AU2019279421A1 - Heterocyclic derivatives and use thereof - Google Patents
Heterocyclic derivatives and use thereof Download PDFInfo
- Publication number
- AU2019279421A1 AU2019279421A1 AU2019279421A AU2019279421A AU2019279421A1 AU 2019279421 A1 AU2019279421 A1 AU 2019279421A1 AU 2019279421 A AU2019279421 A AU 2019279421A AU 2019279421 A AU2019279421 A AU 2019279421A AU 2019279421 A1 AU2019279421 A1 AU 2019279421A1
- Authority
- AU
- Australia
- Prior art keywords
- pyrazin
- pyrido
- bromo
- imidazo
- mmol
- 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.)
- Abandoned
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 37
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 100
- 229960001340 histamine Drugs 0.000 claims abstract description 50
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 19
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- 239000000203 mixture Substances 0.000 claims description 49
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- GCBPTLCOBQPYQZ-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-8-nitro-1H-imidazo[1,2-a]quinoxalin-2-one Chemical compound CN1CCN(CC1)C=1C=2N(C3=CC(=CC=C3N=1)[N+](=O)[O-])CC(N=2)=O GCBPTLCOBQPYQZ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- ZIBHXXPQKCMASQ-UHFFFAOYSA-N 12-bromo-11-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CCN(CC2)C)N=C1Cl ZIBHXXPQKCMASQ-UHFFFAOYSA-N 0.000 claims description 5
- PSZHUGUONMGRGX-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound ClC=1C=CC=2N=C(C=3N(C=2N=1)CC(N=3)=O)N1CCN(CC1)C PSZHUGUONMGRGX-UHFFFAOYSA-N 0.000 claims description 5
- YHXOULSAORZYSW-UHFFFAOYSA-N 8-bromo-4-[3-(methylamino)azetidin-1-yl]-1H-imidazo[1,2-a]quinoxalin-2-one Chemical compound BrC1=CC=C2N=C(C=3N(C2=C1)CC(N=3)=O)N1CC(C1)NC YHXOULSAORZYSW-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- QLDFGFZMONUCFU-UHFFFAOYSA-N 11-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,12-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one Chemical compound ClC1=CC=2N=C(C=3N(C=2C=N1)CC(N=3)=O)N1CCN(CC1)C QLDFGFZMONUCFU-UHFFFAOYSA-N 0.000 claims description 4
- DVYWJRJQVBKHCC-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,3,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2NC(N=3)=O)N2CCN(CC2)C)N=C1 DVYWJRJQVBKHCC-UHFFFAOYSA-N 0.000 claims description 4
- ZAPPYODPYLXGJG-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-3-one Chemical compound BrC1=CC2=C(N=C(C=3N2C(NN=3)=O)N2CCN(CC2)C)N=C1 ZAPPYODPYLXGJG-UHFFFAOYSA-N 0.000 claims description 4
- VNTNDZPEKVLQKC-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CCN(CC2)C)N=C1 VNTNDZPEKVLQKC-UHFFFAOYSA-N 0.000 claims description 4
- ZTPXIEDATPKEPA-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,5,8,11-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CCN(CC2)C)C=N1 ZTPXIEDATPKEPA-UHFFFAOYSA-N 0.000 claims description 4
- BJSCTIOVIMAHAT-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-4lambda6-thia-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaene 4,4-dioxide Chemical compound BrC1=CC2=C(N=C(C=3N2CS(N=3)(=O)=O)N2CCN(CC2)C)N=C1 BJSCTIOVIMAHAT-UHFFFAOYSA-N 0.000 claims description 4
- ANOKGZCOHQWALX-SECBINFHSA-N 12-bromo-7-[(3R)-3-(methylamino)pyrrolidin-1-yl]-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2C[C@@H](CC2)NC)N=C1 ANOKGZCOHQWALX-SECBINFHSA-N 0.000 claims description 4
- ANOKGZCOHQWALX-VIFPVBQESA-N 12-bromo-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2C[C@H](CC2)NC)N=C1 ANOKGZCOHQWALX-VIFPVBQESA-N 0.000 claims description 4
