OA11123A - 6-Phenylpyridyl-2-amine derivatives useful as nos inhibitors - Google Patents

6-Phenylpyridyl-2-amine derivatives useful as nos inhibitors Download PDF

Info

Publication number: OA11123A
Authority: OA; OAPI
Prior art keywords: phenyl; pyridin; ylamine; nmr; methyl
Prior art date: 1996-12-06

Application number

OA9900115A

Other languages

English (en)

Inventor

Lowe John Adams Iii

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1996-12-06

Filing date

1999-06-01

Publication date

2003-04-07

1999-06-01 Application filed by Pfizer filed Critical Pfizer

2003-04-07 Publication of OA11123A publication Critical patent/OA11123A/en

Links

239000003112 inhibitor Substances 0.000 title abstract description 6
102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 26
108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 26
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 89
-1 hydroxy, methyl Chemical group 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 24
125000003710 aryl alkyl group Chemical group 0.000 claims description 23
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
241000124008 Mammalia Species 0.000 claims description 16
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 16
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 15
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 15
230000001154 acute effect Effects 0.000 claims description 15
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201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 15
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
208000002193 Pain Diseases 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
230000002401 inhibitory effect Effects 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 10
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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229910052757 nitrogen Inorganic materials 0.000 claims description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
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125000001246 bromo group Chemical group Br* 0.000 claims description 4
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125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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RDUSFASPCBUTSL-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethylidene]-1-methylindol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1=C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 RDUSFASPCBUTSL-UHFFFAOYSA-N 0.000 claims description 2
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230000006378 damage Effects 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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206010012601 diabetes mellitus Diseases 0.000 claims 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
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125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
ZOMWHUFJIVHYTM-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethyl]-1-methyl-3h-indol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 ZOMWHUFJIVHYTM-UHFFFAOYSA-N 0.000 claims 1
AFXPRGRPBFUARV-UHFFFAOYSA-N 3-[(6-aminopyridin-2-yl)-phenylmethylidene]-1-[2-(dimethylamino)ethyl]indol-2-one Chemical compound C12=CC=CC=C2N(CCN(C)C)C(=O)C1=C(C=1N=C(N)C=CC=1)C1=CC=CC=C1 AFXPRGRPBFUARV-UHFFFAOYSA-N 0.000 claims 1
MNUHYQZBNHDABI-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1NCC2C(N)C21 MNUHYQZBNHDABI-UHFFFAOYSA-N 0.000 claims 1
208000025865 Ulcer Diseases 0.000 claims 1
208000027418 Wounds and injury Diseases 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
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125000003386 piperidinyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 5
210000003169 central nervous system Anatomy 0.000 abstract description 2
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
230000002265 prevention Effects 0.000 abstract 1
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238000005160 1H NMR spectroscopy Methods 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
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229910000073 phosphorus hydride Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
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BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
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NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 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
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OA9900115A 1996-12-06 1999-06-01 6-Phenylpyridyl-2-amine derivatives useful as nos inhibitors OA11123A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3279396P	1996-12-06	1996-12-06

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OA11123A true OA11123A (en)	2003-04-07

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OA9900115A OA11123A (en)	1996-12-06	1999-06-01	6-Phenylpyridyl-2-amine derivatives useful as nos inhibitors

