TWI698435B - 作為吲哚胺２,３-二加氧酶和/或色氨酸２,３-二加氧酶抑制劑之新穎之５或８-取代之咪唑並［１，５－ａ］吡啶 - Google Patents
作為吲哚胺２,３-二加氧酶和/或色氨酸２,３-二加氧酶抑制劑之新穎之５或８-取代之咪唑並［１，５－ａ］吡啶 Download PDFInfo
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- TWI698435B TWI698435B TW105111144A TW105111144A TWI698435B TW I698435 B TWI698435 B TW I698435B TW 105111144 A TW105111144 A TW 105111144A TW 105111144 A TW105111144 A TW 105111144A TW I698435 B TWI698435 B TW I698435B
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- Prior art keywords
- alkyl
- haloalkyl
- compound
- aryl
- heteroaryl
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title abstract description 16
- 229960004799 tryptophan Drugs 0.000 title abstract description 10
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000006035 Tryptophane Substances 0.000 title abstract 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 title 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
- -1 8-substituted imidazo[1,5-a]pyridines Chemical class 0.000 claims abstract description 159
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 300
- 125000000217 alkyl group Chemical group 0.000 claims description 180
- 125000003118 aryl group Chemical group 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 118
- 229910052736 halogen Inorganic materials 0.000 claims description 111
- 150000002367 halogens Chemical class 0.000 claims description 111
- 125000001072 heteroaryl group Chemical group 0.000 claims description 111
- 239000001257 hydrogen Substances 0.000 claims description 108
- 125000000623 heterocyclic group Chemical group 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 106
- 150000002431 hydrogen Chemical class 0.000 claims description 79
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 66
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000000304 alkynyl group Chemical group 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- 102100040061 Indoleamine 2,3-dioxygenase 1 Human genes 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 101001037256 Homo sapiens Indoleamine 2,3-dioxygenase 1 Proteins 0.000 claims description 35
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 29
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 16
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical group C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 206010009944 Colon cancer Diseases 0.000 claims description 10
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
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- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 9
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 7
- 208000030507 AIDS Diseases 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 201000001441 melanoma Diseases 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims description 5
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
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- 206010014733 Endometrial cancer Diseases 0.000 claims description 5
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- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 206010038389 Renal cancer Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
- 208000009956 adenocarcinoma Diseases 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
- 201000010881 cervical cancer Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 201000004101 esophageal cancer Diseases 0.000 claims description 5
- 201000010536 head and neck cancer Diseases 0.000 claims description 5
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 201000010982 kidney cancer Diseases 0.000 claims description 5
- 201000007270 liver cancer Diseases 0.000 claims description 5
- 208000014018 liver neoplasm Diseases 0.000 claims description 5
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 201000002510 thyroid cancer Diseases 0.000 claims description 5
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
- 208000020790 biliary tract neoplasm Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 201000009036 biliary tract cancer Diseases 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 2
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 238000010839 reverse transcription Methods 0.000 claims 1
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- 239000011734 sodium Substances 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 122
- 239000007787 solid Substances 0.000 description 122
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- 239000012043 crude product Substances 0.000 description 103
