NO760054L - - Google Patents
Info
- Publication number
- NO760054L NO760054L NO760054A NO760054A NO760054L NO 760054 L NO760054 L NO 760054L NO 760054 A NO760054 A NO 760054A NO 760054 A NO760054 A NO 760054A NO 760054 L NO760054 L NO 760054L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- biphenyl
- methoxy
- propionic acid
- ethyl
- Prior art date
Links
- -1 biphenyloxy Chemical class 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000012954 diazonium Substances 0.000 claims description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 235000013312 flour Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000005904 alkaline hydrolysis reaction Methods 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 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- UPTARWRVITZABZ-UHFFFAOYSA-N 4-[4-(2-aminoethyl)phenyl]phenol Chemical group C1=CC(CCN)=CC=C1C1=CC=C(O)C=C1 UPTARWRVITZABZ-UHFFFAOYSA-N 0.000 description 6
- 238000005661 deetherification reaction Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- HKWQCCDPHAMDBW-UHFFFAOYSA-N 5-chloro-n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2-methoxybenzamide Chemical group COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 HKWQCCDPHAMDBW-UHFFFAOYSA-N 0.000 description 5
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 3
- JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OPHSRZJQIZXQKC-UHFFFAOYSA-N 4-[4-(3-aminopropyl)phenyl]phenol Chemical group C1=CC(CCCN)=CC=C1C1=CC=C(O)C=C1 OPHSRZJQIZXQKC-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
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WGIIOGRUHSJKMI-UHFFFAOYSA-N ethyl 2-methyl-2-phenoxypropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC=C1 WGIIOGRUHSJKMI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- MKYZAVWWTBRCTE-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2,4-dimethoxybenzamide Chemical group COC1=CC(OC)=CC=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 MKYZAVWWTBRCTE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- ZNPWFAWDQBGQFW-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(4-methoxyphenyl)benzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(CCCl)C=C1 ZNPWFAWDQBGQFW-UHFFFAOYSA-N 0.000 description 1
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical group COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 1
- GNBRZRRANUHHGT-UHFFFAOYSA-N 1-phenylcyclohexa-2,4-dien-1-ol Chemical group C=1C=CC=CC=1C1(O)CC=CC=C1 GNBRZRRANUHHGT-UHFFFAOYSA-N 0.000 description 1
- KVIUXRJCBBXEGJ-UHFFFAOYSA-N 2,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1 KVIUXRJCBBXEGJ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- SUSAZDLJYMQAEJ-UHFFFAOYSA-N 2-[4-(4-hydroxyphenyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=C(O)C=C1 SUSAZDLJYMQAEJ-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- WDBAWEYZZRFJPP-UHFFFAOYSA-N 2-[4-[4-(2-benzamidoethyl)phenyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=CC=C1 WDBAWEYZZRFJPP-UHFFFAOYSA-N 0.000 description 1
- LTDMWFQGGFGTJW-UHFFFAOYSA-N 2-[4-[4-[2-[(2-methoxybenzoyl)amino]ethyl]phenyl]phenoxy]-2-methylpropanoic acid Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(C=2C=CC(OC(C)(C)C(O)=O)=CC=2)C=C1 LTDMWFQGGFGTJW-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 1
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 1
- TVFYBZHKKIJXRG-UHFFFAOYSA-N 3-[4-(4-methoxyphenyl)phenyl]propan-1-amine Chemical group C1=CC(OC)=CC=C1C1=CC=C(CCCN)C=C1 TVFYBZHKKIJXRG-UHFFFAOYSA-N 0.000 description 1
- WLUHPIINCCXDJY-UHFFFAOYSA-N 3-[4-(4-methoxyphenyl)phenyl]propan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=C(CCCN)C=C1 WLUHPIINCCXDJY-UHFFFAOYSA-N 0.000 description 1
- QPSRZNBTERPGCN-UHFFFAOYSA-N 3-[4-(4-methoxyphenyl)phenyl]propanenitrile Chemical group C1=CC(OC)=CC=C1C1=CC=C(CCC#N)C=C1 QPSRZNBTERPGCN-UHFFFAOYSA-N 0.000 description 1
