CA2485166A1 - Substituted pyrimidinone and pyridinone compounds - Google Patents
Substituted pyrimidinone and pyridinone compounds Download PDFInfo
- Publication number
- CA2485166A1 CA2485166A1 CA002485166A CA2485166A CA2485166A1 CA 2485166 A1 CA2485166 A1 CA 2485166A1 CA 002485166 A CA002485166 A CA 002485166A CA 2485166 A CA2485166 A CA 2485166A CA 2485166 A1 CA2485166 A1 CA 2485166A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- substituted
- pyrrolidin
- naphthalen
- groups
- 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
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 13
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 title description 7
- 150000005299 pyridinones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 241000124008 Mammalia Species 0.000 claims abstract description 12
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 12
- 125000005605 benzo group Chemical group 0.000 claims abstract description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 12
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- 206010061218 Inflammation Diseases 0.000 claims abstract description 10
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 10
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims abstract description 10
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- -1 3-benzylpiperazin-1-yl Chemical group 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- PEKMHSOHZFDZPF-UHFFFAOYSA-N 5-(3-bromophenyl)-3-methyl-2-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=NC(C=2C=CN=CC=2)=C1C1=CC=CC(Br)=C1 PEKMHSOHZFDZPF-UHFFFAOYSA-N 0.000 claims description 6
- BJKIHSVABYXHSU-UHFFFAOYSA-N 5-chloro-1-methyl-3-naphthalen-2-yl-6-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-4-pyridin-4-ylpyridin-2-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=C(Cl)C(C=2C=CN=CC=2)=C1C1=CC=C(C=CC=C2)C2=C1 BJKIHSVABYXHSU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- BEIGKYIMWQJOAV-UHFFFAOYSA-N 6-(2-chloropyridin-4-yl)-2-[2-(methoxymethyl)pyrrolidin-1-yl]-3-methyl-5-(3-methylphenyl)pyrimidin-4-one Chemical compound COCC1CCCN1C(N(C1=O)C)=NC(C=2C=C(Cl)N=CC=2)=C1C1=CC=CC(C)=C1 BEIGKYIMWQJOAV-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- HEVCAQFJFXOVOH-UHFFFAOYSA-N n-[[1-(6-naphthalen-2-yl-5-pyridin-4-ylpyridazin-3-yl)pyrrolidin-2-yl]methyl]propan-2-amine Chemical compound CC(C)NCC1CCCN1C1=CC(C=2C=CN=CC=2)=C(C=2C=C3C=CC=CC3=CC=2)N=N1 HEVCAQFJFXOVOH-UHFFFAOYSA-N 0.000 claims description 5
- LTNHJKDMINFWSJ-UHFFFAOYSA-N tert-butyl n-[2-[2-(1-methyl-5-naphthalen-2-yl-6-oxo-4-pyridin-4-ylpyridin-2-yl)pyrrolidin-1-yl]ethyl]carbamate Chemical compound C=1C=C2C=CC=CC2=CC=1C=1C(=O)N(C)C(C2N(CCC2)CCNC(=O)OC(C)(C)C)=CC=1C1=CC=NC=C1 LTNHJKDMINFWSJ-UHFFFAOYSA-N 0.000 claims description 5
- KRKFYVSYDWBYRY-UHFFFAOYSA-N 3-methyl-5-naphthalen-2-yl-2-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=NC(C=2C=CN=CC=2)=C1C1=CC=C(C=CC=C2)C2=C1 KRKFYVSYDWBYRY-UHFFFAOYSA-N 0.000 claims description 4
- SYWWZJQOHDOFFW-UHFFFAOYSA-N 6-[1-(2-aminoethyl)pyrrolidin-2-yl]-1-methyl-3-naphthalen-2-yl-4-pyridin-4-ylpyridin-2-one Chemical compound C=1C=C2C=CC=CC2=CC=1C=1C(=O)N(C)C(C2N(CCC2)CCN)=CC=1C1=CC=NC=C1 SYWWZJQOHDOFFW-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- QNZCUMOSCXLCNW-UHFFFAOYSA-N tert-butyl n-[2-[3-(1-methyl-5-naphthalen-2-yl-6-oxo-4-pyridin-4-ylpyridin-2-yl)pyrrolidin-1-yl]ethyl]carbamate Chemical compound C=1C=C2C=CC=CC2=CC=1C=1C(=O)N(C)C(C2CN(CCNC(=O)OC(C)(C)C)CC2)=CC=1C1=CC=NC=C1 QNZCUMOSCXLCNW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- SXNBMRCZWKZFGU-UHFFFAOYSA-N 2-[2-(methoxymethyl)pyrrolidin-1-yl]-3-methyl-5-(3-methylphenyl)-6-[2-(1-phenylethylamino)pyridin-4-yl]pyrimidin-4-one Chemical compound COCC1CCCN1C(N(C1=O)C)=NC(C=2C=C(NC(C)C=3C=CC=CC=3)N=CC=2)=C1C1=CC=CC(C)=C1 SXNBMRCZWKZFGU-UHFFFAOYSA-N 0.000 claims description 3
- FULZVEMXIUGOPT-UHFFFAOYSA-N 5-(3-ethenylphenyl)-3-methyl-2-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=NC(C=2C=CN=CC=2)=C1C1=CC=CC(C=C)=C1 FULZVEMXIUGOPT-UHFFFAOYSA-N 0.000 claims description 3
