ES2524423T3 - Inhibidores de KAT II - Google Patents
Inhibidores de KAT II Download PDFInfo
- Publication number
- ES2524423T3 ES2524423T3 ES11804801.6T ES11804801T ES2524423T3 ES 2524423 T3 ES2524423 T3 ES 2524423T3 ES 11804801 T ES11804801 T ES 11804801T ES 2524423 T3 ES2524423 T3 ES 2524423T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- compound
- cycloalkyl
- 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.)
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- 239000003112 inhibitor Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 163
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 95
- 125000003118 aryl group Chemical group 0.000 claims abstract description 91
- 125000001424 substituent group Chemical group 0.000 claims abstract description 88
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 239000007787 solid Substances 0.000 claims abstract description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 45
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- 125000005843 halogen group Chemical group 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 208000010877 cognitive disease Diseases 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 206010012289 Dementia Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 208000028698 Cognitive impairment Diseases 0.000 claims description 12
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- 241000124008 Mammalia Species 0.000 claims description 10
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- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
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- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
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- 208000021642 Muscular disease Diseases 0.000 claims description 3
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- 208000017442 Retinal disease Diseases 0.000 claims description 3
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- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 3
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 3
- 208000009205 Tinnitus Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 201000004810 Vascular dementia Diseases 0.000 claims description 3
- 206010047700 Vomiting Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
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- 208000006752 brain edema Diseases 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 230000007882 cirrhosis Effects 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 231100000040 eye damage Toxicity 0.000 claims description 3
- 230000010370 hearing loss Effects 0.000 claims description 3
- 231100000888 hearing loss Toxicity 0.000 claims description 3
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- 230000002218 hypoglycaemic effect Effects 0.000 claims description 3
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- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
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- 206010027599 migraine Diseases 0.000 claims description 3
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- 230000000926 neurological effect Effects 0.000 claims description 3
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- 208000033300 perinatal asphyxia Diseases 0.000 claims description 3
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 210000000278 spinal cord Anatomy 0.000 claims description 3
- 231100000886 tinnitus Toxicity 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- YEHNWRNMGIYLAL-NSHDSACASA-N (5s)-5-amino-2-benzyl-7-hydroxy-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@@H](C(N(O)C1=N2)=O)N)C1=CN2CC1=CC=CC=C1 YEHNWRNMGIYLAL-NSHDSACASA-N 0.000 claims description 2
- VRCGFKBFAAAERR-LBPRGKRZSA-N (5s)-5-amino-3-benzyl-2-ethyl-7-hydroxy-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@H](N)C(=O)N(O)C1=NN2CC)C1=C2CC1=CC=CC=C1 VRCGFKBFAAAERR-LBPRGKRZSA-N 0.000 claims description 2
- ABBLRYAESUTTSD-NSHDSACASA-N (5s)-5-amino-3-benzyl-7-hydroxy-1-methyl-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound O=C([C@@H](N)CC=12)N(O)C=1N(C)N=C2CC1=CC=CC=C1 ABBLRYAESUTTSD-NSHDSACASA-N 0.000 claims description 2
