CS266593B2 - Method of 2-(2-hydroxy-3-phenosypropylamine) ethoxyphenolh's derivativesprodduction - Google Patents
Method of 2-(2-hydroxy-3-phenosypropylamine) ethoxyphenolh's derivativesprodduction Download PDFInfo
- Publication number
- CS266593B2 CS266593B2 CS865735A CS573586A CS266593B2 CS 266593 B2 CS266593 B2 CS 266593B2 CS 865735 A CS865735 A CS 865735A CS 573586 A CS573586 A CS 573586A CS 266593 B2 CS266593 B2 CS 266593B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- group
- hydroxy
- amino
- pharmaceutically acceptable
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- -1 phenoxyacetic acid ethers Chemical class 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxy-acetic acid Natural products OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 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 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 102100038239 Protein Churchill Human genes 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- SREGRRJATITKGT-UHFFFAOYSA-N 2-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenol Chemical class C=1C=CC=CC=1OCC(O)CNCCOC1=CC=CC=C1O SREGRRJATITKGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 abstract description 8
- 235000020824 obesity Nutrition 0.000 abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 150000002170 ethers Chemical class 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000011343 solid material Substances 0.000 description 11
- 238000004452 microanalysis Methods 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 230000000476 thermogenic effect Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- DVPLHEDOLZCKHJ-UHFFFAOYSA-N 2-phenoxyacetic acid;hydrochloride Chemical compound Cl.OC(=O)COC1=CC=CC=C1 DVPLHEDOLZCKHJ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229960001317 isoprenaline Drugs 0.000 description 4
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZBUOFYWAPOFSQS-UHFFFAOYSA-N 4-[2-(benzylamino)ethoxy]phenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1OCCNCC1=CC=CC=C1 ZBUOFYWAPOFSQS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000035924 thermogenesis Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QEIPKCFBHGRHFL-UHFFFAOYSA-N 3-(2-bromoethoxy)phenol Chemical compound OC1=CC=CC(OCCBr)=C1 QEIPKCFBHGRHFL-UHFFFAOYSA-N 0.000 description 2
- QRIQOOIPQYJNNA-UHFFFAOYSA-N 3-[2-(benzylamino)ethoxy]phenol;hydrochloride Chemical compound Cl.OC1=CC=CC(OCCNCC=2C=CC=CC=2)=C1 QRIQOOIPQYJNNA-UHFFFAOYSA-N 0.000 description 2
- JADOYZZQMNOBML-UHFFFAOYSA-N 4-[2-(benzylamino)ethoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCNCC1=CC=CC=C1 JADOYZZQMNOBML-UHFFFAOYSA-N 0.000 description 2
- SYNLIGYCDMFOQE-UHFFFAOYSA-N 4-[2-[benzyl-(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenol Chemical compound C=1C=C(O)C=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC1=CC=CC=C1 SYNLIGYCDMFOQE-UHFFFAOYSA-N 0.000 description 2
- BYTGPDJRALBAPX-UHFFFAOYSA-N 4-[2-[benzyl-[3-(2-fluorophenoxy)-2-hydroxypropyl]amino]ethoxy]phenol Chemical compound C=1C=C(O)C=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC1=CC=CC=C1F BYTGPDJRALBAPX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001404 mediated effect 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
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- XVNKNFCMXHXIPO-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid;hydrate Chemical compound O.C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 XVNKNFCMXHXIPO-UHFFFAOYSA-N 0.000 description 1
- ZGBJAUZQXAADQJ-UHFFFAOYSA-N 2-[(2-fluorophenoxy)methyl]oxirane Chemical compound FC1=CC=CC=C1OCC1OC1 ZGBJAUZQXAADQJ-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- PDROUWAJYLGJRS-UHFFFAOYSA-N 2-phenoxyacetamide;hydrochloride Chemical compound Cl.NC(=O)COC1=CC=CC=C1 PDROUWAJYLGJRS-UHFFFAOYSA-N 0.000 description 1
