JP2007506680A5 - - Google Patents
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- Publication number
- JP2007506680A5 JP2007506680A5 JP2006527054A JP2006527054A JP2007506680A5 JP 2007506680 A5 JP2007506680 A5 JP 2007506680A5 JP 2006527054 A JP2006527054 A JP 2006527054A JP 2006527054 A JP2006527054 A JP 2006527054A JP 2007506680 A5 JP2007506680 A5 JP 2007506680A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonitrile
- fluorophenyl
- methoxy
- methoxyquinoline
- quinoline
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 206010003119 arrhythmia Diseases 0.000 claims 7
- -1 R 42 Chemical compound 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- YEZMUYCDDZUGJI-UHFFFAOYSA-N 2-(2,3-dihydroxypropoxy)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(OCC(O)CO)C(C#N)=C1C1=CC=CC(F)=C1 YEZMUYCDDZUGJI-UHFFFAOYSA-N 0.000 claims 2
- MOWNLMCRBFQKJO-UHFFFAOYSA-N 2-(4,5-dihydroxypentoxy)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(OCCCC(O)CO)C(C#N)=C1C1=CC=CC(F)=C1 MOWNLMCRBFQKJO-UHFFFAOYSA-N 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 2
- YGBXGOQOFLJVOE-RTBURBONSA-N 2-[(3r,4r)-3,4-dihydroxypyrrolidin-1-yl]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1N1C[C@@H](O)[C@H](O)C1 YGBXGOQOFLJVOE-RTBURBONSA-N 0.000 claims 2
- YGBXGOQOFLJVOE-OALUTQOASA-N 2-[(3s,4s)-3,4-dihydroxypyrrolidin-1-yl]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1N1C[C@H](O)[C@@H](O)C1 YGBXGOQOFLJVOE-OALUTQOASA-N 0.000 claims 2
- ONKQEYXHYCOZSE-CQSZACIVSA-N 2-[[(2r)-2,3-dihydroxypropyl]amino]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(NC[C@@H](O)CO)C(C#N)=C1C1=CC=CC(F)=C1 ONKQEYXHYCOZSE-CQSZACIVSA-N 0.000 claims 2
- ONKQEYXHYCOZSE-AWEZNQCLSA-N 2-[[(2s)-2,3-dihydroxypropyl]amino]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(NC[C@H](O)CO)C(C#N)=C1C1=CC=CC(F)=C1 ONKQEYXHYCOZSE-AWEZNQCLSA-N 0.000 claims 2
- IVURGAGPZMKVDK-UHFFFAOYSA-N 2-chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(Cl)C(C#N)=C1C1=CC=CC(F)=C1 IVURGAGPZMKVDK-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- BYUIJSYHQUHPFS-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-(4-methylimidazol-1-yl)quinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(N2C=C(C)N=C2)C(C#N)=C1C1=CC=CC(F)=C1 BYUIJSYHQUHPFS-UHFFFAOYSA-N 0.000 claims 2
- HIBMVIQPPVERIZ-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-[(2-oxo-1,3-oxazolidin-5-yl)methoxy]quinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1OCC1CNC(=O)O1 HIBMVIQPPVERIZ-UHFFFAOYSA-N 0.000 claims 2
- VIYLPCZQZDHAEK-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-[(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)methoxy]quinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1OCC(ON=1)=NC=1C1=CC=CN=C1 VIYLPCZQZDHAEK-UHFFFAOYSA-N 0.000 claims 2
- QPEXTHITXVHCQT-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-pent-4-enoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(OCCCC=C)C(C#N)=C1C1=CC=CC(F)=C1 QPEXTHITXVHCQT-UHFFFAOYSA-N 0.000 claims 2
- WBGMOBHUCJXUHA-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-prop-2-enoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(OCC=C)C(C#N)=C1C1=CC=CC(F)=C1 WBGMOBHUCJXUHA-UHFFFAOYSA-N 0.000 claims 2
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 2
- 206010003662 Atrial flutter Diseases 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000003734 Supraventricular Tachycardia Diseases 0.000 claims 2
- 208000001435 Thromboembolism Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
- YHBCRXAIIVZWEW-UHFFFAOYSA-N 2-[3-(diaminomethylideneamino)phenyl]-3-sulfanylpropanoic acid Chemical compound NC(=N)NC1=CC=CC(C(CS)C(O)=O)=C1 YHBCRXAIIVZWEW-UHFFFAOYSA-N 0.000 claims 1
- JPOQGDJGHIWRMZ-UHFFFAOYSA-N 2-chloro-4-(3-chlorophenyl)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(Cl)C(C#N)=C1C1=CC=CC(Cl)=C1 JPOQGDJGHIWRMZ-UHFFFAOYSA-N 0.000 claims 1
- QOVRZLUUCNBPRQ-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(2-hydroxyethylamino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=C(NCCO)C(C#N)=C1C1=CC=CC(Cl)=C1 QOVRZLUUCNBPRQ-UHFFFAOYSA-N 0.000 claims 1
- UKRYIAFMNZEZJV-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-methoxy-2-(oxolan-2-ylmethylamino)quinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(Cl)C=CC=2)C2=CC(OC)=CC=C2N=C1NCC1CCCO1 UKRYIAFMNZEZJV-UHFFFAOYSA-N 0.000 claims 1
