992-03-26 |
| HU903384D0 (en) | 1991-05-28 |
| CA2015705A1 (en) | 1990-11-05 |
| ZW6790A1 (en) | 1991-02-27 |
| DE69006178D1 (de) | 1994-03-03 |
| JPH03506037A (ja) | 1991-12-26 |
| PL285062A1 (en) | 1992-01-13 |
| ES2062526T3 (es) | 1994-12-16 |
| IE63533B1 (en) | 1995-05-03 |
| EP0426804B1 (en) | 1994-01-19 |
| GB8910374D0 (en) | 1989-06-21 |
| KR920701123A (ko) | 1992-08-11 |
| GR900100332A (en) | 1991-10-10 |
| CN1047857A (zh) | 1990-12-19 |
| PT93954A (pt) | 1991-01-08 |
| GB9008867D0 (en) | 1990-06-20 |
| EP0426804A1 (en) | 1991-05-15 |
| NO910033L (no) | 1991-03-04 |
| HUT58277A (en) | 1992-02-28 |
| BG93509A (bg) | 1993-12-24 |
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