OA13080A - Purine compounds and uses thereof as cannabinoid receptor ligands. - Google Patents

Purine compounds and uses thereof as cannabinoid receptor ligands. Download PDF

Info

Publication number: OA13080A
Authority: OA; OAPI
Prior art keywords: alkyl; alkylamino; aryl; partially; membered
Prior art date: 2002-10-28

Application number

OA1200500128A

Other languages

English (en)

Inventor

David Andrew Griffith

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.)

2002-10-28

Filing date

2003-10-21

Publication date

2006-11-10

2003-10-21 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-11-10 Publication of OA13080A publication Critical patent/OA13080A/en

Links

102000018208 Cannabinoid Receptor Human genes 0.000 title abstract description 17
108050007331 Cannabinoid receptor Proteins 0.000 title abstract description 17
239000003446 ligand Substances 0.000 title abstract description 15
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 290
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
201000010099 disease Diseases 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims description 226
-1 hydroxy, amino Chemical group 0.000 claims description 210
229920006395 saturated elastomer Polymers 0.000 claims description 153
125000003118 aryl group Chemical group 0.000 claims description 142
125000003282 alkyl amino group Chemical group 0.000 claims description 138
125000001072 heteroaryl group Chemical group 0.000 claims description 124
229910052739 hydrogen Inorganic materials 0.000 claims description 122
239000001257 hydrogen Substances 0.000 claims description 122
125000000623 heterocyclic group Chemical group 0.000 claims description 104
239000000203 mixture Substances 0.000 claims description 86
125000002252 acyl group Chemical group 0.000 claims description 84
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 77
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
125000003545 alkoxy group Chemical group 0.000 claims description 69
239000000126 substance Substances 0.000 claims description 68
150000002431 hydrogen Chemical group 0.000 claims description 59
125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 56
239000005977 Ethylene Substances 0.000 claims description 48
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
150000003951 lactams Chemical group 0.000 claims description 42
229940002612 prodrug Drugs 0.000 claims description 39
239000000651 prodrug Substances 0.000 claims description 39
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
239000001301 oxygen Substances 0.000 claims description 38
229910052760 oxygen Inorganic materials 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 38
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
150000002596 lactones Chemical group 0.000 claims description 37
239000011593 sulfur Chemical group 0.000 claims description 37
229910052717 sulfur Inorganic materials 0.000 claims description 37
125000004423 acyloxy group Chemical group 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 35
125000004442 acylamino group Chemical group 0.000 claims description 34
239000003795 chemical substances by application Substances 0.000 claims description 26
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 25
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
150000001408 amides Chemical class 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
125000005842 heteroatom Chemical group 0.000 claims description 21
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
239000000546 pharmaceutical excipient Substances 0.000 claims description 16
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
125000003107 substituted aryl group Chemical group 0.000 claims description 14
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239000003085 diluting agent Substances 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
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239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
239000004031 partial agonist Substances 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
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239000003536 cannabinoid receptor antagonist Substances 0.000 claims description 5
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SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 5
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238000004519 manufacturing process Methods 0.000 claims description 3
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
LGRHTFQDJMGCCC-UHFFFAOYSA-N 1-[9-(4-chlorophenyl)-8-(2-fluorophenyl)-2-methylpurin-6-yl]-4-(propan-2-ylamino)piperidine-4-carboxamide Chemical compound C1CC(NC(C)C)(C(N)=O)CCN1C1=NC(C)=NC2=C1N=C(C=1C(=CC=CC=1)F)N2C1=CC=C(Cl)C=C1 LGRHTFQDJMGCCC-UHFFFAOYSA-N 0.000 claims description 2
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VNOGOEOTNFURPS-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyrimidin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CN=3)=C2N=C1C1=CC=C(Cl)C=C1Cl VNOGOEOTNFURPS-UHFFFAOYSA-N 0.000 claims description 2
UNAZAADNBYXMIV-UHFFFAOYSA-N otenabant Chemical compound C1CC(NCC)(C(N)=O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 UNAZAADNBYXMIV-UHFFFAOYSA-N 0.000 claims description 2
LGBUKOHYRKYGMR-UHFFFAOYSA-N 1-(ethylamino)piperidine-4-carboxamide Chemical compound CCNN1CCC(C(N)=O)CC1 LGBUKOHYRKYGMR-UHFFFAOYSA-N 0.000 claims 1
IBYUCEFFHNVUDP-UHFFFAOYSA-N 1-(propylamino)piperidine-4-carboxamide Chemical compound C(CC)NN1CCC(CC1)C(=O)N IBYUCEFFHNVUDP-UHFFFAOYSA-N 0.000 claims 1
SQSZXZKMVHUPRD-UHFFFAOYSA-N 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(propan-2-ylamino)piperidine-4-carboxamide Chemical compound C1CC(NC(C)C)(C(N)=O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 SQSZXZKMVHUPRD-UHFFFAOYSA-N 0.000 claims 1
HDPLEFUIDWOLLX-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyridin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1Cl HDPLEFUIDWOLLX-UHFFFAOYSA-N 0.000 claims 1
PPNKCVSOPVJBPB-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-[(2-methylpropan-2-yl)oxy]purine Chemical compound N=1C=2C(OC(C)(C)C)=NC=NC=2N(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl PPNKCVSOPVJBPB-UHFFFAOYSA-N 0.000 claims 1
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Classifications