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 63
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 39
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Immunology (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015076296 | 2015-04-10 | ||
| WOPCT/CN2015/076296 | 2015-04-10 |
Publications (2)
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| TW201706270A TW201706270A (zh) | 2017-02-16 |
| TWI698435B true TWI698435B (zh) | 2020-07-11 |
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| TW105111144A TWI698435B (zh) | 2015-04-10 | 2016-04-08 | 作為吲哚胺２,３-二加氧酶和/或色氨酸２,３-二加氧酶抑制劑之新穎之５或８-取代之咪唑並［１，５－ａ］吡啶 |
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| US (2) | US10280163B2 (enExample) |
| EP (1) | EP3280715B1 (enExample) |
| JP (1) | JP6806342B2 (enExample) |
| KR (1) | KR20170137165A (enExample) |
| CN (2) | CN107531693B (enExample) |
| TW (1) | TWI698435B (enExample) |
| WO (1) | WO2016161960A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI755426B (zh) * | 2016-09-24 | 2022-02-21 | 英屬開曼群島商百濟神州有限公司 | 作為吲哚胺2,3-二加氧酶和/或色胺酸2,3-二加氧酶選擇性抑制劑的新穎的5或8-取代的咪唑並[1,5-a]吡啶 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3280715B1 (en) | 2015-04-10 | 2020-11-25 | Beigene, Ltd. | NOVEL 5 OR 8-SUBSTITUTED IMIDAZO [1, 5-a]PYRIDINES AS INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES |
| GB201511790D0 (en) | 2015-07-06 | 2015-08-19 | Iomet Pharma Ltd | Pharmaceutical compound |
| WO2018036414A1 (zh) * | 2016-08-23 | 2018-03-01 | 北京诺诚健华医药科技有限公司 | 稠杂环类衍生物、其制备方法及其在医学上的应用 |
| TW201815766A (zh) | 2016-09-22 | 2018-05-01 | 美商普雷辛肯公司 | 用於ｉｄｏ及ｔｄｏ調節之化合物及方法以及其適應症 |
| WO2018136437A2 (en) * | 2017-01-17 | 2018-07-26 | Tesaro, Inc. | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| TW201920202A (zh) * | 2017-08-17 | 2019-06-01 | 瑞士商愛杜西亞製藥有限公司 | 吲哚胺2,3-二氧酶及/或色胺酸2,3-二氧酶的抑制劑 |
| KR102891807B1 (ko) * | 2017-08-22 | 2025-12-01 | 길리애드 사이언시즈, 인코포레이티드 | 치료 헤테로시클릭 화합물 |
| CN111601808B (zh) * | 2017-10-19 | 2023-09-08 | 捷思英达医药技术（上海）有限公司 | 杂环化合物及其组合物和使用方法 |
| WO2019076358A1 (en) * | 2017-10-19 | 2019-04-25 | Js Innopharm (Shanghai) Ltd | HETEROCYCLIC COMPOUNDS, COMPOSITIONS COMPRISING THE HETEROCYCLIC COMPOUND, AND METHODS OF USE THEREOF |
| CN107721915A (zh) * | 2017-11-12 | 2018-02-23 | 刘磊 | 一种氯羟吡啶毒性杂质dcal的制备及纯化方法 |
| US11472788B2 (en) | 2017-11-25 | 2022-10-18 | Beigene, Ltd. | Benzoimidazoles as selective inhibitors of indoleamine 2,3-dioxygenases |
| ES2907282T3 (es) * | 2018-01-15 | 2022-04-22 | Idorsia Pharmaceuticals Ltd | Inhibidores de la indoleamina 2,3-dioxigenasa y/o de la triptófano dioxigenasa |
| CN110092750B (zh) | 2018-01-29 | 2023-07-21 | 北京诺诚健华医药科技有限公司 | 五氟硫烷基取代的酰胺类化合物、其制备方法及其在医药学上的应用 |
| US11149011B2 (en) | 2018-03-20 | 2021-10-19 | Plexxikon Inc. | Compounds and methods for IDO and TDO modulation, and indications therefor |
| CN110526898A (zh) | 2018-05-25 | 2019-12-03 | 北京诺诚健华医药科技有限公司 | 3-吲唑啉酮类化合物、其制备方法及其在医药学上的应用 |
| EP3823604A4 (en) | 2018-07-17 | 2022-03-16 | Board of Regents, The University of Texas System | COMPOUNDS AS INHIBITORS OF INDOLAMINE-2,3-DIOXYGENASE AND/OR TRYPTOPHANE DIOXYGENASE |
| EP3873608A1 (en) | 2018-10-31 | 2021-09-08 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
| EP4371987B9 (en) | 2018-10-31 | 2025-11-26 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds as hpk1 inhibitors |
| CN109293588B (zh) * | 2018-11-14 | 2022-02-01 | 四川大学 | 一种具有ido1/tdo双靶点的小分子化合物及其制备方法与应用 |
| US11453681B2 (en) | 2019-05-23 | 2022-09-27 | Gilead Sciences, Inc. | Substituted eneoxindoles and uses thereof |
| US20220259212A1 (en) | 2019-07-11 | 2022-08-18 | Idorsia Pharmaceuticals Ltd | Inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan 2,3-dioxygenase |
| US11839659B2 (en) | 2020-07-02 | 2023-12-12 | Northwestern University | Proteolysis-targeting chimeric molecules (PROTACs) that induce degradation of indoleamine 2,3-dioxygenase (IDO) protein |
| TW202246259A (zh) | 2021-01-29 | 2022-12-01 | 瑞士商赫孚孟拉羅股份公司 | 吡唑醯胺衍生物 |
| BR112023017582A2 (pt) | 2021-03-05 | 2023-12-05 | Univ Basel | Composições para o tratamento de doenças ou condições associadas ao ebv |
| EP4052705A1 (en) | 2021-03-05 | 2022-09-07 | Universität Basel Vizerektorat Forschung | Compositions for the treatment of ebv associated diseases or conditions |
| WO2023133524A1 (en) * | 2022-01-06 | 2023-07-13 | Terran Biosciences, Inc. | A process for synthesizing ketanserin |
