CA2960274A1 - Isoxazole carboxamide compounds - Google Patents
Isoxazole carboxamide compounds Download PDFInfo
- Publication number
- CA2960274A1 CA2960274A1 CA2960274A CA2960274A CA2960274A1 CA 2960274 A1 CA2960274 A1 CA 2960274A1 CA 2960274 A CA2960274 A CA 2960274A CA 2960274 A CA2960274 A CA 2960274A CA 2960274 A1 CA2960274 A1 CA 2960274A1
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- Prior art keywords
- cancer
- alkyl
- cell
- tumor
- carcinoma
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- 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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- LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical class NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 title abstract description 90
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
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- 102000004169 proteins and genes Human genes 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 480
- -1 hydroxy, amino Chemical group 0.000 claims description 204
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 152
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
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- 239000001257 hydrogen Substances 0.000 claims description 89
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 125000003282 alkyl amino group Chemical group 0.000 claims description 86
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 84
- 150000002431 hydrogen Chemical group 0.000 claims description 50
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 44
- 125000005518 carboxamido group Chemical group 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
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- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 210000003289 regulatory T cell Anatomy 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
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- 229940100486 rice starch Drugs 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
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- 229940005550 sodium alginate Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- 238000007614 solvation Methods 0.000 description 1
- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- WPGLRFGDZJSQGI-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(N)C1 WPGLRFGDZJSQGI-UHFFFAOYSA-N 0.000 description 1
- KLKBCNDBOVRQIJ-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CN)CC1 KLKBCNDBOVRQIJ-UHFFFAOYSA-N 0.000 description 1
- JYUQEWCJWDGCRX-UHFFFAOYSA-N tert-butyl 4-formylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)CC1 JYUQEWCJWDGCRX-UHFFFAOYSA-N 0.000 description 1
- VXWAFKKVTFBTIW-UHFFFAOYSA-N tert-butyl N-[6-[(5-cyclopropyl-1,2-oxazole-3-carbonyl)amino]-2-bicyclo[3.3.1]nonanyl]carbamate Chemical compound C1(CC1)C1=CC(=NO1)C(=O)NC1C2CCC(C(CC1)C2)NC(OC(C)(C)C)=O VXWAFKKVTFBTIW-UHFFFAOYSA-N 0.000 description 1
- ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
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- 238000013519 translation Methods 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
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- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462048759P | 2014-09-10 | 2014-09-10 | |
| US62/048,759 | 2014-09-10 | ||
| US201562146794P | 2015-04-13 | 2015-04-13 | |
| US62/146,794 | 2015-04-13 | ||
| PCT/US2015/049213 WO2016040498A1 (en) | 2014-09-10 | 2015-09-09 | Isoxazole carboxamide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2960274A1 true CA2960274A1 (en) | 2016-03-17 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2960274A Abandoned CA2960274A1 (en) | 2014-09-10 | 2015-09-09 | Isoxazole carboxamide compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US10428029B2 (enExample) |
| EP (1) | EP3193603A4 (enExample) |
| JP (1) | JP2017526706A (enExample) |
| AU (1) | AU2015315167A1 (enExample) |
| CA (1) | CA2960274A1 (enExample) |
| WO (1) | WO2016040498A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2015315171A1 (en) | 2014-09-10 | 2017-03-16 | Epizyme, Inc. | Substituted cyclohexylamine compounds |
| MX2017002986A (es) | 2014-09-10 | 2017-10-24 | Epizyme Inc | Compuestos de piperidina sustituidos. |