- HJYALFQOHNHTGI-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-(2-morpholin-4-ylethylamino)quinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1NCCN1CCOCC1 HJYALFQOHNHTGI-UHFFFAOYSA-N 0.000 claims 1
- WWSGDWSHRMFPDK-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methoxy-2-[2-(4-methylpiperidin-1-yl)ethylamino]quinoline-3-carbonitrile Chemical compound N#CC1=C(C=2C=C(F)C=CC=2)C2=CC(OC)=CC=C2N=C1NCCN1CCC(C)CC1 WWSGDWSHRMFPDK-UHFFFAOYSA-N 0.000 claims 1
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 claims 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 101000953562 Dendroaspis angusticeps Kunitz-type serine protease inhibitor homolog calcicludine Proteins 0.000 claims 1
- 101000723297 Dendroaspis polylepis polylepis Calciseptin Proteins 0.000 claims 1
- 229940123583 Factor Xa inhibitor Drugs 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims 1
- 108091007262 P2T receptors Proteins 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 229940126495 T-type calcium channel blocker Drugs 0.000 claims 1
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 claims 1
- 229940122388 Thrombin inhibitor Drugs 0.000 claims 1
- 229940122202 Thromboxane receptor antagonist Drugs 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 claims 1
- 239000003420 antiserotonin agent Substances 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940097217 cardiac glycoside Drugs 0.000 claims 1
- 239000002368 cardiac glycoside Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 229960003009 clopidogrel Drugs 0.000 claims 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000013003 healing agent Substances 0.000 claims 1
- 229920000669 heparin Polymers 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 239000003055 low molecular weight heparin Substances 0.000 claims 1
- 229940127215 low-molecular weight heparin Drugs 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000033764 rhythmic process Effects 0.000 claims 1
- 229930002534 steroid glycoside Natural products 0.000 claims 1
- 239000003868 thrombin inhibitor Substances 0.000 claims 1
- 239000002396 thromboxane receptor blocking agent Substances 0.000 claims 1
- 229960005001 ticlopidine Drugs 0.000 claims 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims 1
- 229960005080 warfarin Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50520203P | 2003-09-23 | 2003-09-23 | |
| US60/505,202 | 2003-09-23 | ||
| PCT/US2004/030485 WO2005030129A2 (en) | 2003-09-23 | 2004-09-17 | Quinoline potassium channel inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007506680A JP2007506680A (ja) | 2007-03-22 |
| JP2007506680A5 true JP2007506680A5 (enExample) | 2007-10-25 |
| JP4722851B2 JP4722851B2 (ja) | 2011-07-13 |
Family
ID=34392989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006527054A Expired - Fee Related JP4722851B2 (ja) | 2003-09-23 | 2004-09-17 | キノリンカリウムチャネル阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7692017B2 (enExample) |
| EP (1) | EP1667683A4 (enExample) |
| JP (1) | JP4722851B2 (enExample) |
| CN (1) | CN1856307A (enExample) |
| AU (1) | AU2004275719B2 (enExample) |
| CA (1) | CA2539707C (enExample) |
| WO (1) | WO2005030129A2 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05007485A (es) | 2003-01-14 | 2006-01-30 | Arena Pharm Inc | Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia. |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| US7569589B2 (en) | 2004-07-29 | 2009-08-04 | Merck & Co., Inc. | Potassium channel inhibitors |
| CN1993347A (zh) | 2004-07-29 | 2007-07-04 | 默克公司 | 钾通道抑制剂 |
| DE102004042607A1 (de) * | 2004-09-03 | 2006-03-09 | Bayer Healthcare Ag | Substituierte Phenylaminothiazole und ihre Verwendung |
| EP1891039A1 (en) | 2005-05-20 | 2008-02-27 | Vertex Pharmaceuticals Incorporated | Quinoline derivatives useful as modulators of ion channels |
| KR20080089416A (ko) * | 2005-12-21 | 2008-10-06 | 페인셉터 파마 코포레이션 | 개폐 이온 통로를 조절하기 위한 조성물 및 방법 |
| DE102006042143A1 (de) * | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
