ZA200208894B - Pharmaceutically active piperidine derivatives, in particular as modulators of chemokine receptor activity. - Google Patents
Pharmaceutically active piperidine derivatives, in particular as modulators of chemokine receptor activity. Download PDFInfo
- Publication number
- ZA200208894B ZA200208894B ZA200208894A ZA200208894A ZA200208894B ZA 200208894 B ZA200208894 B ZA 200208894B ZA 200208894 A ZA200208894 A ZA 200208894A ZA 200208894 A ZA200208894 A ZA 200208894A ZA 200208894 B ZA200208894 B ZA 200208894B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- heteroaryl
- alkoxy
- compound
- optionally substituted
- Prior art date
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- 230000000694 effects Effects 0.000 title claims description 6
- 102000009410 Chemokine receptor Human genes 0.000 title description 2
- 108050000299 Chemokine receptor Proteins 0.000 title description 2
- 150000003053 piperidines Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 293
- 125000001072 heteroaryl group Chemical group 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 58
- -1 nitro, hydroxy Chemical group 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 102000005962 receptors Human genes 0.000 claims description 9
- 108020003175 receptors Proteins 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 239000000126 substance Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
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- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- 108010012236 Chemokines Proteins 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- 108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002975 chemoattractant Substances 0.000 description 3
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- 210000000440 neutrophil Anatomy 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
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- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 2
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- 108010035886 connective tissue-activating peptide Proteins 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
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Classifications
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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
- C07D401/04—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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- A61P11/02—Nasal agents, e.g. decongestants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| MXPA02008770A (es) * | 2000-03-06 | 2004-09-10 | Acadia Pharm Inc | Compuestos azaciclicos para uso en el tratamiento de enfermedades relacionadas con la serotonina. |
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| JP4508650B2 (ja) | 2002-01-29 | 2010-07-21 | グラクソ グループ リミテッド | アミノピペリジン化合物、当該化合物の製法および当該化合物を含有する医薬組成物 |
| EP2181996A1 (en) | 2002-01-29 | 2010-05-05 | Glaxo Group Limited | Aminopiperidine derivatives |
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| WO2003099773A1 (en) * | 2002-05-24 | 2003-12-04 | Millennium Pharmaceuticals, Inc. | Ccr9 inhibitors and methods of use thereof |
| US7253186B2 (en) | 2002-06-24 | 2007-08-07 | Carl-Magnus Andersson | N-substituted piperidine derivatives as serotonin receptor agents |
| CA2490397A1 (en) | 2002-06-24 | 2003-12-31 | Acadia Pharmaceuticals Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
| US7538222B2 (en) | 2002-06-24 | 2009-05-26 | Acadia Pharmaceuticals, Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
| AR040336A1 (es) | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de piperidina, uso del mismo para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para preparar dicho compuesto |
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| ATE555087T1 (de) | 2002-11-27 | 2012-05-15 | Incyte Corp | 3-aminopyrrolidinderivate als modulatoren von chemokinrezeptoren |
| AR042628A1 (es) * | 2002-12-20 | 2005-06-29 | Astrazeneca Ab | Derivados de piperidina como moduladores del receptor ccr5 |
