AP848A - 6-Phenylpyridyl-2-amine derivatives useful as NOS inhibitors. - Google Patents
6-Phenylpyridyl-2-amine derivatives useful as NOS inhibitors. Download PDFInfo
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- AP848A AP848A APAP/P/1997/001156A AP9701156A AP848A AP 848 A AP848 A AP 848A AP 9701156 A AP9701156 A AP 9701156A AP 848 A AP848 A AP 848A
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- 239000003112 inhibitor Substances 0.000 title abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract 9
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 hydroxy, methyl Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229960005181 morphine Drugs 0.000 claims description 5
- 210000002569 neuron Anatomy 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- MNUHYQZBNHDABI-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-6-amine Chemical group C1NCC2C(N)C21 MNUHYQZBNHDABI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 8
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 8
- 230000001154 acute effect Effects 0.000 claims 8
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 8
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 230000002401 inhibitory effect Effects 0.000 claims 6
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- 125000003118 aryl group Chemical group 0.000 claims 4
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- 239000000126 substance Substances 0.000 claims 4
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- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- XDWUSBKLDNVDDQ-UHFFFAOYSA-N 6-phenylpyridin-2-amine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=N1 XDWUSBKLDNVDDQ-UHFFFAOYSA-N 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 82
- 238000005160 1H NMR spectroscopy Methods 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 56
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 33
- 239000003921 oil Substances 0.000 description 32
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
- 239000000047 product Substances 0.000 description 30
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 8
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- HTNVCPGFIZOGBR-UHFFFAOYSA-N 6-(4-piperidin-4-ylphenyl)pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)C2CCNCC2)=N1 HTNVCPGFIZOGBR-UHFFFAOYSA-N 0.000 description 6
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- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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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 2
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Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Neurosurgery (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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US3279396P | 1996-12-06 | 1996-12-06 | |
PCT/IB1997/001446 WO1998024766A1 (en) | 1996-12-06 | 1997-11-17 | 6-phenylpyridyl-2-amine derivatives useful as nos inhibitors |
Publications (2)
Publication Number | Publication Date |
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AP9701156A0 AP9701156A0 (en) | 1998-01-31 |
AP848A true AP848A (en) | 2000-06-09 |
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APAP/P/1997/001156A AP848A (en) | 1996-12-06 | 1997-12-04 | 6-Phenylpyridyl-2-amine derivatives useful as NOS inhibitors. |
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EP (1) | EP0946512B1 (cs) |
JP (2) | JP3604399B2 (cs) |
KR (1) | KR100360633B1 (cs) |
CN (1) | CN1117077C (cs) |
AP (1) | AP848A (cs) |
AR (1) | AR010331A1 (cs) |
AT (1) | ATE251612T1 (cs) |
AU (2) | AU4791797A (cs) |