- DWEALSNXOHBFBK-UHFFFAOYSA-N 3-chloro-n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]benzamide Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=CC(Cl)=C1 DWEALSNXOHBFBK-UHFFFAOYSA-N 0.000 description 1
- QTEULXFWUJXYPF-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)phenol Chemical group CC1=CC(N)=CC=C1C1=CC=C(O)C=C1 QTEULXFWUJXYPF-UHFFFAOYSA-N 0.000 description 1
- QVCDBOQTJPSXRP-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]phenol Chemical group C1=CC(CN)=CC=C1C1=CC=C(O)C=C1 QVCDBOQTJPSXRP-UHFFFAOYSA-N 0.000 description 1
- HHYRZUNYTGIDRI-UHFFFAOYSA-N 4-bromo-n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]benzamide Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=C(Br)C=C1 HHYRZUNYTGIDRI-UHFFFAOYSA-N 0.000 description 1
- NMCMDPRNCWZHBW-UHFFFAOYSA-N 4-chloro-n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]benzamide Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 NMCMDPRNCWZHBW-UHFFFAOYSA-N 0.000 description 1
- QQXVZGWCVOCPDR-UHFFFAOYSA-N 4-ethylisoindole-1,3-dione Chemical compound CCC1=CC=CC2=C1C(=O)NC2=O QQXVZGWCVOCPDR-UHFFFAOYSA-N 0.000 description 1
- KLXMCHGJMOJZPI-UHFFFAOYSA-N 4-fluoro-n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]benzamide Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=C(F)C=C1 KLXMCHGJMOJZPI-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- XZCPHKOHGCYKFP-UHFFFAOYSA-N 5-chloro-n-[2-[4-[4-(1-hydroxy-2-methylpropan-2-yl)oxyphenyl]phenyl]ethyl]-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C=2C=CC(OC(C)(C)CO)=CC=2)C=C1 XZCPHKOHGCYKFP-UHFFFAOYSA-N 0.000 description 1
- ATPRUYUZRSHDBE-UHFFFAOYSA-N 5-chloro-n-[3-[4-(4-hydroxyphenyl)phenyl]propyl]-2-methoxybenzamide Chemical group COC1=CC=C(Cl)C=C1C(=O)NCCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 ATPRUYUZRSHDBE-UHFFFAOYSA-N 0.000 description 1
- KLFXTDPWWDUYFP-UHFFFAOYSA-N 5-chloro-n-[[4-(4-hydroxyphenyl)phenyl]methyl]-2-methoxybenzamide Chemical group COC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 KLFXTDPWWDUYFP-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001201614 Prays Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FCGNMLIQOMBQTQ-UHFFFAOYSA-N cyclohexyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OC1CCCCC1 FCGNMLIQOMBQTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- NROWRXJHDZHLPF-UHFFFAOYSA-N ethyl 2-[4-[4-(2-acetamidoethyl)phenyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C1=CC=C(CCNC(C)=O)C=C1 NROWRXJHDZHLPF-UHFFFAOYSA-N 0.000 description 1
- XHENYRFBPOJRKW-UHFFFAOYSA-N ethyl 2-[4-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC XHENYRFBPOJRKW-UHFFFAOYSA-N 0.000 description 1
- IGBUZMBHLXBNLR-UHFFFAOYSA-N ethyl 2-methyl-2-[4-[4-[2-[(4-methylbenzoyl)amino]ethyl]phenyl]phenoxy]propanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=C(C)C=C1 IGBUZMBHLXBNLR-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CLJAWWBXVXWHFD-UHFFFAOYSA-N methyl 2-[4-(4-chlorophenyl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC)=CC=C1C1=CC=C(Cl)C=C1 CLJAWWBXVXWHFD-UHFFFAOYSA-N 0.000 description 1
- PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- ADNAPSAPLXEECH-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)-2-[4-(4-hydroxyphenyl)phenyl]acetamide Chemical group COC1=CC=C(Cl)C=C1NC(=O)CC1=CC=C(C=2C=CC(O)=CC=2)C=C1 ADNAPSAPLXEECH-UHFFFAOYSA-N 0.000 description 1
- KCZOHSCPMWSZEC-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(N)C=C1 KCZOHSCPMWSZEC-UHFFFAOYSA-N 0.000 description 1
- IESGYPDWRWZPEH-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(N)C=C1 IESGYPDWRWZPEH-UHFFFAOYSA-N 0.000 description 1
- ABWLZCWWRKIKNQ-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2,6-dimethoxybenzamide Chemical group COC1=CC=CC(OC)=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 ABWLZCWWRKIKNQ-UHFFFAOYSA-N 0.000 description 1
