CA2725573A1 - Novel 1,2,4 oxadiazole compounds and methods of use thereof - Google Patents

Novel 1,2,4 oxadiazole compounds and methods of use thereof Download PDF

Info

Publication number: CA2725573A1
Authority: CA; Canada
Prior art keywords: pyridin; oxadiazole; oxadiazol; compound; benzo
Prior art date: 2008-06-06
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA2725573A

Other languages

English (en)

French (fr)

Inventor

Jianguo Ji

Chih-Hung Lee

Kevin B. Sippy

Tao Li

Murali Gopalakrishnan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott Laboratories

Original Assignee

Abbott Laboratories

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.)

2008-06-06

Filing date

2008-06-06

Publication date

2009-12-10

2008-06-06 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2009-12-10 Publication of CA2725573A1 publication Critical patent/CA2725573A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 201
150000005071 1,2,4-oxadiazoles Chemical class 0.000 title abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 49
150000001875 compounds Chemical class 0.000 claims description 370
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 100
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 100
125000000217 alkyl group Chemical group 0.000 claims description 53
239000003446 ligand Substances 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 42
125000001072 heteroaryl group Chemical group 0.000 claims description 41
125000004076 pyridyl group Chemical group 0.000 claims description 34
208000002193 Pain Diseases 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 29
230000036407 pain Effects 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
239000000556 agonist Substances 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 19
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000003373 pyrazinyl group Chemical group 0.000 claims description 15
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
239000004031 partial agonist Substances 0.000 claims description 13
125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
230000006870 function Effects 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000002098 pyridazinyl group Chemical group 0.000 claims description 9
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 7
206010012289 Dementia Diseases 0.000 claims description 7
SSFWHRNFIGPQCE-UHFFFAOYSA-N 3-pyrimidin-5-yl-5-(2,3,4,5-tetrafluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=C(F)C(F)=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1F SSFWHRNFIGPQCE-UHFFFAOYSA-N 0.000 claims description 6
YGMLSLFSBADKNJ-UHFFFAOYSA-N 3-pyrimidin-5-yl-5-(2,3,6-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(N=2)C=2C=NC=NC=2)=C1F YGMLSLFSBADKNJ-UHFFFAOYSA-N 0.000 claims description 6
HZKYACYTOVWXMR-UHFFFAOYSA-N 5-(1,2,3-benzothiadiazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2N=C(ON=2)C=2C=C3N=NSC3=CC=2)=C1 HZKYACYTOVWXMR-UHFFFAOYSA-N 0.000 claims description 6
JCHFRGRJFXLBOC-UHFFFAOYSA-N 5-(2,3-difluorophenyl)-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1F JCHFRGRJFXLBOC-UHFFFAOYSA-N 0.000 claims description 6
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
125000003368 amide group Chemical group 0.000 claims description 6
210000003169 central nervous system Anatomy 0.000 claims description 6
208000010877 cognitive disease Diseases 0.000 claims description 6
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
125000004306 triazinyl group Chemical group 0.000 claims description 6
WAWPCRPMSZYPQY-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-5-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=C(F)C(F)=CC=C1C1=NOC(C=2C=NC=NC=2)=N1 WAWPCRPMSZYPQY-UHFFFAOYSA-N 0.000 claims description 5