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BR (1) | BR9714381A (cs) |
CA (1) | CA2273479C (cs) |
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DZ (1) | DZ2361A1 (cs) |
EA (1) | EA002907B1 (cs) |
ES (1) | ES2206691T3 (cs) |
HN (2) | HN1997000027A (cs) |
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IL (1) | IL130111A0 (cs) |
IS (1) | IS5053A (cs) |
MA (1) | MA26453A1 (cs) |
NO (1) | NO313517B1 (cs) |
NZ (1) | NZ335733A (cs) |
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PA (1) | PA8442201A1 (cs) |
PE (1) | PE46499A1 (cs) |
PL (1) | PL333918A1 (cs) |
PT (1) | PT946512E (cs) |
SI (1) | SI0946512T1 (cs) |
SK (1) | SK70899A3 (cs) |
TN (1) | TNSN97198A1 (cs) |
TR (1) | TR199901259T2 (cs) |
TW (1) | TW491840B (cs) |
UA (1) | UA59379C2 (cs) |
UY (1) | UY24799A1 (cs) |
WO (1) | WO1998024766A1 (cs) |
YU (1) | YU25399A (cs) |
ZA (1) | ZA9710906B (cs) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
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JP3455229B2 (ja) * | 1996-03-29 | 2003-10-14 | ファイザー インク. | 6―フェニルピリジル―2―アミン誘導体 |
US20010049379A1 (en) | 1997-08-27 | 2001-12-06 | Lowe John Adams | 2-aminopyridines containing fused ring substituents |
HN1998000118A (es) | 1997-08-27 | 1999-02-09 | Pfizer Prod Inc | 2 - aminopiridinas que contienen sustituyentes de anillos condensados. |
HN1998000125A (es) * | 1997-08-28 | 1999-02-09 | Pfizer Prod Inc | 2-aminopiridinas con sustituyentes alcoxi ramificados |
NZ508057A (en) | 1998-06-03 | 2003-07-25 | Pfizer Prod Inc | 2-aminopyridines containing fused ring substituents as nitric oxide synthase inhibitors |
FR2791674A1 (fr) * | 1999-04-02 | 2000-10-06 | Sod Conseils Rech Applic | Nouveaux derives de 2-aminopyridines, leur utilisation en tant que medicaments et compositions pharmaceutiques les contenant |
FR2780971B1 (fr) * | 1998-07-08 | 2001-09-28 | Sod Conseils Rech Applic | Nouveaux derives de 2-aminopyridines, leur application en tant que medicaments et compositions pharmaceutiques les contenant |
AR019190A1 (es) * | 1998-07-08 | 2001-12-26 | Sod Conseils Rech Applic | Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos |
AP2001002067A0 (en) * | 1998-08-11 | 2001-03-31 | Pfizer Prod Inc | New pharmaceutical uses for nos inhibitors. |
SE9803710L (sv) | 1998-09-25 | 2000-03-26 | A & Science Invest Ab | Användning av vissa substanser för behandling av nervrotsskador |
US7115557B2 (en) | 1998-09-25 | 2006-10-03 | Sciaticon Ab | Use of certain drugs for treating nerve root injury |
ES2200813T3 (es) | 1999-02-25 | 2004-03-16 | Pfizer Products Inc. | 2-aminopiridinas que contienen sustituyentes de anillo condesado. |
HK1046645A1 (zh) * | 1999-07-23 | 2003-01-24 | 盐野义制药株式会社 | Th2分化抑制剂 |
FR2804429B1 (fr) * | 2000-01-31 | 2003-05-09 | Adir | Nouveaux derives de 4-sulfonamides piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
WO2002080853A2 (en) * | 2001-04-09 | 2002-10-17 | Bristol-Myers Squibb Company | Fused heterocyclic inhibitors of factor xa |
US20030045449A1 (en) * | 2001-08-15 | 2003-03-06 | Pfizer, Inc. | Pharmaceutical combinations for the treatment of neurodegenerative diseases |
CA2522323C (en) * | 2003-04-14 | 2009-09-15 | Pfizer Products Inc. | 3-azabicyclo[3.2.1]octane derivatives as opioid receptor ligands |
CN1295216C (zh) * | 2003-07-04 | 2007-01-17 | 中国人民解放军军事医学科学院毒物药物研究所 | 吲哚酮类衍生物及其用于制备抗肿瘤药物的用途 |
US20080070952A1 (en) * | 2005-02-21 | 2008-03-20 | Proximagen Ltd., | Inhibition or Treatment of Dyskinesia |
WO2006105795A1 (en) * | 2005-04-08 | 2006-10-12 | Leo Pharma A/S | Novel indolinone derivatives |