| WO2024117205A1 (ja) * | 2022-11-30 | 2024-06-06 | 北興化学工業株式会社 | 双環式ピリジン誘導体およびその塩、並びに、当該誘導体又はその塩を有効成分として含有することを特徴とする有害生物防除剤 |
| CN117534669A (zh) * | 2023-11-01 | 2024-02-09 | 上海凌凯医药科技有限公司 | 五元氮杂环并吡啶醇的制备方法 |
| WO2025260150A1 (en) * | 2024-06-21 | 2025-12-26 | Microbiológica Química E Farmacêutica Ltda. | Novel n-benzyl phthalimides for the treatment of pain. methods of preparation and therapeutic use |
| CN119707787B (zh) * | 2024-12-24 | 2025-09-19 | 陕西师范大学 | 一种光连续流动合成4-烷基吡啶类化合物的方法 |
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| JPH0971586A (ja) * | 1995-09-07 | 1997-03-18 | Yamanouchi Pharmaceut Co Ltd | 新規な二環性縮合イミダゾール誘導体 |
| WO2012142237A1 (en) * | 2011-04-15 | 2012-10-18 | Newlink Geneticks Corporation | Fused imidazole derivatives useful as ido inhibitors |
| WO2014159248A1 (en) * | 2013-03-14 | 2014-10-02 | Newlink Genetics Corporation | Tricyclic compounds as inhibitors of immunosuppression mediated by tryptophan metabolization |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2489560A1 (en) | 2002-06-27 | 2004-01-08 | Schering Aktiengesellschaft | Substituted quinoline ccr5 receptor antagonists |
| JP2006505570A (ja) | 2002-10-17 | 2006-02-16 | アムジエン・インコーポレーテツド | ベンズイミダゾール誘導体およびそれのバニロイド受容体リガンドとしての使用 |
| GB0226724D0 (en) * | 2002-11-15 | 2002-12-24 | Merck Sharp & Dohme | Therapeutic agents |
| US7432278B2 (en) | 2004-03-08 | 2008-10-07 | The University Of North Carolina At Chapel Hill | Dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents |
| FR2906250B1 (fr) | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| WO2008110523A1 (en) * | 2007-03-09 | 2008-09-18 | Probiodrug Ag | Imidazo [1,5-a] pyridine derivatives as inhibitors of glutaminyl cyclase |
| CN102532144B (zh) * | 2012-01-20 | 2014-09-10 | 辽宁思百得医药科技有限公司 | 一种新型吲哚胺-2,3-双加氧酶抑制剂及其制备方法和用途 |
| EP3280715B1 (en) | 2015-04-10 | 2020-11-25 | Beigene, Ltd. | NOVEL 5 OR 8-SUBSTITUTED IMIDAZO [1, 5-a]PYRIDINES AS INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES |
| JP2019528301A (ja) | 2016-08-26 | 2019-10-10 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | インドールアミン２，３−ジオキシゲナーゼの阻害剤およびその使用方法 |
| EP3515914A4 (en) | 2016-09-24 | 2020-04-15 | BeiGene, Ltd. | INNOVATIVE 5- OR 8-SUBSTITUTED IMIDAZO [1,5-A] PYRIDINE AS SELECTIVE INHIBITORS OF INDOLEAMINE AND / OR TRYPTOPHANE-2,3-DIOXYGENASES |
| US11472788B2 (en) | 2017-11-25 | 2022-10-18 | Beigene, Ltd. | Benzoimidazoles as selective inhibitors of indoleamine 2,3-dioxygenases |
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2016
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- 2016-04-08 JP JP2017552439A patent/JP6806342B2/ja active Active
- 2016-04-08 CN CN201680020381.7A patent/CN107531693B/zh not_active Expired - Fee Related
- 2016-04-08 US US15/564,666 patent/US10280163B2/en active Active
- 2016-04-08 WO PCT/CN2016/078787 patent/WO2016161960A1/en not_active Ceased
- 2016-04-08 CN CN201910357804.XA patent/CN110872289A/zh active Pending
- 2016-04-08 KR KR1020177032633A patent/KR20170137165A/ko not_active Abandoned
- 2016-04-08 TW TW105111144A patent/TWI698435B/zh not_active IP Right Cessation
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2019
- 2019-03-27 US US16/366,353 patent/US10647714B2/en active Active
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| JPH0971586A (ja) * | 1995-09-07 | 1997-03-18 | Yamanouchi Pharmaceut Co Ltd | 新規な二環性縮合イミダゾール誘導体 |
| WO2012142237A1 (en) * | 2011-04-15 | 2012-10-18 | Newlink Geneticks Corporation | Fused imidazole derivatives useful as ido inhibitors |
| WO2014159248A1 (en) * | 2013-03-14 | 2014-10-02 | Newlink Genetics Corporation | Tricyclic compounds as inhibitors of immunosuppression mediated by tryptophan metabolization |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI755426B (zh) * | 2016-09-24 | 2022-02-21 | 英屬開曼群島商百濟神州有限公司 | 作為吲哚胺2,3-二加氧酶和/或色胺酸2,3-二加氧酶選擇性抑制劑的新穎的5或8-取代的咪唑並[1,5-a]吡啶 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018514518A (ja) | 2018-06-07 |
| EP3280715A4 (en) | 2019-03-13 |
| KR20170137165A (ko) | 2017-12-12 |
| US10280163B2 (en) | 2019-05-07 |
| US20190284184A1 (en) | 2019-09-19 |
| HK1244787A1 (zh) | 2018-08-17 |
| JP6806342B2 (ja) | 2021-01-06 |
| CN110872289A (zh) | 2020-03-10 |
| CN107531693B (zh) | 2021-07-06 |
| US10647714B2 (en) | 2020-05-12 |
| CN107531693A (zh) | 2018-01-02 |
| WO2016161960A1 (en) | 2016-10-13 |
| EP3280715A1 (en) | 2018-02-14 |
| EP3280715B1 (en) | 2020-11-25 |
| TW201706270A (zh) | 2017-02-16 |
| US20180072716A1 (en) | 2018-03-15 |
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