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US (3)	US6235750B1 (fr)
EP (1)	EP0946512B1 (fr)
JP (2)	JP3604399B2 (fr)
KR (1)	KR100360633B1 (fr)
CN (1)	CN1117077C (fr)
AP (1)	AP848A (fr)
AR (1)	AR010331A1 (fr)
AT (1)	ATE251612T1 (fr)
AU (2)	AU4791797A (fr)
BG (1)	BG103540A (fr)
BR (1)	BR9714381A (fr)
CA (1)	CA2273479C (fr)
CZ (1)	CZ293863B6 (fr)
DE (1)	DE69725465T2 (fr)
DK (1)	DK0946512T3 (fr)
DZ (1)	DZ2361A1 (fr)
EA (1)	EA002907B1 (fr)
ES (1)	ES2206691T3 (fr)
HN (2)	HN1997000027A (fr)
HR (1)	HRP970664A2 (fr)
HU (1)	HUP0001848A3 (fr)
ID (1)	ID19056A (fr)
IL (1)	IL130111A0 (fr)
IS (1)	IS5053A (fr)
MA (1)	MA26453A1 (fr)
NO (1)	NO313517B1 (fr)
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OA (1)	OA11123A (fr)
PA (1)	PA8442201A1 (fr)
PE (1)	PE46499A1 (fr)
PL (1)	PL333918A1 (fr)
PT (1)	PT946512E (fr)
SI (1)	SI0946512T1 (fr)
SK (1)	SK70899A3 (fr)
TN (1)	TNSN97198A1 (fr)
TR (1)	TR199901259T2 (fr)
TW (1)	TW491840B (fr)
UA (1)	UA59379C2 (fr)
UY (1)	UY24799A1 (fr)
WO (1)	WO1998024766A1 (fr)
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EP2152270B1 (fr)	2007-06-08	2015-03-04	Janssen Pharmaceutica, N.V.	Dérivés de piperidine/piperazine
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PE20100083A1 (es)	2008-06-05	2010-02-17	Janssen Pharmaceutica Nv	Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar
UA105182C2 (ru)	2008-07-03	2014-04-25	Ньюрексон, Інк.	Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
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RU2764243C2 (ru)	2017-09-22	2022-01-14	ДЖУБИЛАНТ ЭПИПЭД ЭлЭлСи	Гетероциклические соединения в качестве ингибиторов PAD
CN111225915B (zh)	2017-10-18	2023-03-07	朱比兰特埃皮帕德有限公司	作为pad抑制剂的咪唑并吡啶化合物
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RS65576B1 (sr)	2017-11-24	2024-06-28	Jubilant Episcribe Llc	Heterociklična jedinjenja kao inhibitori prmt5
CN112105610B (zh)	2018-03-13	2024-01-26	朱比连特普罗德尔有限责任公司	作为pd1/pd-l1相互作用/活化的抑制剂的双环化合物
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1997
- 1997-02-18 HN HN1997000027A patent/HN1997000027A/es unknown
- 1997-11-17 DE DE69725465T patent/DE69725465T2/de not_active Expired - Fee Related
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- 1997-11-17 SI SI9730597T patent/SI0946512T1/xx unknown
- 1997-11-17 TR TR1999/01259T patent/TR199901259T2/xx unknown
- 1997-11-17 WO PCT/IB1997/001446 patent/WO1998024766A1/fr not_active Ceased
- 1997-11-17 UA UA99063103A patent/UA59379C2/uk unknown
- 1997-11-17 PL PL97333918A patent/PL333918A1/xx unknown
- 1997-11-17 CN CN97180350A patent/CN1117077C/zh not_active Expired - Fee Related
- 1997-11-17 CZ CZ19992017A patent/CZ293863B6/cs not_active IP Right Cessation
- 1997-11-17 YU YU25399A patent/YU25399A/sh unknown
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- 1997-11-17 AU AU47917/97A patent/AU4791797A/en not_active Abandoned
- 1997-11-17 KR KR1019997004981A patent/KR100360633B1/ko not_active Expired - Fee Related
- 1997-11-17 DK DK97910587T patent/DK0946512T3/da active
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- 1997-11-17 EP EP97910587A patent/EP0946512B1/fr not_active Expired - Lifetime
- 1997-11-17 HU HU0001848A patent/HUP0001848A3/hu unknown
- 1997-11-17 BR BR9714381-2A patent/BR9714381A/pt not_active Application Discontinuation
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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 DZ DZ970211A patent/DZ2361A1/fr active
- 1997-12-03 TN TNTNSN97198A patent/TNSN97198A1/fr unknown
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- 1997-12-03 MA MA24884A patent/MA26453A1/fr unknown
- 1997-12-04 AP APAP/P/1997/001156A patent/AP848A/en active
- 1997-12-04 HR HR60/032,793A patent/HRP970664A2/hr not_active Application Discontinuation
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- 1997-12-04 ZA ZA9710906A patent/ZA9710906B/xx unknown
- 1997-12-04 PA PA19978442201A patent/PA8442201A1/es unknown
- 1997-12-05 ID IDP973838A patent/ID19056A/id unknown
1999
- 1999-05-18 IS IS5053A patent/IS5053A/is unknown
- 1999-06-01 OA OA9900115A patent/OA11123A/en unknown
- 1999-06-03 US US09/325,480 patent/US6235750B1/en not_active Expired - Fee Related
- 1999-06-04 NO NO19992725A patent/NO313517B1/no unknown
- 1999-06-30 BG BG103540A patent/BG103540A/bg unknown
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
2004
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Also Published As