WO2008021849A2 (en) * | 2006-08-09 | 2008-02-21 | Smithkline Beecham Corporation | Novel compounds as antagonists or inverse agonists at opioid receptors |
US8835437B2 (en) | 2007-06-08 | 2014-09-16 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
EP2152270B1 (en) | 2007-06-08 | 2015-03-04 | Janssen Pharmaceutica, N.V. | Piperidine/piperazine derivatives |
EP2152269B1 (en) | 2007-06-08 | 2014-04-23 | Janssen Pharmaceutica, N.V. | Piperidine/piperazine derivatives |
CA2725933C (en) | 2008-06-05 | 2018-01-16 | Janssen Pharmaceutica Nv | Drug combinations comprising a dgat inhibitor and a ppar-agonist |
UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
US8889674B2 (en) * | 2009-03-05 | 2014-11-18 | Shionogi & Co., Ltd. | Piperidine and pyrrolidine derivatives having NPY Y5 receptor antagonism |
US11013844B2 (en) * | 2014-11-20 | 2021-05-25 | City Of Hope | Treatment device for plasma virus inactivation |
TWI874960B (zh) | 2016-08-12 | 2025-03-01 | 美商亞瑟尼克斯公司 | 聯芳組成物和調控激酶級聯之方法 |
PT3684767T (pt) | 2017-09-22 | 2024-07-29 | Jubilant Epipad LLC | Compostos heterocíclicos como inibidores de pad |
ES2941512T3 (es) | 2017-10-18 | 2023-05-23 | Jubilant Epipad LLC | Compuestos de imidazo-piridina como inhibidores de PAD |
SG11202004143XA (en) | 2017-11-06 | 2020-06-29 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
KR102780935B1 (ko) | 2017-11-24 | 2025-03-12 | 주빌런트 에피스크라이브 엘엘씨 | Prmt5 억제제로서의 헤테로사이클릭 화합물 |
JP7279063B6 (ja) | 2018-03-13 | 2024-02-15 | ジュビラント プローデル エルエルシー | Pd1/pd-l1相互作用/活性化の阻害剤としての二環式化合物 |
CN114206843A (zh) * | 2019-06-14 | 2022-03-18 | Srx心脏有限责任公司 | 用于调节前蛋白转化酶枯草杆菌蛋白酶/Kexin 9型(PCSK9)的化合物 |
US12115154B2 (en) * | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
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WO1992014780A1 (en) | 1991-02-19 | 1992-09-03 | Akzo N.V. | Stabilized carbon monoxide-olefin copolymers |
EP0674627A1 (en) * | 1992-12-18 | 1995-10-04 | The Wellcome Foundation Limited | Pyrimidine, pyridine, pteridinone and indazole derivatives as enzyme inhibitors |
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AU4515696A (en) * | 1994-12-12 | 1996-07-03 | Merck & Co., Inc. | Substituted 2-aminopyridines as inhibitors of nitric oxide synthase |
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1997
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- 1997-11-17 DE DE69725465T patent/DE69725465T2/de not_active Expired - Fee Related
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- 1997-11-17 DK DK97910587T patent/DK0946512T3/da active
- 1997-11-17 HU HU0001848A patent/HUP0001848A3/hu unknown
- 1997-11-17 CZ CZ19992017A patent/CZ293863B6/cs not_active IP Right Cessation
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- 1997-11-22 TW TW086117501A patent/TW491840B/zh active
- 1997-12-01 PE PE1997001080A patent/PE46499A1/es not_active Application Discontinuation
- 1997-12-03 MA MA24884A patent/MA26453A1/fr unknown
- 1997-12-03 TN TNTNSN97198A patent/TNSN97198A1/fr unknown
- 1997-12-03 UY UY24799A patent/UY24799A1/es unknown
- 1997-12-03 DZ DZ970211A patent/DZ2361A1/xx active
- 1997-12-04 AR ARP970105713A patent/AR010331A1/es not_active Application Discontinuation
- 1997-12-04 AP APAP/P/1997/001156A patent/AP848A/en active
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1999
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2001
- 2001-03-08 US US09/802,086 patent/US20020032191A1/en not_active Abandoned
- 2001-09-13 AU AU72050/01A patent/AU766080B2/en not_active Ceased
- 2001-09-27 US US09/965,564 patent/US20020103227A1/en not_active Abandoned
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2004
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