ZA200506976B - Substituted pyrimidinones - Google Patents
Substituted pyrimidinones Download PDFInfo
- Publication number
- ZA200506976B ZA200506976B ZA200506976A ZA200506976A ZA200506976B ZA 200506976 B ZA200506976 B ZA 200506976B ZA 200506976 A ZA200506976 A ZA 200506976A ZA 200506976 A ZA200506976 A ZA 200506976A ZA 200506976 B ZA200506976 B ZA 200506976B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- alkoxy
- independently
- halogen
- groups
- Prior art date
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 555
- 125000003545 alkoxy group Chemical group 0.000 claims description 168
- 229910052736 halogen Inorganic materials 0.000 claims description 132
- 150000002367 halogens Chemical class 0.000 claims description 131
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 98
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
- 125000001589 carboacyl group Chemical group 0.000 claims description 81
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 78
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 76
- -1 arylthiocalkoxy Chemical group 0.000 claims description 57
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 32
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 30
- 125000002757 morpholinyl group Chemical group 0.000 claims description 28
- 125000004193 piperazinyl group Chemical group 0.000 claims description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000003386 piperidinyl group Chemical group 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 22
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 14
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 12
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000005495 pyridazyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
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- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- 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
- C07D403/02—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 two hetero rings
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- C—CHEMISTRY; METALLURGY
- 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
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- C—CHEMISTRY; METALLURGY
- 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
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Publications (1)
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| US20070167621A1 (en) * | 2003-04-03 | 2007-07-19 | Pharmacia Corporation | Substituted pyrimidinones |
| DE602005010714D1 (de) | 2004-08-12 | 2008-12-11 | Pfizer | Der p38-map-kinase |
| CA2584246C (en) * | 2004-10-13 | 2011-08-09 | Pharmacia & Upjohn Company Llc | Crystalline forms of 3-[5-chloro-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6h)-yl]-n-(2-hydroxyethyl)-4-methylbenzamide |
| CA2580497A1 (en) * | 2004-10-13 | 2006-04-20 | Pharmacia & Upjohn Company Llc | Substituted n-alkylpyrimidinones |
| WO2007081901A2 (en) * | 2006-01-05 | 2007-07-19 | The Scripps Research Institute | Pyrimidinone derivatives as protein kinase inhibitors |
| WO2007091176A1 (en) * | 2006-02-10 | 2007-08-16 | Pfizer Products Inc. | Pyridinone pyrazole urea and pyrimidinone pyrazole urea derivatives |
| US7588924B2 (en) * | 2006-03-07 | 2009-09-15 | Procter & Gamble Company | Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase |
| LT3357911T (lt) * | 2006-06-26 | 2022-08-10 | Akebia Therapeutics Inc. | Prolilo hidroksilazės inhibitoriai ir naudojimo būdai |
| EP2069327B1 (en) | 2006-08-25 | 2013-10-16 | Boehringer Ingelheim International GmbH | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
| TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
| TW200845994A (en) * | 2007-01-12 | 2008-12-01 | Smithkline Beecham Corp | N-substituted glycine derivatives: prolyl hydroxylase inhibitors |
| CA2689607A1 (en) * | 2007-06-06 | 2008-12-18 | Tyrogenex, Inc. | Kinase inhibitor compounds |
| WO2010138585A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Sharp & Dohme Corp. | Pyrimidinones as pde10 inhibitors |
| RS52870B (sr) | 2009-11-06 | 2013-12-31 | Aerpio Therapeutics Inc. | Inhibitori prolil hidroksilaze |
| US8563558B2 (en) | 2010-12-06 | 2013-10-22 | Confluence Life Sciences, Inc. | Substituted pyridine urea compounds |
| WO2012078674A1 (en) | 2010-12-06 | 2012-06-14 | Confluence Life Sciences, Inc. | Substituted indole/indazole-pyrimidinyl compounds |
| JP5848775B2 (ja) | 2010-12-06 | 2016-01-27 | コンフルエンス・ライフ・サイエンシズ，インコーポレーテッド | 置換ピリジノンピリジニル化合物 |
| US9359300B2 (en) | 2010-12-06 | 2016-06-07 | Confluence Life Sciences, Inc. | Methyl/difluorophenyl-methoxy substituted pyridinone-pyridinyl compounds, methyl-pyridinyl-methoxy substituted pyridinone-pyridinyl compounds, and methyl-pyrimidinyl-methoxy substituted pyridinone-pyridinyl compounds |
| NO2686520T3 (xx) | 2011-06-06 | 2018-03-17 | ||
