JP2012515152A5 - - Google Patents
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- Publication number
- JP2012515152A5 JP2012515152A5 JP2011544892A JP2011544892A JP2012515152A5 JP 2012515152 A5 JP2012515152 A5 JP 2012515152A5 JP 2011544892 A JP2011544892 A JP 2011544892A JP 2011544892 A JP2011544892 A JP 2011544892A JP 2012515152 A5 JP2012515152 A5 JP 2012515152A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- amine
- alkyl
- compound
- thiazolo
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000002947 alkylene group Chemical group 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 230000002265 prevention Effects 0.000 claims 14
- -1 6-methylpyridin-2-yl Chemical group 0.000 claims 8
- 208000015114 central nervous system disease Diseases 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 206010012289 Dementia Diseases 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 206010012218 Delirium Diseases 0.000 claims 4
- 208000012661 Dyskinesia Diseases 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 206010044565 Tremor Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 230000033001 locomotion Effects 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 206010008748 Chorea Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000027534 Emotional disease Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 206010029350 Neurotoxicity Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010034010 Parkinsonism Diseases 0.000 claims 2
- 206010044221 Toxic encephalopathy Diseases 0.000 claims 2
- 125000005275 alkylenearyl group Chemical group 0.000 claims 2
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000012601 choreatic disease Diseases 0.000 claims 2
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 229960004502 levodopa Drugs 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 230000003227 neuromodulating effect Effects 0.000 claims 2
- 230000007135 neurotoxicity Effects 0.000 claims 2
- 231100000228 neurotoxicity Toxicity 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 230000002085 persistent effect Effects 0.000 claims 2
- 208000019899 phobic disease Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- LJPUMHSOHJXQPU-UHFFFAOYSA-N 2-methyl-1-[2-(pyridin-2-ylamino)-4,5-dihydropyrazolo[4,3-e][1,3]benzothiazol-6-yl]propan-1-one Chemical compound CC(C)C(=O)N1N=CC(C=2N=3)=C1CCC=2SC=3NC1=CC=CC=N1 LJPUMHSOHJXQPU-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000002381 Brain Hypoxia Diseases 0.000 claims 1
- SRGWKMSEGDYAJD-UHFFFAOYSA-N CC1(C2=C(C=3C=NNC3C1)N=C(S2)NC2=NC=CC=N2)C.CC2(C1=C(C=3C=NNC3C2)N=C(S1)NC1=NC=CC=C1)C Chemical compound CC1(C2=C(C=3C=NNC3C1)N=C(S2)NC2=NC=CC=N2)C.CC2(C1=C(C=3C=NNC3C2)N=C(S1)NC1=NC=CC=C1)C SRGWKMSEGDYAJD-UHFFFAOYSA-N 0.000 claims 1
- QQKDNJWNXHEVMQ-UHFFFAOYSA-N CC1C2=C(C=3C=NNC3C1)N=C(S2)NC2=NC=CC=C2.FC2=CC=CC(=N2)NC=2SC1=C(C=3C=NNC3CC1)N2 Chemical compound CC1C2=C(C=3C=NNC3C1)N=C(S2)NC2=NC=CC=C2.FC2=CC=CC(=N2)NC=2SC1=C(C=3C=NNC3CC1)N2 QQKDNJWNXHEVMQ-UHFFFAOYSA-N 0.000 claims 1
- YJNXVKMMBQVJAJ-UHFFFAOYSA-N CN1N=C(C=C1)NC=1SC2=C(C=3C=NNC3CCC2)N1.N1=C(N=CC=C1)NC=1SC2=C(C=3C=NNC3CC2)N1 Chemical compound CN1N=C(C=C1)NC=1SC2=C(C=3C=NNC3CCC2)N1.N1=C(N=CC=C1)NC=1SC2=C(C=3C=NNC3CC2)N1 YJNXVKMMBQVJAJ-UHFFFAOYSA-N 0.000 claims 1
- ODWYOBDWCRZXKB-UHFFFAOYSA-N COC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.FC=1C(=NC=CC1)NC=1SC2=C(C=3C=NNC3CCC2)N1 Chemical compound COC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.FC=1C(=NC=CC1)NC=1SC2=C(C=3C=NNC3CCC2)N1 ODWYOBDWCRZXKB-UHFFFAOYSA-N 0.000 claims 1
