JP2018538253A5 - - Google Patents
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- JP2018538253A5 JP2018538253A5 JP2018522572A JP2018522572A JP2018538253A5 JP 2018538253 A5 JP2018538253 A5 JP 2018538253A5 JP 2018522572 A JP2018522572 A JP 2018522572A JP 2018522572 A JP2018522572 A JP 2018522572A JP 2018538253 A5 JP2018538253 A5 JP 2018538253A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- methylpyrimidin
- indoline
- compound
- formula
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 35
- -1 2-methylpyrimidine- 5-yl Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 208000011117 substance-related disease Diseases 0.000 claims 10
- 208000024891 symptom Diseases 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 claims 7
- 125000003277 amino group Chemical group 0.000 claims 7
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 230000003287 optical effect Effects 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000003566 oxetanyl group Chemical group 0.000 claims 6
- 208000007848 Alcoholism Diseases 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 5
- 208000019901 Anxiety disease Diseases 0.000 claims 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 5
- 206010003805 Autism Diseases 0.000 claims 5
- 208000020706 Autistic disease Diseases 0.000 claims 5
- 208000023275 Autoimmune disease Diseases 0.000 claims 5
- 208000020925 Bipolar disease Diseases 0.000 claims 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims 5
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 5
- 208000000094 Chronic Pain Diseases 0.000 claims 5
- 208000028698 Cognitive impairment Diseases 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 206010017533 Fungal infection Diseases 0.000 claims 5
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 5
- 208000023105 Huntington disease Diseases 0.000 claims 5
- 208000019022 Mood disease Diseases 0.000 claims 5
- 206010052904 Musculoskeletal stiffness Diseases 0.000 claims 5
- 208000031888 Mycoses Diseases 0.000 claims 5
- 208000029726 Neurodevelopmental disease Diseases 0.000 claims 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 5
- 208000018737 Parkinson disease Diseases 0.000 claims 5
- 201000009006 Partial Sensory Epilepsy Diseases 0.000 claims 5
- 208000017442 Retinal disease Diseases 0.000 claims 5
- 208000020764 Sensation disease Diseases 0.000 claims 5
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims 5
- 208000036142 Viral infection Diseases 0.000 claims 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 5
- 206010003246 arthritis Diseases 0.000 claims 5
- 208000006673 asthma Diseases 0.000 claims 5
- 208000030963 borderline personality disease Diseases 0.000 claims 5
- 208000015114 central nervous system disease Diseases 0.000 claims 5
- DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 claims 5
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 206010013663 drug dependence Diseases 0.000 claims 5
- 230000000694 effects Effects 0.000 claims 5
- 206010015037 epilepsy Diseases 0.000 claims 5
- 208000027866 inflammatory disease Diseases 0.000 claims 5
- 230000002757 inflammatory effect Effects 0.000 claims 5
- 208000024714 major depressive disease Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 5
