ZA200305770B - Chemical compounds. - Google Patents
Chemical compounds. Download PDFInfo
- Publication number
- ZA200305770B ZA200305770B ZA200305770A ZA200305770A ZA200305770B ZA 200305770 B ZA200305770 B ZA 200305770B ZA 200305770 A ZA200305770 A ZA 200305770A ZA 200305770 A ZA200305770 A ZA 200305770A ZA 200305770 B ZA200305770 B ZA 200305770B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- carboxylic acid
- ethylamino
- chlorophenyl
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 116
- 239000000203 mixture Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- 239000000556 agonist Substances 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 17
- 108040006818 beta-adrenergic receptor activity proteins Proteins 0.000 claims description 12
- 102000015005 beta-adrenergic receptor activity proteins Human genes 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000000048 adrenergic agonist Substances 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- QWYBUWOMJOUHER-IBGZPJMESA-N 2-[3-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]thiophene-3-carboxylic acid Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=1)=CC=CC=1C=1SC=CC=1C(O)=O QWYBUWOMJOUHER-IBGZPJMESA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 101000780539 Homo sapiens Beta-3 adrenergic receptor Proteins 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- BQYBTKTZDVRZNT-VLIAUNLRSA-N 2-[3-[[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]furan-3-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)NC(C=1)=CC=CC=1C=1OC=CC=1C(O)=O BQYBTKTZDVRZNT-VLIAUNLRSA-N 0.000 claims description 2
- BHSXWAJCDNDMAX-VLIAUNLRSA-N 2-[3-[[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]thiophene-3-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)NC(C=1)=CC=CC=1C=1SC=CC=1C(O)=O BHSXWAJCDNDMAX-VLIAUNLRSA-N 0.000 claims description 2
- YFYQFWWLQLLILT-VLIAUNLRSA-N 2-[4-[[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]furan-3-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)NC(C=C1)=CC=C1C=1OC=CC=1C(O)=O YFYQFWWLQLLILT-VLIAUNLRSA-N 0.000 claims description 2
- MSMOXLIFEHLUGV-VLIAUNLRSA-N 2-[4-[[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]thiophene-3-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)NC(C=C1)=CC=C1C=1SC=CC=1C(O)=O MSMOXLIFEHLUGV-VLIAUNLRSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- HMWZLYLDLHPPCO-IBGZPJMESA-N 2-[3-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]furan-3-carboxylic acid Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=1)=CC=CC=1C=1OC=CC=1C(O)=O HMWZLYLDLHPPCO-IBGZPJMESA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000543 intermediate Substances 0.000 description 30
- 239000007787 solid Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- -1 oxalic Chemical class 0.000 description 7
- 125000006308 propyl amino group Chemical group 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZKHQSQYLKSSYIP-UHFFFAOYSA-N methyl furan-3-carboxylate Chemical compound COC(=O)C=1C=COC=1 ZKHQSQYLKSSYIP-UHFFFAOYSA-N 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- ZTRAEMILTFNZSM-UHFFFAOYSA-N methyl thiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1 ZTRAEMILTFNZSM-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- JRRSINSJEXMVLY-UHFFFAOYSA-N ethyl 2-(3-aminophenyl)furan-3-carboxylate;hydrochloride Chemical compound Cl.C1=COC(C=2C=C(N)C=CC=2)=C1C(=O)OCC JRRSINSJEXMVLY-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229960001317 isoprenaline Drugs 0.000 description 3
- AMNGOSWPHVUAFF-UHFFFAOYSA-N methyl 2-(3-aminophenyl)furan-3-carboxylate Chemical compound C1=COC(C=2C=C(N)C=CC=2)=C1C(=O)OC AMNGOSWPHVUAFF-UHFFFAOYSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NRQHBNNTBIDSRK-YRNVUSSQSA-N (4e)-4-[(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one Chemical compound C1=CC(OC)=CC=C1\C=C\1C(=O)OC(C)=N/1 NRQHBNNTBIDSRK-YRNVUSSQSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HIIQKULKTXGUQJ-UHFFFAOYSA-N 2-(3-nitrophenyl)furan-3-carboxylic acid Chemical compound C1=COC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1C(=O)O HIIQKULKTXGUQJ-UHFFFAOYSA-N 0.000 description 2
- OCWKBBVFZPOJIQ-UHFFFAOYSA-N 2-(4-nitrophenyl)furan-3-carboxylic acid Chemical compound C1=COC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C(=O)O OCWKBBVFZPOJIQ-UHFFFAOYSA-N 0.000 description 2
- DWVRCBVUNGHZMG-UHFFFAOYSA-N 2-(4-nitrophenyl)thiophene-3-carboxylic acid Chemical compound C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C(=O)O DWVRCBVUNGHZMG-UHFFFAOYSA-N 0.000 description 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-M 3-furoate Chemical compound [O-]C(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-M 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 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 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BXECCFVRKBIUCJ-UHFFFAOYSA-N methyl 2-(3-nitrophenyl)furan-3-carboxylate Chemical compound C1=COC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1C(=O)OC BXECCFVRKBIUCJ-UHFFFAOYSA-N 0.000 description 2
- ABYFVPZBYVMVPV-UHFFFAOYSA-N methyl 2-(3-nitrophenyl)thiophene-3-carboxylate Chemical compound C1=CSC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1C(=O)OC ABYFVPZBYVMVPV-UHFFFAOYSA-N 0.000 description 2
- JMGKXLZRODFPNG-UHFFFAOYSA-N methyl 2-(4-aminophenyl)furan-3-carboxylate Chemical compound C1=COC(C=2C=CC(N)=CC=2)=C1C(=O)OC JMGKXLZRODFPNG-UHFFFAOYSA-N 0.000 description 2
- PLDISUWQYUVIOM-UHFFFAOYSA-N methyl 2-(4-nitrophenyl)furan-3-carboxylate Chemical compound C1=COC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C(=O)OC PLDISUWQYUVIOM-UHFFFAOYSA-N 0.000 description 2
- PTLXXPNEMPVVHV-UHFFFAOYSA-N methyl 2-(4-nitrophenyl)thiophene-3-carboxylate Chemical compound C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C(=O)OC PTLXXPNEMPVVHV-UHFFFAOYSA-N 0.000 description 2
- GCYZAGHQPYXHAR-WSZABJOTSA-N methyl 2-[3-[[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]amino]phenyl]thiophene-3-carboxylate hydrochloride Chemical compound Cl.COC(=O)C1=C(SC=C1)C1=CC(=CC=C1)NC[C@@H](C)NC[C@H](O)C1=CC(=CC=C1)Cl GCYZAGHQPYXHAR-WSZABJOTSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
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- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GIISOKXJNMYXHH-SFHVURJKSA-N tert-butyl n-[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3-chlorophenyl)ethyl]-n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(CC=O)C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(Cl)=C1 GIISOKXJNMYXHH-SFHVURJKSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000000476 thermogenic effect Effects 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- External Artificial Organs (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0102408.2A GB0102408D0 (en) | 2001-01-31 | 2001-01-31 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305770B true ZA200305770B (en) | 2004-10-25 |
Family
ID=9907834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305770A ZA200305770B (en) | 2001-01-31 | 2003-07-25 | Chemical compounds. |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1366033B1 (cs) |
| JP (1) | JP2004521895A (cs) |
| KR (1) | KR20030070923A (cs) |
| CN (1) | CN1487928A (cs) |
| AT (1) | ATE294167T1 (cs) |
| AU (1) | AU2002246720B2 (cs) |
| BR (1) | BR0116854A (cs) |
| CA (1) | CA2434853A1 (cs) |
