CA2960271A1 - Substituted cyclohexylamine compounds - Google Patents
Substituted cyclohexylamine compounds Download PDFInfo
- Publication number
- CA2960271A1 CA2960271A1 CA2960271A CA2960271A CA2960271A1 CA 2960271 A1 CA2960271 A1 CA 2960271A1 CA 2960271 A CA2960271 A CA 2960271A CA 2960271 A CA2960271 A CA 2960271A CA 2960271 A1 CA2960271 A1 CA 2960271A1
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- Prior art keywords
- cancer
- cell
- tumor
- carcinoma
- lymphoma
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- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- 150000003839 salts Chemical class 0.000 claims abstract description 75
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- 239000012453 solvate Substances 0.000 claims abstract description 62
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- 125000000217 alkyl group Chemical group 0.000 claims description 249
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 50
- 125000003282 alkyl amino group Chemical group 0.000 claims description 45
- 210000004027 cell Anatomy 0.000 claims description 45
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
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- JFDCTNUZMWJXLE-CBZIJGRNSA-N tert-butyl N-[(2R)-4-[[(1S,3R,4S)-3-ethyl-4-[(5-ethyl-1,2-oxazole-3-carbonyl)amino]cyclohexyl]amino]-4-oxobutan-2-yl]carbamate Chemical compound C(C)[C@@H]1C[C@H](CC[C@@H]1NC(=O)C1=NOC(=C1)CC)NC(C[C@@H](C)NC(OC(C)(C)C)=O)=O JFDCTNUZMWJXLE-CBZIJGRNSA-N 0.000 description 1
- JFDCTNUZMWJXLE-DFGXFYAUSA-N tert-butyl N-[(2S)-4-[[(1S,3R,4S)-3-ethyl-4-[(5-ethyl-1,2-oxazole-3-carbonyl)amino]cyclohexyl]amino]-4-oxobutan-2-yl]carbamate Chemical compound C(C)[C@@H]1C[C@H](CC[C@@H]1NC(=O)C1=NOC(=C1)CC)NC(C[C@H](C)NC(OC(C)(C)C)=O)=O JFDCTNUZMWJXLE-DFGXFYAUSA-N 0.000 description 1
- VTORJPDWMOIOIQ-UHFFFAOYSA-N tert-butyl(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](C(C)(C)C)C1=CC=CC=C1 VTORJPDWMOIOIQ-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 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
- 229940100445 wheat starch Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- 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
- C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462048756P | 2014-09-10 | 2014-09-10 | |
| US62/048,756 | 2014-09-10 | ||
| PCT/US2015/049217 WO2016040502A1 (en) | 2014-09-10 | 2015-09-09 | Substituted cyclohexylamine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2960271A1 true CA2960271A1 (en) | 2016-03-17 |
Family
ID=55459525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2960271A Abandoned CA2960271A1 (en) | 2014-09-10 | 2015-09-09 | Substituted cyclohexylamine compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10106510B2 (enExample) |
| EP (1) | EP3190891B1 (enExample) |
| JP (1) | JP2017527576A (enExample) |
| AU (1) | AU2015315171A1 (enExample) |
| CA (1) | CA2960271A1 (enExample) |
| WO (1) | WO2016040502A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017526706A (ja) | 2014-09-10 | 2017-09-14 | エピザイム,インコーポレイティド | イソオキサゾールカルボキサミド化合物 |
| 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 |
| AU2024258350A1 (en) * | 2023-04-19 | 2025-10-30 | Alcon Inc. | N-substituted c6 cyclyl carboxamide compounds and uses thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060089398A1 (en) * | 2003-03-19 | 2006-04-27 | Gang Liu | Isoxazole carboxamide derivatives as ghrelin receptor modulators |
| GB0317484D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| WO2008065500A2 (en) * | 2006-11-30 | 2008-06-05 | Pfizer Products Inc. | Heteroaryl amides as type i glycine transport inhibitors |
| WO2008137834A2 (en) * | 2007-05-04 | 2008-11-13 | Osi Pharmaceuticals, Inc. | Crystal structure of smyd3 protein |
| CA2721065C (en) * | 2008-05-27 | 2016-09-27 | Astrazeneca Ab | Phenoxypyridinylamide derivatives and their use as pde4 inhibitors |
| SI2310356T1 (sl) * | 2008-07-25 | 2014-02-28 | H. Lundbeck A/S | Adamantil diamid derivati in uporaba le-teh |
| JP6135391B2 (ja) | 2013-08-16 | 2017-05-31 | ソニー株式会社 | 撮像装置、画像処理装置、および画像処理方法、並びにプログラム |
| 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 |
| JP2017526706A (ja) | 2014-09-10 | 2017-09-14 | エピザイム,インコーポレイティド | イソオキサゾールカルボキサミド化合物 |
| US20170247326A1 (en) | 2014-09-10 | 2017-08-31 | Epizyme, Inc. | Substituted Pyrrolidine Carboxamide Compounds |
| US20170253601A1 (en) | 2014-09-10 | 2017-09-07 | Epizyme, Inc. | Substituted Pyrrolidine Compounds |
-
2015
- 2015-09-09 AU AU2015315171A patent/AU2015315171A1/en not_active Abandoned
- 2015-09-09 EP EP15839333.0A patent/EP3190891B1/en active Active
- 2015-09-09 US US15/510,605 patent/US10106510B2/en active Active
- 2015-09-09 JP JP2017513205A patent/JP2017527576A/ja active Pending
- 2015-09-09 CA CA2960271A patent/CA2960271A1/en not_active Abandoned
- 2015-09-09 WO PCT/US2015/049217 patent/WO2016040502A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3190891A4 (en) | 2018-03-28 |
| US10106510B2 (en) | 2018-10-23 |
| US20170362191A1 (en) | 2017-12-21 |
| EP3190891B1 (en) | 2020-01-15 |
| JP2017527576A (ja) | 2017-09-21 |
| AU2015315171A1 (en) | 2017-03-16 |
| WO2016040502A1 (en) | 2016-03-17 |
| EP3190891A1 (en) | 2017-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20200909 |