- 230000004770 neurodegeneration Effects 0.000 claims 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 5
- 201000000980 schizophrenia Diseases 0.000 claims 5
- 208000019116 sleep disease Diseases 0.000 claims 5
- 208000020685 sleep-wake disease Diseases 0.000 claims 5
- 201000009032 substance abuse Diseases 0.000 claims 5
- 231100000736 substance abuse Toxicity 0.000 claims 5
- 230000003612 virological effect Effects 0.000 claims 5
- BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 claims 4
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims 3
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims 2
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical compound CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000000561 anti-psychotic effect Effects 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- 239000002249 anxiolytic agent Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 claims 2
- CDCHDCWJMGXXRH-UHFFFAOYSA-N estazolam Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CDCHDCWJMGXXRH-UHFFFAOYSA-N 0.000 claims 2
- GBBSUAFBMRNDJC-INIZCTEOSA-N eszopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-INIZCTEOSA-N 0.000 claims 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 2
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims 2
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 2
- 239000004050 mood stabilizer Substances 0.000 claims 2
- 229940127237 mood stabilizer Drugs 0.000 claims 2
- 229960002296 paroxetine Drugs 0.000 claims 2
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims 2
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims 2
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 2
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 claims 2
- KTGRHKOEFSJQNS-BDQAORGHSA-N (1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 KTGRHKOEFSJQNS-BDQAORGHSA-N 0.000 claims 1
- ODNKBNRHGJXLNB-HXUWFJFHSA-N (4S)-3-[6-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]pyrazin-2-yl]-4-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C1=CN=CC(=N1)N1C(OC[C@@H]1C(C)C)=O)=O)C ODNKBNRHGJXLNB-HXUWFJFHSA-N 0.000 claims 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims 1
- JHFXUQWHKYTBOM-UHFFFAOYSA-N 1-(5-aminopyridin-3-yl)-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound CC1=NC=C(C=N1)C1=CC=C2C(=C1)N(C(=O)C2(C)C)C1=CC(N)=CN=C1 JHFXUQWHKYTBOM-UHFFFAOYSA-N 0.000 claims 1
- QRISSWTXCLLIRY-UHFFFAOYSA-N 1-(6-aminopyrazin-2-yl)-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-(6-morpholin-4-ylpyrazin-2-yl)indol-2-one Chemical compound Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cncc(N)n1.Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cncc(n1)N1CCOCC1 QRISSWTXCLLIRY-UHFFFAOYSA-N 0.000 claims 1
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 claims 1
- SEJYGLHCGAFLJB-UHFFFAOYSA-N 1-[5-(2-hydroxyethylamino)pyrazin-2-yl]-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound CC1=NC=C(C=N1)C1=CC=C2C(=C1)N(C(=O)C2(C)C)C1=CN=C(NCCO)C=N1 SEJYGLHCGAFLJB-UHFFFAOYSA-N 0.000 claims 1
- XHMUAGQUMQLGOK-UHFFFAOYSA-N 1-[6-(2-methoxyethylamino)pyrazin-2-yl]-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound COCCNC1=NC(=CN=C1)N1C(=O)C(C)(C)C2=CC=C(C=C12)C1=CN=C(C)N=C1 XHMUAGQUMQLGOK-UHFFFAOYSA-N 0.000 claims 1
- YRNXJNDPINRAML-UHFFFAOYSA-N 1-[6-(4-hydroxy-4-methylpiperidin-1-yl)pyrazin-2-yl]-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound CC1=NC=C(C=N1)C1=CC=C2C(=C1)N(C(=O)C2(C)C)C1=CN=CC(=N1)N1CCC(C)(O)CC1 YRNXJNDPINRAML-UHFFFAOYSA-N 0.000 claims 1
- CHYLOBFKSRZDPO-UHFFFAOYSA-N 1-[6-(4-hydroxypiperidin-1-yl)pyrazin-2-yl]-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound OC1CCN(CC1)C1=CN=CC(=N1)N1C(C(C2=CC=C(C=C12)C=1C=NC(=NC=1)C)(C)C)=O CHYLOBFKSRZDPO-UHFFFAOYSA-N 0.000 claims 1
- GSWXBGLBNJBLQU-UHFFFAOYSA-N 1-[6-[2-methoxyethyl(methyl)amino]pyrazin-2-yl]-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound COCCN(C)C1=NC(=CN=C1)N1C(=O)C(C)(C)C2=CC=C(C=C12)C1=CN=C(C)N=C1 GSWXBGLBNJBLQU-UHFFFAOYSA-N 0.000 claims 1
- FYNHUVJPOGRUNU-UHFFFAOYSA-N 1-cyclopropyl-6-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-3,3-dimethylpyrrolo[3,2-c]pyridin-2-one Chemical compound CC1=NC=C(C=N1)C1=CC=C2C(=C1)N(C(=O)C2(C)C)C1=CC2=C(C=N1)C(C)(C)C(=O)N2C1CC1 FYNHUVJPOGRUNU-UHFFFAOYSA-N 0.000 claims 1
- CIMLGGRCZPAAMY-UHFFFAOYSA-N 3,3-dimethyl-1-(3-methylbenzotriazol-5-yl)-6-(2-methylpyrimidin-5-yl)indol-2-one Chemical compound CN1N=NC2=CC=C(C=C12)N1C2=CC(=CC=C2C(C)(C)C1=O)C1=CN=C(C)N=C1 CIMLGGRCZPAAMY-UHFFFAOYSA-N 0.000 claims 1
- HJVNENCFBJMOKQ-UHFFFAOYSA-N 3,3-dimethyl-1-(5-methyl-6-morpholin-4-ylpyrazin-2-yl)-6-(2-methylpyrimidin-5-yl)indol-2-one 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-[6-(oxetan-3-ylamino)pyrazin-2-yl]indol-2-one Chemical compound Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cncc(NC2COC2)n1.Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cnc(C)c(n1)N1CCOCC1 HJVNENCFBJMOKQ-UHFFFAOYSA-N 0.000 claims 1
- PTBUXRUQTQKMPV-UHFFFAOYSA-N 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-(2-morpholin-4-ylpyrimidin-4-yl)indol-2-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C1=NC(=NC=C1)N1CCOCC1)=O)C PTBUXRUQTQKMPV-UHFFFAOYSA-N 0.000 claims 1
- FLBCXONXVFHNGV-UHFFFAOYSA-N 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-(4-morpholin-4-ylpyrimidin-2-yl)indol-2-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C1=NC=CC(=N1)N1CCOCC1)=O)C FLBCXONXVFHNGV-UHFFFAOYSA-N 0.000 claims 1
- FJAUJHZRDQNZAQ-HDICACEKSA-N 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-[5-[(1S,5R)-3-oxa-6-azabicyclo[3.1.1]heptan-6-yl]pyrazin-2-yl]indol-2-one Chemical compound Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cnc(cn1)N1[C@H]2C[C@@H]1COC2 FJAUJHZRDQNZAQ-HDICACEKSA-N 0.000 claims 1
- LEPAQXWVAPQELT-HDICACEKSA-N 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-[6-[(1R,5S)-3-oxa-6-azabicyclo[3.1.1]heptan-6-yl]pyrazin-2-yl]indol-2-one Chemical compound Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cncc(n1)N1[C@H]2C[C@@H]1COC2 LEPAQXWVAPQELT-HDICACEKSA-N 0.000 claims 1
- PQZGEFNMZYVGCJ-HDICACEKSA-N 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-[6-[(1R,5S)-6-oxa-3-azabicyclo[3.1.1]heptan-3-yl]pyrazin-2-yl]indol-2-one Chemical compound Cc1ncc(cn1)-c1ccc2c(c1)N(C(=O)C2(C)C)c1cncc(n1)N1C[C@@H]2C[C@H](C1)O2 PQZGEFNMZYVGCJ-HDICACEKSA-N 0.000 claims 1
- LWVHHVOPXGLKST-UHFFFAOYSA-N 3-[6-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]pyrazin-2-yl]-1,3-oxazolidin-2-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C1=CN=CC(=N1)N1C(OCC1)=O)=O)C LWVHHVOPXGLKST-UHFFFAOYSA-N 0.000 claims 1