- JSYLBTJBEBAHKT-UHFFFAOYSA-N 3-[2-[benzyl-(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenol Chemical compound C=1C=CC(O)=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC1=CC=CC=C1 JSYLBTJBEBAHKT-UHFFFAOYSA-N 0.000 description 1
- QSDOKFGRSJQNMX-UHFFFAOYSA-N 4-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=C(O)C=C1 QSDOKFGRSJQNMX-UHFFFAOYSA-N 0.000 description 1
- ARULEAIJJGDJPB-UHFFFAOYSA-N 4-(2-aminoethoxy)phenol;hydrochloride Chemical compound Cl.NCCOC1=CC=C(O)C=C1 ARULEAIJJGDJPB-UHFFFAOYSA-N 0.000 description 1
- YKHKGUAWZWOFDH-UHFFFAOYSA-N 4-(2-bromoethoxy)phenol Chemical compound OC1=CC=C(OCCBr)C=C1 YKHKGUAWZWOFDH-UHFFFAOYSA-N 0.000 description 1
- YZLRERGTVPWECP-UHFFFAOYSA-N 4-[2-(benzylamino)ethyl]phenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1CCNCC1=CC=CC=C1 YZLRERGTVPWECP-UHFFFAOYSA-N 0.000 description 1
- LAYZACJCZJBWNB-UHFFFAOYSA-N 4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenol;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OCC(O)CNCCOC1=CC=C(O)C=C1 LAYZACJCZJBWNB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 102220608146 TYRO protein tyrosine kinase-binding protein_D50Q_mutation Human genes 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000001085 differential centrifugation Methods 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 230000008280 toxic mechanism Effects 0.000 description 1
- 239000003981 vehicle Substances 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
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
-
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858519154A GB8519154D0 (en) | 1985-07-30 | 1985-07-30 | Aromatic ethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS573586A2 CS573586A2 (en) | 1989-04-14 |
| CS266593B2 true CS266593B2 (en) | 1990-01-12 |
Family
ID=10583042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS865735A CS266593B2 (en) | 1985-07-30 | 1986-07-30 | Method of 2-(2-hydroxy-3-phenosypropylamine) ethoxyphenolh's derivativesprodduction |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4772631A (hu) |
| EP (1) | EP0210849B1 (hu) |
| JP (2) | JPH0651661B2 (hu) |
| KR (1) | KR870001142A (hu) |
| CN (1) | CN1014516B (hu) |
| AR (1) | AR242176A1 (hu) |
| AT (1) | ATE55980T1 (hu) |
| AU (1) | AU603987B2 (hu) |
| CA (1) | CA1283122C (hu) |
| CS (1) | CS266593B2 (hu) |
| DD (1) | DD251551A5 (hu) |
| DE (1) | DE3673722D1 (hu) |
| DK (1) | DK168761B1 (hu) |
| ES (1) | ES2002720A6 (hu) |
| FI (1) | FI88030C (hu) |
| GB (1) | GB8519154D0 (hu) |
| GR (1) | GR861994B (hu) |
| HU (1) | HUT44757A (hu) |
| IE (1) | IE60157B1 (hu) |
| IL (1) | IL79447A0 (hu) |
| NO (1) | NO170480C (hu) |
| NZ (1) | NZ217011A (hu) |
| PH (1) | PH22503A (hu) |
| PL (1) | PL152320B1 (hu) |
| PT (1) | PT83085B (hu) |
| SU (1) | SU1632370A3 (hu) |
| ZA (1) | ZA865097B (hu) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3866984D1 (en) * | 1987-07-21 | 1992-01-30 | Hoffmann La Roche | Phenoxypropanolamine. |
| GB8801306D0 (en) * | 1988-01-21 | 1988-02-17 | Ici Plc | Chemical compounds |
| GB8905336D0 (en) * | 1989-03-08 | 1989-04-19 | Ici Plc | Chemical compounds |
| GB8910374D0 (en) * | 1989-05-05 | 1989-06-21 | Ici Plc | Chemical compounds |
| KR920005952B1 (ko) * | 1989-05-26 | 1992-07-25 | 이사무 이와이 | 오수정화조의 여과재 순환 정화장치 |
| GB8925032D0 (en) * | 1989-11-06 | 1989-12-28 | Ici Plc | Chemical compounds |
| GB8926083D0 (en) * | 1989-11-17 | 1990-01-10 | Ici Plc | Therapeutic agents |
| GB9003185D0 (en) * | 1990-02-13 | 1990-04-11 | Ici Plc | Pharmaceutical compositions |
| US5061727A (en) * | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| US5245053A (en) * | 1990-05-04 | 1993-09-14 | American Cyanamid Company | Substituted 5-(2-(2-aryl-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxoles |
| US5106867A (en) * | 1990-05-04 | 1992-04-21 | American Cyanamid Company | Method of increasing lean meat in edible animals |
| US5151439A (en) * | 1990-05-04 | 1992-09-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| GB9016655D0 (en) * | 1990-07-30 | 1990-09-12 | Ici Plc | Therapeutic agents |
| GB9111425D0 (en) * | 1991-05-28 | 1991-07-17 | Ici Plc | Chemical compounds |
| GB9111426D0 (en) * | 1991-05-28 | 1991-07-17 | Ici Plc | Chemical compounds |
| US5502078A (en) * | 1991-05-28 | 1996-03-26 | Zeneca Limited | Chemical compounds |
| GB9224740D0 (en) * | 1992-11-26 | 1993-01-13 | Ici Plc | Therapeutic agents |
| US5578638A (en) * | 1993-11-05 | 1996-11-26 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3 -adrenergic agonists |
| US5563171A (en) * | 1993-11-05 | 1996-10-08 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3-adrenergic agonists |
| US5776983A (en) * | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5488064A (en) * | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| US5491134A (en) * | 1994-09-16 | 1996-02-13 | Bristol-Myers Squibb Company | Sulfonic, phosphonic or phosphiniic acid β3 agonist derivatives |
| US5541204A (en) * | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| US5770615A (en) * | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5808080A (en) * | 1996-09-05 | 1998-09-15 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| ES2171839T3 (es) | 1996-09-05 | 2002-09-16 | Lilly Co Eli | Analogos de carbazol como agonistas adrenergicos selectivos de beta3. |
| CO5011072A1 (es) * | 1997-12-05 | 2001-02-28 | Lilly Co Eli | Etanolaminas pirazinil substituidas como agfonistas de los receptores |
| GB9812709D0 (en) * | 1998-06-13 | 1998-08-12 | Glaxo Group Ltd | Chemical compounds |
| US6344481B1 (en) | 1999-03-01 | 2002-02-05 | Pfizer Inc. | Thyromimetic antiobesity agents |
| GB0102407D0 (en) | 2001-01-31 | 2001-03-14 | Glaxo Group Ltd | Process |
| US7709677B2 (en) * | 2001-01-31 | 2010-05-04 | Glaxosmithkline Llc | Process of preparing arylethanoldiamines |
| US7504435B2 (en) * | 2001-01-31 | 2009-03-17 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method for stimulating weight loss and/or for lowering triglycerides in patients |
| US7202222B2 (en) * | 2003-01-06 | 2007-04-10 | National Bioscience Corporation | Methods for treatment of obesity and effective fat loss promotion |
| WO2008106213A1 (en) * | 2007-02-27 | 2008-09-04 | Titan Pharmaceuticals, Inc. | Administration of 3,5-diiodothyropropionic acid for stimulating weight loss, and/or lowering triglyceride levels, and/or treatment of metabolic syndrome. |
| US9044606B2 (en) | 2010-01-22 | 2015-06-02 | Ethicon Endo-Surgery, Inc. | Methods and devices for activating brown adipose tissue using electrical energy |
| US8476227B2 (en) | 2010-01-22 | 2013-07-02 | Ethicon Endo-Surgery, Inc. | Methods of activating a melanocortin-4 receptor pathway in obese subjects |
| US9907767B2 (en) | 2010-08-03 | 2018-03-06 | Velicept Therapeutics, Inc. | Pharmaceutical compositions and the treatment of overactive bladder |
| US9522129B2 (en) | 2010-08-03 | 2016-12-20 | Velicept Therapeutics, Inc. | Pharmaceutical Combination |
| CA2866080C (en) * | 2012-03-01 | 2021-01-19 | University Of Cincinnati | Ros-activated compounds as selective anti-cancer therapeutics |
| KR20170086659A (ko) | 2014-12-03 | 2017-07-26 | 벨리셉트 테라퓨틱스, 인크. | 하부 요로 증상을 위한 변형 방출형 솔라베그론을 이용한 조성물 및 방법 |
| US10080884B2 (en) | 2014-12-29 | 2018-09-25 | Ethicon Llc | Methods and devices for activating brown adipose tissue using electrical energy |
| US10092738B2 (en) | 2014-12-29 | 2018-10-09 | Ethicon Llc | Methods and devices for inhibiting nerves when activating brown adipose tissue |
| PL3365321T3 (pl) | 2015-10-23 | 2024-03-25 | B3Ar Therapeutics, Inc. | Jon obojnaczy solabegronu i jego zastosowania |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE368197B (hu) * | 1968-11-18 | 1974-06-24 | Pfizer | |
| GB1245148A (en) * | 1968-11-18 | 1971-09-08 | Pfizer Ltd | Propanolamine derivatives |
| SE354851B (hu) * | 1970-02-18 | 1973-03-26 | Haessle Ab | |
| US4146638A (en) * | 1976-02-17 | 1979-03-27 | Boehringer Ingelheim Gmbh | N-(3-phenoxy-2-hydroxy-propyl)-n-(2-phenyl-2-hydroxy-ethyl)-amines |
| US4191765A (en) * | 1976-05-25 | 1980-03-04 | Hoechst Aktiengesellschaft | 1-Aryloxy-2-hydroxy-3-aminopropanes |
| CH632987A5 (en) * | 1976-10-07 | 1982-11-15 | Haessle Ab | Process for preparing novel amines |
| SE416545B (sv) * | 1976-10-07 | 1981-01-19 | Haessle Ab | Forfarande for framstellning av nya hjertaktiva 1-frnoxi-3-aminopropan-2-ol-derivat |
| DE2965655D1 (en) * | 1978-06-28 | 1983-07-21 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| SE7807408L (sv) * | 1978-06-30 | 1979-12-31 | Haessle Ab | Hjertaktiva foreningar |
| US4338333A (en) * | 1979-06-16 | 1982-07-06 | Beecham Group Limited | Ethanamine derivatives their preparation and use in pharmaceutical compositions |
| EP0028105B1 (en) * | 1979-10-25 | 1983-01-19 | Beecham Group Plc | Secondary amines, their preparation and use in pharmaceutical compositions |
| IL65541A0 (en) * | 1981-05-06 | 1982-07-30 | Haessle Ab | Alkylamino-2-propanols,process for their preparation and pharmaceutical preparations containing same |
| GB8415377D0 (en) * | 1984-06-15 | 1984-07-18 | Beecham Group Plc | Compounds |
| GB8510146D0 (en) * | 1985-04-20 | 1985-05-30 | Smith Kline French Lab | Chemical compounds & processes |
-
1985
- 1985-07-30 GB GB858519154A patent/GB8519154D0/en active Pending
-
1986
- 1986-07-07 IE IE182786A patent/IE60157B1/en not_active IP Right Cessation
- 1986-07-08 ZA ZA865097A patent/ZA865097B/xx unknown
- 1986-07-09 FI FI862896A patent/FI88030C/fi not_active IP Right Cessation
- 1986-07-09 PH PH33996A patent/PH22503A/en unknown
- 1986-07-10 AU AU60029/86A patent/AU603987B2/en not_active Ceased
- 1986-07-17 IL IL79447A patent/IL79447A0/xx not_active IP Right Cessation
- 1986-07-23 PL PL1986260759A patent/PL152320B1/pl unknown
- 1986-07-25 EP EP86305749A patent/EP0210849B1/en not_active Expired - Lifetime
- 1986-07-25 DE DE8686305749T patent/DE3673722D1/de not_active Expired - Lifetime
- 1986-07-25 AT AT86305749T patent/ATE55980T1/de not_active IP Right Cessation
- 1986-07-28 HU HU863206A patent/HUT44757A/hu unknown
- 1986-07-28 US US06/889,857 patent/US4772631A/en not_active Expired - Lifetime
- 1986-07-29 SU SU864027877A patent/SU1632370A3/ru active
- 1986-07-29 PT PT83085A patent/PT83085B/pt unknown
- 1986-07-29 NO NO863061A patent/NO170480C/no unknown
- 1986-07-29 DD DD86293056A patent/DD251551A5/de not_active IP Right Cessation
- 1986-07-29 GR GR861994A patent/GR861994B/el unknown
- 1986-07-29 CA CA000514820A patent/CA1283122C/en not_active Expired - Lifetime
- 1986-07-29 DK DK359986A patent/DK168761B1/da not_active IP Right Cessation
- 1986-07-29 NZ NZ217011A patent/NZ217011A/en unknown
- 1986-07-30 CS CS865735A patent/CS266593B2/cs unknown
- 1986-07-30 CN CN86105400A patent/CN1014516B/zh not_active Expired
- 1986-07-30 JP JP61177914A patent/JPH0651661B2/ja not_active Expired - Lifetime
- 1986-07-30 AR AR86304733A patent/AR242176A1/es active
- 1986-07-30 ES ES8600729A patent/ES2002720A6/es not_active Expired
- 1986-07-30 KR KR1019860006278A patent/KR870001142A/ko not_active Ceased
-
1993
- 1993-12-24 JP JP5327984A patent/JPH0819062B2/ja not_active Ceased
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