JP2009509986A5 - - Google Patents
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- Publication number
- JP2009509986A5 JP2009509986A5 JP2008532645A JP2008532645A JP2009509986A5 JP 2009509986 A5 JP2009509986 A5 JP 2009509986A5 JP 2008532645 A JP2008532645 A JP 2008532645A JP 2008532645 A JP2008532645 A JP 2008532645A JP 2009509986 A5 JP2009509986 A5 JP 2009509986A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- heterocycloalkyl
- cycloalkyl
- heteroaryl
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 claims description 49
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 9
- -1 wherein Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 224
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 29
- 229910052731 fluorine Inorganic materials 0.000 claims 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229920001577 copolymer Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012305 Demyelination Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 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 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- JKKQHWBKENNTLX-UHFFFAOYSA-N ethyl 2-chloro-3-oxo-6-phenylmethoxyhexanoate Chemical compound CCOC(=O)C(Cl)C(=O)CCCOCC1=CC=CC=C1 JKKQHWBKENNTLX-UHFFFAOYSA-N 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- ZGGLXDWYBLNMDD-UHFFFAOYSA-N ethyl 3-oxo-6-phenylmethoxyhexanoate Chemical compound CCOC(=O)CC(=O)CCCOCC1=CC=CC=C1 ZGGLXDWYBLNMDD-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- HLCHESOMJVGDSJ-LOYHVIPDSA-N (3r)-n-[(2r)-3-(4-chlorophenyl)-1-[4-cyclohexyl-4-(1,2,4-triazol-1-ylmethyl)piperidin-1-yl]-1-oxopropan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C[C@H](C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)[C@@H]1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-LOYHVIPDSA-N 0.000 description 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
- DIWGYCJCIRPVEF-UHFFFAOYSA-N 1-[2-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-(4-chlorophenyl)-2-oxoethyl]-1-amino-3,4-dihydro-2h-naphthalene-2-carboxamide Chemical compound O=C1N(C)N=C2CCN(C(=O)C(C=3C=CC(Cl)=CC=3)C3(N)C4=CC=CC=C4CCC3C(N)=O)CC21CC1=CC=CC=C1 DIWGYCJCIRPVEF-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 description 1
- OXPFZPRRMMRQTA-UHFFFAOYSA-N 3-[2-methoxy-4-[[4-(3-methylsulfonylpropyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C=1C=C(C=2NC(=O)ON=2)C(OC)=CC=1OCC(=C(N=1)CCCS(C)(=O)=O)SC=1C1=CC=C(C(F)(F)F)C=C1 OXPFZPRRMMRQTA-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- MUIHXQKLDLLIPG-UHFFFAOYSA-P COc(cc(cc1)OCc2c(CCC[S+](C)(O)=O)nc(-c3ccc(C(F)(F)F)cc3)[s]2)c1C(N1)=NOC1=O Chemical compound COc(cc(cc1)OCc2c(CCC[S+](C)(O)=O)nc(-c3ccc(C(F)(F)F)cc3)[s]2)c1C(N1)=NOC1=O MUIHXQKLDLLIPG-UHFFFAOYSA-P 0.000 description 1
- ZBGIVPIGYBHEME-UHFFFAOYSA-N COc1cc(OCc2c(CCCSC)nc(-c3ccc(C(F)(F)F)cc3)[s]2)ccc1C(N1)=NOC1=O Chemical compound COc1cc(OCc2c(CCCSC)nc(-c3ccc(C(F)(F)F)cc3)[s]2)ccc1C(N1)=NOC1=O ZBGIVPIGYBHEME-UHFFFAOYSA-N 0.000 description 1
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DHHKPEUQJIEKOA-UHFFFAOYSA-N tert-butyl 2-[6-(nitromethyl)-6-bicyclo[3.2.0]hept-3-enyl]acetate Chemical compound C1C=CC2C(CC(=O)OC(C)(C)C)(C[N+]([O-])=O)CC21 DHHKPEUQJIEKOA-UHFFFAOYSA-N 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05021235 | 2005-09-29 | ||
| PCT/EP2006/009298 WO2007039172A1 (en) | 2005-09-29 | 2006-09-26 | Phenyl- and pyridyl-i, 2 , 4 -oxadiazolone derivatives with phenyl group, processes for their preparation and their use as pharmaceuticals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009509986A JP2009509986A (ja) | 2009-03-12 |
| JP2009509986A5 true JP2009509986A5 (enExample) | 2009-11-05 |
Family
ID=35809809
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008532645A Abandoned JP2009509986A (ja) | 2005-09-29 | 2006-09-26 | フェニル基を有する、フェニル−及びピリジル−１，２，４−オキサジアゾロン誘導体、その製造方法、及び医薬品としてのその使用 |