- AUAOKUNOKVGYJP-JTQLQIEISA-N (5s)-5-amino-7-hydroxy-2-phenyl-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@@H](C(N(O)C1=N2)=O)N)C1=CN2C1=CC=CC=C1 AUAOKUNOKVGYJP-JTQLQIEISA-N 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 208000027691 Conduct disease Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- YAYRMUVEORJPCX-UHFFFAOYSA-N pyrazolo[3,4-b]pyridin-3-one Chemical compound C1=CC=C2C(=O)N=NC2=N1 YAYRMUVEORJPCX-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 109
- 230000015572 biosynthetic process Effects 0.000 description 98
- 238000003786 synthesis reaction Methods 0.000 description 97
- 238000005160 1H NMR spectroscopy Methods 0.000 description 83
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
- 238000000034 method Methods 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 75
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 61
- 239000000243 solution Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 54
- 239000000203 mixture Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 27
- 238000000746 purification Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000005842 heteroatom Chemical group 0.000 description 21
- 238000010898 silica gel chromatography Methods 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
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- 230000002829 reductive effect Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000002367 halogens Chemical group 0.000 description 18
- 239000000651 prodrug Substances 0.000 description 18
- 229940002612 prodrug Drugs 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
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- 229910052736 halogen Inorganic materials 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
- 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 10
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
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- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 7
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Gastroenterology & Hepatology (AREA)
- Addiction (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41880210P | 2010-12-01 | 2010-12-01 | |
| US418802P | 2010-12-01 | ||
| PCT/IB2011/055158 WO2012073143A1 (en) | 2010-12-01 | 2011-11-17 | Kat ii inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2524423T3 true ES2524423T3 (es) | 2014-12-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11804801.6T Active ES2524423T3 (es) | 2010-12-01 | 2011-11-17 | Inhibidores de KAT II |
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| Country | Link |
|---|---|
| US (2) | US8598200B2 (enExample) |
| EP (1) | EP2646443B1 (enExample) |
| JP (1) | JP2013544277A (enExample) |
| KR (1) | KR101544290B1 (enExample) |
| CN (1) | CN103228660A (enExample) |
| AU (1) | AU2011336214B2 (enExample) |
| CA (1) | CA2819102A1 (enExample) |
| DK (1) | DK2646443T3 (enExample) |
| ES (1) | ES2524423T3 (enExample) |
| MX (1) | MX2013005773A (enExample) |
| SG (1) | SG190207A1 (enExample) |
| WO (1) | WO2012073143A1 (enExample) |
| ZA (1) | ZA201303360B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101522803B1 (ko) | 2010-12-01 | 2015-05-26 | 화이자 인코포레이티드 | Kat ii 억제제 |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| WO2015163339A1 (ja) * | 2014-04-23 | 2015-10-29 | 田辺三菱製薬株式会社 | 新規二環性または三環性複素環化合物 |
| WO2016164703A1 (en) | 2015-04-09 | 2016-10-13 | Eisai R & D Management Co., Ltd. | Fgfr4 inhibitors |
| WO2016164754A1 (en) | 2015-04-09 | 2016-10-13 | Eisai R&D Management Co., Ltd. | Fgfr4 inhibitors |
| EP3372601B1 (en) * | 2015-10-22 | 2022-09-21 | Mitsubishi Tanabe Pharma Corporation | Novel bicyclic heterocyclic compound |
| CN114599650A (zh) * | 2019-06-20 | 2022-06-07 | 肯塔基大学研究基金会 | DCN1/2介导的cullin类泛素化修饰的药学活性吡唑并-吡啶酮调节剂 |
| CR20220280A (es) | 2019-11-22 | 2022-09-02 | Incyte Corp | Terapia de combinación que comprende un inhibidor de alk2 y un inhibidor de jak2 |
| CN115916754A (zh) | 2020-05-05 | 2023-04-04 | 纽威伦特公司 | 杂芳族大环醚化学治疗剂 |