- PIPRDOCPXFVYKC-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2-methoxybenzamide Chemical group COC1=CC=CC=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 PIPRDOCPXFVYKC-UHFFFAOYSA-N 0.000 description 1
- YKXMXFXDKAKGDU-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2-methylbenzamide Chemical group CC1=CC=CC=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 YKXMXFXDKAKGDU-UHFFFAOYSA-N 0.000 description 1
- KOWQCHNCLOUKTE-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-2-phenylacetamide Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1CCNC(=O)CC1=CC=CC=C1 KOWQCHNCLOUKTE-UHFFFAOYSA-N 0.000 description 1
- YFNBRUHUMCKDNA-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-3,5-dimethoxybenzamide Chemical group COC1=CC(OC)=CC(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 YFNBRUHUMCKDNA-UHFFFAOYSA-N 0.000 description 1
- FWZWFHJZZGOHKK-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]-4-methylbenzamide Chemical group C1=CC(C)=CC=C1C(=O)NCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 FWZWFHJZZGOHKK-UHFFFAOYSA-N 0.000 description 1
- PEAWYDSXWVGXLQ-UHFFFAOYSA-N n-[2-[4-(4-hydroxyphenyl)phenyl]ethyl]acetamide Chemical group C1=CC(CCNC(=O)C)=CC=C1C1=CC=C(O)C=C1 PEAWYDSXWVGXLQ-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500692 DE2500692C3 (de) | 1975-01-09 | Derivate des 4-Amidoalkylen-4'oxy diphenyle | |
| DE19752547872 DE2547872A1 (de) | 1975-10-25 | 1975-10-25 | Verfahren zur herstellung von biphenyloxy-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO760054L true NO760054L (uk) | 1976-07-12 |
Family
ID=25768333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO760054A NO760054L (uk) | 1975-01-09 | 1976-01-08 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4010279A (uk) |
| JP (1) | JPS5195047A (uk) |
| AT (1) | AT341512B (uk) |
| CA (1) | CA1061347A (uk) |
| CS (1) | CS188263B2 (uk) |
| DD (1) | DD125199A5 (uk) |
| DK (1) | DK5976A (uk) |
| ES (1) | ES443415A1 (uk) |
| FI (1) | FI753702A (uk) |
| FR (1) | FR2297037A1 (uk) |
| GB (1) | GB1501541A (uk) |
| GR (1) | GR59482B (uk) |
| HU (1) | HU172100B (uk) |
| IL (1) | IL48806A (uk) |
| LU (1) | LU74139A1 (uk) |
| NL (1) | NL7600144A (uk) |
| NO (1) | NO760054L (uk) |
| PH (1) | PH13633A (uk) |
| PL (1) | PL101301B1 (uk) |
| PT (1) | PT64680B (uk) |
| RO (1) | RO70525A (uk) |
| SE (1) | SE7600139L (uk) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517229A1 (de) * | 1975-04-18 | 1976-10-28 | Boehringer Mannheim Gmbh | Phenylalkylcarbonsaeure-derivate und verfahren zu ihrer herstellung |
| DE2541342A1 (de) * | 1975-09-17 | 1977-03-31 | Boehringer Mannheim Gmbh | Neue phenoxyalkylcarbonsaeuren und verfahren zur herstellung derselben |
| DE2546996C2 (de) * | 1975-10-21 | 1984-07-05 | Boehringer Mannheim Gmbh, 6800 Mannheim | Phenoxyalkylcarbonsäure-Derivate, Verfahren zur Herstellung derselben sowie Arzneimittel, die diese Verbindungen als Wirkstoff enthalten |
| US4214094A (en) * | 1977-03-30 | 1980-07-22 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-phenyl substituted-alkyl ethers and the preparation thereof |
| US6617351B1 (en) | 1998-07-31 | 2003-09-09 | Eli Lilly And Company | Amide, carbamate, and urea derivatives |
| PE20000942A1 (es) * | 1998-07-31 | 2000-09-28 | Lilly Co Eli | Derivados de amida, carbamato y urea |
| US7122580B2 (en) | 2002-08-09 | 2006-10-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| WO2005014532A1 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| US7208601B2 (en) | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| WO2005014533A2 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| KR101328273B1 (ko) | 2004-12-28 | 2013-11-14 | 키넥스 파마슈티컬즈, 엘엘씨 | 세포 증식 질환의 치료를 위한 조성물 및 방법 |