- LPQZXFAKLZIAFI-UHFFFAOYSA-N 5-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-1,3,3-trimethylpyrrolo[2,3-b]pyridin-2-one Chemical compound CN1C2=NC=C(C=C2C(C)(C)C1=O)N1C2=CC(=CC=C2C(C)(C)C1=O)C1=CN=C(C)N=C1 LPQZXFAKLZIAFI-UHFFFAOYSA-N 0.000 claims 1
- NHRJZHBUNAXEAH-UHFFFAOYSA-N 5-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-1-methyl-3H-imidazo[4,5-b]pyrazin-2-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C=1N=C2C(=NC=1)N(C(N2)=O)C)=O)C NHRJZHBUNAXEAH-UHFFFAOYSA-N 0.000 claims 1
- MXWCLVXVUNZMRJ-UHFFFAOYSA-N 6-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-1,3,3-trimethylpyrrolo[2,3-b]pyridin-2-one Chemical compound CN1C2=NC(=CC=C2C(C)(C)C1=O)N1C2=CC(=CC=C2C(C)(C)C1=O)C1=CN=C(C)N=C1 MXWCLVXVUNZMRJ-UHFFFAOYSA-N 0.000 claims 1
- JPMJOWQKHQVHID-UHFFFAOYSA-N 6-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-4-methyl-1,4-benzoxazin-3-one Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC=1)C)C1=CC2=C(OCC(N2C)=O)C=C1)=O)C JPMJOWQKHQVHID-UHFFFAOYSA-N 0.000 claims 1
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 1
- WKXGYHSGPGJMAH-UHFFFAOYSA-N 7-cyclopropyl-3-[3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-2-oxoindol-1-yl]-5,5-dimethylpyrrolo[2,3-c]pyridazin-6-one Chemical compound C1(CC1)N1C(C(C2=C1N=NC(=C2)N1C(C(C2=CC=C(C=C12)C=1C=NC(=NC=1)C)(C)C)=O)(C)C)=O WKXGYHSGPGJMAH-UHFFFAOYSA-N 0.000 claims 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 1
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- HWBNVFHGWZVKCO-UHFFFAOYSA-N CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC1)C)C1=C2C(=CN=C1)NC=C2)=O)C.N2C=CC1=C(C=CC=C21)N2C(C(C1=CC=C(C=C21)C=2C=NC(=NC2)C)(C)C)=O Chemical compound CC1(C(N(C2=CC(=CC=C12)C=1C=NC(=NC1)C)C1=C2C(=CN=C1)NC=C2)=O)C.N2C=CC1=C(C=CC=C21)N2C(C(C1=CC=C(C=C21)C=2C=NC(=NC2)C)(C)C)=O HWBNVFHGWZVKCO-UHFFFAOYSA-N 0.000 claims 1
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| EP15193355 | 2015-11-06 | ||
| EP15193355.3 | 2015-11-06 | ||
| PCT/EP2016/076315 WO2017076842A1 (en) | 2015-11-06 | 2016-11-02 | Indolin-2-one derivatives |
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| HUE050083T2 (hu) | 2015-11-06 | 2020-11-30 | Hoffmann La Roche | Indolin-2-on származékok |
| EP3371170B1 (en) | 2015-11-06 | 2019-07-31 | H. Hoffnabb-La Roche Ag | Indolin-2-one derivatives useful in the treatment of cns diseases |
| EP3371174B1 (en) | 2015-11-06 | 2021-03-17 | H. Hoffnabb-La Roche Ag | Indolin-2-one derivatives |
| CN108349942B (zh) | 2015-11-06 | 2021-03-30 | 豪夫迈·罗氏有限公司 | 用于治疗cns和相关疾病的二氢吲哚-2-酮衍生物 |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| CN114787363A (zh) | 2019-10-01 | 2022-07-22 | 恩派瑞安神经科学公司 | 对真菌进行遗传工程化以调节色胺表达 |
| WO2021231933A1 (en) * | 2020-05-15 | 2021-11-18 | Neucyte Pharmaceuticals | Anti-epileptic pharmaceutical compositions and use thereof |
| WO2023130078A2 (en) | 2021-12-31 | 2023-07-06 | Empyrean Neuroscience, Inc. | Genetically modified mycelium for producing psychotropic alkaloids |
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| DE3935514A1 (de) | 1989-10-25 | 1991-05-02 | Boehringer Mannheim Gmbh | Neue bicyclo-imidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| TW251284B (cg-RX-API-DMAC7.html) | 1992-11-02 | 1995-07-11 | Pfizer | |