| KR102496364B1 (ko) | 2014-09-10 | 2023-02-06 | 에피자임, 인코포레이티드 | Ｓｍｙｄ 억제제 |
| JP2017528460A (ja) | 2014-09-10 | 2017-09-28 | エピザイム インコーポレイテッド | 不可逆的ｓｍｙｄ阻害剤としてのイソオキサゾールカルボキサミド |
| WO2016204006A1 (ja) | 2015-06-17 | 2016-12-22 | 住友化学株式会社 | 有害節足動物防除剤 |
| CU20210018A7 (es) * | 2018-09-21 | 2021-10-12 | Novartis Ag | Compuestos de isoxazol-3-carboxamida |
| CN109879868B (zh) * | 2019-03-07 | 2022-04-22 | 南通大学 | 含2-芳基噁唑结构的吡唑酰胺类化合物的制备和应用 |
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| US3065225A (en) * | 1960-02-05 | 1962-11-20 | Hoffmann La Roche | N', n4-di-isoxazolylcarbonyl-sulfanilamide derivatives |
| DE19930075A1 (de) * | 1999-06-30 | 2001-01-04 | Bayer Ag | Neue Amino- und Amidosulfonamide als antivirale Mittel |
| GB0017518D0 (en) * | 2000-07-17 | 2000-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| AU2002338334B8 (en) * | 2001-04-03 | 2008-09-18 | Merck & Co., Inc. | N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B antagonists |
| CA2449249A1 (en) * | 2001-06-12 | 2002-12-19 | Merck & Co., Inc. | Nr2b receptor antagonists for the treatment or prevention of migraines |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2005004810A2 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Arylsulfonamide derivatives |
| US7709645B2 (en) * | 2004-07-27 | 2010-05-04 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| CA2589773A1 (en) * | 2004-12-22 | 2006-06-29 | Astrazeneca Ab | Pyridine carboxamide derivatives for use as anticancer agents |
| US7291743B2 (en) * | 2005-03-29 | 2007-11-06 | Geneblue Corporation | Isoxazole derivatives and methods of treating nitric oxide mediated diseases |
| NL2000284C2 (nl) * | 2005-11-04 | 2007-09-28 | Pfizer Ltd | Pyrazine-derivaten. |
| WO2008040149A1 (en) * | 2006-09-05 | 2008-04-10 | Dexian Dou | Composition and method for treating immune-mediated skin disorders |
| KR20100007956A (ko) * | 2007-05-03 | 2010-01-22 | 화이자 리미티드 | 나트륨 채널 조절제로서의 2-피리딘 카복스아마이드 유도체 |
| WO2008137834A2 (en) * | 2007-05-04 | 2008-11-13 | Osi Pharmaceuticals, Inc. | Crystal structure of smyd3 protein |
| EP2528925B1 (en) * | 2010-01-29 | 2017-07-05 | Hanmi Science Co., Ltd. | THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON PROTEIN KINASES |
| WO2013043826A1 (en) * | 2011-09-21 | 2013-03-28 | Abbvie Inc. | Tricyclic compounds useful as protein kinase inhibitors |
| US9919129B2 (en) * | 2012-12-18 | 2018-03-20 | Alcyone Lifesciences, Inc. | Systems and methods for reducing or preventing backflow in a delivery system |
| EP2968266B1 (en) * | 2013-03-15 | 2019-05-01 | Shifa Biomedical Corporation | Anti-proprotein convertase subtilisin kexin type 9 (anti-pcsk9) compounds in the treatment and/or prevention of cardiovascular diseases |
| MX2017002986A (es) | 2014-09-10 | 2017-10-24 | Epizyme Inc | Compuestos de piperidina sustituidos. |
| AU2015315171A1 (en) | 2014-09-10 | 2017-03-16 | Epizyme, Inc. | Substituted cyclohexylamine compounds |
| US20170247326A1 (en) | 2014-09-10 | 2017-08-31 | Epizyme, Inc. | Substituted Pyrrolidine Carboxamide Compounds |
| KR102496364B1 (ko) | 2014-09-10 | 2023-02-06 | 에피자임, 인코포레이티드 | Ｓｍｙｄ 억제제 |
| JP2017528460A (ja) | 2014-09-10 | 2017-09-28 | エピザイム インコーポレイテッド | 不可逆的ｓｍｙｄ阻害剤としてのイソオキサゾールカルボキサミド |
| US20170253601A1 (en) * | 2014-09-10 | 2017-09-07 | Epizyme, Inc. | Substituted Pyrrolidine Compounds |
-
2015
- 2015-09-09 JP JP2017513199A patent/JP2017526706A/ja active Pending
- 2015-09-09 EP EP15839331.4A patent/EP3193603A4/en not_active Withdrawn
- 2015-09-09 US US15/510,593 patent/US10428029B2/en active Active
- 2015-09-09 WO PCT/US2015/049213 patent/WO2016040498A1/en not_active Ceased
- 2015-09-09 AU AU2015315167A patent/AU2015315167A1/en not_active Abandoned
- 2015-09-09 CA CA2960274A patent/CA2960274A1/en not_active Abandoned
-
2019
- 2019-09-30 US US16/588,209 patent/US20200148650A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015315167A1 (en) | 2017-03-16 |
| JP2017526706A (ja) | 2017-09-14 |
| US20200148650A1 (en) | 2020-05-14 |
| US20170190676A1 (en) | 2017-07-06 |
| EP3193603A4 (en) | 2018-02-28 |
| EP3193603A1 (en) | 2017-07-26 |
| US10428029B2 (en) | 2019-10-01 |
| WO2016040498A1 (en) | 2016-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20211201 |
|
| FZDE | Discontinued |
Effective date: 20211201 |