TWI504604B - 雜環化合物及其用途 - Google Patents
雜環化合物及其用途 Download PDFInfo
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- TWI504604B TWI504604B TW100128311A TW100128311A TWI504604B TW I504604 B TWI504604 B TW I504604B TW 100128311 A TW100128311 A TW 100128311A TW 100128311 A TW100128311 A TW 100128311A TW I504604 B TWI504604 B TW I504604B
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- optionally substituted
- halogen atom
- substituted
- compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
- -1 tetrahydrofuranyloxy Chemical group 0.000 claims description 354
- 150000001875 compounds Chemical class 0.000 claims description 331
- 125000005843 halogen group Chemical group 0.000 claims description 269
- 125000001424 substituent group Chemical group 0.000 claims description 202
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 150
- 150000003839 salts Chemical class 0.000 claims description 126
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 119
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 100
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 96
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 78
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 66
- 239000003814 drug Substances 0.000 claims description 62
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 56
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 56
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 51
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 238000011282 treatment Methods 0.000 claims description 36
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 31
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 30
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 30
- 125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 26
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 25
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
- 201000000980 schizophrenia Diseases 0.000 claims description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 23
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 108090000078 AMPA Receptors Proteins 0.000 claims description 21
- 102000003678 AMPA Receptors Human genes 0.000 claims description 21
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 19
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 19
- 230000036961 partial effect Effects 0.000 claims description 19
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 17
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 17
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 16
- 229930192474 thiophene Natural products 0.000 claims description 16
- 208000024827 Alzheimer disease Diseases 0.000 claims description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
- 150000001924 cycloalkanes Chemical class 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- 125000006612 decyloxy group Chemical group 0.000 claims description 11
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 10
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 10
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 10
- 229940126585 therapeutic drug Drugs 0.000 claims description 10
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 claims description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 7
- YIISYHGSPQJEBJ-UHFFFAOYSA-N C1=CCCC1.N1N=CC=CC2=C1C=CC=C2 Chemical compound C1=CCCC1.N1N=CC=CC2=C1C=CC=C2 YIISYHGSPQJEBJ-UHFFFAOYSA-N 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000003623 enhancer Substances 0.000 claims description 7
- 206010022437 insomnia Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 241000534944 Thia Species 0.000 claims description 4
- 201000002859 sleep apnea Diseases 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 133
- 235000002639 sodium chloride Nutrition 0.000 description 118
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 125000000623 heterocyclic group Chemical group 0.000 description 65
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000002904 solvent Substances 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- 229910052757 nitrogen Inorganic materials 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 229940079593 drug Drugs 0.000 description 54
- 238000000034 method Methods 0.000 description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 description 50
- 239000002585 base Substances 0.000 description 49
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 229910052731 fluorine Inorganic materials 0.000 description 36
- 125000003277 amino group Chemical class 0.000 description 33
- 125000001153 fluoro group Chemical group F* 0.000 description 33
- 230000035484 reaction time Effects 0.000 description 30
- 229910052717 sulfur Inorganic materials 0.000 description 30
- 150000001335 aliphatic alkanes Chemical class 0.000 description 28
- 125000004429 atom Chemical group 0.000 description 28
- 125000005842 heteroatom Chemical group 0.000 description 28
- 125000004430 oxygen atom Chemical group O* 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- 238000010511 deprotection reaction Methods 0.000 description 27
- 125000004434 sulfur atom Chemical group 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 17
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
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- 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 14
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 14
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- 230000007062 hydrolysis Effects 0.000 description 14
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 125000002950 monocyclic group Chemical group 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
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- 125000006239 protecting group Chemical group 0.000 description 14
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- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 13
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- 125000000524 functional group Chemical group 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
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- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 10
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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| SI2603513T1 (sl) * | 2010-08-10 | 2020-07-31 | Takeda Pharmaceutical Company Limited | Heterociklična spojina in njena uporaba kot pozitivni alosterični modulator receptorja AMPA |
| WO2012137982A2 (en) * | 2011-04-05 | 2012-10-11 | Takeda Pharmaceutical Company Limited | Sulfonamide derivative and use thereof |
| US9493484B2 (en) | 2012-02-08 | 2016-11-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| BR112015031249A2 (pt) * | 2013-06-13 | 2017-07-25 | Veroscience Llc | método de tratamento, método para tratar um distúrbio metabólico ou um elemento chave do mesmo, método para normalizar um ritmo diário de liberação de dopamina no sumn, método para estimular a liberação de dopamina de neurônios dopaminérgicos no sumn de um indivíduo e composição farmacêutica |
| CN105324376B (zh) | 2013-06-27 | 2017-06-23 | 辉瑞大药厂 | 杂芳族化合物及其作为多巴胺d1配体的用途 |
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| MD4889C1 (ro) | 2013-12-03 | 2024-10-31 | Фмк Корпорейшн | Pirolidinone în calitate de erbicide |
| WO2016003997A1 (en) | 2014-07-02 | 2016-01-07 | E. I. Du Pont De Nemours And Company | Piperidinone herbicides |
| JP6611816B2 (ja) | 2014-12-08 | 2019-11-27 | エフ エム シー コーポレーション | ３−オキソ−３−（アリールアミノ）プロパノエイト、その製造方法、およびピロリジノンの製造におけるその使用 |
| US10405547B2 (en) | 2015-04-10 | 2019-09-10 | Fmc Corporation | Substituted cyclic amides as herbicides |
| EP3288928B1 (en) | 2015-04-27 | 2021-10-13 | FMC Corporation | Butyrolactones as herbicides |
| AU2016255431B2 (en) * | 2015-04-29 | 2020-05-07 | Janssen Pharmaceutica Nv | Imidazopyrazines and pyrazolopyrimidines and their use as AMPA receptor modulators |
| HRP20210403T1 (hr) | 2015-04-29 | 2021-10-29 | Janssen Pharmaceutica Nv | Azabenzimidazoli i njihova uporaba kao modulatora ampa receptora |
| CA2980643C (en) | 2015-05-12 | 2023-10-17 | E I Du Pont De Nemours And Company | Aryl substituted bicyclic compounds as herbicides |
| CA2983590C (en) | 2015-05-29 | 2021-11-30 | E I Du Pont De Nemours And Company | Substituted cyclic amides as herbicides |
| JP6949730B2 (ja) | 2015-06-02 | 2021-10-13 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | 置換環状アミドおよび除草剤としてのそれらの使用 |
| AU2016303209B2 (en) | 2015-07-31 | 2021-04-01 | Fmc Corporation | Cyclic N-carboxamide compounds useful as herbicides |
| PL3331892T3 (pl) * | 2015-08-06 | 2019-11-29 | Hoffmann La Roche | Sposób wytwarzania pochodnych kwasu GalNAc |
| US20170181292A1 (en) * | 2015-12-16 | 2017-06-22 | Rohm And Haas Electronic Materials Llc | Method for forming organic coating on nickel surface |
| CN105669731B (zh) * | 2016-01-10 | 2017-06-30 | 沧州普瑞东方科技有限公司 | 一种4‑(4‑烷基环己氧基)苯硼酸的合成方法 |
| BR112019012910B1 (pt) | 2016-12-21 | 2023-10-17 | Fmc Corporation | Composto, composição herbicida, mistura herbicida e método para controlar o crescimento de vegetação indesejável |
| CN107892697B (zh) | 2016-12-26 | 2020-11-03 | 郑州泰基鸿诺医药股份有限公司 | 一种[1,3]噻嗪-2-胺类化合物及应用，药物组合物 |
| SG11201908640TA (en) | 2017-03-21 | 2019-10-30 | Fmc Corp | Pyrrolidinones and a process to prepare them |
| BR112019019551A2 (pt) | 2017-03-21 | 2020-04-22 | Fmc Corp | mistura, e, método para controlar o crescimento de vegetação indesejada |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| JP7250686B2 (ja) * | 2017-10-06 | 2023-04-03 | 武田薬品工業株式会社 | 複素環化合物 |
| EP3693360B1 (en) * | 2017-10-06 | 2023-12-13 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds |
| PL4031552T3 (pl) | 2019-09-16 | 2025-03-17 | Takeda Pharmaceutical Company Limited | Pochodne azolowo-skondensowanych pirydazyn-3(2h)-onów |
| TW202207944A (zh) * | 2020-05-15 | 2022-03-01 | 日商武田藥品工業股份有限公司 | 抑鬱症之治療 |
| CN113943294A (zh) * | 2020-07-15 | 2022-01-18 | 成都海博为药业有限公司 | 一种作为btk抑制剂的化合物及其制备方法与用途 |
| WO2025226591A1 (en) | 2024-04-22 | 2025-10-30 | Neurocrine Biosciences, Inc. | Methods of administering 9-[4-(cyclohexyloxy)phenyl]-7-methyl-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide without side effects |
| WO2026050231A1 (en) | 2024-08-27 | 2026-03-05 | Neurocrine Biosciences, Inc. | Method of treating a bipolar disorder |
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| JPH0285851A (ja) * | 1988-09-22 | 1990-03-27 | Konica Corp | 新規な写真用カプラー |
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