- ZELPPFUKNQILQT-UHFFFAOYSA-N 12-bromo-7-[3-(methylamino)azetidin-1-yl]-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CC(C2)NC)N=C1 ZELPPFUKNQILQT-UHFFFAOYSA-N 0.000 claims description 4
- APZVRNBQZIJZQE-UHFFFAOYSA-N 12-bromo-7-[3-(methylamino)azetidin-1-yl]-2,5,8,11-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CC(C2)NC)C=N1 APZVRNBQZIJZQE-UHFFFAOYSA-N 0.000 claims description 4
- SWNFCLJMNLSBPE-UHFFFAOYSA-N 12-bromo-7-[3-(methylamino)azetidin-1-yl]-2,5,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC=1C=CC=2N=C(C=3N(C=2N=1)CC(N=3)=O)N1CC(C1)NC SWNFCLJMNLSBPE-UHFFFAOYSA-N 0.000 claims description 4
- DSQYZQXDAWHCSX-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound ClC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CCN(CC2)C)N=C1 DSQYZQXDAWHCSX-UHFFFAOYSA-N 0.000 claims description 4
- KSLIBLYDYHJQFP-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,11-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one hydrochloride Chemical compound Cl.ClC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CCN(CC2)C)C=N1 KSLIBLYDYHJQFP-UHFFFAOYSA-N 0.000 claims description 4
- APHAHZQZEILDSM-UHFFFAOYSA-N 12-chloro-7-[3-(methylamino)azetidin-1-yl]-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound ClC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CC(C2)NC)N=C1 APHAHZQZEILDSM-UHFFFAOYSA-N 0.000 claims description 4
- RDFVSFSLLQXPQM-UHFFFAOYSA-N 12-chloro-7-[3-(methylamino)azetidin-1-yl]-2,5,8,11-tetrazatricyclo[7.4.0.02,6]trideca-1(13),5,7,9,11-pentaen-4-one hydrochloride Chemical compound Cl.ClC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CC(C2)NC)C=N1 RDFVSFSLLQXPQM-UHFFFAOYSA-N 0.000 claims description 4
- SOBRKCBLXIFLQB-UHFFFAOYSA-N 12-chloro-7-[3-(methylamino)azetidin-1-yl]-2,5,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound ClC=1C=CC=2N=C(C=3N(C=2N=1)CC(N=3)=O)N1CC(C1)NC SOBRKCBLXIFLQB-UHFFFAOYSA-N 0.000 claims description 4
- PGFHKUHIZMGNNB-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-bromo-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-4-one Chemical compound BrC1=CC2=C(N=C(C=3N2CC(N=3)=O)N2CC3N(CC2)CCC3)N=C1 PGFHKUHIZMGNNB-UHFFFAOYSA-N 0.000 claims description 4
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- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- LHUFQYUQIUJJIB-UHFFFAOYSA-N tert-butyl n-(azetidin-3-yl)-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1CNC1 LHUFQYUQIUJJIB-UHFFFAOYSA-N 0.000 description 1
- XYKYUXYNQDXZTD-MRVPVSSYSA-N tert-butyl n-methyl-n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@@H]1CCNC1 XYKYUXYNQDXZTD-MRVPVSSYSA-N 0.000 description 1
- XYKYUXYNQDXZTD-QMMMGPOBSA-N tert-butyl n-methyl-n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@H]1CCNC1 XYKYUXYNQDXZTD-QMMMGPOBSA-N 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- 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
-
- 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
- C07D513/12—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 three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20180062254 | 2018-05-31 | ||
| KR10-2018-0062254 | 2018-05-31 | ||
| PCT/KR2019/006553 WO2019231270A1 (en) | 2018-05-31 | 2019-05-31 | Heterocyclic derivatives and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2019279421A1 true AU2019279421A1 (en) | 2020-12-03 |
Family
ID=68698381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2019279421A Abandoned AU2019279421A1 (en) | 2018-05-31 | 2019-05-31 | Heterocyclic derivatives and use thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20210198259A1 (https=) |