| WO2013012723A1 (en) | 2011-07-13 | 2013-01-24 | Novartis Ag | Novel 2-piperidin-1-yl-acetamide compounds for use as tankyrase inhibitors |
| US9227982B2 (en) | 2011-07-13 | 2016-01-05 | Novartis Ag | 4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrminidinyl compounds for use as tankyrase inhibitors |
| EP2731940B1 (en) | 2011-07-13 | 2015-08-19 | Novartis AG | 4 - piperidinyl compounds for use as tankyrase inhibitors |
| WO2013086208A1 (en) | 2011-12-06 | 2013-06-13 | Confluence Life Sciences, Inc. | Substituted pyrimidinone-phenyl-pyrimidinyl compounds |
| US9365540B2 (en) | 2012-01-12 | 2016-06-14 | Takeda Pharmaceutical Company Limited | Benzimidazole derivatives as MCH receptor antagonists |
| ES2716008T3 (es) * | 2012-07-18 | 2019-06-07 | Sunshine Lake Pharma Co Ltd | Derivados heterocíclicos nitrogenados y su aplicación en fármacos |
| JP6699909B2 (ja) | 2013-06-07 | 2020-05-27 | アクラリス セラピューティクス，インコーポレイテッド | メチル／フルオロ−ピリジニル−メトキシ置換ピリジノン−ピリジニル化合物及びフルオロ−ピリミジニル−メトキシ置換ピリジノン−ピリジニル化合物 |
| SG11201509998WA (en) | 2013-06-13 | 2016-01-28 | Akebia Therapeutics Inc | Compositions and methods for treating anemia |
| AU2015253040B2 (en) | 2014-05-01 | 2020-04-09 | Celgene Quanticel Research, Inc. | Inhibitors of lysine specific demethylase-1 |
| WO2015200619A1 (en) * | 2014-06-26 | 2015-12-30 | Rodin Therapeutics, Inc. | Inhibitors of histone deacetylase |
| DK3186242T3 (da) | 2014-08-29 | 2021-12-20 | Tes Pharma S R L | Alfa-amino-beta-carboxymuconsyre-semialdehyd-decarboxylasehæmmere |
| BR112017015852A2 (pt) | 2015-01-23 | 2018-03-27 | Akebia Therapeutics Inc | forma de cristal, sal hemicálcico, sal hemicálcico di-hidratado, sal monossódico hidratado, sal bissódico monoidratado, sal monossódico anidro e método para preparar o composto 1 |
| TWI794725B (zh) | 2015-04-01 | 2023-03-01 | 美商阿克比治療有限公司 | 用於治療貧血之組合物及方法 |
| EP3790863A1 (en) | 2018-05-09 | 2021-03-17 | Akebia Therapeutics Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| GB201820450D0 (en) | 2018-12-14 | 2019-01-30 | Z Factor Ltd | Compound and its use for the treatment of alpha1-antitryspin deficiency |
| AU2021244609A1 (en) | 2020-03-27 | 2022-09-15 | Aclaris Therapeutics, Inc. | Oral compositions of MK2 pathway inhibitor for treatment of immune conditions |
| CN112209886A (zh) * | 2020-11-09 | 2021-01-12 | 沈阳药科大学 | 2-(3-氰基-4-烷氧基)苯基嘧啶衍生物及其制备方法和用途 |
| BR112023015584A2 (pt) | 2021-02-02 | 2023-10-24 | Liminal Biosciences Ltd | Antagonistas de gpr84 e usos dos mesmos |
| CA3215746A1 (en) * | 2021-03-31 | 2022-10-06 | Xinthera, Inc. | Mk2 inhibitors and uses thereof |
| AU2022307534B2 (en) | 2021-07-09 | 2025-12-04 | Xinthera, Inc. | Pyridinone mk2 inhibitors and uses thereof |
| CA3259871A1 (en) * | 2022-06-21 | 2025-03-25 | Kumiai Chemical Industry Co., Ltd. | PROCESS FOR PRODUCING A SULFONE DERIVATIVE USING HALOACETIC ACID |
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| JPS61205261A (ja) * | 1985-03-08 | 1986-09-11 | Sagami Chem Res Center | ６―置換―５―フルオロウラシル誘導体 |
| AU7798994A (en) * | 1993-10-20 | 1995-05-08 | Upjohn Company, The | Pyrimidinones as antiarthritic and anti-inflammatories |
| HUP0001140A3 (en) * | 1996-12-05 | 2002-05-28 | Amgen Inc Thousand Oaks | Substituted pyrimidinone and pyridone compounds and methods of use |
| JP2002517486A (ja) * | 1998-06-12 | 2002-06-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | ｐ３８のインヒビター |
| WO2001029010A1 (en) * | 1999-10-21 | 2001-04-26 | Merck & Co., Inc. | Gram-positive selective antibacterial compounds, compositions containing such compounds and methods of treatment |
| EP1553949B1 (en) * | 2002-08-13 | 2007-04-18 | Warner-Lambert Company LLC | Pyrimidine-2,4-dione derivatives as matrix metalloproteinase inhibitors |
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| OA13113A (en) | 2006-11-10 |
| MXPA05010621A (es) | 2005-11-23 |
| EA009743B1 (ru) | 2008-04-28 |
| JP3981398B1 (ja) | 2007-09-26 |
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| WO2004087677A2 (en) | 2004-10-14 |
| JP2007528353A (ja) | 2007-10-11 |
| KR100776120B1 (ko) | 2007-11-16 |
| WO2004087677A3 (en) | 2004-12-16 |
| CR8007A (es) | 2006-02-13 |
| ECSP056072A (es) | 2006-03-01 |
| MA27754A1 (fr) | 2006-02-01 |
| EA200501332A1 (ru) | 2006-06-30 |
| CA2521081C (en) | 2010-09-07 |
| BRPI0408990A (pt) | 2006-04-04 |
| CA2521081A1 (en) | 2004-10-14 |
| NZ542139A (en) | 2008-11-28 |
| AU2004226165B2 (en) | 2007-11-08 |
| AU2004226165C1 (en) | 2008-07-03 |
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| UA81658C2 (xx) | 2008-01-25 |
| CN1968937A (zh) | 2007-05-23 |
| AU2004226165A2 (en) | 2004-10-14 |
| KR20060006906A (ko) | 2006-01-20 |
| US7183287B2 (en) | 2007-02-27 |
| AU2004226165A1 (en) | 2004-10-14 |
| AP2005003403A0 (en) | 2005-12-31 |
| EP1753731A2 (en) | 2007-02-21 |
| US20040242608A1 (en) | 2004-12-02 |
| TNSN05250A1 (fr) | 2007-07-10 |
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