JP2000510150A - 置換１，３―ベンゾジオキソール - Google Patents
置換１，３―ベンゾジオキソールInfo
- Publication number
- JP2000510150A JP2000510150A JP09541097A JP54109797A JP2000510150A JP 2000510150 A JP2000510150 A JP 2000510150A JP 09541097 A JP09541097 A JP 09541097A JP 54109797 A JP54109797 A JP 54109797A JP 2000510150 A JP2000510150 A JP 2000510150A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- chloro
- hydroxy
- benzo
- dioxole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000005529 1,3-benzodioxoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 276
- 150000003839 salts Chemical class 0.000 claims abstract description 131
- 238000000034 method Methods 0.000 claims abstract description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 86
- 239000001257 hydrogen Substances 0.000 claims abstract description 81
- 239000000203 mixture Substances 0.000 claims abstract description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 170
- -1 2-tert-butoxy-ethyl Chemical group 0.000 claims description 87
- 150000002148 esters Chemical class 0.000 claims description 78
- JEDJMKTVUPSHFW-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C=1C=C2OC(C(O)=O)(C(O)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JEDJMKTVUPSHFW-UHFFFAOYSA-N 0.000 claims description 60
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 18
- 150000004702 methyl esters Chemical class 0.000 claims description 11
- 239000006187 pill Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 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 description 6
- 208000008589 Obesity Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- JEDJMKTVUPSHFW-ABAIWWIYSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(O)=O)C(O)=O)C)=CC=CC(Cl)=C1 JEDJMKTVUPSHFW-ABAIWWIYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims description 3
- KVJUIGSWTPMWJL-UHFFFAOYSA-N 1,3-dioxole-2,2-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)OC=CO1 KVJUIGSWTPMWJL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- DDLJLQQNSYZHDP-UHFFFAOYSA-N 5-[2-[2-(3-chlorophenyl)-1,3-oxazolidin-3-yl]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C=1C=C2OC(C(O)=O)(C(O)=O)OC2=CC=1CC(C)N1CCOC1C1=CC=CC(Cl)=C1 DDLJLQQNSYZHDP-UHFFFAOYSA-N 0.000 claims description 2
- JHYORHSRKUXTSS-UHFFFAOYSA-N C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC(C=1C=CC=CC=1)C1=CC=CC=C1 JHYORHSRKUXTSS-UHFFFAOYSA-N 0.000 claims description 2
- ZGWJVQQEZHERFY-UHFFFAOYSA-N OC(=O)OCC1=CC=CC(Cl)=C1 Chemical compound OC(=O)OCC1=CC=CC(Cl)=C1 ZGWJVQQEZHERFY-UHFFFAOYSA-N 0.000 claims description 2
- WMWHRXNMXHUDHU-UYHPJTEGSA-N bis(3-phenylmethoxypropyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCCCOCC=1C=CC=CC=1)C(=O)OCCCOCC1=CC=CC=C1 WMWHRXNMXHUDHU-UYHPJTEGSA-N 0.000 claims description 2
- XNHDAXYFERIURL-REBFLZFKSA-N bis(4-phenylmethoxybut-2-enyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC=CCOCC=1C=CC=CC=1)C(=O)OCC=CCOCC1=CC=CC=C1 XNHDAXYFERIURL-REBFLZFKSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims 5
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 3
- 150000007970 thio esters Chemical class 0.000 claims 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- OXRWICUICBZVAE-UHFFFAOYSA-N 4-methylpent-1-yne Chemical compound CC(C)CC#C OXRWICUICBZVAE-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 16
- 230000003579 anti-obesity Effects 0.000 abstract description 8
- 230000002058 anti-hyperglycaemic effect Effects 0.000 abstract description 7
- 230000003178 anti-diabetic effect Effects 0.000 abstract description 6
- 239000003472 antidiabetic agent Substances 0.000 abstract description 5
- 125000004404 heteroalkyl group Chemical group 0.000 abstract description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005353 silylalkyl group Chemical group 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 136
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 112
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000007787 solid Substances 0.000 description 96
- 238000005481 NMR spectroscopy Methods 0.000 description 75
- 239000000243 solution Substances 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- 239000011541 reaction mixture Substances 0.000 description 47
- 238000000921 elemental analysis Methods 0.000 description 40
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000011734 sodium Substances 0.000 description 24
- 239000000725 suspension Substances 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- 239000012153 distilled water Substances 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 150000003840 hydrochlorides Chemical class 0.000 description 15
- 239000008280 blood Substances 0.000 description 14
- 210000004369 blood Anatomy 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 10
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 241000400611 Eucalyptus deanei Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 108060003345 Adrenergic Receptor Proteins 0.000 description 6
- 102000017910 Adrenergic receptor Human genes 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- JYHIJPMNTUZEAY-UHFFFAOYSA-N diethyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCC)(C(=O)OCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JYHIJPMNTUZEAY-UHFFFAOYSA-N 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 244000144977 poultry Species 0.000 description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 4
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- FUIZGVJPURUILK-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C=1C=C2OC(C(O)=O)(C(O)=O)OC2=CC=1CC(C)N(C(=O)OC(C)(C)C)CC(O)C1=CC=CC(Cl)=C1 FUIZGVJPURUILK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- 206010008531 Chills Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 3
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 3
- 240000001414 Eucalyptus viminalis Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- CJSNUAXCJPOSFZ-UHFFFAOYSA-N bis(1-ethoxy-1-oxopropan-2-yl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OC(C)C(=O)OCC)(C(=O)OC(C)C(=O)OCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 CJSNUAXCJPOSFZ-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
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- MRGNGLHCBRTELY-UHFFFAOYSA-N diethyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCC)(C(=O)OCC)OC2=CC=C1CC(C)N(C(=O)OC(C)(C)C)CC(O)C1=CC=CC(Cl)=C1 MRGNGLHCBRTELY-UHFFFAOYSA-N 0.000 description 1
- FZRUHORICRDKKU-UHFFFAOYSA-N diethyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate;hydrochloride Chemical compound Cl.C1=C2OC(C(=O)OCC)(C(=O)OCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 FZRUHORICRDKKU-UHFFFAOYSA-N 0.000 description 1
- REILEOOPSNTBHF-UHFFFAOYSA-N diheptyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCCCCCC)(C(=O)OCCCCCCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 REILEOOPSNTBHF-UHFFFAOYSA-N 0.000 description 1
- GRHWEUAYZZFBLE-UHFFFAOYSA-N dipropan-2-yl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical class C1=C2OC(C(=O)OC(C)C)(C(=O)OC(C)C)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 GRHWEUAYZZFBLE-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RKEVLNCQYZEAAM-UHFFFAOYSA-L disilver;5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Ag+].[Ag+].C=1C=C2OC(C([O-])=O)(C([O-])=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 RKEVLNCQYZEAAM-UHFFFAOYSA-L 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- FUZBPOHHSBDTJQ-UHFFFAOYSA-L disodium;5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Na+].[Na+].C=1C=C2OC(C([O-])=O)(C([O-])=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 FUZBPOHHSBDTJQ-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000035611 feeding Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- HNJMSLJLLQCWDB-UHFFFAOYSA-N iodomethyl 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C(=O)OCI HNJMSLJLLQCWDB-UHFFFAOYSA-N 0.000 description 1
- PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 1
- KWIBRJGXWFDQNU-UHFFFAOYSA-N iodomethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCI KWIBRJGXWFDQNU-UHFFFAOYSA-N 0.000 description 1
- BPRVJFRRXJYYQF-UHFFFAOYSA-N iodomethyl 3,3-dimethylbutanoate Chemical compound CC(C)(C)CC(=O)OCI BPRVJFRRXJYYQF-UHFFFAOYSA-N 0.000 description 1
- NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 1
- KCQMUFYIGUHOMQ-UHFFFAOYSA-N iodomethyl benzoate Chemical compound ICOC(=O)C1=CC=CC=C1 KCQMUFYIGUHOMQ-UHFFFAOYSA-N 0.000 description 1
- AIEFWPONAXOMOR-UHFFFAOYSA-N iodomethyl butanoate Chemical compound CCCC(=O)OCI AIEFWPONAXOMOR-UHFFFAOYSA-N 0.000 description 1
- HXNVZZWJJDAMHS-UHFFFAOYSA-N iodomethyl cyclohexanecarboxylate Chemical compound ICOC(=O)C1CCCCC1 HXNVZZWJJDAMHS-UHFFFAOYSA-N 0.000 description 1
- AHWAPPBPAIVQBI-UHFFFAOYSA-N iodomethyl heptanoate Chemical compound CCCCCCC(=O)OCI AHWAPPBPAIVQBI-UHFFFAOYSA-N 0.000 description 1
- IFZADQLLMDQVOK-UHFFFAOYSA-N iodomethyl hexanoate Chemical compound CCCCCC(=O)OCI IFZADQLLMDQVOK-UHFFFAOYSA-N 0.000 description 1
- JSPZULPOZBGXGJ-UHFFFAOYSA-N iodomethyl pentanoate Chemical compound CCCCC(=O)OCI JSPZULPOZBGXGJ-UHFFFAOYSA-N 0.000 description 1
- GLQOBGUEBABWDN-UHFFFAOYSA-N iodomethyl propanoate Chemical compound CCC(=O)OCI GLQOBGUEBABWDN-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PCPUMGYALMOCHF-UHFFFAOYSA-N oxolan-3-ylmethanol Chemical compound OCC1CCOC1 PCPUMGYALMOCHF-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 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
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000000636 white adipocyte Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64597096A | 1996-05-14 | 1996-05-14 | |
| US08/645,970 | 1996-05-14 | ||
| PCT/US1997/008148 WO1997043273A1 (fr) | 1996-05-14 | 1997-05-09 | 1,3-benzodioxoles substitues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000510150A true JP2000510150A (ja) | 2000-08-08 |
Family
ID=24591209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09541097A Pending JP2000510150A (ja) | 1996-05-14 | 1997-05-09 | 置換１，３―ベンゾジオキソール |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0901484A1 (fr) |
| JP (1) | JP2000510150A (fr) |
| KR (1) | KR20000011001A (fr) |
| AU (1) | AU730659B2 (fr) |
| BR (1) | BR9708948A (fr) |
| CA (1) | CA2254120A1 (fr) |
| HU (1) | HUP9902088A2 (fr) |
| IL (1) | IL126780A0 (fr) |
| NZ (1) | NZ332713A (fr) |
| WO (1) | WO1997043273A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3797108B1 (fr) | 2018-05-21 | 2022-07-20 | Constellation Pharmaceuticals, Inc. | Modulateurs de l'enzyme méthyl modifiant, compositions et leur utilisation. |
| CA3148444A1 (fr) * | 2019-07-24 | 2021-01-28 | Constellation Pharmaceuticals, Inc. | Therapies d'inhibition d'ezh2 pour le traitement des cancers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061727A (en) * | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| US5482971A (en) * | 1993-10-01 | 1996-01-09 | American Cyanamid Company | Beta3 -adrenergic agents and their use in pharmaceutical compositions |
-
1997
- 1997-05-05 EP EP97924720A patent/EP0901484A1/fr not_active Withdrawn
- 1997-05-05 HU HU9902088A patent/HUP9902088A2/hu unknown
- 1997-05-09 NZ NZ332713A patent/NZ332713A/xx unknown
- 1997-05-09 KR KR1019980709151A patent/KR20000011001A/ko not_active Application Discontinuation
- 1997-05-09 JP JP09541097A patent/JP2000510150A/ja active Pending
- 1997-05-09 CA CA002254120A patent/CA2254120A1/fr not_active Abandoned
- 1997-05-09 BR BR9708948A patent/BR9708948A/pt unknown
- 1997-05-09 WO PCT/US1997/008148 patent/WO1997043273A1/fr not_active Application Discontinuation
- 1997-05-09 AU AU30067/97A patent/AU730659B2/en not_active Ceased
- 1997-05-09 IL IL12678097A patent/IL126780A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL126780A0 (en) | 1999-08-17 |
| BR9708948A (pt) | 1999-08-03 |
| CA2254120A1 (fr) | 1997-11-20 |
| HUP9902088A2 (hu) | 2001-04-28 |
| WO1997043273A1 (fr) | 1997-11-20 |
| KR20000011001A (ko) | 2000-02-25 |
| AU730659B2 (en) | 2001-03-08 |
| AU3006797A (en) | 1997-12-05 |
| EP0901484A1 (fr) | 1999-03-17 |
| NZ332713A (en) | 2000-07-28 |
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