- COQUZYSSDACVLD-UHFFFAOYSA-N 6-[1-(2-hydroxy-2-methylpropyl)pyrrolidin-3-yl]-1-methyl-3-naphthalen-2-yl-4-pyridin-4-ylpyridin-2-one Chemical compound C=1C=C2C=CC=CC2=CC=1C=1C(=O)N(C)C(C2CN(CC(C)(C)O)CC2)=CC=1C1=CC=NC=C1 COQUZYSSDACVLD-UHFFFAOYSA-N 0.000 claims description 3
- CWQOZLXGDDPKEE-UHFFFAOYSA-N 6-[1-(2-hydroxypropyl)pyrrolidin-3-yl]-1-methyl-3-naphthalen-2-yl-4-pyridin-4-ylpyridin-2-one Chemical compound C1N(CC(O)C)CCC1C(N(C1=O)C)=CC(C=2C=CN=CC=2)=C1C1=CC=C(C=CC=C2)C2=C1 CWQOZLXGDDPKEE-UHFFFAOYSA-N 0.000 claims description 3
- JNLTXQCRJFPAPA-UHFFFAOYSA-N 3-methyl-5-(3-methylphenyl)-2-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=NC(C=2C=CN=CC=2)=C1C1=CC=CC(C)=C1 JNLTXQCRJFPAPA-UHFFFAOYSA-N 0.000 claims description 2
- BDUZZXNVSKUYIR-UHFFFAOYSA-N 5-(3-cyclopropylphenyl)-3-methyl-2-[2-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound CC(C)NCC1CCCN1C(N(C1=O)C)=NC(C=2C=CN=CC=2)=C1C1=CC=CC(C2CC2)=C1 BDUZZXNVSKUYIR-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
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| US7666568B2 (en) * | 2007-10-23 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Composition and method for providing a patterned metal layer having high conductivity |
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| EP2430022B1 (en) | 2009-05-12 | 2013-11-20 | Janssen Pharmaceuticals, Inc. | 1,2,4-Triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| JP5707390B2 (ja) | 2009-05-12 | 2015-04-30 | ジャンセン ファーマシューティカルズ， インコーポレイテッド | １，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体の正のアロステリック調節因子としてのその使用 |
| EP2661435B1 (en) | 2010-11-08 | 2015-08-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| WO2012062750A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| CA2814998C (en) | 2010-11-08 | 2019-10-29 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| JP6085866B2 (ja) | 2011-02-28 | 2017-03-01 | アレイ バイオファーマ、インコーポレイテッド | セリン／トレオニンキナーゼインヒビター |
| BR112014002675A2 (pt) | 2011-08-04 | 2017-02-21 | Array Biopharma Inc | "quinazolina como inibidores de serina/treonina quinase, seus usos, e composição" |
| WO2013066729A1 (en) * | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
| US10531655B2 (en) | 2011-12-02 | 2020-01-14 | The Regents Of The University Of California | Reperfusion protection solution and uses thereof |
| PL2820009T3 (pl) * | 2012-03-01 | 2018-09-28 | Array Biopharma, Inc. | Inhibitory kinaz serynowo/treoninowych |
| CA2882750A1 (en) | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
| AU2015208233B2 (en) | 2014-01-21 | 2019-08-29 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US11178870B2 (en) * | 2017-04-11 | 2021-11-23 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
| KR102730718B1 (ko) * | 2017-08-23 | 2024-11-14 | 스프린트 바이오사이언스 아베 | 피리딜피리돈 화합물 |
| ES2929424T3 (es) * | 2017-08-23 | 2022-11-29 | Sprint Bioscience Ab | Compuestos de piridinamina-piridona y pirimidinamina-piridona |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| JP2023553809A (ja) | 2020-11-25 | 2023-12-26 | デシフェラ・ファーマシューティカルズ，エルエルシー | ウイルス感染の治療に使用するためのｖｓｐ３４阻害剤としてのピリジルピリドン誘導体 |
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- 2003-05-15 PL PL376575A patent/PL376575A1/pl not_active Application Discontinuation
- 2003-05-15 EP EP03728971A patent/EP1506186A1/en not_active Withdrawn
- 2003-05-21 TW TW092113725A patent/TW200406399A/zh unknown
- 2003-05-22 AR ARP030101777A patent/AR039842A1/es not_active Application Discontinuation
-
2010
- 2010-07-09 JP JP2010157000A patent/JP2010280669A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1506186A1 (en) | 2005-02-16 |
| WO2003099808A8 (en) | 2009-02-05 |
| TW200406399A (en) | 2004-05-01 |
| JP2005530810A (ja) | 2005-10-13 |
| AU2003234628A1 (en) | 2003-12-12 |
| AR039842A1 (es) | 2005-03-02 |
| US20050038010A1 (en) | 2005-02-17 |
| PL376575A1 (pl) | 2006-01-09 |
| JP4606161B2 (ja) | 2011-01-05 |
| US7026326B2 (en) | 2006-04-11 |
| WO2003099808A1 (en) | 2003-12-04 |
| JP2010280669A (ja) | 2010-12-16 |
| AU2003234628B2 (en) | 2007-08-23 |
| MXPA04011470A (es) | 2005-02-14 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Dead |