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| WO2004064738A2 (en) | 2003-01-16 | 2004-08-05 | Acadia Pharmaceuticals Inc. | Selective serotonin 2a/2c receptor inverse agonists as therapeutics for neurodegenerative diseases |
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| US7521462B2 (en) | 2004-02-27 | 2009-04-21 | Eli Lilly And Company | 4-Amino-piperidine derivatives as monoamine uptake inhibitors |
| TW200610761A (en) * | 2004-04-23 | 2006-04-01 | Astrazeneca Ab | Chemical compounds |
| US7820695B2 (en) | 2004-05-21 | 2010-10-26 | Acadia Pharmaceuticals, Inc. | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US20050261278A1 (en) | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| CN1329374C (zh) * | 2004-06-09 | 2007-08-01 | 上海靶点药物有限公司 | 作为ccr5拮抗剂的化合物 |
| KR100905260B1 (ko) * | 2004-06-09 | 2009-06-30 | 상해 타킷 드러그 주식회사 | 씨씨알5 길항제로서의 화합물 |
| SE0401656D0 (sv) * | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | Chemical compounds |
| AU2005283326B2 (en) * | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| AU2005289635A1 (en) * | 2004-09-27 | 2006-04-06 | Acadia Pharmaceuticals Inc. | Salts of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide and their preparation |
| US7790899B2 (en) | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| SE0403106D0 (sv) * | 2004-12-20 | 2004-12-20 | Astrazeneca Ab | Chemical compounds |
| CA2612325A1 (en) * | 2005-06-15 | 2006-12-28 | Anormed Inc. | Chemokine receptor binding compounds |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| EP1943250A1 (en) | 2005-09-09 | 2008-07-16 | Euro-Celtique S.A. | Fused and spirocycle compounds and the use thereof |
| SI1928821T1 (sl) | 2005-09-21 | 2009-04-30 | Pfizer Ltd | Derivati karboksamida kot antagonisti muskarinskih receptorjev |
| HUP0500879A2 (en) | 2005-09-22 | 2007-05-29 | Sanofi Aventis | Amide derivatives as ccr3 receptor ligands, process for producing them, pharmaceutical compositions containing them and their use and intermediates |
| CN101291905A (zh) | 2005-10-19 | 2008-10-22 | 弗·哈夫曼-拉罗切有限公司 | 苯乙酰胺nnrt抑制剂 |
| BRPI0708731A2 (pt) | 2006-03-10 | 2011-06-07 | Ono Pharmaceutical Co | derivado heterocìclico nitrogenado, e agente farmacêutico compreendendo o derivado como ingrediente ativo |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| WO2007118854A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| WO2007118853A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| EP2102889B1 (en) * | 2006-12-12 | 2020-10-07 | Evatec AG | Rf substrate bias with high power impulse magnetron sputtering (hipims) |
| KR101475091B1 (ko) | 2006-12-13 | 2014-12-22 | 에프. 호프만-라 로슈 아게 | 비뉴클레오시드 역전사 효소 억제제로서 2-(피페리딘-4-일)-4-페녹시- 또는 페닐아미노-피리미딘 유도체 |
| US20090053329A1 (en) | 2007-03-19 | 2009-02-26 | Acadia Pharmaceuticals, Inc. | Combinations of 5-ht2a inverse agonists and antagonists with antipsychotics |
| WO2008124118A1 (en) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| EP2173715A2 (en) * | 2007-07-13 | 2010-04-14 | Euroscreen S.A. | Use of piperidine derivatives as agonists of chemokine receptor activity |
| DK2200610T3 (en) * | 2007-09-21 | 2018-04-23 | Acadia Pharm Inc | ADMINISTRATION OF PIMAVANSERIN WITH OTHER AGENTS |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| WO2009058923A1 (en) * | 2007-10-31 | 2009-05-07 | Smithkline Beecham Corporation | Ccr5 antagonists as therapeutic agents |
| WO2009058924A1 (en) * | 2007-10-31 | 2009-05-07 | Smithkline Beecham Corporation | Ccr5 antagonists as therapeutic agents |
| WO2009075960A1 (en) * | 2007-12-12 | 2009-06-18 | Smithkline Beecham Corporation | Ccr5 antagonists as therapeutic agents |
| EA201200829A1 (ru) | 2008-01-10 | 2012-11-30 | Такеда Фармасьютикал Компани Лимитед | Состав капсулы |
| CN102140104B (zh) * | 2010-02-03 | 2014-11-12 | 中国科学院上海药物研究所 | 1-(3-(s)-氨基丙基)-哌啶-4-氨基酰胺类化合物、其药物组合物及其制备方法和用途 |
| WO2012113103A1 (en) * | 2011-02-25 | 2012-08-30 | Helsinn Healthcare S.A. | Asymmetric ureas and medical uses thereof |
| CN103130709B (zh) * | 2011-11-22 | 2017-04-12 | 常州亚邦制药有限公司 | 具有抗hiv活性的3‑氨基丙酸哌啶酰胺类化合物，合成方法及用途 |
| EP3233077A4 (en) | 2014-12-19 | 2018-08-08 | The Broad Institute Inc. | Dopamine d2 receptor ligands |
| EP3233799B1 (en) * | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| CN107108467B (zh) * | 2014-12-24 | 2022-08-19 | 北京生命科学研究所 | 细胞坏死抑制剂 |
