AU2004218456A1 - Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists. - Google Patents
Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists. Download PDFInfo
- Publication number
- AU2004218456A1 AU2004218456A1 AU2004218456A AU2004218456A AU2004218456A1 AU 2004218456 A1 AU2004218456 A1 AU 2004218456A1 AU 2004218456 A AU2004218456 A AU 2004218456A AU 2004218456 A AU2004218456 A AU 2004218456A AU 2004218456 A1 AU2004218456 A1 AU 2004218456A1
- Authority
- AU
- Australia
- Prior art keywords
- methylquinolin
- ethyl
- ylamino
- amine
- phenyl
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 18
- 108050002984 Urotensin II receptors Proteins 0.000 title description 11
- 102000012327 Urotensin II receptors Human genes 0.000 title description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 5
- 239000002464 receptor antagonist Substances 0.000 title description 5
- 229940044551 receptor antagonist Drugs 0.000 title description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 271
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 201
- -1 benzoheteroaryl Chemical group 0.000 claims description 144
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 125
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 43
- 150000001412 amines Chemical class 0.000 claims description 41
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000010992 reflux Methods 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 108010018369 Urotensin II Proteins 0.000 claims description 9
- 102000050488 Urotensin II Human genes 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 claims description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 7
- 230000006870 function Effects 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- KPPYVLQMFQUNSU-UHFFFAOYSA-N 6-n-[2-(4-benzylpiperidin-1-yl)ethyl]-4-n-(2-methylquinolin-4-yl)pyrimidine-4,6-diamine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(N=CN=1)=CC=1NCCN(CC1)CCC1CC1=CC=CC=C1 KPPYVLQMFQUNSU-UHFFFAOYSA-N 0.000 claims description 4
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
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- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical group C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 claims description 2
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- MYOYGUUBXOBIAC-UHFFFAOYSA-N n-[2-(2,2-dimethylpropylamino)ethyl]-3-[(2-methylquinolin-4-yl)amino]benzamide Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC1=CC=CC(C(=O)NCCNCC(C)(C)C)=C1 MYOYGUUBXOBIAC-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/14—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 three or more hetero rings
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45108903P | 2003-02-28 | 2003-02-28 | |
| US60/451,089 | 2003-02-28 | ||
| PCT/US2004/005150 WO2004078114A2 (en) | 2003-02-28 | 2004-02-20 | Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists. |
Publications (1)
| Publication Number | Publication Date |
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| AU2004218456A1 true AU2004218456A1 (en) | 2004-09-16 |
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Family Applications (1)
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| AU2004218456A Abandoned AU2004218456A1 (en) | 2003-02-28 | 2004-02-20 | Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists. |
Country Status (6)
| Country | Link |
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| US (2) | US7265122B2 (enExample) |
| EP (1) | EP1603884A4 (enExample) |
| JP (1) | JP2006519258A (enExample) |
| AU (1) | AU2004218456A1 (enExample) |
| CA (1) | CA2517166A1 (enExample) |
| WO (1) | WO2004078114A2 (enExample) |
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| WO2005070891A2 (en) | 2004-01-23 | 2005-08-04 | Amgen Inc | Compounds and methods of use |
| MXPA06014129A (es) * | 2004-06-04 | 2007-03-07 | Arena Pharm Inc | Derivados de arilo y heteroarilo sustituidos como moduladores del metabolismo y profilaxis y tratamiento de trastornos relacionados con los mismos. |
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| ES2450566T3 (es) | 2004-11-30 | 2014-03-25 | Amgen Inc. | Análogos de quinazolina y quinolinas y su uso como medicamentos para tratar el cáncer |
| US20060167044A1 (en) * | 2004-12-20 | 2006-07-27 | Arnaiz Damian O | Piperidine derivatives and their use as anti-inflammatory agents |
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| JP2010522766A (ja) * | 2007-03-28 | 2010-07-08 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | １１ベータ−ｈｓｄ１活性化合物 |
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| PA8782701A1 (es) | 2007-06-07 | 2009-01-23 | Janssen Pharmaceutica Nv | Antagonistas del receptor de urotensina ii |