| DE4427648A1 (de) | 1994-08-04 | 1996-02-08 | Basf Ag | N-Stubstituierte 3-Azabicyclo[3,2,0,]heptan-Derivate, ihre Herstellung und Verwendung |
| FR2757157B1 (fr) | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| WO2000040581A1 (en) | 1999-01-07 | 2000-07-13 | American Home Products Corporation | 3,4-dihydro-2h-benzo[1,4]oxazine derivatives |
| JP2004501192A (ja) | 2000-06-29 | 2004-01-15 | ニューロサーチ、アクティーゼルスカブ | Ｋｃｎｑカリウムチャネルモジュレーターとしての３−置換オキシインドール誘導体の使用方法 |
| WO2004060902A2 (en) | 2002-12-31 | 2004-07-22 | John K Buolamwini | Novel nucleoside transport inhibitors |
| KR20070011552A (ko) | 2004-05-11 | 2007-01-24 | 에지스 지오기스제르기아르 엔와이알티. | ５-ｈｔ７ 수용체 활성제로서 알킬 옥스인돌의 피리딘유도체 |
| US20060253263A1 (en) | 2005-04-11 | 2006-11-09 | Meshkin Brian J | Method to optimize drug selection, dosing and evaluation and to help predict therapeutic response and toxicity from immunosuppressant therapy |
| AR056317A1 (es) | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| AR053713A1 (es) | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
| CA2655829A1 (en) | 2006-06-26 | 2008-01-03 | Helicon Therapeutics, Inc. | Method of modulating neurite outgrowth by the use of a galanin-3 receptor antagonist |
| WO2008046083A2 (en) | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Use of oxindole compounds as therapeutic agents |
| PT2114921E (pt) | 2006-12-30 | 2013-03-26 | Abbott Gmbh & Co Kg | Derivado de oxindol substituído e sua utilização como ligante do recetor de vasopressina |
| UY30846A1 (es) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
| JO3126B1 (ar) * | 2007-11-14 | 2017-09-20 | Janssen Pharmaceutica Nv | مثبطات ناقل نيوكليوسيد متوازن اي ان تي 1 |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| JO3265B1 (ar) | 2008-12-09 | 2018-09-16 | Novartis Ag | مثبطات بيريديلوكسى اندولات vegf-r2 واستخدامها لعلاج المرض |
| SG11201501923WA (en) | 2012-09-13 | 2015-04-29 | Hoffmann La Roche | 2-oxo-2,3-dihydro-indoles for the treatment of cns disorders |
| KR101811549B1 (ko) * | 2013-06-19 | 2017-12-26 | 에프. 호프만-라 로슈 아게 | 인돌린-2-온 또는 피롤로-피리딘/피리미딘-2-온 유도체 |
| FR3017867A1 (fr) * | 2014-02-21 | 2015-08-28 | Inventiva | Nouveaux composes de type phenylazetidine carboxylate ou carboxamide |
| PE20161476A1 (es) * | 2014-06-26 | 2017-01-07 | Hoffmann La Roche | Derivados de indolin-2-ona o pirrolo-piridin-2-ona |
| HUE050083T2 (hu) | 2015-11-06 | 2020-11-30 | Hoffmann La Roche | Indolin-2-on származékok |
| CN108349942B (zh) | 2015-11-06 | 2021-03-30 | 豪夫迈·罗氏有限公司 | 用于治疗cns和相关疾病的二氢吲哚-2-酮衍生物 |
| EP3371174B1 (en) | 2015-11-06 | 2021-03-17 | H. Hoffnabb-La Roche Ag | Indolin-2-one derivatives |
| EP3371170B1 (en) | 2015-11-06 | 2019-07-31 | H. Hoffnabb-La Roche Ag | Indolin-2-one derivatives useful in the treatment of cns diseases |
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- 2016-11-02 WO PCT/EP2016/076315 patent/WO2017076842A1/en not_active Ceased
- 2016-11-02 JP JP2018522572A patent/JP6839184B2/ja active Active
- 2016-11-02 CN CN201680056575.2A patent/CN108137561B/zh active Active
- 2016-11-04 TW TW105135829A patent/TWI614244B/zh not_active IP Right Cessation
- 2016-11-04 AR ARP160103364A patent/AR106589A1/es unknown
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2018
- 2018-05-04 US US15/971,368 patent/US10519140B2/en active Active
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