| BR112022022530A2 (pt) | 2020-05-05 | 2023-02-23 | Nuvalent Inc | Composto, composição farmacêutica, método de tratamento de câncer, método de inibição seletiva, método de redução de um nível de ros1 ou alk |
| WO2022165382A1 (en) * | 2021-01-29 | 2022-08-04 | Neurawell Therapeutics | Phenylethylidenehydrazine combination therapies |
| MX2024003738A (es) | 2021-10-01 | 2024-06-19 | Nuvalent Inc | Formas solidas, composiciones farmaceuticas y preparacion de compuestos de eter macrociclico heteroaromatico. |
| WO2025096956A1 (en) | 2023-11-03 | 2025-05-08 | Cellarity, Inc. | Dcn-1 modulating compounds and methods of use thereof |
| US12435087B2 (en) | 2023-11-03 | 2025-10-07 | Cellarity, Inc. | Modulators of DCN-1 and methods of use thereof |
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| US4282361A (en) | 1978-03-16 | 1981-08-04 | Massachusetts Institute Of Technology | Synthesis for 7-alkylamino-3-methylpyrazolo [4,3-d]pyrimidines |
| US5519055A (en) * | 1993-08-06 | 1996-05-21 | University Of Maryland At Baltimore | Substituted kynurenines and process for their preparation |
| US7276608B2 (en) * | 2003-07-11 | 2007-10-02 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
| GT200500186A (es) | 2004-07-07 | 2006-03-02 | Regimenes anticonceptivos con antagonistas del receptor de progesterona y kits | |
| WO2006046135A2 (en) | 2004-10-28 | 2006-05-04 | Pharmacia & Upjohn Company Llc | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
| CA2626897A1 (en) | 2005-11-03 | 2007-05-18 | Joshua Close | Histone deacetylase inhibitors with aryl-pyrazolyl motifs |
| US20090012075A1 (en) | 2006-01-12 | 2009-01-08 | Miller Thomas A | Fluorinated Arylamide Derivatives |
| EP2049548A1 (en) | 2006-07-27 | 2009-04-22 | UCB Pharma, S.A. | Fused oxazoles & thiazoles as histamine h3- receptor ligands |
| WO2009064836A2 (en) * | 2007-11-15 | 2009-05-22 | University Of Maryland, Baltimore | Kynurenine-aminotransferase inhibitors |
| WO2009095752A1 (en) * | 2008-01-29 | 2009-08-06 | Glenmark Pharmaceuticals, S.A. | Fused pyrazole derivatives as cannabinoid receptor modulators |
| WO2010014688A2 (en) | 2008-07-30 | 2010-02-04 | Bal Seal Engineering | Canted coil multi-metallic wire |
| DK2443092T3 (en) * | 2009-06-18 | 2015-04-27 | Pfizer | Bicyclic and tricyclic compounds as CAT-II inhibitors |
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2011
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- 2011-11-17 MX MX2013005773A patent/MX2013005773A/es active IP Right Grant
- 2011-11-17 KR KR1020137014065A patent/KR101544290B1/ko not_active Expired - Fee Related
- 2011-11-17 JP JP2013541446A patent/JP2013544277A/ja not_active Ceased
- 2011-11-17 AU AU2011336214A patent/AU2011336214B2/en not_active Expired - Fee Related
- 2011-11-17 CN CN2011800578092A patent/CN103228660A/zh active Pending
- 2011-11-17 SG SG2013035399A patent/SG190207A1/en unknown
- 2011-11-17 ES ES11804801.6T patent/ES2524423T3/es active Active
- 2011-11-17 CA CA2819102A patent/CA2819102A1/en not_active Abandoned
- 2011-11-17 WO PCT/IB2011/055158 patent/WO2012073143A1/en not_active Ceased
- 2011-11-17 DK DK11804801.6T patent/DK2646443T3/en active
- 2011-11-30 US US13/307,636 patent/US8598200B2/en not_active Expired - Fee Related
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2013
- 2013-05-09 ZA ZA2013/03360A patent/ZA201303360B/en unknown
- 2013-10-31 US US14/068,707 patent/US8933095B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20140057938A1 (en) | 2014-02-27 |
| ZA201303360B (en) | 2014-07-30 |
| SG190207A1 (en) | 2013-06-28 |
| US8598200B2 (en) | 2013-12-03 |
| EP2646443A1 (en) | 2013-10-09 |
| DK2646443T3 (en) | 2014-11-17 |
| JP2013544277A (ja) | 2013-12-12 |
| CN103228660A (zh) | 2013-07-31 |
| MX2013005773A (es) | 2013-06-18 |
| AU2011336214B2 (en) | 2015-08-20 |
| US20120302599A1 (en) | 2012-11-29 |
| AU2011336214A1 (en) | 2013-05-30 |
| KR101544290B1 (ko) | 2015-08-12 |
| WO2012073143A1 (en) | 2012-06-07 |
| US8933095B2 (en) | 2015-01-13 |
| EP2646443B1 (en) | 2014-09-24 |
| CA2819102A1 (en) | 2012-06-07 |
| KR20130108618A (ko) | 2013-10-04 |
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