UZBVGTWVANRPSH-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-6-yl-5-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CC2=NC=CN2C=C1C(N=1)=NOC=1C1=CC=CN=C1 UZBVGTWVANRPSH-UHFFFAOYSA-N 0.000 claims description 5
FDMIHNAUNHYRCH-UHFFFAOYSA-N 5-(1-benzofuran-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2OC=CC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 FDMIHNAUNHYRCH-UHFFFAOYSA-N 0.000 claims description 5
FWQNYUFEBHHAKR-UHFFFAOYSA-N 5-(1h-indazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=C2C=NNC2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 FWQNYUFEBHHAKR-UHFFFAOYSA-N 0.000 claims description 5
GHAREMXDWNPSTJ-UHFFFAOYSA-N 5-(1h-indol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2NC=CC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 GHAREMXDWNPSTJ-UHFFFAOYSA-N 0.000 claims description 5
JSIGOTKXTWWRMH-UHFFFAOYSA-N 5-(1h-indol-6-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=C2NC=CC2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 JSIGOTKXTWWRMH-UHFFFAOYSA-N 0.000 claims description 5
YLVUXYOKZKLSBP-UHFFFAOYSA-N 5-(2,2-difluoro-1,3-benzodioxol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=C2OC(F)(F)OC2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 YLVUXYOKZKLSBP-UHFFFAOYSA-N 0.000 claims description 5
GVTZFKOAJWQMLQ-UHFFFAOYSA-N 5-(2-chloropyridin-4-yl)-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=NC(Cl)=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1 GVTZFKOAJWQMLQ-UHFFFAOYSA-N 0.000 claims description 5
YFLNOUOMLKAOFS-UHFFFAOYSA-N 5-(2-methyl-1-benzofuran-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2OC(C)=CC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 YFLNOUOMLKAOFS-UHFFFAOYSA-N 0.000 claims description 5
HAKNWMQSYTUVTB-UHFFFAOYSA-N 5-(2h-benzotriazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2N=C(ON=2)C=2C=C3N=NNC3=CC=2)=C1 HAKNWMQSYTUVTB-UHFFFAOYSA-N 0.000 claims description 5
MGLARUUXINDDDZ-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-3-pyridazin-4-yl-1,2,4-oxadiazole Chemical compound C1=C(F)C(F)=CC=C1C1=NC(C=2C=NN=CC=2)=NO1 MGLARUUXINDDDZ-UHFFFAOYSA-N 0.000 claims description 5
FWZYMIREVMRKCN-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=C(F)C(F)=CC=C1C1=NC(C=2C=NC=NC=2)=NO1 FWZYMIREVMRKCN-UHFFFAOYSA-N 0.000 claims description 5
SDRBNZCCJUCMRV-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-3-pyridazin-4-yl-1,2,4-oxadiazole Chemical compound FC1=CC(F)=CC(C=2ON=C(N=2)C=2C=NN=CC=2)=C1 SDRBNZCCJUCMRV-UHFFFAOYSA-N 0.000 claims description 5
MMIAFCROZZBCJZ-UHFFFAOYSA-N 5-(4-fluorophenyl)-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1C1=NC(C=2C=NC=NC=2)=NO1 MMIAFCROZZBCJZ-UHFFFAOYSA-N 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
238000000159 protein binding assay Methods 0.000 claims description 5
LEFGPCSKXLZVKF-UHFFFAOYSA-N 2-fluoro-n,n-dimethyl-4-(3-pyrimidin-5-yl-1,2,4-oxadiazol-5-yl)aniline Chemical compound C1=C(F)C(N(C)C)=CC=C1C1=NC(C=2C=NC=NC=2)=NO1 LEFGPCSKXLZVKF-UHFFFAOYSA-N 0.000 claims description 4
PHZVVPBVYLKKCC-UHFFFAOYSA-N 3-(3-pyridazin-4-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2C=NN=CC=2)=C1 PHZVVPBVYLKKCC-UHFFFAOYSA-N 0.000 claims description 4
SNLNVICSRLZXNP-UHFFFAOYSA-N 3-(3-pyrimidin-5-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1 SNLNVICSRLZXNP-UHFFFAOYSA-N 0.000 claims description 4
DCXSZTNPKYMMND-UHFFFAOYSA-N 3-pyridazin-4-yl-5-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2ON=C(N=2)C=2C=NN=CC=2)=C1 DCXSZTNPKYMMND-UHFFFAOYSA-N 0.000 claims description 4
SXTLSYOEVLEDKM-UHFFFAOYSA-N 3-pyridazin-4-yl-5-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound N1=NC=CC(C=2N=C(ON=2)C=2C=NC=NC=2)=C1 SXTLSYOEVLEDKM-UHFFFAOYSA-N 0.000 claims description 4
OWUYNXNJBUAJEF-UHFFFAOYSA-N 3-pyridin-3-yl-5-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2N=C(ON=2)C=2C=NC=NC=2)=C1 OWUYNXNJBUAJEF-UHFFFAOYSA-N 0.000 claims description 4
XSDSUSNYXCJJHC-UHFFFAOYSA-N 5-imidazo[1,5-a]pyridin-6-yl-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CC2=CN=CN2C=C1C(ON=1)=NC=1C1=CC=CN=C1 XSDSUSNYXCJJHC-UHFFFAOYSA-N 0.000 claims description 4
YBHIOMKTJJRELV-UHFFFAOYSA-N 5-pyridazin-4-yl-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2N=C(ON=2)C=2C=NN=CC=2)=C1 YBHIOMKTJJRELV-UHFFFAOYSA-N 0.000 claims description 4
BOUFDXTWCFJBDX-UHFFFAOYSA-N 5-pyridin-3-yl-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound C1=CN=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1 BOUFDXTWCFJBDX-UHFFFAOYSA-N 0.000 claims description 4
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
ANJTVLIZGCUXLD-UHFFFAOYSA-N ent-cytisine Natural products C1NCC2CN3C(=O)C=CC=C3C1C2 ANJTVLIZGCUXLD-UHFFFAOYSA-N 0.000 claims description 4
229960002870 gabapentin Drugs 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 4
230000007246 mechanism Effects 0.000 claims description 4
230000037361 pathway Effects 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
FCWPUHGNNDBBTG-UHFFFAOYSA-N 1,3-dimethyl-5-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)benzimidazol-2-one Chemical compound C1=C2N(C)C(=O)N(C)C2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 FCWPUHGNNDBBTG-UHFFFAOYSA-N 0.000 claims description 3
PEHCLLOSMABJQY-UHFFFAOYSA-N 3-pyridazin-4-yl-5-(2,3,4-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=C(F)C(F)=CC=C1C1=NC(C=2C=NN=CC=2)=NO1 PEHCLLOSMABJQY-UHFFFAOYSA-N 0.000 claims description 3
LCGOKTHPLXQEJZ-UHFFFAOYSA-N 3-pyridazin-4-yl-5-(2,3,6-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(N=2)C=2C=NN=CC=2)=C1F LCGOKTHPLXQEJZ-UHFFFAOYSA-N 0.000 claims description 3
KYZNWNGJIDEHNX-UHFFFAOYSA-N 3-pyridazin-4-yl-5-(3,4,5-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=C(F)C(F)=CC(C=2ON=C(N=2)C=2C=NN=CC=2)=C1 KYZNWNGJIDEHNX-UHFFFAOYSA-N 0.000 claims description 3
BEMIUTKPJNJPRB-UHFFFAOYSA-N 3-pyridin-3-yl-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-1,2,4-oxadiazole Chemical compound C=1N=C2NC=CC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 BEMIUTKPJNJPRB-UHFFFAOYSA-N 0.000 claims description 3
QQHNTTTZOKVJDS-UHFFFAOYSA-N 3-pyridin-3-yl-5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,2,4-oxadiazole Chemical compound C=1N2C=NN=C2C=CC=1C(ON=1)=NC=1C1=CC=CN=C1 QQHNTTTZOKVJDS-UHFFFAOYSA-N 0.000 claims description 3
ZVRXXQXCCAAIEJ-UHFFFAOYSA-N 3-pyrimidin-5-yl-5-(2,3,4-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=C(F)C(F)=CC=C1C1=NC(C=2C=NC=NC=2)=NO1 ZVRXXQXCCAAIEJ-UHFFFAOYSA-N 0.000 claims description 3
RDUMUBOETLFKKX-UHFFFAOYSA-N 5-(1,3-benzothiazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2SC=NC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 RDUMUBOETLFKKX-UHFFFAOYSA-N 0.000 claims description 3
PHSLPBFPDPJLOL-UHFFFAOYSA-N 5-(1-methylbenzimidazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2N(C)C=NC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 PHSLPBFPDPJLOL-UHFFFAOYSA-N 0.000 claims description 3
RYPJNLKGNOYEJR-UHFFFAOYSA-N 5-(2,7-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound CC=1N2N=C(C)C=C2N=CC=1C(ON=1)=NC=1C1=CC=CN=C1 RYPJNLKGNOYEJR-UHFFFAOYSA-N 0.000 claims description 3
JOJKTEMAJLOFNV-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-pyridazin-4-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2C=NN=CC=2)=C1 JOJKTEMAJLOFNV-UHFFFAOYSA-N 0.000 claims description 3
RMBLEYJQWAKZEH-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-pyrimidin-5-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2C=NC=NC=2)=C1 RMBLEYJQWAKZEH-UHFFFAOYSA-N 0.000 claims description 3
DTNIDIQIBDPKTM-UHFFFAOYSA-N 5-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C2NC(=O)NC2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 DTNIDIQIBDPKTM-UHFFFAOYSA-N 0.000 claims description 3
MLORQGUCNNDACK-UHFFFAOYSA-N 5-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)-1,3-dihydrobenzimidazole-2-thione Chemical compound C1=C2NC(=S)NC2=CC=C1C(ON=1)=NC=1C1=CC=CN=C1 MLORQGUCNNDACK-UHFFFAOYSA-N 0.000 claims description 3
QTSCFRXMHBFFPS-UHFFFAOYSA-N 5-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2OC(=O)NC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 QTSCFRXMHBFFPS-UHFFFAOYSA-N 0.000 claims description 3
BQVJLWIOHBVTCS-UHFFFAOYSA-N 5-(3h-benzimidazol-5-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C=1C=C2NC=NC2=CC=1C(ON=1)=NC=1C1=CC=CN=C1 BQVJLWIOHBVTCS-UHFFFAOYSA-N 0.000 claims description 3
BWDMGSVZNSZQOB-UHFFFAOYSA-N 5-(4-fluorophenyl)-3-pyridazin-4-yl-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1C1=NC(C=2C=NN=CC=2)=NO1 BWDMGSVZNSZQOB-UHFFFAOYSA-N 0.000 claims description 3
VMXBVMWRUSVYDV-UHFFFAOYSA-N 5-(5-pyridin-3-yl-1,2,4-oxadiazol-3-yl)-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2OC(=O)NC2=CC=1C(N=1)=NOC=1C1=CC=CN=C1 VMXBVMWRUSVYDV-UHFFFAOYSA-N 0.000 claims description 3
HJTYSZYUPTVZOE-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-3-imidazo[1,2-a]pyridin-6-yl-1,2,4-oxadiazole Chemical compound C1=NC(Cl)=CC=C1C1=NC(C2=CN3C=CN=C3C=C2)=NO1 HJTYSZYUPTVZOE-UHFFFAOYSA-N 0.000 claims description 3
QGHLSZNGYRXFGV-UHFFFAOYSA-N 5-[5-(6-chloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=NC(Cl)=CC=C1C1=NC(C=2C=C3NC(=O)OC3=CC=2)=NO1 QGHLSZNGYRXFGV-UHFFFAOYSA-N 0.000 claims description 3
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KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
CJNWEJQNKRUGOX-UHFFFAOYSA-N pyrido[1,2]pyrano[3,5-b]azepine Chemical class C1=CC=NC2=CC3=NC=CC=C3OC2=C1 CJNWEJQNKRUGOX-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
238000011808 rodent model Methods 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
230000020341 sensory perception of pain Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229960001945 sparteine Drugs 0.000 description 1
SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000003594 spinal ganglia Anatomy 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000012414 sterilization procedure Methods 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
210000000225 synapse Anatomy 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YQEXHAAQOMABEK-UHFFFAOYSA-N tert-butyl n-[[3-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 YQEXHAAQOMABEK-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
210000001103 thalamus Anatomy 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011285 therapeutic regimen Methods 0.000 description 1
125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
125000005305 thiadiazolinyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000000085 vanilloid receptor antagonist Substances 0.000 description 1
208000021331 vascular occlusion disease Diseases 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA2725573A 2008-06-06 2008-06-06 Novel 1,2,4 oxadiazole compounds and methods of use thereof Abandoned CA2725573A1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US2008/066002 WO2009148452A1 (en)	2008-06-06	2008-06-06	Novel 1,2,4 oxadiazole compounds and methods of use thereof

Publications (1)

Publication Number	Publication Date
CA2725573A1 true CA2725573A1 (en)	2009-12-10

Family

ID=41398367

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2725573A Abandoned CA2725573A1 (en)	2008-06-06	2008-06-06	Novel 1,2,4 oxadiazole compounds and methods of use thereof

Country Status (6)

Country	Link
EP (1)	EP2297140A4 (de)
JP (1)	JP2011522818A (de)
CN (1)	CN102089297A (de)
CA (1)	CA2725573A1 (de)
MX (1)	MX2010013399A (de)
WO (1)	WO2009148452A1 (de)

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US8486979B2 (en)	2006-12-12	2013-07-16	Abbvie Inc.	1,2,4 oxadiazole compounds and methods of use thereof
US20080167286A1 (en)	2006-12-12	2008-07-10	Abbott Laboratories	Pharmaceutical compositions and their methods of use
UY30846A1 (es)	2006-12-30	2008-07-31	Abbott Gmbh & Amp	Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos
WO2010009775A1 (de)	2007-12-07	2010-01-28	Abbott Gmbh & Co. Kg	Carbamat-substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen
JP5701607B2 (ja)	2007-12-07	2015-04-15	アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー	アミドメチル置換オキシインドール誘導体およびバソプレッシン依存性疾患の治療へのこれらの使用
EP2231644B1 (de)	2007-12-07	2014-01-15	AbbVie Deutschland GmbH & Co KG	5,6-Disubstitutierte Oxindol-Derivate und ihre Verwendung zur Herstellung eines Medikaments zur Behandlung von Vasopressin-abhängigen Erkrankungen
KR20100097195A (ko)	2007-12-07	2010-09-02	애보트 게엠베하 운트 콤파니 카게	５－할로겐－치환된 옥스인돌 유도체 및 바소프레신－의존성 질병을 치료하기 위한 이의 용도
EP2435080A2 (de)	2009-05-29	2012-04-04	Abbott Laboratories	Pharmazeutische zusammensetzungen zur schmerzbehandlung
BR112012033402A2 (pt) *	2010-07-02	2017-01-24	Gilead Sciences Inc	moduladores de canais de íons conforme os compostos heterocíclicos fundidos
WO2012052412A1 (de) *	2010-10-22	2012-04-26	Bayer Cropscience Ag	Neue heterocylische verbindungen als schädlingsbekämpfungsmittel
CA2834164A1 (en)	2011-05-10	2012-11-15	Gilead Sciences, Inc.	Fused benzoxazinones as ion channel modulators
TW201837023A (zh)	2011-07-01	2018-10-16	美商基利科學股份有限公司	作為離子通道調節劑之稠合雜環化合物
NO3175985T3 (de)	2011-07-01	2018-04-28
WO2013057101A1 (de) *	2011-10-17	2013-04-25	Bayer Intellectual Property Gmbh	Substituierte oxadiazolylpyridinone und - pyridazinone als hif - hemmer
EP2867230B1 (de)	2012-07-02	2020-02-12	Monsanto Technology LLC	Verfahren zur herstellung von 3,5-disubstituierten 1,2,4-oxadiazolen
CN106316885B (zh) *	2015-07-03	2019-02-12	普济生物科技（台州）有限公司	一种3-[5-(2-氟苯基)-1,2,4-噁二唑-3-基]苯甲酸的制备方法
IL271149B2 (en) *	2017-06-14	2024-05-01	Trevena Inc	Compounds for modulating s1p1 activity and methods of using the same
RU2671563C1 (ru) *	2017-11-13	2018-11-02	Федеральное государственное бюджетное учреждение науки Южный научный центр Российской академии наук	2-фенил-5-(3,4,5-триэтоксифенил)-1,3,4-оксадиазол с люминесцентной активностью
EP4061352A4 (de)	2019-11-19	2024-02-28	Trevena, Inc.	Verbindungen und verfahren zur herstellung von s1p1-modulierenden verbindungen
IL293340A (en) *	2019-12-02	2022-07-01	Storm Therapeutics Ltd	Polyheterocyclic compounds as mettl3 inhibitors
CN111138376A (zh) *	2019-12-24	2020-05-12	中山大学	一种3,5-二取代苯基-1,2,4-噁二唑衍生物及其制备方法和应用

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2008
- 2008-06-06 CN CN2008801303362A patent/CN102089297A/zh active Pending
- 2008-06-06 WO PCT/US2008/066002 patent/WO2009148452A1/en not_active Ceased
- 2008-06-06 EP EP08770247A patent/EP2297140A4/de not_active Withdrawn
- 2008-06-06 MX MX2010013399A patent/MX2010013399A/es not_active Application Discontinuation
- 2008-06-06 CA CA2725573A patent/CA2725573A1/en not_active Abandoned
- 2008-06-06 JP JP2011512428A patent/JP2011522818A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
EP2297140A4 (de)	2012-05-02
CN102089297A (zh)	2011-06-08
MX2010013399A (es)	2010-12-21
WO2009148452A1 (en)	2009-12-10
EP2297140A1 (de)	2011-03-23
JP2011522818A (ja)	2011-08-04

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Publication	Publication Date	Title
US8486979B2 (en)	2013-07-16	1,2,4 oxadiazole compounds and methods of use thereof
US9040568B2 (en)	2015-05-26	Pharmaceutical compositions for the treatment of pain
US9186407B2 (en)	2015-11-17	Pharmaceutical compositions and their methods of use
CA2725573A1 (en)	2009-12-10	Novel 1,2,4 oxadiazole compounds and methods of use thereof
US20080255203A1 (en)	2008-10-16	Heterocyclic compounds and their methods of use
JP2012521429A (ja)	2012-09-13	疼痛治療用のｐ２ｘ３受容体アンタゴニスト
RS64828B1 (sr)	2023-12-29	Jedinjenja piridazinona i njihove upotrebe
AU2014284616A2 (en)	2016-06-09	Novel bicyclic bromodomain inhibitors
BR112015001502B1 (pt)	2023-03-07	Uso de derivados de tipo azaindazol ou diazaindazol no tratamento ou prevenção de dor
WO2018130869A1 (en)	2018-07-19	Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment
Shook et al.	2013	Substituted thieno [2, 3-d] pyrimidines as adenosine A2A receptor antagonists
JP2016528266A (ja)	2016-09-15	位相変位睡眠障害を処置するためのＶ１ａアンタゴニスト
TW202220990A (zh)	2022-06-01	雜芳基取代的螺哌啶基衍生物及其藥物用途
CN101605542A (zh)	2009-12-16	药物组合物以及其使用方法
HK1144381A (en)	2011-02-18	Pharmaceutical compositions and their methods of use
OA20303A (en)	2022-05-10	Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment.
HK40049071B (zh)	2024-10-25	用於治疗认知损害的苯并二氮杂环庚三烯衍生物，组合物和方法