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| SG10201902963PA (en) | 2014-10-06 | 2019-05-30 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
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| AU2017240685B2 (en) | 2016-03-31 | 2021-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| EP3241874B1 (en) | 2016-05-04 | 2019-08-14 | Agfa Nv | Acylphosphine oxide photoinitiators |
| GEP20217329B (en) | 2016-09-30 | 2021-12-10 | Vertex Pharma | Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| HUE052205T2 (hu) | 2016-12-09 | 2021-04-28 | Vertex Pharma | Cisztás fibrózis transzmembrán vezetõképesség szabályzó modulátora, gyógyszerészeti készítmények, kezelési eljárások és eljárás a modulátor elõállítására |
| PT3562821T (pt) | 2016-12-28 | 2021-03-03 | Minoryx Therapeutics S L | Compostos de isoquinolina, métodos para a sua preparação e utilizações terapêuticas dos mesmos em condições associadas à alteração da atividade da beta-galactosidade |
| JP7017797B2 (ja) * | 2017-02-24 | 2022-02-09 | 深▲チェン▼市霊蘭生物医薬科技有限公司 | 新規なドーパミンｄ３受容体選択的リガンド及びびその調製方法並びに医薬使用 |
| BR112019025801A2 (pt) | 2017-06-08 | 2020-07-07 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| BR112020000941A2 (pt) | 2017-07-17 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| US11434201B2 (en) | 2017-08-02 | 2022-09-06 | Vertex Pharmaceuticals Incorporated | Processes for preparing pyrrolidine compounds |
| CA3078893A1 (en) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of cftr modulators |
| CA3085006A1 (en) | 2017-12-08 | 2019-06-13 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| EP3774825A1 (en) | 2018-04-13 | 2021-02-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| CN110938021A (zh) * | 2019-12-18 | 2020-03-31 | 荆门市丽康源纺织科技有限公司 | 一种染料中间体3-(β-羟乙基砜基)苯胺的制备方法 |
| CN111170897A (zh) * | 2019-12-18 | 2020-05-19 | 荆门市丽康源纺织科技有限公司 | 一种间位酯的制备方法及间位酯 |
| MX2023003476A (es) * | 2020-09-25 | 2023-06-22 | Escient Pharmaceuticals Inc | Moduladores del receptor x2 de proteína g relacionado con mas y productos y métodos relacionados. |
| CN114890946B (zh) * | 2022-05-20 | 2023-10-27 | 沈阳药科大学 | 含有吗啉丙基的[(喹啉-4-基)氨基]苯甲酰胺类化合物及其制备与应用 |
Family Cites Families (16)
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| US2419199A (en) * | 1945-02-09 | 1947-04-22 | Parke Davis & Co | Quinoline compounds and process of making same |
| GB974348A (en) * | 1961-01-25 | 1964-11-04 | Parke Davis & Co | Basic 7-chloroquinoline-1-oxide derivatives and methods for their production |
| BE687335A (enExample) | 1965-12-10 | 1967-03-01 | ||
| US3919238A (en) * | 1973-06-06 | 1975-11-11 | Morton Norwich Products Inc | 9-(Substituted amino)imidazo(4,5-f) quinolines |
| CH593266A5 (enExample) * | 1973-09-20 | 1977-11-30 | Delalande Sa | |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| WO2002062787A1 (en) * | 2001-02-02 | 2002-08-15 | Glaxo Group Limited | Pyrazoles as tgf inhibitors |
| AR033879A1 (es) | 2001-05-07 | 2004-01-07 | Smithkline Beecham Corp | Compuesto sulfonamida, composicion farmaceutica que lo comprende, su uso para preparar dicha composicion y procedimiento para la obtencion de dicho compuesto |
| WO2002090337A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| JP2005508852A (ja) | 2001-05-07 | 2005-04-07 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| WO2002089793A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| WO2002089785A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| EP1385841A4 (en) | 2001-05-07 | 2005-03-02 | Smithkline Beecham Corp | SULPHONAMIDES |
| RS63204A (sr) * | 2002-01-17 | 2006-10-27 | Neurogen Corporation | Supstituisani analozi hinazolin-4-ilamina kao modulatori kapsaicina |
| EP2402310A1 (en) | 2002-05-24 | 2012-01-04 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
| AU2003270186A1 (en) | 2002-09-17 | 2004-04-08 | Actelion Pharmaceuticals Ltd | 1-pyridin-4-yl-urea derivatives |
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2004
- 2004-02-20 EP EP04713383A patent/EP1603884A4/en not_active Withdrawn
- 2004-02-20 US US10/783,916 patent/US7265122B2/en not_active Expired - Fee Related
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- 2004-02-20 WO PCT/US2004/005150 patent/WO2004078114A2/en not_active Ceased
- 2004-02-20 JP JP2006508787A patent/JP2006519258A/ja not_active Withdrawn
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2007
- 2007-05-25 US US11/807,047 patent/US20080004312A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2517166A1 (en) | 2004-09-16 |
| JP2006519258A (ja) | 2006-08-24 |
| WO2004078114A2 (en) | 2004-09-16 |
| EP1603884A2 (en) | 2005-12-14 |
| US20080004312A1 (en) | 2008-01-03 |
| EP1603884A4 (en) | 2008-05-28 |
| US7265122B2 (en) | 2007-09-04 |
| US20040186102A1 (en) | 2004-09-23 |
| WO2004078114A3 (en) | 2005-02-17 |
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