| EP (1) | EP3807282A4 (https=) |
| JP (1) | JP2021525738A (https=) |
| KR (1) | KR102344295B1 (https=) |
| CN (1) | CN112204032A (https=) |
| AU (1) | AU2019279421A1 (https=) |
| BR (1) | BR112020023946A2 (https=) |
| CA (1) | CA3098825A1 (https=) |
| MX (1) | MX2020011955A (https=) |
| SG (1) | SG11202010985TA (https=) |
| TW (1) | TW202021969A (https=) |
| WO (1) | WO2019231270A1 (https=) |
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| US20230107927A1 (en) | 2020-02-28 | 2023-04-06 | First Wave Bio, Inc. | Methods of treating iatrogenic autoimmune colitis |
| IL298760A (en) | 2020-06-05 | 2023-02-01 | Kinnate Biopharma Inc | Fibroblast growth factor receptor kinase inhibitors |
| EP4067357A1 (en) * | 2021-03-30 | 2022-10-05 | JW Pharmaceutical Corporation | Novel crystalline form of 1-(8-bromopyrido[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-n-methylazetidin-3-amine hydrogen sulfate monohydrate |
| CN113929634A (zh) * | 2021-11-22 | 2022-01-14 | 山西永津集团有限公司 | 一种2,3-二溴喹喔啉的合成方法 |
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| SE358395B (https=) * | 1967-09-27 | 1973-07-30 | Siegfried Ag | |
| BRPI0407926A (pt) * | 2003-03-27 | 2006-02-21 | Pfizer Prod Inc | 4-amino[1,2,4]triazol[4,3-a]quinoxalinas substituìdas |
| TW201024297A (en) * | 2008-09-10 | 2010-07-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| TW201204727A (en) * | 2010-03-10 | 2012-02-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| TW201206936A (en) * | 2010-07-19 | 2012-02-16 | Alcon Res Ltd | Methods and compositions for the treatment of allergy |
| TWI551600B (zh) * | 2011-09-30 | 2016-10-01 | Ｃ＆Ｃ新藥研究所 | 新穎雜環衍生物及其用途 |
| CA2904364A1 (en) * | 2013-03-15 | 2014-09-25 | Epigenetix, Inc. | Oxazolo[5,4-c]quinolin-2-one compounds as bromodomain inhibitors |
| JP2018537450A (ja) * | 2015-11-16 | 2018-12-20 | ファンダシオン パラ ラ インベスティガシオン メディカ アプリカダＦｕｎｄａｃｉｏｎ Ｐａｒａ Ｌａ Ｉｎｖｅｓｔｉｇａｓｉｏｎ Ｍｅｄｉｃａ Ａｐｌｉｃａｄａ | Ｄｎａメチルトランスフェラーゼ阻害剤としての新規化合物 |
| JP7212612B2 (ja) * | 2016-07-28 | 2023-01-25 | プロメガ コーポレイション | セレンテラジン類縁体 |
-
2019
- 2019-05-30 TW TW108118749A patent/TW202021969A/zh unknown
- 2019-05-31 JP JP2020566706A patent/JP2021525738A/ja not_active Withdrawn
- 2019-05-31 US US17/057,753 patent/US20210198259A1/en not_active Abandoned
- 2019-05-31 AU AU2019279421A patent/AU2019279421A1/en not_active Abandoned
- 2019-05-31 CA CA3098825A patent/CA3098825A1/en active Pending
- 2019-05-31 MX MX2020011955A patent/MX2020011955A/es unknown
- 2019-05-31 SG SG11202010985TA patent/SG11202010985TA/en unknown
- 2019-05-31 EP EP19810281.6A patent/EP3807282A4/en not_active Withdrawn
- 2019-05-31 CN CN201980035540.4A patent/CN112204032A/zh active Pending
- 2019-05-31 BR BR112020023946-1A patent/BR112020023946A2/pt not_active Application Discontinuation
- 2019-05-31 WO PCT/KR2019/006553 patent/WO2019231270A1/en not_active Ceased
- 2019-05-31 KR KR1020190064284A patent/KR102344295B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20210198259A1 (en) | 2021-07-01 |
| TW202021969A (zh) | 2020-06-16 |
| BR112020023946A2 (pt) | 2021-02-23 |
| EP3807282A1 (en) | 2021-04-21 |
| MX2020011955A (es) | 2021-01-15 |
| CN112204032A (zh) | 2021-01-08 |
| SG11202010985TA (en) | 2020-12-30 |
| CA3098825A1 (en) | 2019-12-05 |
| WO2019231270A1 (en) | 2019-12-05 |
| EP3807282A4 (en) | 2022-03-02 |
| JP2021525738A (ja) | 2021-09-27 |
| KR20190137013A (ko) | 2019-12-10 |
| KR102344295B1 (ko) | 2021-12-29 |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |