AU2015280138B2 - Phosphatidylinositol 3-kinase inhibitors - Google Patents
Phosphatidylinositol 3-kinase inhibitors Download PDFInfo
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- AU2015280138B2 AU2015280138B2 AU2015280138A AU2015280138A AU2015280138B2 AU 2015280138 B2 AU2015280138 B2 AU 2015280138B2 AU 2015280138 A AU2015280138 A AU 2015280138A AU 2015280138 A AU2015280138 A AU 2015280138A AU 2015280138 B2 AU2015280138 B2 AU 2015280138B2
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- Australia
- Prior art keywords
- oxo
- diamino
- optionally substituted
- alkylene
- compound
- Prior art date
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- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 101
- 108091007960 PI3Ks Proteins 0.000 claims abstract description 43
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 7
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 401
- -1 azido, carbamoyl Chemical group 0.000 claims description 255
- 239000000203 mixture Substances 0.000 claims description 119
- 229910052739 hydrogen Inorganic materials 0.000 claims description 118
- 239000001257 hydrogen Substances 0.000 claims description 115
- 125000005843 halogen group Chemical group 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 201000006417 multiple sclerosis Diseases 0.000 claims description 109
- 125000001188 haloalkyl group Chemical group 0.000 claims description 99
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 94
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 73
- 125000001153 fluoro group Chemical group F* 0.000 claims description 57
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
- 230000000694 effects Effects 0.000 claims description 49
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 49
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- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000003107 substituted aryl group Chemical group 0.000 claims description 39
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 38
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 37
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- 125000004429 atom Chemical group 0.000 claims description 30
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- 125000003725 azepanyl group Chemical group 0.000 claims description 24
- 125000003566 oxetanyl group Chemical group 0.000 claims description 24
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- 125000001424 substituent group Chemical group 0.000 claims description 24
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 13
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 12
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- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
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- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
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- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 5
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
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- AHRQYOSAXZQCIG-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=C=NC=N[CH]1 AHRQYOSAXZQCIG-UHFFFAOYSA-N 0.000 claims 14
- LTJDTZLNOJTXMS-KRWDZBQOSA-N 2,4-diamino-6-[(2S)-2-[3-(3-fluorophenyl)-5-methylsulfonyl-4-oxoquinazolin-2-yl]pyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CCC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC=C1)F)=O)S(=O)(=O)C LTJDTZLNOJTXMS-KRWDZBQOSA-N 0.000 claims 3
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- UBCROLIANMOUOT-IBYPIGCZSA-N 2,4-diamino-6-[(2S)-2-[5-chloro-3-(3,5-difluorophenyl)-4-oxoquinazolin-2-yl]-4-methoxypyrrolidin-1-yl]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N1[C@@H](CC(C1)OC)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)F)=O)Cl UBCROLIANMOUOT-IBYPIGCZSA-N 0.000 claims 2
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- NRJSHKSODUMLII-FQEVSTJZSA-N 2,4-diamino-6-[[(S)-[3-(3-cyano-5-fluorophenyl)-5-methyl-4-oxoquinazolin-2-yl]-cyclopropylmethyl]amino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)N)C#N)N[C@@H](C1CC1)C1=NC2=CC=CC(=C2C(N1C1=CC(=CC(=C1)F)C#N)=O)C NRJSHKSODUMLII-FQEVSTJZSA-N 0.000 claims 2
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Classifications
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- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Landscapes
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| US20140213630A1 (en) | 2011-03-08 | 2014-07-31 | Thomas Diacovo | Methods and pharmaceutical compositions for treating lymphoid malignancy |
| CA2952018A1 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Quinazolinone derivatives as phosphatidylinositol 3-kinase inhibitors |
| JP6455995B2 (ja) | 2014-06-13 | 2019-01-23 | ギリアード サイエンシーズ， インコーポレイテッド | ホスファチジルイノシトール３−キナーゼ阻害剤 |
| CA2952025A1 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| EP3154958B1 (en) | 2014-06-13 | 2020-10-07 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| UA115296C2 (uk) | 2014-07-04 | 2017-10-10 | Люпін Лімітед | Хінолізинонові похідні як інгібітори pi3k |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) * | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| CN106632077B (zh) * | 2016-10-10 | 2019-01-22 | 上海再启生物技术有限公司 | 一种2-氨基-4-溴嘧啶的制备方法 |
| US10396145B2 (en) * | 2017-01-12 | 2019-08-27 | Micron Technology, Inc. | Memory cells comprising ferroelectric material and including current leakage paths having different total resistances |
| WO2018237007A1 (en) * | 2017-06-22 | 2018-12-27 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of phosphoinositide 3-kinase and histone deacetylase for treatment of cancer |
| RU2020108454A (ru) * | 2017-07-31 | 2021-09-02 | Дзе Трастиз Оф Коламбия Юниверсити Ин Дзе Сити Оф Нью Йорк | Соединения, композиции и способы лечения t-клеточного острого лимфобластного лейкоза |
| AU2019209960B2 (en) | 2018-01-20 | 2023-11-23 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| EA202190880A1 (ru) * | 2018-09-27 | 2021-06-28 | Шанхай Инли Фармасьютикал Ко., Лтд | Кристаллическая форма морфолинохиназолинового соединения, способ ее получения и ее применение |
| US20220348558A1 (en) * | 2019-09-05 | 2022-11-03 | Wisconsin Alumni Research Foundation | Inhibitors of encephalitic alphaviruses |
| CN110590681B (zh) * | 2019-09-30 | 2021-06-01 | 中山大学 | 一种新型喹唑啉酮类化合物及其制备方法和应用 |
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| WO2013032591A1 (en) * | 2011-08-29 | 2013-03-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2014100767A1 (en) * | 2012-12-21 | 2014-06-26 | Gilead Calistoga Llc | Isoquinolinone or quinazolinone phosphatidylinositol 3-kinase inhibitors |
| WO2015081127A2 (en) * | 2013-11-26 | 2015-06-04 | Gilead Sciences, Inc. | Therapies for treating myeloproliferative disorders |
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| KR20170015521A (ko) | 2017-02-08 |
| CA2953820A1 (en) | 2015-12-30 |
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| AU2015280138A1 (en) | 2016-12-22 |
| SG11201610341PA (en) | 2017-01-27 |
| WO2015200352A1 (en) | 2015-12-30 |
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| CN106459008A (zh) | 2017-02-22 |
| NZ727185A (en) | 2018-04-27 |
| US20160024054A1 (en) | 2016-01-28 |
| HK1231474A1 (zh) | 2017-12-22 |
| JP6391718B2 (ja) | 2018-09-19 |
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