| DE102006056739A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Substituierte 4-Amino-3,5-dicyano-2-thiopyridine und ihre Verwendung |
| DE102006056740A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Cyclisch substituierte 3,5-Dicyano-2-thiopyridine und ihre Verwendung |
| US8063220B2 (en) | 2007-06-22 | 2011-11-22 | Richter Gedeon Nyrt. | Sulfonyl-quinoline derivatives |
| DE102007035367A1 (de) | 2007-07-27 | 2009-01-29 | Bayer Healthcare Ag | Substituierte Aryloxazole und ihre Verwendung |
| DE102007036076A1 (de) | 2007-08-01 | 2009-02-05 | Bayer Healthcare Aktiengesellschaft | Dipeptoid-Produgs und ihre Verwendung |
| DE102007061764A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
| DE102007061763A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte azabicyclische Verbindungen und ihre Verwendung |
| DE102008013587A1 (de) * | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| WO2009143992A1 (de) * | 2008-05-29 | 2009-12-03 | Bayer Schering Pharma Aktiengesellschaft | 2-alkoxy-substituierte dicyanopyridine und ihre verwendung |
| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
| DE102009006602A1 (de) * | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
| EP2496234A1 (en) | 2009-11-07 | 2012-09-12 | Merck Patent GmbH | Heteroarylaminoquinolines as tgf-beta receptor kinase inhibitors |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
| US20120058983A1 (en) | 2010-09-02 | 2012-03-08 | Bayer Pharma Aktiengesellschaft | Adenosine A1 agonists for the treatment of glaucoma and ocular hypertension |
| EP3323818A1 (en) | 2010-09-22 | 2018-05-23 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| IN2014CN03234A (enExample) | 2011-11-03 | 2015-07-03 | Merck Sharp & Dohme | |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| WO2017216726A1 (en) | 2016-06-13 | 2017-12-21 | Glaxosmithkline Intellectual Property Development Limited | Substituted pyridines as inhibitors of dnmt1 |
| 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 |
| 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 |
| 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 |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| KR20220087497A (ko) | 2019-10-18 | 2022-06-24 | 더 리전츠 오브 더 유니버시티 오브 캘리포니아 | 병원성 혈관을 표적화하기 위한 화합물 및 방법 |
| US12590298B2 (en) | 2019-10-18 | 2026-03-31 | The Regents Of The University Of California | Ex vivo tumor angiogenesis model |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63301821A (ja) * | 1986-03-05 | 1988-12-08 | Otsuka Pharmaceut Co Ltd | 抗不整脈剤 |
| EP0446604A3 (en) * | 1990-03-16 | 1992-02-19 | American Cyanamid Company | Pyridine and related aza heterocycle derivatives as cardiovascular agents |
| JP2000095759A (ja) * | 1998-07-21 | 2000-04-04 | Takeda Chem Ind Ltd | 三環性化合物、その製造法および剤 |
| PT1133474E (pt) * | 1998-12-04 | 2007-04-30 | Bristol Myers Squibb Co | Derivados da 4-arilquinolin-2-ona substituidos em 3 posições utilizados como moduladores do canal de potássio. |
| AU2002212969B2 (en) * | 2000-09-20 | 2006-07-06 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| WO2002024686A2 (en) * | 2000-09-25 | 2002-03-28 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinoline and quinazoline derivatives |
| FR2842524B1 (fr) * | 2002-07-16 | 2005-04-22 | Aventis Pharma Sa | Compositions pharmaceutiques contenant un derive de 3-guanidinocarbonyl-1-heteroaryl-pyrrole, leur procede de preparation a titre de medicaments |
| FR2842525B1 (fr) * | 2002-07-16 | 2005-05-13 | Aventis Pharma Sa | Derives de 3-guanidinocarbonyl-1-heteroaryl-indole, procede de preparation a titre de medicaments et compositions pharmaceutiques les renfermant |
-
2004
- 2004-09-17 CN CNA2004800273747A patent/CN1856307A/zh active Pending
- 2004-09-17 EP EP04784369A patent/EP1667683A4/en not_active Withdrawn
- 2004-09-17 CA CA2539707A patent/CA2539707C/en not_active Expired - Fee Related
- 2004-09-17 JP JP2006527054A patent/JP4722851B2/ja not_active Expired - Fee Related
- 2004-09-17 AU AU2004275719A patent/AU2004275719B2/en not_active Ceased
- 2004-09-17 US US10/571,841 patent/US7692017B2/en not_active Expired - Fee Related
- 2004-09-17 WO PCT/US2004/030485 patent/WO2005030129A2/en not_active Ceased
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