JP2018519253A5 - - Google Patents
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- Publication number
- JP2018519253A5 JP2018519253A5 JP2017556818A JP2017556818A JP2018519253A5 JP 2018519253 A5 JP2018519253 A5 JP 2018519253A5 JP 2017556818 A JP2017556818 A JP 2017556818A JP 2017556818 A JP2017556818 A JP 2017556818A JP 2018519253 A5 JP2018519253 A5 JP 2018519253A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- indoline
- carboxamide
- fluoro
- ethyl
- 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
Links
- -1 pyridindiyl Chemical group 0.000 claims description 640
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 28
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 9
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 208000035475 disorder Diseases 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 238000011282 treatment Methods 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 12
- 230000002265 prevention Effects 0.000 claims 12
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 11
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 11
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 208000016285 Movement disease Diseases 0.000 claims 8
- 208000028017 Psychotic disease Diseases 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 8
- 208000019901 Anxiety disease Diseases 0.000 claims 7
- 230000036506 anxiety Effects 0.000 claims 7
- 208000027776 Extrapyramidal disease Diseases 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 6
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 6
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 201000000980 schizophrenia Diseases 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 5
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 208000027626 Neurocognitive disease Diseases 0.000 claims 5
- 208000018300 basal ganglia disease Diseases 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- 208000012661 Dyskinesia Diseases 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 230000006399 behavior Effects 0.000 claims 4
- 230000037361 pathway Effects 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- VUPPNIBEGQJLEG-UHFFFAOYSA-N 2,3-dihydro-1h-indole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1CCN2 VUPPNIBEGQJLEG-UHFFFAOYSA-N 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 230000006870 function Effects 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 208000009017 Athetosis Diseases 0.000 claims 2
- 208000030336 Bipolar and Related disease Diseases 0.000 claims 2
- 206010008748 Chorea Diseases 0.000 claims 2
- 206010012239 Delusion Diseases 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 208000004547 Hallucinations Diseases 0.000 claims 2
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- LQSZIELGYRULLD-UHFFFAOYSA-N N-[4-[(3,4,5-trifluorophenyl)methyl]pyridin-2-yl]-2,3-dihydro-1H-indole-4-carboxamide Chemical compound N1CCC=2C(=CC=CC1=2)C(=O)NC1=NC=CC(=C1)CC1=CC(=C(C(=C1)F)F)F LQSZIELGYRULLD-UHFFFAOYSA-N 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 102000003946 Prolactin Human genes 0.000 claims 2
- 108010057464 Prolactin Proteins 0.000 claims 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims 2
- 208000018839 Wilson disease Diseases 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 2
- 208000012601 choreatic disease Diseases 0.000 claims 2
- 230000007585 cortical function Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 231100000868 delusion Toxicity 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 210000001652 frontal lobe Anatomy 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- 230000007106 neurocognition Effects 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 229940097325 prolactin Drugs 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 208000016686 tic disease Diseases 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- ORFUKCGRDYFOFJ-UHFFFAOYSA-N 1-[1-oxido-5-[[3-(trifluoromethyl)phenyl]methyl]pyridin-1-ium-3-yl]-2,3-dihydroindole-4-carboxamide Chemical compound C(N)(=O)C1=C2CCN(C2=CC=C1)C=1C=[N+](C=C(C=1)CC1=CC(=CC=C1)C(F)(F)F)[O-] ORFUKCGRDYFOFJ-UHFFFAOYSA-N 0.000 claims 1
- WMFACUQHPBZUMK-FQEVSTJZSA-N 1-[1-oxido-5-[[3-(trifluoromethyl)phenyl]methyl]pyridin-1-ium-3-yl]-N-[(3S)-oxolan-3-yl]-2,3-dihydroindole-4-carboxamide Chemical compound O1C[C@H](CC1)NC(=O)C1=C2CCN(C2=CC=C1)C=1C=[N+](C=C(C=1)CC1=CC(=CC=C1)C(F)(F)F)[O-] WMFACUQHPBZUMK-FQEVSTJZSA-N 0.000 claims 1
- DBJWCTAEEGRBFM-UHFFFAOYSA-N 1-[4-[(3,5-difluorophenyl)methyl]pyridin-2-yl]-N-methyl-2,3-dihydroindole-4-carboxamide Chemical compound FC=1C=C(CC2=CC(=NC=C2)N2CCC=3C(=CC=CC2=3)C(=O)NC)C=C(C=1)F DBJWCTAEEGRBFM-UHFFFAOYSA-N 0.000 claims 1
- BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims 1
- 206010000117 Abnormal behaviour Diseases 0.000 claims 1
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 206010001540 Akathisia Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 206010058504 Ballismus Diseases 0.000 claims 1
- 208000011597 CGF1 Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000000269 Hyperkinesis Diseases 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- HJQCELFTHPDMIP-UHFFFAOYSA-N OCCNC(=O)C=1C=2CCN(C=2C=CC=1)C1=NC=CC(=C1)CC1=CC(=C(C(=C1)F)F)F Chemical compound OCCNC(=O)C=1C=2CCN(C=2C=CC=1)C1=NC=CC(=C1)CC1=CC(=C(C(=C1)F)F)F HJQCELFTHPDMIP-UHFFFAOYSA-N 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 208000001431 Psychomotor Agitation Diseases 0.000 claims 1
- 208000024791 Schizotypal Personality disease Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 206010042008 Stereotypy Diseases 0.000 claims 1
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 206010044565 Tremor Diseases 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- 230000009471 action Effects 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000006986 amnesia Effects 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 229940005530 anxiolytics Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 229960001948 caffeine Drugs 0.000 claims 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 206010007776 catatonia Diseases 0.000 claims 1
- 230000001054 cortical effect Effects 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000001066 destructive effect Effects 0.000 claims 1
- 201000002545 drug psychosis Diseases 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002996 emotional effect Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000000380 hallucinogen Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000035873 hypermotility Effects 0.000 claims 1
- 208000031424 hyperprolactinemia Diseases 0.000 claims 1
- 230000005032 impulse control Effects 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 240000004308 marijuana Species 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004899 motility Effects 0.000 claims 1
- 230000008450 motivation Effects 0.000 claims 1
- 230000002151 myoclonic effect Effects 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 claims 1
- 230000000701 neuroleptic effect Effects 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 230000001314 paroxysmal effect Effects 0.000 claims 1
- 229940049953 phenylacetate Drugs 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 229940125723 sedative agent Drugs 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
- 208000015891 sexual disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 230000004039 social cognition Effects 0.000 claims 1
- 201000001716 specific phobia Diseases 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000000021 stimulant Substances 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562154523P | 2015-04-29 | 2015-04-29 | |
| US62/154,523 | 2015-04-29 | ||
| PCT/US2016/030105 WO2016176571A1 (en) | 2015-04-29 | 2016-04-29 | 1-heteroaryl-indoline-4-carboxamides as modulators of gpr52 useful for the treatment or prevention of disorders related thereto |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018519253A JP2018519253A (ja) | 2018-07-19 |
| JP2018519253A5 true JP2018519253A5 (https=) | 2019-06-06 |
| JP6673939B2 JP6673939B2 (ja) | 2020-04-01 |
Family
ID=56015108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556818A Active JP6673939B2 (ja) | 2015-04-29 | 2016-04-29 | Ｇｐｒ５２に関連する障害の治療または予防に有用なｇｐｒ５２のモジュレーターとしての１−ヘテロアリール−インドリン−４−カルボキサミド |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9676758B2 (https=) |
| EP (1) | EP3292114B1 (https=) |
| JP (1) | JP6673939B2 (https=) |
| KR (1) | KR20180004193A (https=) |
| CN (1) | CN108174603B (https=) |
| AU (1) | AU2016255510A1 (https=) |
| BR (1) | BR112017022987A2 (https=) |
| CA (1) | CA2984153A1 (https=) |
| CL (1) | CL2017002738A1 (https=) |
| EA (1) | EA034244B1 (https=) |
| ES (1) | ES2784316T3 (https=) |
| IL (1) | IL255185A0 (https=) |
| MX (1) | MX373876B (https=) |
| PH (1) | PH12017501961A1 (https=) |
| WO (1) | WO2016176571A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111792990A (zh) * | 2019-04-09 | 2020-10-20 | 中国科学院上海药物研究所 | 一种不饱和酮类化合物、其制备方法和用途 |
| CA3156474A1 (en) * | 2019-11-08 | 2021-05-14 | Heptares Therapeutics Limited | GPR52 MODULATING COMPOUNDS |
| GB202003668D0 (en) | 2020-03-13 | 2020-04-29 | Heptares Therapeutics Ltd | GPR52 Modulator compounds |
| BR112022018996A2 (pt) * | 2020-03-30 | 2022-11-01 | Boehringer Ingelheim Int | 3-fenoxiazetidin-1-il-pirazinas substituídas apresentando atividade agonística do gpr52". |
| TW202206413A (zh) * | 2020-04-22 | 2022-02-16 | 美商紐羅克里生物科學有限公司 | Gpr52調節劑及其使用方法 |
| GB202013558D0 (en) | 2020-08-28 | 2020-10-14 | Heptares Therapeutics Ltd | GRP52 Modularor compounds |
| EP4330232A1 (en) | 2021-04-26 | 2024-03-06 | Neurocrine Biosciences, Inc. | Gpr52 modulators and methods of use |
| US12115157B2 (en) | 2021-09-14 | 2024-10-15 | Boehringer Ingelheim International Gmbh | 3-phenoxyazetidin-1-yl-heteroaryl pyrrolidine derivatives and the use thereof as medicament |
| GB202113186D0 (en) | 2021-09-15 | 2021-10-27 | Heptares Therapeutics Ltd | GPR52 Modulator compounds |
| WO2024091541A1 (en) * | 2022-10-26 | 2024-05-02 | Neurocrine Biosciences, Inc. | Compounds and compositions as gpr52 modulators |
| JP2026508053A (ja) * | 2022-10-26 | 2026-03-10 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | Ｇｐｒ５２モジュレーターとしての化合物および組成物 |
| WO2024091542A1 (en) * | 2022-10-26 | 2024-05-02 | Neurocrine Biosciences, Inc. | Compounds and compositions as gpr52 modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2043744A2 (en) * | 2006-07-13 | 2009-04-08 | SmithKline Beecham Corporation | Chemical compounds |
| WO2009107391A1 (ja) * | 2008-02-27 | 2009-09-03 | 武田薬品工業株式会社 | ６員芳香環含有化合物 |
| FR2928645A1 (fr) * | 2008-03-14 | 2009-09-18 | Sanofi Aventis Sa | Nouveaux derives de carbazole inhibiteurs d'hsp90, compositions les contenant et utilisation |
| JPWO2009157196A1 (ja) * | 2008-06-25 | 2011-12-08 | 武田薬品工業株式会社 | アミド化合物 |
| US20100041891A1 (en) | 2008-08-12 | 2010-02-18 | Takeda Pharmaceutical Company Limited | Amide compound |
| AR077214A1 (es) * | 2009-06-24 | 2011-08-10 | Neurocrine Biosciences Inc | Heterociclos nitrogenados y composiciones farmaceuticas que los contienen |
| JP2012082175A (ja) * | 2010-10-14 | 2012-04-26 | Daiichi Sankyo Co Ltd | インドリン化合物を含有する医薬組成物 |
-
2016
- 2016-04-29 KR KR1020177034516A patent/KR20180004193A/ko not_active Withdrawn
- 2016-04-29 WO PCT/US2016/030105 patent/WO2016176571A1/en not_active Ceased
- 2016-04-29 EA EA201792375A patent/EA034244B1/ru not_active IP Right Cessation
- 2016-04-29 ES ES16723592T patent/ES2784316T3/es active Active
- 2016-04-29 BR BR112017022987A patent/BR112017022987A2/pt not_active Application Discontinuation
- 2016-04-29 CA CA2984153A patent/CA2984153A1/en not_active Abandoned
- 2016-04-29 AU AU2016255510A patent/AU2016255510A1/en not_active Abandoned
- 2016-04-29 US US15/143,026 patent/US9676758B2/en active Active
- 2016-04-29 EP EP16723592.8A patent/EP3292114B1/en active Active
- 2016-04-29 MX MX2017013853A patent/MX373876B/es active IP Right Grant
- 2016-04-29 CN CN201680038190.3A patent/CN108174603B/zh active Active
- 2016-04-29 JP JP2017556818A patent/JP6673939B2/ja active Active
-
2017
- 2017-10-22 IL IL255185A patent/IL255185A0/en unknown
- 2017-10-27 PH PH12017501961A patent/PH12017501961A1/en unknown
- 2017-10-30 CL CL2017002738A patent/CL2017002738A1/es unknown
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