EA002124B1 - Производные хинолина - Google Patents
Производные хинолина Download PDFInfo
- Publication number
- EA002124B1 EA002124B1 EA199800477A EA199800477A EA002124B1 EA 002124 B1 EA002124 B1 EA 002124B1 EA 199800477 A EA199800477 A EA 199800477A EA 199800477 A EA199800477 A EA 199800477A EA 002124 B1 EA002124 B1 EA 002124B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compound
- group
- och
- pharmaceutically acceptable
- Prior art date
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 250
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 239000012453 solvate Substances 0.000 claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 19
- 125000004429 atom Chemical group 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract description 12
- 230000027455 binding Effects 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000006413 ring segment Chemical group 0.000 claims abstract description 10
- 241000124008 Mammalia Species 0.000 claims abstract description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 230000000638 stimulation Effects 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 102000007124 Tachykinin Receptors Human genes 0.000 claims abstract description 6
- 108010072901 Tachykinin Receptors Proteins 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 6
- 238000011321 prophylaxis Methods 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005977 Ethylene Substances 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 11
- 102000005962 receptors Human genes 0.000 claims description 21
- 108020003175 receptors Proteins 0.000 claims description 21
- 229910052700 potassium Inorganic materials 0.000 claims description 19
- 239000005557 antagonist Substances 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 210000003169 central nervous system Anatomy 0.000 claims description 6
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 5
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- 102000002003 Neurokinin-3 Receptors Human genes 0.000 abstract description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000002746 neurokinin 2 receptor antagonist Substances 0.000 abstract 2
- 239000002740 neurokinin 3 receptor antagonist Substances 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 abstract 1
- 102100037342 Substance-K receptor Human genes 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
- 239000000203 mixture Substances 0.000 description 60
- 239000011541 reaction mixture Substances 0.000 description 51
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- 238000002844 melting Methods 0.000 description 40
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- 239000000243 solution Substances 0.000 description 33
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- 238000005481 NMR spectroscopy Methods 0.000 description 22
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- SRCMBPJTOJHJEN-UHFFFAOYSA-N NCCOC=1C(=NC2=CC=CC=C2C=1C(=O)N)C1=CC=CC=C1 Chemical compound NCCOC=1C(=NC2=CC=CC=C2C=1C(=O)N)C1=CC=CC=C1 SRCMBPJTOJHJEN-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
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- 210000001428 peripheral nervous system Anatomy 0.000 description 5
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- WZYBQONKMQQIDY-UHFFFAOYSA-N 3-amino-2-phenylquinoline-4-carboxylic acid Chemical compound N1=C2C=CC=CC2=C(C(O)=O)C(N)=C1C1=CC=CC=C1 WZYBQONKMQQIDY-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI952461 IT1276170B1 (it) | 1995-11-24 | 1995-11-24 | Derivati chinolinici |
| ITMI961689 IT1307331B1 (it) | 1996-08-02 | 1996-08-02 | Derivati chinolinici |