| PT3325444T (pt) | 2015-07-20 | 2021-09-22 | Acadia Pharm Inc | Métodos para preparar n-(4-fluorobenzil)-n-(1-metilpiperidina-4-il)-n'-(4-(2-metilpropiloxi)fenilmetil)carbamida e o seu sal de tartarato e forma polimórfica c |
| US10525048B2 (en) | 2015-09-18 | 2020-01-07 | Memorial Sloan Kettering Cancer Center | Methods and compositions of inhibiting DCN1-UBC12 interaction |
| EA037040B1 (ru) | 2016-03-22 | 2021-01-29 | Хелсинн Хелскеа Са | Асимметричные бензолсульфонилмочевины и их применение в качестве модуляторов рецептора грелина |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| EP3615028A1 (en) | 2017-04-28 | 2020-03-04 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| US20210077479A1 (en) | 2017-08-30 | 2021-03-18 | Acadia Pharmaceuticals Inc. | Formulations of pimavanserin |
| TW202317528A (zh) | 2021-06-24 | 2023-05-01 | 美商富曼西公司 | 用於防治無脊椎有害生物的唑類化合物 |
| CN113582915B (zh) * | 2021-07-25 | 2024-03-08 | 河南师范大学 | 一种4-取代吡啶类化合物的合成方法 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1220440B (de) * | 1962-02-14 | 1966-07-07 | Sanol Arznei Schwarz Gmbh | Verfahren zur Herstellung von Derivaten des 1-(o-Bromphenoxy)-2-hydroxy-3-amino-propans und deren Saeureadditionssalzen |
| US3577432A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-phenoxypyrrolidines |
| US4029801A (en) * | 1970-09-03 | 1977-06-14 | John Wyeth & Brother Limited | Pharmaceutical compositions and methods of treating hypertension |
| US3755584A (en) * | 1972-04-03 | 1973-08-28 | Abbott Lab | Tranquilizers |
| US3818017A (en) * | 1973-01-04 | 1974-06-18 | Janssen Pharmaceutica Nv | 1-{8 1-(2-hydroxy-3-aryloxypropyl)-4-piperidyl{9 -2-benzimidazolinones and related compounds |
| US3894030A (en) * | 1973-01-04 | 1975-07-08 | Janssen Pharmaceutica Nv | 1-{8 1-(2-Hydroxy-3-aryloxypropyl)-4-piperidyl{9 -2-benzimidazolinones and related compounds |
| GB1425354A (en) * | 1973-10-10 | 1976-02-18 | Wyeth John & Brother Ltd | Indole derivatives |
| JPS5285174A (en) * | 1976-01-05 | 1977-07-15 | Yoshitomi Pharmaceut Ind Ltd | Novel urea or thiourea derivatives |
| FR2361880A1 (fr) * | 1976-04-29 | 1978-03-17 | Science Union & Cie | Nouvelles 4-amino piperidines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| GB1538543A (en) * | 1976-06-23 | 1979-01-24 | Wyeth John & Brother Ltd | N-aminoalkyl piperidine derivatives |
| GB1532671A (en) * | 1976-07-16 | 1978-11-15 | Wyeth John & Brother Ltd | Piperidine derivatives |
| GB1586468A (en) * | 1976-10-29 | 1981-03-18 | Anphar Sa | Piperidine derivatives |
| US4166119A (en) * | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4264613A (en) * | 1979-08-01 | 1981-04-28 | Science Union Et Cie, Societe Francaise De Recherche Medicale | Piperidylbenzimidazolinone compounds |
| FR2469411A1 (fr) * | 1979-11-15 | 1981-05-22 | Science Union & Cie | Nouveaux derives de la piperidylbenzimidazolinone, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| US5614533A (en) * | 1987-03-13 | 1997-03-25 | Bio-Mega/Boehringer Ingelheim Research, Inc. | Substituted pipecolinic acid derivatives as HIV protease inhibitors |
| JPH02104568A (ja) * | 1988-06-22 | 1990-04-17 | Yoshitomi Pharmaceut Ind Ltd | 神経成長因子産生促進作用剤 |
| DK386089A (da) * | 1988-08-12 | 1990-02-13 | Japan Tobacco Inc | Katekolderivater |
| GB9005014D0 (en) * | 1990-03-06 | 1990-05-02 | Janssen Pharmaceutica Nv | N.(4.piperidinyl)(dihydrobenzofuran or dihydro.2h.benzopyran)carboxamide derivatives |
| FR2662162B1 (fr) * | 1990-05-18 | 1995-01-20 | Adir | Nouveaux derives de l'amino piperidine, de l'amino pyrrolidine et de l'amino perhydroazepine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5595872A (en) * | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
| CA2123728A1 (en) * | 1993-05-21 | 1994-11-22 | Noriyoshi Sueda | Urea derivatives and their use as acat inhibitors |
| US5789402A (en) * | 1995-01-17 | 1998-08-04 | Eli Lilly Company | Compounds having effects on serotonin-related systems |
| US5614523A (en) * | 1995-01-17 | 1997-03-25 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5576321A (en) * | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5741789A (en) * | 1995-01-17 | 1998-04-21 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5627196A (en) * | 1995-01-17 | 1997-05-06 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5696267A (en) * | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
| US5688960A (en) * | 1995-05-02 | 1997-11-18 | Schering Corporation | Substituted oximes, hydrazones and olefins useful as neurokinin antagonists |
| JP2002510327A (ja) * | 1997-07-25 | 2002-04-02 | メルク エンド カンパニー インコーポレーテッド | 環状アミンケモカイン受容体活性調節剤 |
| HUP0004200A3 (en) * | 1997-11-18 | 2001-04-28 | Dupont Pharmaceuticals Res Lab | Cyclic amine derivatives and their use as drugs |
| EP1086078B1 (en) * | 1998-06-08 | 2003-02-05 | Schering Corporation | Neuropeptide y5 receptor antagonists |
| EP1013276A1 (en) * | 1998-12-23 | 2000-06-28 | Pfizer Inc. | Aminoazacycloalkanes as CCR5 modulators |
| WO2000076973A1 (en) * | 1999-06-11 | 2000-12-21 | Merck & Co., Inc. | N-cyclopentyl modulators of chemokine receptor activity |
| AU5473800A (en) * | 1999-06-11 | 2001-01-02 | Merck & Co., Inc. | Cyclopentyl modulators of chemokine receptor activity |
| SE9902987D0 (sv) * | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| WO2001070689A1 (fr) * | 2000-03-24 | 2001-09-27 | Meiji Seika Kaisha, Ltd. | DERIVES DE LA DIPHENYLALKYLAMINE UTILES COMME AGONISTES DU RECEPTEUR DE L'OPIOIDE $g(d) |
| US20020094989A1 (en) * | 2000-10-11 | 2002-07-18 | Hale Jeffrey J. | Pyrrolidine modulators of CCR5 chemokine receptor activity |
| GB0104050D0 (en) * | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0107228D0 (en) * | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
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2001
- 2001-05-14 CZ CZ20023777A patent/CZ20023777A3/cs unknown
- 2001-05-14 CA CA002407258A patent/CA2407258A1/en not_active Abandoned
- 2001-05-14 JP JP2001584235A patent/JP2003533510A/ja active Pending
- 2001-05-14 KR KR1020027015475A patent/KR20030001511A/ko not_active Application Discontinuation
- 2001-05-14 BR BR0110767-4A patent/BR0110767A/pt not_active IP Right Cessation
- 2001-05-14 IL IL15241801A patent/IL152418A0/xx unknown
- 2001-05-14 US US10/276,430 patent/US20040006081A1/en not_active Abandoned
- 2001-05-14 CN CN01812747A patent/CN1441781A/zh active Pending
- 2001-05-14 EP EP01932457A patent/EP1289957A1/en not_active Withdrawn
- 2001-05-14 SK SK1615-2002A patent/SK16152002A3/sk unknown
- 2001-05-14 RU RU2002128614/04A patent/RU2002128614A/ru not_active Application Discontinuation
- 2001-05-14 PL PL01365118A patent/PL365118A1/xx not_active Application Discontinuation
- 2001-05-14 MX MXPA02011304A patent/MXPA02011304A/es unknown
- 2001-05-14 EE EEP200200647A patent/EE200200647A/xx unknown
- 2001-05-14 AU AU2001258981A patent/AU2001258981A1/en not_active Abandoned
- 2001-05-14 HU HU0302153A patent/HUP0302153A2/hu unknown
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- 2001-05-16 AR ARP010102321A patent/AR032331A1/es not_active Application Discontinuation
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2002
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2003
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Also Published As
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| HUP0302153A2 (hu) | 2003-10-28 |
| AU2001258981A1 (en) | 2001-11-26 |
| CA2407258A1 (en) | 2001-11-22 |
| WO2001087839A1 (en) | 2001-11-22 |
| IL152418A0 (en) | 2003-05-29 |
| EE200200647A (et) | 2004-08-16 |
| NO20025430L (no) | 2002-12-18 |
| NO20025430D0 (no) | 2002-11-13 |
| HK1052507A1 (zh) | 2003-09-19 |
| GB0011838D0 (en) | 2000-07-05 |
| KR20030001511A (ko) | 2003-01-06 |
| RU2002128614A (ru) | 2004-02-27 |
| IS6608A (is) | 2002-11-07 |
| CN1441781A (zh) | 2003-09-10 |
| JP2003533510A (ja) | 2003-11-11 |
| AR032331A1 (es) | 2003-11-05 |
| SK16152002A3 (sk) | 2003-05-02 |
| EP1289957A1 (en) | 2003-03-12 |
| PL365118A1 (en) | 2004-12-27 |
| BR0110767A (pt) | 2003-02-11 |
| US20040006081A1 (en) | 2004-01-08 |
| WO2001087839A8 (en) | 2004-04-08 |
| CZ20023777A3 (cs) | 2003-05-14 |
| MXPA02011304A (es) | 2003-04-25 |
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