| US7968574B2 (en) | 2004-12-28 | 2011-06-28 | Kinex Pharmaceuticals, Llc | Biaryl compositions and methods for modulating a kinase cascade |
| EP2041071B1 (en) * | 2006-06-29 | 2014-06-18 | Kinex Pharmaceuticals, LLC | Biaryl compositions and methods for modulating a kinase cascade |
| US7939529B2 (en) * | 2007-05-17 | 2011-05-10 | Kinex Pharmaceuticals, Llc | Process for the preparation of compositions for modulating a kinase cascade and methods of use thereof |
| US7935697B2 (en) * | 2006-12-28 | 2011-05-03 | Kinex Pharmaceuticals, Llc | Compositions for modulating a kinase cascade and methods of use thereof |
| WO2009009041A2 (en) * | 2007-07-06 | 2009-01-15 | Kinex Pharmaceuticals, Llc | Compositions and methods for modulating a kinase cascade |
| CA2703615C (en) * | 2007-10-20 | 2017-09-19 | Kinex Pharmaceuticals, Llc | Pharmaceutical compositions for modulating a kinase cascade and methods of use thereof |
| US8748423B2 (en) | 2010-04-16 | 2014-06-10 | Kinex Pharmaceuticals, Llc | Compositions and methods for the prevention and treatment of cancer |
| KR102346033B1 (ko) | 2012-08-30 | 2021-12-30 | 아테넥스, 인크. | 단백질 타이로신 키나아제 조절인자로서의 ｎ-(3-플루오로벤질)-2-(5-(4-모르폴리노페닐)피리딘-2-일)아세트아미드 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH543472A (fr) * | 1969-01-31 | 1973-10-31 | Orchimed Sa | Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques |
| DE2230383C3 (de) * | 1971-10-01 | 1981-12-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Phenoxyalkylcarbonsäurederivate und Verfahren zur Herstellung derselben |
-
1975
- 1975-11-21 AT AT886775A patent/AT341512B/de not_active IP Right Cessation
- 1975-12-11 ES ES443415A patent/ES443415A1/es not_active Expired
- 1975-12-12 DD DD190114A patent/DD125199A5/xx unknown
- 1975-12-23 US US05/643,700 patent/US4010279A/en not_active Expired - Lifetime
- 1975-12-30 FI FI753702A patent/FI753702A/fi not_active Application Discontinuation
-
1976
- 1976-01-03 GR GR49714A patent/GR59482B/el unknown
- 1976-01-06 CS CS7673A patent/CS188263B2/cs unknown
- 1976-01-07 PH PH17944A patent/PH13633A/en unknown
- 1976-01-07 LU LU74139A patent/LU74139A1/xx unknown
- 1976-01-07 HU HU76TO00001019A patent/HU172100B/hu unknown
- 1976-01-08 JP JP51001822A patent/JPS5195047A/ja active Pending
- 1976-01-08 NO NO760054A patent/NO760054L/no unknown
- 1976-01-08 CA CA243,207A patent/CA1061347A/en not_active Expired
- 1976-01-08 PT PT64680A patent/PT64680B/pt unknown
- 1976-01-08 DK DK5976*#A patent/DK5976A/da not_active Application Discontinuation
- 1976-01-08 IL IL48806A patent/IL48806A/xx unknown
- 1976-01-08 RO RO7684441A patent/RO70525A/ro unknown
- 1976-01-08 NL NL7600144A patent/NL7600144A/xx not_active Application Discontinuation
- 1976-01-08 SE SE7600139A patent/SE7600139L/xx unknown
- 1976-01-08 PL PL1976186408A patent/PL101301B1/pl unknown
- 1976-01-08 GB GB669/76A patent/GB1501541A/en not_active Expired
- 1976-01-09 FR FR7600483A patent/FR2297037A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1501541A (en) | 1978-02-15 |
| AT341512B (de) | 1978-02-10 |
| AU1011476A (en) | 1977-07-14 |
| PT64680B (fr) | 1978-01-04 |
| LU74139A1 (uk) | 1977-03-18 |
| HU172100B (hu) | 1978-05-28 |
| DK5976A (da) | 1976-07-10 |
| DD125199A5 (uk) | 1977-04-06 |
| NL7600144A (nl) | 1976-07-13 |
| RO70525A (ro) | 1981-09-24 |
| US4010279A (en) | 1977-03-01 |
| ATA886775A (de) | 1977-06-15 |
| IL48806A (en) | 1978-10-31 |
| SE7600139L (sv) | 1976-07-12 |
| JPS5195047A (uk) | 1976-08-20 |
| FR2297037B1 (uk) | 1979-09-21 |
| ES443415A1 (es) | 1977-04-16 |
| PL101301B1 (pl) | 1978-12-30 |
| FI753702A (uk) | 1976-07-10 |
| FR2297037A1 (fr) | 1976-08-06 |
| CS188263B2 (en) | 1979-02-28 |
| IL48806A0 (en) | 1976-03-31 |
| CA1061347A (en) | 1979-08-28 |
| PH13633A (en) | 1980-08-14 |
| PT64680A (fr) | 1976-05-01 |
| GR59482B (en) | 1978-01-30 |
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