| JP2008532648A Expired - Fee Related JP5183479B2 (ja) | 2005-09-29 | 2006-09-26 | フェニル基を有するフェニル−［１，２，４］−オキサジアゾール−５−オン誘導体、その製造方法、及び医薬品としてのその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008532648A Expired - Fee Related JP5183479B2 (ja) | 2005-09-29 | 2006-09-26 | フェニル基を有するフェニル−［１，２，４］−オキサジアゾール−５−オン誘導体、その製造方法、及び医薬品としてのその使用 |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US20080287409A1 (enExample) |
| EP (2) | EP1931660B1 (enExample) |
| JP (2) | JP2009509986A (enExample) |
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| EP1586573B1 (en) * | 2004-04-01 | 2007-02-07 | Sanofi-Aventis Deutschland GmbH | Oxadiazolones, processes for their preparation and their use as pharmaceuticals |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
| ES2399071T3 (es) | 2006-10-16 | 2013-03-25 | Bionomics Limited | Nuevos compuestos ansiolíticos |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| US20210130285A1 (en) * | 2008-03-19 | 2021-05-06 | Aurimmed Pharma, Inc. | Novel compounds advantageous in the treatment of central nervous system diseases and disorders |
| US10793515B2 (en) * | 2008-03-19 | 2020-10-06 | Aurimmed Pharma, Inc. | Compounds advantageous in the treatment of central nervous system diseases and disorders |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| DK2470552T3 (en) | 2009-08-26 | 2014-02-17 | Sanofi Sa | NOVEL, CRYSTALLINE, heteroaromatic FLUORGLYCOSIDHYDRATER, MEDICINES COVERING THESE COMPOUNDS AND THEIR USE |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8916593B2 (en) | 2010-05-04 | 2014-12-23 | Pfizer Inc. | Alkoxy-substituted 2-aminopyridines as ALK inhibitors |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| JP2014510065A (ja) | 2011-03-02 | 2014-04-24 | バイオノミックス リミテッド | 治療薬としての新規な小分子 |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| JP6055817B2 (ja) | 2011-05-12 | 2016-12-27 | バイオノミックス リミテッド | ナフチリジンの調製方法 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| HK1200824A1 (en) * | 2012-01-18 | 2015-08-14 | Daiichi Sankyo Company, Limited | Substituted phenylazole derivative |
| MX2014015265A (es) | 2012-06-14 | 2015-08-12 | Basf Se | Metodos plaguicidas que utilizan compuestos de 3-piridiltiazol sustituido y derivados para combatir plagas de animales. |
| US10258672B2 (en) | 2014-10-09 | 2019-04-16 | Case Western Reserve University | Compositions and methods of treating root avulsion injury |
| CN106616029B (zh) * | 2016-12-08 | 2020-05-01 | 西南大学 | 一种提高虹鳟抗病能力的饲料添加剂及其制备方法 |
| CN108976150B (zh) * | 2017-06-05 | 2022-11-18 | 重庆博腾制药科技股份有限公司 | 一种3-乙基-4-氟苯腈的制备方法 |
| EP3651785B1 (en) * | 2017-07-11 | 2025-11-12 | Case Western Reserve University | Compositions and methods for treating myelin disorders |
| AU2019318209B2 (en) | 2018-08-10 | 2025-09-25 | Diapin Therapeutics, Llc | Tri-peptides and treatment of metabolic, cardiovascular and inflammatory disorders |
| WO2021092279A1 (en) * | 2019-11-06 | 2021-05-14 | Board Of Regents, The University Of Texas System | Methods for the treatment of dysmyelinating/demyelinating diseases |
| JP7858636B2 (ja) | 2020-09-10 | 2026-05-14 | ガシャーブラム・バイオ・インコーポレイテッド | ヘテロ環ｇｌｐ－１アゴニスト |
| WO2025237291A1 (zh) * | 2024-05-13 | 2025-11-20 | 上海翰森生物医药科技有限公司 | 一种异丙基异喹啉类化合物的制备方法及其中间体 |
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| US5783593A (en) | 1993-11-04 | 1998-07-21 | Abbott Laboratories | Inhibitors of squalene synthetase and protein farnesyltransferase |
| US5641796A (en) * | 1994-11-01 | 1997-06-24 | Eli Lilly And Company | Oral hypoglycemic agents |
| JP2000511883A (ja) | 1996-04-19 | 2000-09-12 | ノボ ノルディスク アクティーゼルスカブ | ホスホチロシン認識ユニットを有する分子のモジュレーター |
| JP4345230B2 (ja) * | 1998-03-10 | 2009-10-14 | 小野薬品工業株式会社 | カルボン酸誘導体およびその誘導体を有効成分として含有する薬剤 |
| CA2377246A1 (en) * | 1999-06-18 | 2000-12-28 | Ranjit C. Desai | Arylthiazolidinedione and aryloxazolidinedione derivatives |
| GB9914977D0 (en) | 1999-06-25 | 1999-08-25 | Glaxo Group Ltd | Chemical compounds |
| DE10112768A1 (de) | 2001-03-16 | 2002-09-19 | Merck Patent Gmbh | Phenylderivate 3 |
| GB0111523D0 (en) | 2001-05-11 | 2001-07-04 | Glaxo Group Ltd | Chemical compounds |