Publication number	Publication date
CA2273479C (fr)	2006-02-07
TNSN97198A1 (fr)	2005-03-15
ES2206691T3 (es)	2004-05-16
JP3604399B2 (ja)	2004-12-22
BR9714381A (pt)	2000-05-02
SI0946512T1 (en)	2004-04-30
AU766080B2 (en)	2003-10-09
DE69725465T2 (de)	2004-05-06
UA59379C2 (uk)	2003-09-15
EP0946512A1 (fr)	1999-10-06
YU25399A (sh)	2001-07-10
PL333918A1 (en)	2000-01-31
CA2273479A1 (fr)	1998-06-11
HN1997000149A (es)	1997-12-26
AP9701156A0 (en)	1998-01-31
JP2005170924A (ja)	2005-06-30
UY24799A1 (es)	2001-08-27
ATE251612T1 (de)	2003-10-15
CZ293863B6 (cs)	2004-08-18
US20020103227A1 (en)	2002-08-01
HUP0001848A2 (hu)	2001-04-28
NO992725D0 (no)	1999-06-04
AR010331A1 (es)	2000-06-07
JP2000505814A (ja)	2000-05-16
US6235750B1 (en)	2001-05-22
EA002907B1 (ru)	2002-10-31
TW491840B (en)	2002-06-21
BG103540A (bg)	2000-12-29
EA199900448A1 (ru)	2000-02-28
ID19056A (id)	1998-06-11
NO992725L (no)	1999-06-04
CN1117077C (zh)	2003-08-06
CZ201799A3 (cs)	2000-07-12
PE46499A1 (es)	1999-05-12
EP0946512B1 (fr)	2003-10-08
IS5053A (is)	1999-05-18
PA8442201A1 (es)	2000-05-24
HRP970664A2 (en)	1998-10-31
PT946512E (pt)	2004-01-30
DK0946512T3 (da)	2004-01-12
NO313517B1 (no)	2002-10-14
AU4791797A (en)	1998-06-29
SK70899A3 (en)	2002-04-04
IL130111A0 (en)	2000-06-01
NZ335733A (en)	2001-01-26
AP848A (en)	2000-06-09
AU7205001A (en)	2001-11-15
WO1998024766A1 (fr)	1998-06-11
TR199901259T2 (xx)	1999-08-23
KR100360633B1 (ko)	2002-11-13
CN1239952A (zh)	1999-12-29
MA26453A1 (fr)	2004-12-20
DE69725465D1 (de)	2003-11-13
HUP0001848A3 (en)	2002-03-28
DZ2361A1 (fr)	2002-12-28
KR20000057413A (ko)	2000-09-15
US20020032191A1 (en)	2002-03-14
HN1997000027A (es)	1997-06-05
ZA9710906B (en)	1999-06-09

Publication	Publication Date	Title
EP0946512B1 (fr)	2003-10-08	Derives de 6-phenylpyridyl-2-amine utilises comme inhibiteurs de nos
AP1213A (en)	2003-10-07	2-aminopyridines containing fused ring substituents.
AU2022279504A1 (en)	2023-02-02	Substituted 4-Phenyl Pyridine Compounds As Non-Systemic TGR5 Agonists
OA11294A (en)	2003-10-22	Branched alkoxy-substituted 2-aminopyridines as nos inhibitors.
US20260092070A1 (en)	2026-04-02	Inhibitors of canine janus kinase and uses thereof
CN115197221A (zh)	2022-10-18	二氢吡唑并嘧啶酮类大环衍生物及其用途
EP1084109B1 (fr)	2005-01-26	2-aminopyridines contenant des substituants a anneaux condenses et convenant comme inhibiteurs de synthase de l'oxyde nitrique
ES2275917T3 (es)	2007-06-16	2-amino-6-(fenil-2,4,5-sustituido)-piridinas para usar como inhibidores de la oxido nitrico sintasa.
EP4167982A1 (fr)	2023-04-26	Méthodes et composés pour la restauration d'une fonction de mutants de p53
US20040142924A1 (en)	2004-07-22	6-Phenylpyridyl-2-amine derivatives useful as NOS inhibitors
US20010049379A1 (en)	2001-12-06	2-aminopyridines containing fused ring substituents
AU2002341234A1 (en)	2003-04-22	2-amino-6-(2,4,5-substituted-phenyl)-pyridines for use as nitric oxide synthase inhibitors