| CZ (1) | CZ20032085A3 (cs) |
| DE (1) | DE60110468T2 (cs) |
| DK (1) | DK1366033T3 (cs) |
| ES (1) | ES2240557T3 (cs) |
| GB (1) | GB0102408D0 (cs) |
| HU (1) | HUP0303026A3 (cs) |
| IL (2) | IL156639A0 (cs) |
| MX (1) | MXPA03006847A (cs) |
| NO (1) | NO20033401L (cs) |
| NZ (1) | NZ526846A (cs) |
| PL (1) | PL363359A1 (cs) |
| PT (1) | PT1366033E (cs) |
| WO (1) | WO2002060885A1 (cs) |
| ZA (1) | ZA200305770B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1424079A1 (en) * | 2002-11-27 | 2004-06-02 | Boehringer Ingelheim International GmbH | Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9207964D0 (en) * | 1992-04-10 | 1992-05-27 | Ici Plc | Chemical compounds |
| AU2737295A (en) * | 1994-06-09 | 1996-01-04 | Glaxo Group Limited | Phenethanolamine derivatives and their use as atypical beta-adrenoceptor agonists |
| GB9525177D0 (en) * | 1995-12-08 | 1996-02-07 | Glaxo Group Ltd | Chemical compounds |
| GB9812709D0 (en) * | 1998-06-13 | 1998-08-12 | Glaxo Group Ltd | Chemical compounds |
-
2001
- 2001-01-31 GB GBGB0102408.2A patent/GB0102408D0/en not_active Ceased
- 2001-12-17 IL IL15663901A patent/IL156639A0/xx active IP Right Grant
- 2001-12-17 PT PT01994312T patent/PT1366033E/pt unknown
- 2001-12-17 BR BR0116854-1A patent/BR0116854A/pt not_active Application Discontinuation
- 2001-12-17 WO PCT/US2001/049299 patent/WO2002060885A1/en active IP Right Grant
- 2001-12-17 CN CNA018224415A patent/CN1487928A/zh active Pending
- 2001-12-17 KR KR10-2003-7010057A patent/KR20030070923A/ko not_active Ceased
- 2001-12-17 JP JP2002561035A patent/JP2004521895A/ja active Pending
- 2001-12-17 DE DE60110468T patent/DE60110468T2/de not_active Expired - Lifetime
- 2001-12-17 ES ES01994312T patent/ES2240557T3/es not_active Expired - Lifetime
- 2001-12-17 AT AT01994312T patent/ATE294167T1/de not_active IP Right Cessation
- 2001-12-17 PL PL01363359A patent/PL363359A1/xx not_active Application Discontinuation
- 2001-12-17 CZ CZ20032085A patent/CZ20032085A3/cs unknown
- 2001-12-17 AU AU2002246720A patent/AU2002246720B2/en not_active Ceased
- 2001-12-17 HU HU0303026A patent/HUP0303026A3/hu unknown
- 2001-12-17 CA CA002434853A patent/CA2434853A1/en not_active Abandoned
- 2001-12-17 EP EP01994312A patent/EP1366033B1/en not_active Expired - Lifetime
- 2001-12-17 MX MXPA03006847A patent/MXPA03006847A/es active IP Right Grant
- 2001-12-17 NZ NZ526846A patent/NZ526846A/en unknown
- 2001-12-17 DK DK01994312T patent/DK1366033T3/da active
-
2003
- 2003-06-25 IL IL156639A patent/IL156639A/en not_active IP Right Cessation
- 2003-07-25 ZA ZA200305770A patent/ZA200305770B/en unknown
- 2003-07-30 NO NO20033401A patent/NO20033401L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303026A2 (hu) | 2003-12-29 |
| CN1487928A (zh) | 2004-04-07 |
| WO2002060885A1 (en) | 2002-08-08 |
| JP2004521895A (ja) | 2004-07-22 |
| DK1366033T3 (da) | 2005-08-15 |
| NO20033401D0 (no) | 2003-07-30 |
| DE60110468D1 (de) | 2005-06-02 |
| CZ20032085A3 (cs) | 2003-12-17 |
| NZ526846A (en) | 2004-10-29 |
| EP1366033A1 (en) | 2003-12-03 |
| ES2240557T3 (es) | 2005-10-16 |
| AU2002246720B2 (en) | 2004-07-22 |
| MXPA03006847A (es) | 2003-11-13 |
| KR20030070923A (ko) | 2003-09-02 |
| PT1366033E (pt) | 2005-08-31 |
| PL363359A1 (en) | 2004-11-15 |
| DE60110468T2 (de) | 2006-02-23 |
| IL156639A (en) | 2006-12-31 |
| CA2434853A1 (en) | 2002-08-08 |
| ATE294167T1 (de) | 2005-05-15 |
| GB0102408D0 (en) | 2001-03-14 |
| HUP0303026A3 (en) | 2007-06-28 |
| HK1060883A1 (en) | 2004-08-27 |
| NO20033401L (no) | 2003-09-30 |
| EP1366033B1 (en) | 2005-04-27 |
| BR0116854A (pt) | 2004-02-25 |
| IL156639A0 (en) | 2004-01-04 |
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