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Publication number	Publication date
AU2003269368B2 (en)	2008-10-30
ZA200503378B (en)	2006-07-26
NO20052512L (no)	2005-05-25
IS7801A (is)	2005-04-14
EP1558615B1 (en)	2007-08-29
EP1558615B8 (en)	2007-10-10
TNSN05121A1 (fr)	2007-05-14
PE20040781A1 (es)	2004-11-20
KR100674560B1 (ko)	2007-02-28
HRP20050378A2 (en)	2005-12-31
PT1558615E (pt)	2007-11-08
EP1558615A1 (en)	2005-08-03
EG24662A (en)	2010-04-07
CR7812A (es)	2005-06-08
DOP2003000742A (es)	2004-04-30
KR20050070093A (ko)	2005-07-05
AP2005003290A0 (en)	2005-06-30
ECSP055767A (es)	2005-08-11
US20040092520A1 (en)	2004-05-13
DE60316012D1 (de)	2007-10-11
HK1099762A1 (zh)	2007-08-24
CN100439369C (zh)	2008-12-03
CO5560546A2 (es)	2005-09-30
US20060241120A1 (en)	2006-10-26
NO332195B1 (no)	2012-07-23
HK1081189A1 (zh)	2006-05-12
JP2007099779A (ja)	2007-04-19
JP3954618B2 (ja)	2007-08-08
DE60316012T2 (de)	2008-05-29
RS20050306A (sr)	2007-04-10
CU23535A3 (es)	2010-06-17
UY28044A1 (es)	2004-05-31
DK1558615T3 (da)	2007-12-03
RS20050395A (sr)	2007-04-10
ATE371658T1 (de)	2007-09-15
AU2003269368A1 (en)	2004-05-13
CN100478343C (zh)	2009-04-15
NL1024643A1 (nl)	2004-05-03
NZ539589A (en)	2007-10-26
EA200500520A1 (ru)	2005-12-29
AP1916A (en)	2008-11-10
MY140010A (en)	2009-11-30
EA008176B1 (ru)	2007-04-27
UA79507C2 (en)	2007-06-25
AR041835A1 (es)	2005-06-01
ES2291669T3 (es)	2008-03-01
US7129239B2 (en)	2006-10-31
JP2006505581A (ja)	2006-02-16
CN1708499A (zh)	2005-12-14
CY1107505T1 (el)	2013-03-13
CN1955181A (zh)	2007-05-02
MA27479A1 (fr)	2005-08-01
WO2004037823A1 (en)	2004-05-06
CN1955182A (zh)	2007-05-02
SG148071A1 (en)	2008-12-31
BR0314918A (pt)	2005-08-02
GEP20084325B (en)	2008-03-25
TWI327567B (en)	2010-07-21
CA2503900A1 (en)	2004-05-06
IS2602B (is)	2010-04-15
TW200424202A (en)	2004-11-16
MXPA05003882A (es)	2005-06-22
CA2503900C (en)	2009-06-02
PL376311A1 (en)	2005-12-27
NO20052512D0 (no)	2005-05-25
GT200300232A (es)	2004-06-23
NL1024643C2 (nl)	2005-02-01

Publication	Publication Date	Title
CA2503900C (en)	2009-06-02	Purine compounds and use thereof as cannabinoid receptor ligands
CA2515596C (en)	2008-07-29	Cannabinoid receptor ligands and uses thereof
OA12980A (en)	2006-10-13	Pyrazolo[1,5-A][1,3,5]triazine derivatives as cannabinoid receptor ligands.
US20040214837A1 (en)	2004-10-28	Cannabinoid receptor ligands and uses thereof
AU2004245316A1 (en)	2004-12-16	Cannabinoid receptor ligands and uses thereof
HK1081189B (en)	2009-08-07	Purine compounds and use thereof as cannabinoid receptor ligands
HK1099762B (en)	2009-12-04	Purine compounds and use thereof as cannabinoid receptor ligands