| PCT/EP1996/005203 WO1997021680A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199800477A1 EA199800477A1 (ru) | 1998-12-24 |
| EA002124B1 true EA002124B1 (ru) | 2001-12-24 |
Family
ID=26331326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199800477A EA002124B1 (ru) | 1995-11-24 | 1996-11-22 | Производные хинолина |
Country Status (26)
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ290470B6 (cs) | 1991-10-18 | 2002-07-17 | Monsanto Technology Llc | 5 či 6 členné aromáty jako fungicidy pro kontrolu stéblolamu rostlin, způsob kontroly a fungicidní směs k provedení tohoto způsobu |
| SE9703407D0 (sv) * | 1997-09-19 | 1997-09-19 | Astra Ab | New use |
| SE9802073D0 (sv) | 1998-06-11 | 1998-06-11 | Astra Ab | New use |
| GB9825554D0 (en) * | 1998-11-20 | 1999-01-13 | Smithkline Beecham Spa | Novel Compounds |
| US7037922B1 (en) | 2000-03-10 | 2006-05-02 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands |
| ATE247652T1 (de) | 1999-03-29 | 2003-09-15 | Neurogen Corp | 4-substituierte chinolinderivate als nk-3 und/oder gaba(a) rezeptor liganden |
| AU4802500A (en) | 1999-04-26 | 2000-11-10 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| EP1659120A1 (en) * | 2001-04-11 | 2006-05-24 | GlaxoSmithKline S.p.A. | 3-substituted quinoline-4-carboxamide derivatives as NK-3 and NK-2 receptor antagonists |
| WO2002089802A2 (en) * | 2001-05-08 | 2002-11-14 | Schering Corporation | Use of neurokinin receptor antagonists to treat androgen-dependent diseases |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| DE602004028678D1 (de) | 2003-01-28 | 2010-09-23 | Ironwood Pharmaceuticals Inc | Zusammensetzungen zur Behandlung von Magen-Darm-Störungen |
| GB0303086D0 (en) | 2003-02-11 | 2003-03-19 | Merck Sharp & Dohme | New compounds |
| GB0419192D0 (en) | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| SG155229A1 (en) * | 2004-11-09 | 2009-09-30 | Smithkline Beecham Corp | Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof |
| GB0425077D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| JP2009504641A (ja) * | 2005-08-11 | 2009-02-05 | アストラゼネカ・アクチエボラーグ | Ｎｋ−３受容体の調節剤としてのアルキルピリジルキノリン |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| TW200804288A (en) * | 2005-12-12 | 2008-01-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| CA2701120A1 (en) * | 2007-09-28 | 2009-04-09 | Glaxosmithkline Llc | Glycogen phosphorylase inhibitor compound and pharmaceutical composition thereof |
| EA201000392A1 (ru) * | 2007-09-28 | 2010-10-29 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Соединение, представляющее собой ингибитор гликогенфосфорилазы, и его фармацевтическая композиция |
| CA2930674A1 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| JP2011528375A (ja) | 2008-07-16 | 2011-11-17 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| KR20220042487A (ko) | 2008-12-31 | 2022-04-05 | 알데릭스, 인코포레이티드 | 체액 저류 또는 염 과부하와 연관된 장애 및 위장관 장애의 치료 시에 ｎｈｅ-매개된 역수송을 억제하는 화합물 및 방법 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| JP6392754B2 (ja) | 2012-08-21 | 2018-09-19 | アーデリクス，インコーポレーテッド | 体液貯留又は塩過負荷に関係する疾患及び消化管疾患の治療におけるｎｈｅ仲介の逆輸送を阻害するための化合物並びに方法 |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| BR112015025805A2 (pt) | 2013-04-12 | 2017-07-25 | Ardelyx Inc | compostos de ligação de nh3 e métodos para inibir o transporte de fosfato |
| WO2014170648A1 (en) | 2013-04-19 | 2014-10-23 | Astrazeneca Ab | A nk3 receptor antagonist compound (nk3ra) for use in a method for the treatment of polycystic ovary syndrome (pcos) |
| EP4424697A3 (en) | 2013-06-05 | 2024-12-25 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| WO2017072629A1 (en) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Pharmaceutical combination of nk3 receptor antagonist and biguanides |
| WO2018129552A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| BR112019013963A2 (pt) | 2017-01-09 | 2020-04-28 | Ardelyx Inc | inibidores de antiporte mediado por nhe |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| JPS6399057A (ja) * | 1986-06-27 | 1988-04-30 | Nippon Shinyaku Co Ltd | グリシン誘導体 |
| DE69531458T2 (de) * | 1994-05-27 | 2004-08-05 | Glaxosmithkline S.P.A. | Chinolinderivate als tachykinin nk3 rezeptor antagonisten |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
-
1996
- 1996-11-22 US US09/077,151 patent/US6277862B1/en not_active Expired - Fee Related
- 1996-11-22 JP JP9521658A patent/JP2000501104A/ja active Pending
- 1996-11-22 BR BR9611820A patent/BR9611820A/pt not_active Application Discontinuation
- 1996-11-22 KR KR1019980703873A patent/KR19990071597A/ko not_active Withdrawn
- 1996-11-22 TR TR1998/00924T patent/TR199800924T2/xx unknown
- 1996-11-22 WO PCT/EP1996/005203 patent/WO1997021680A1/en not_active Ceased
- 1996-11-22 IL IL12452296A patent/IL124522A0/xx unknown
- 1996-11-22 CZ CZ981579A patent/CZ157998A3/cs unknown
- 1996-11-22 DE DE69634416T patent/DE69634416T2/de not_active Expired - Fee Related
- 1996-11-22 EP EP96941023A patent/EP0876347B1/en not_active Expired - Lifetime
- 1996-11-22 EA EA199800477A patent/EA002124B1/ru not_active IP Right Cessation
- 1996-11-22 AP APAP/P/1998/001237A patent/AP9801237A0/en unknown
- 1996-11-22 PL PL96326967A patent/PL326967A1/xx unknown
- 1996-11-22 ES ES96941023T patent/ES2236757T3/es not_active Expired - Lifetime
- 1996-11-22 SK SK667-98A patent/SK66798A3/sk unknown
- 1996-11-22 NZ NZ323387A patent/NZ323387A/en unknown
- 1996-11-22 CN CN96199753A patent/CN1207730A/zh active Pending
- 1996-11-22 AT AT96941023T patent/ATE289994T1/de not_active IP Right Cessation
- 1996-11-22 CA CA002238298A patent/CA2238298A1/en not_active Abandoned
- 1996-11-23 TW TW085114500A patent/TW353066B/zh active
- 1996-11-25 AR ARP960105317A patent/AR004972A1/es not_active Application Discontinuation
-
1997
- 1997-09-30 UY UY24733A patent/UY24733A1/es not_active Application Discontinuation
-
1998
- 1998-05-22 MX MX9804107A patent/MX9804107A/es unknown
- 1998-05-22 NO NO19982331A patent/NO311212B1/no unknown
- 1998-05-22 OA OA9800061A patent/OA11010A/en unknown
- 1998-06-18 BG BG102558A patent/BG102558A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0876347B1 (en) | 2005-03-02 |
| NO311212B1 (no) | 2001-10-29 |
| PL326967A1 (en) | 1998-11-09 |
| SK66798A3 (en) | 1999-01-11 |
| UY24733A1 (es) | 2001-08-27 |
| BG102558A (bg) | 1999-03-31 |
| CN1207730A (zh) | 1999-02-10 |
| JP2000501104A (ja) | 2000-02-02 |
| EA199800477A1 (ru) | 1998-12-24 |
| TW353066B (en) | 1999-02-21 |
| KR19990071597A (ko) | 1999-09-27 |
| MX9804107A (es) | 1998-09-30 |
| AR004972A1 (es) | 1999-04-07 |
| DE69634416T2 (de) | 2005-12-29 |
| EP0876347A1 (en) | 1998-11-11 |
| NZ323387A (en) | 2000-02-28 |
| OA11010A (en) | 2003-03-06 |
| CZ157998A3 (cs) | 1998-12-16 |
| ATE289994T1 (de) | 2005-03-15 |
| DE69634416D1 (de) | 2005-04-07 |
| US6277862B1 (en) | 2001-08-21 |
| TR199800924T2 (xx) | 1998-08-21 |
| CA2238298A1 (en) | 1997-06-19 |
| BR9611820A (pt) | 1999-07-13 |
| NO982331D0 (no) | 1998-05-22 |
| AP9801237A0 (en) | 1998-06-30 |
| WO1997021680A1 (en) | 1997-06-19 |
| NO982331L (no) | 1998-07-22 |
| IL124522A0 (en) | 1998-12-06 |
| ES2236757T3 (es) | 2005-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |