ZA200603594B - Bicyclic pyrazolyl and imidazolyl compounds and uses thereof - Google Patents

Bicyclic pyrazolyl and imidazolyl compounds and uses thereof Download PDF

Info

Publication number: ZA200603594B
Authority: ZA; South Africa
Prior art keywords: chlorophenyl; compound; alkyl; azulen; triaza
Prior art date: 2003-11-07

Application number

ZA200603594A

Other languages

English (en)

Inventor

Carpino Philip Albert

Griffith David Andrew

Dow Robert Lee

Original Assignee

Pfizer Prod Inc

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.)

2003-11-07

Filing date

2006-05-05

Publication date

2007-09-26

2006-05-05 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2007-09-26 Publication of ZA200603594B publication Critical patent/ZA200603594B/en

Links

125000002883 imidazolyl group Chemical group 0.000 title description 2
-1 arvi Chemical group 0.000 claims description 74
150000001875 compounds Chemical class 0.000 claims description 70
125000001424 substituent group Chemical group 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 55
125000003118 aryl group Chemical group 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
125000001072 heteroaryl group Chemical group 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 18
239000012453 solvate Substances 0.000 claims description 18
239000000126 substance Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000002837 carbocyclic group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000005557 antagonist Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
239000011593 sulfur Chemical group 0.000 claims description 8
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
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125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
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125000005843 halogen group Chemical group 0.000 claims description 6
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 4
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NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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VBQDMCVGFGCEHT-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-5,6-dihydroimidazo[4,5-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)C)CCOC(N2C=3C=CC(Cl)=CC=3)=C1N=C2C1=CC=CC=C1Cl VBQDMCVGFGCEHT-UHFFFAOYSA-N 0.000 claims description 2
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NMDXWGLMBYRKCQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2,2-trifluoroethyl)-5,6-dihydro-4h-pyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound O=C1N(CC(F)(F)F)CCNC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 NMDXWGLMBYRKCQ-UHFFFAOYSA-N 0.000 claims 1
LRZXYARISQFUKT-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluorobutyl)-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)CC)CCOC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 LRZXYARISQFUKT-UHFFFAOYSA-N 0.000 claims 1
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ZA200603594A 2003-11-07 2006-05-05 Bicyclic pyrazolyl and imidazolyl compounds and uses thereof ZA200603594B (en)

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DE10138275A1 (de) *	2001-08-10	2003-02-27	Boehringer Ingelheim Pharma	Verbindungen zur Beseitigung der Anhedonie
WO2004083388A2 (en) *	2003-03-14	2004-09-30	Bristol-Myers Squibb Company	Polynucleotide encoding a novel human g-protein coupled receptor variant of hm74, hgprbmy74
US7151097B2 (en) *	2003-11-07	2006-12-19	Pfizer Inc.	Bicyclic pyrazolyl and imidazolyl compounds and uses thereof
ITMI20041032A1 (it) *	2004-05-24	2004-08-24	Neuroscienze S C A R L	Compositi farmaceutici
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
US20060025448A1 (en)	2004-07-22	2006-02-02	Cadila Healthcare Limited	Hair growth stimulators
KR20070051921A (ko) *	2004-09-27	2007-05-18	화이자 프로덕츠 인코포레이티드	이환 피라졸릴 화합물의 제조 방법
PA8660701A1 (es)	2005-02-04	2006-09-22	Pfizer Prod Inc	Agonistas de pyy y sus usos
JP2008536909A (ja) *	2005-04-20	2008-09-11	ファイザー・プロダクツ・インク	カンナビノイド受容体リガンドとしてのアシルアミノ二環複素芳香族化合物
JP2008542255A (ja) *	2005-05-27	2008-11-27	ファイザー・プロダクツ・インク	肥満症の治療または体重減量の維持のためのカンナビノイド−１受容体アンタゴニストおよびミクロソームトリグリセリド輸送タンパク質阻害物質の併用
US7825151B2 (en) *	2005-09-23	2010-11-02	Janssen Pharmaceutica Nv	Hexahydro-cyclooctyl pyrazole cannabinoid modulators
US8378117B2 (en) *	2005-09-23	2013-02-19	Janssen Pharmaceutica N.V.	Hexahydro-cycloheptapyrazole cannabinoid modulators
US8378096B2 (en) *	2005-09-23	2013-02-19	Janssen Pharmaceutica N.V.	Hexahydro-cycloheptapyrazole cannabinoid modulators
US7872006B2 (en)	2005-10-21	2011-01-18	Mitsubishi Tanabe Pharma Corporation	Pyrazole compounds having cannabinoid receptor (CB1) antagonizing activity
WO2007060525A2 (en)	2005-11-28	2007-05-31	Pfizer Products Inc.	Process for preparing bicyclic pyrazolyl and imidazolyl compounds
ES2402581T3 (es) *	2006-02-23	2013-05-06	Pfizer Limited	Piperidinoilpirrolidinas como agonistas del receptor de melanocortina tipo 4
WO2007132841A1 (ja) *	2006-05-16	2007-11-22	Takeda Pharmaceutical Company Limited	縮合複素環化合物およびその用途
WO2008048648A2 (en) *	2006-10-17	2008-04-24	Acadia Pharmaceuticals Inc.	Cb1-modulating compounds and their use
MX2009004314A (es)	2006-11-13	2009-05-05	Pfizer Prod Inc	Diaril, dipiridinil y arilpiridinilderivados y usos de los mismos.
WO2009032754A2 (en) *	2007-08-31	2009-03-12	Kalypsys, Inc.	Heterocyclodiazepine cannabinoid receptor modulators for treatment of disease
JP2010043063A (ja)	2008-05-09	2010-02-25	Agency For Science Technology & Research	川崎病の診断及び治療
WO2010015972A1 (en) *	2008-08-06	2010-02-11	Pfizer Limited	Diazepine and diazocane compounds as mc4 agonists
US9549006B2 (en) *	2013-07-31	2017-01-17	Cisco Technology, Inc.	Self-adaptive sample period for content sharing in communication sessions
EA201991770A1 (ru) *	2013-11-08	2019-12-30	Инсайт Холдингс Корпорейшн	Способ синтеза ингибитора индоламин-2,3-диоксигеназы
US11504416B2 (en)	2018-09-04	2022-11-22	Paw Power, Inc.	Formulation with cannabinoids
WO2020060761A2 (en)	2018-09-04	2020-03-26	Skodda Anja	Pet food formulation with cannabinoids
BR112021025970A2 (pt)	2019-08-09	2022-02-15	Nihon Nohyaku Co Ltd	Derivado de oxazepinona, inseticida agrícola/hortícola contendo o derivado e método para uso do mesmo

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6653304B2 (en)	2000-02-11	2003-11-25	Bristol-Myers Squibb Co.	Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases
EP1421077A4 (en)	2001-08-31	2004-11-17	Univ Connecticut	NEW PYRAZOLANALOGS ON CANNABINOID RECEPTORS
ES2252524T3 (es) *	2001-09-24	2006-05-16	Bayer Pharmaceuticals Corporation	Preparacion y uso de derivados de 1,5,6,7-tetrahidropirrolo(3,2-c)piridina para el tratamiento de la obesidad.
GB0207249D0 (en)	2002-03-27	2002-05-08	Glaxo Group Ltd	Novel compounds
EP1556373A1 (en) *	2002-10-18	2005-07-27	Pfizer Products Inc.	Cannabinoid receptor ligands and uses thereof
US7129239B2 (en) *	2002-10-28	2006-10-31	Pfizer Inc.	Purine compounds and uses thereof
US7247628B2 (en) *	2002-12-12	2007-07-24	Pfizer, Inc.	Cannabinoid receptor ligands and uses thereof
US7329658B2 (en) *	2003-02-06	2008-02-12	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
US7176210B2 (en) *	2003-02-10	2007-02-13	Pfizer Inc.	Cannabinoid receptor ligands and uses thereof
US7145012B2 (en)	2003-04-23	2006-12-05	Pfizer Inc.	Cannabinoid receptor ligands and uses thereof
US20040214856A1 (en)	2003-04-23	2004-10-28	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
US7141669B2 (en) *	2003-04-23	2006-11-28	Pfizer Inc.	Cannabiniod receptor ligands and uses thereof
US7268133B2 (en) *	2003-04-23	2007-09-11	Pfizer, Inc. Patent Department	Cannabinoid receptor ligands and uses thereof
US7423031B2 (en)	2003-05-01	2008-09-09	Irm Llc	Compounds and compositions as protein kinase inhibitors
WO2004099157A1 (en) *	2003-05-07	2004-11-18	Pfizer Products Inc.	Cannabinoid receptor ligands and uses thereof
US7232823B2 (en)	2003-06-09	2007-06-19	Pfizer, Inc.	Cannabinoid receptor ligands and uses thereof
US20040259887A1 (en)	2003-06-18	2004-12-23	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
US20050026983A1 (en)	2003-07-30	2005-02-03	Pfizer Inc	Imidazole compounds and uses thereof
US7151097B2 (en) *	2003-11-07	2006-12-19	Pfizer Inc.	Bicyclic pyrazolyl and imidazolyl compounds and uses thereof
KR20070051921A (ko) *	2004-09-27	2007-05-18	화이자 프로덕츠 인코포레이티드	이환 피라졸릴 화합물의 제조 방법

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Publication number	Publication date
HRP20060166A2 (en)	2006-10-31
JP4056549B2 (ja)	2008-03-05
PE20050576A1 (es)	2005-09-14
US20050101592A1 (en)	2005-05-12
JP2007510707A (ja)	2007-04-26
DOP2004001024A (es)	2005-05-14
GT200400226A (es)	2005-09-06
MA28151A1 (fr)	2006-09-01
EP1682554A1 (en)	2006-07-26
OA13280A (en)	2007-01-31
NO20062618L (no)	2006-08-07
NL1027434C2 (nl)	2007-11-27
CR8387A (es)	2007-05-30
AP2006003601A0 (en)	2006-04-30
EA009742B1 (ru)	2008-04-28
IS8426A (is)	2006-04-21
MXPA06005023A (es)	2006-07-06
IL175283A0 (en)	2006-09-05
TW200526669A (en)	2005-08-16
US7151097B2 (en)	2006-12-19
EA200600647A1 (ru)	2006-10-27
KR20060086396A (ko)	2006-07-31
AU2004286909A1 (en)	2005-05-19
BRPI0416299A (pt)	2007-01-23
AR046831A1 (es)	2005-12-28
JP2007302685A (ja)	2007-11-22
PA8616801A1 (es)	2006-05-16
TWI280245B (en)	2007-05-01
ECSP066549A (es)	2006-10-17
CN1886407A (zh)	2006-12-27
CA2544752A1 (en)	2005-05-19
TNSN06129A1 (fr)	2007-11-15
TW200716135A (en)	2007-05-01
WO2005044822A1 (en)	2005-05-19
NL1027434A1 (nl)	2005-05-10
US20070027133A1 (en)	2007-02-01

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