CN106632082A - 一类对gpr84具有激动作用的化合物及其制备方法和用途 - Google Patents
一类对gpr84具有激动作用的化合物及其制备方法和用途 Download PDFInfo
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- CN106632082A CN106632082A CN201510745971.3A CN201510745971A CN106632082A CN 106632082 A CN106632082 A CN 106632082A CN 201510745971 A CN201510745971 A CN 201510745971A CN 106632082 A CN106632082 A CN 106632082A
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- compound
- alkyl
- dissolved
- phenyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 102100033864 G-protein coupled receptor 84 Human genes 0.000 title abstract description 30
- 101001069589 Homo sapiens G-protein coupled receptor 84 Proteins 0.000 title abstract 2
- 230000001270 agonistic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 5
- 206010040047 Sepsis Diseases 0.000 claims abstract description 3
- 208000013223 septicemia Diseases 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- -1 acetenyl Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 150000002431 hydrogen Chemical class 0.000 claims description 5
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- 238000006467 substitution reaction Methods 0.000 claims description 5
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
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- C—CHEMISTRY; METALLURGY
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- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
6-OAU起始浓度 | 6-OAU配样板浓度 | 6-OAU最终工作浓度 |
10mM(含100%DMSO) | 30μM(含3%DMSO) | 100μM(含1%DMSO) |
1mM(含100%DMSO) | 30μM(含3%DMSO) | 10μM(含1%DMSO) |
100μM(含100%DMSO) | 3μM(含3%DMSO) | 1μM(含1%DMSO) |
10μM(含100%DMSO) | 300nM(含3%DMSO) | 100nM(含1%DMSO) |
1μM(含100%DMSO) | 30nM(含3%DMSO) | 10nM(含1%DMSO) |
100nM(含100%DMSO) | 3nM(含3%DMSO) | 1nM(含1%DMSO) |
10nM(含100%DMSO) | 0.3nM(含3%DMSO) | 0.1nM(含1%DMSO) |
100%DMSO | 3%DMSO | 1%DMSO |
Claims (8)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510745971.3A CN106632082B (zh) | 2015-11-04 | 2015-11-04 | 一类对gpr84具有激动作用的化合物及其制备方法和用途 |
PCT/CN2016/104165 WO2017076264A1 (zh) | 2015-11-04 | 2016-11-01 | 一类对gpr84具有激动作用的化合物及其制备方法和用途 |
EP16861532.6A EP3372590A4 (en) | 2015-11-04 | 2016-11-01 | Compounds having agonistic effect for gpr84, preparation method for compounds and use of compounds |
JP2018522950A JP2019500322A (ja) | 2015-11-04 | 2016-11-01 | Gpr84に対してアゴニスト作用を有する化合物及びその製造方法、並びに使用 |
US15/772,105 US20180237399A1 (en) | 2015-11-04 | 2016-11-01 | Compounds having agonistic effect against gpr84, preparation method for compounds and use of compounds |
KR1020187015198A KR20180073671A (ko) | 2015-11-04 | 2016-11-01 | Gpr84에 대하여 작용 효과를 구비하는 화합물 및 이의 제조방법과 용도 |
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CN201510745971.3A CN106632082B (zh) | 2015-11-04 | 2015-11-04 | 一类对gpr84具有激动作用的化合物及其制备方法和用途 |
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CN106632082A true CN106632082A (zh) | 2017-05-10 |
CN106632082B CN106632082B (zh) | 2020-10-09 |
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US (1) | US20180237399A1 (zh) |
EP (1) | EP3372590A4 (zh) |
JP (1) | JP2019500322A (zh) |
KR (1) | KR20180073671A (zh) |
CN (1) | CN106632082B (zh) |
WO (1) | WO2017076264A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115279758A (zh) * | 2020-01-10 | 2022-11-01 | 皮莱环球有限责任公司 | 用于慢性障碍的化合物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021123394A1 (en) | 2019-12-20 | 2021-06-24 | University Of Copenhagen | G protein-coupled receptor modulators and a pharmaceutical composition |
WO2022223831A2 (en) * | 2021-04-23 | 2022-10-27 | Universität Zürich | A hydroxycarboxylic acid for the treatment of cancer |
EP4355743A1 (en) | 2021-06-18 | 2024-04-24 | University of Copenhagen | Polysubstituted 4-hydroxypyridine and 4-hydroxyquinoline derivatives as gpr84 antagonists |
WO2024028364A1 (en) * | 2022-08-02 | 2024-02-08 | Liminal Biosciences Limited | Aryl-triazolyl and related gpr84 antagonists and uses thereof |
WO2024028365A1 (en) * | 2022-08-02 | 2024-02-08 | Liminal Biosciences Limited | Substituted pyridone gpr84 antagonists and uses thereof |
Citations (5)
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US3974162A (en) * | 1972-12-21 | 1976-08-10 | American Home Products Corporation | 4-Pyrimidinylthioacetic acid derivatives |
CN1134697A (zh) * | 1993-11-12 | 1996-10-30 | 厄普约翰公司 | 嘧啶-硫烷基和烷基醚化合物 |
WO2011101740A1 (en) * | 2010-02-16 | 2011-08-25 | Actavis Group Ptc Ehf | Improved processes for preparing ticagrelor intermediate, 4,6-dichloro-5-nitro-2-(propylthio)pyrimidine |
CN104781731A (zh) * | 2012-12-04 | 2015-07-15 | Az电子材料卢森堡有限公司 | 正性工作光敏材料 |
WO2015108938A1 (en) * | 2014-01-17 | 2015-07-23 | Valent Biosciences Corporation | S-benzylthiouracil compounds and methods of enhancing plant root growth |
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US2513550A (en) * | 1946-12-23 | 1950-07-04 | American Cyanamid Co | Preparation of 2-substituted pyrimidines |
US2635960A (en) * | 1950-04-18 | 1953-04-21 | Gen Aniline & Film Corp | High-speed silver dye bleachout taking and printing film |
CH509039A (de) * | 1967-10-02 | 1971-06-30 | Ici Ltd | Handelsfähiges fungizides Mittel und Verwendung zur Bekämpfung von Pilzkrankheiten von Pflanzen |
US4478635A (en) * | 1982-01-11 | 1984-10-23 | Ciba-Geigy Corporation | N-Arylsulfonyl-N'-pyrimidinylureas |
US4912100A (en) * | 1986-10-15 | 1990-03-27 | Toray Industries, Inc. | Platinum complex, process for preparing same and antitumor agent |
AU2001231154A1 (en) * | 2000-01-24 | 2001-07-31 | Adherex Technologies Inc. | Peptidomimetic modulators of cell adhesion |
CN1976905A (zh) * | 2004-03-30 | 2007-06-06 | 大正制药株式会社 | 嘧啶衍生物以及与其应用有关的治疗方法 |
WO2009086303A2 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
CA2724733A1 (en) * | 2008-05-19 | 2009-11-26 | The University Of Tennessee Research Foundation | Pyrimidine classical cannabinoid compounds and related methods of use |
-
2015
- 2015-11-04 CN CN201510745971.3A patent/CN106632082B/zh active Active
-
2016
- 2016-11-01 US US15/772,105 patent/US20180237399A1/en not_active Abandoned
- 2016-11-01 KR KR1020187015198A patent/KR20180073671A/ko not_active Application Discontinuation
- 2016-11-01 EP EP16861532.6A patent/EP3372590A4/en not_active Withdrawn
- 2016-11-01 WO PCT/CN2016/104165 patent/WO2017076264A1/zh active Application Filing
- 2016-11-01 JP JP2018522950A patent/JP2019500322A/ja active Pending
Patent Citations (5)
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---|---|---|---|---|
US3974162A (en) * | 1972-12-21 | 1976-08-10 | American Home Products Corporation | 4-Pyrimidinylthioacetic acid derivatives |
CN1134697A (zh) * | 1993-11-12 | 1996-10-30 | 厄普约翰公司 | 嘧啶-硫烷基和烷基醚化合物 |
WO2011101740A1 (en) * | 2010-02-16 | 2011-08-25 | Actavis Group Ptc Ehf | Improved processes for preparing ticagrelor intermediate, 4,6-dichloro-5-nitro-2-(propylthio)pyrimidine |
CN104781731A (zh) * | 2012-12-04 | 2015-07-15 | Az电子材料卢森堡有限公司 | 正性工作光敏材料 |
WO2015108938A1 (en) * | 2014-01-17 | 2015-07-23 | Valent Biosciences Corporation | S-benzylthiouracil compounds and methods of enhancing plant root growth |
Non-Patent Citations (9)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115279758A (zh) * | 2020-01-10 | 2022-11-01 | 皮莱环球有限责任公司 | 用于慢性障碍的化合物 |
Also Published As
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EP3372590A4 (en) | 2018-09-26 |
JP2019500322A (ja) | 2019-01-10 |
EP3372590A1 (en) | 2018-09-12 |
CN106632082B (zh) | 2020-10-09 |
US20180237399A1 (en) | 2018-08-23 |
WO2017076264A1 (zh) | 2017-05-11 |
KR20180073671A (ko) | 2018-07-02 |
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