| AU2002323776B2 (en) * | 2001-08-10 | 2008-07-31 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator-responsive receptor Delta |
| JP2005529077A (ja) * | 2002-02-25 | 2005-09-29 | イーライ・リリー・アンド・カンパニー | ペルオキシソーム増殖因子活性化受容体調節物質 |
| JPWO2004080943A1 (ja) | 2003-03-11 | 2006-06-08 | 小野薬品工業株式会社 | シンナミルアルコール誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| US20070054902A1 (en) | 2003-12-02 | 2007-03-08 | Shionogi & Co., Ltd. | Isoxazole derivatives as peroxisome proliferator-activated receptors agonists |
| EP1586573B1 (en) * | 2004-04-01 | 2007-02-07 | Sanofi-Aventis Deutschland GmbH | Oxadiazolones, processes for their preparation and their use as pharmaceuticals |
| KR20060135854A (ko) * | 2004-04-01 | 2006-12-29 | 아벤티스 파마슈티칼스 인크. | Ｐｐａｒ 델타 조절물질로서의 1,3,4-옥사디아졸-2-온 |
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2006
- 2006-09-26 WO PCT/EP2006/009298 patent/WO2007039172A1/en not_active Ceased
- 2006-09-26 CA CA002624093A patent/CA2624093A1/en not_active Abandoned
- 2006-09-26 NZ NZ566878A patent/NZ566878A/en not_active IP Right Cessation
- 2006-09-26 RU RU2008112202/04A patent/RU2008112202A/ru not_active Application Discontinuation
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- 2006-09-26 EP EP06792252A patent/EP1931660B1/en active Active
- 2006-09-26 KR KR1020087007735A patent/KR20080048520A/ko not_active Withdrawn
- 2006-09-26 AU AU2006299092A patent/AU2006299092A1/en not_active Abandoned
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- 2006-09-26 NZ NZ566875A patent/NZ566875A/en not_active IP Right Cessation
- 2006-09-26 ES ES06792252T patent/ES2392181T3/es active Active
- 2006-09-26 BR BRPI0616465-0A patent/BRPI0616465A2/pt not_active Application Discontinuation
- 2006-09-26 EP EP06805857A patent/EP1934206B1/en active Active
- 2006-09-26 AT AT06805857T patent/ATE537167T1/de active
- 2006-09-26 SI SI200631453T patent/SI1931660T1/sl unknown
- 2006-09-26 CN CNA2006800344489A patent/CN101268069A/zh active Pending
- 2006-09-26 PL PL06792252T patent/PL1931660T3/pl unknown
- 2006-09-26 DK DK06792252.6T patent/DK1931660T3/da active
- 2006-09-26 JP JP2008532645A patent/JP2009509986A/ja not_active Abandoned
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- 2006-09-26 BR BRPI0616457-9A patent/BRPI0616457A2/pt not_active IP Right Cessation
- 2006-09-26 WO PCT/EP2006/009304 patent/WO2007039178A2/en not_active Ceased
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- 2006-09-26 JP JP2008532648A patent/JP5183479B2/ja not_active Expired - Fee Related
- 2006-09-26 AU AU2006299086A patent/AU2006299086A1/en not_active Abandoned
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- 2006-09-27 TW TW095135660A patent/TWI398436B/zh not_active IP Right Cessation
- 2006-09-27 DO DO2006000205A patent/DOP2006000205A/es unknown
- 2006-09-27 TW TW095135657A patent/TW200811154A/zh unknown
- 2006-09-27 AR ARP060104225A patent/AR056203A1/es not_active Application Discontinuation
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- 2006-09-28 PE PE2006001178A patent/PE20070545A1/es not_active Application Discontinuation
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- 2006-09-29 UY UY29829A patent/UY29829A1/es not_active Application Discontinuation
- 2006-09-29 UY UY29830A patent/UY29830A1/es not_active Application Discontinuation
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2008
- 2008-02-19 ZA ZA2008/01630A patent/ZA200801630B/en unknown
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- 2008-03-14 NO NO20081367A patent/NO20081367L/no not_active Application Discontinuation
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- 2008-03-17 IL IL190227A patent/IL190227A/en not_active IP Right Cessation
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- 2008-03-24 MA MA30783A patent/MA29807B1/fr unknown
- 2008-03-24 MA MA30780A patent/MA29804B1/fr unknown
- 2008-03-25 KR KR1020087007148A patent/KR101342415B1/ko not_active Expired - Fee Related
- 2008-03-26 US US12/055,793 patent/US20080287409A1/en not_active Abandoned
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