- 206010053942 Cerebral haematoma Diseases 0.000 claims 1
- WHWYWEXNYQSMAI-UHFFFAOYSA-N ClC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.FC=1C=CC(=NC1)NC=1SC2=C(C=3C=NNC3CC2)N1 Chemical compound ClC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.FC=1C=CC(=NC1)NC=1SC2=C(C=3C=NNC3CC2)N1 WHWYWEXNYQSMAI-UHFFFAOYSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 229940123736 Decarboxylase inhibitor Drugs 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000014094 Dystonic disease Diseases 0.000 claims 1
- WWYGFBLODHLLFI-UHFFFAOYSA-N FC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.C1(CCC1)NC=1SC2=C(C=3C=NNC3CC2)N1 Chemical compound FC1=CC=CC(=N1)NC=1SC2=C(C=3C=NNC3CCC2)N1.C1(CCC1)NC=1SC2=C(C=3C=NNC3CC2)N1 WWYGFBLODHLLFI-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- 208000000172 Medulloblastoma Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 208000002740 Muscle Rigidity Diseases 0.000 claims 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 claims 1
- WFWJWEJJNJNNGZ-UHFFFAOYSA-N N1=C(N=CC=C1)NC=1SC2=C(C=3C=NNC3CCC2)N1.C1(CCCC1)NC=1SC2=C(C=3C=NNC3CCC2)N1 Chemical compound N1=C(N=CC=C1)NC=1SC2=C(C=3C=NNC3CCC2)N1.C1(CCCC1)NC=1SC2=C(C=3C=NNC3CCC2)N1 WFWJWEJJNJNNGZ-UHFFFAOYSA-N 0.000 claims 1
- 208000008705 Nocturnal Myoclonus Syndrome Diseases 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 claims 1
- 208000007400 Relapsing-Remitting Multiple Sclerosis Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 229940125516 allosteric modulator Drugs 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 229960004205 carbidopa Drugs 0.000 claims 1
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 claims 1
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000002566 clonic effect Effects 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003954 decarboxylase inhibitor Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 claims 1
- 229960003337 entacapone Drugs 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- MMNFTOZWBIUGDR-UHFFFAOYSA-N n-cyclopropyl-4,5,6,7-tetrahydropyrazolo[2,3]cyclohepta[2,4-b][1,3]thiazol-2-amine Chemical compound C1CC1NC(S1)=NC2=C1CCCC1=C2C=NN1 MMNFTOZWBIUGDR-UHFFFAOYSA-N 0.000 claims 1
- DBISXWCOHGUFSF-UHFFFAOYSA-N n-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[2,3]cyclohepta[2,4-b][1,3]thiazol-2-amine Chemical compound S1C=2CCCC=3NN=CC=3C=2N=C1NC1=CC=CC=N1 DBISXWCOHGUFSF-UHFFFAOYSA-N 0.000 claims 1
- MIOXQGMSPSEKCA-UHFFFAOYSA-N n-pyridin-2-yl-5,6-dihydro-4h-pyrazolo[4,3-e][1,3]benzothiazol-2-amine Chemical compound N=1C=2C=3C=NNC=3CCC=2SC=1NC1=CC=CC=N1 MIOXQGMSPSEKCA-UHFFFAOYSA-N 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 208000023515 periodic limb movement disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940126027 positive allosteric modulator Drugs 0.000 claims 1
- 206010063401 primary progressive multiple sclerosis Diseases 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 238000012954 risk control Methods 0.000 claims 1
- 201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000024794 sputum Diseases 0.000 claims 1
- 210000003802 sputum Anatomy 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0900404.5A GB0900404D0 (en) | 2009-01-12 | 2009-01-12 | New compounds 4 |
| GB0900404.5 | 2009-01-12 | ||
| PCT/EP2010/050304 WO2010079238A1 (en) | 2009-01-12 | 2010-01-12 | Heterotricyclic compounds as positive allosteric modulators of metabotropic glutamate receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012515152A JP2012515152A (ja) | 2012-07-05 |
| JP2012515152A5 true JP2012515152A5 (https=) | 2013-02-21 |
Family
ID=40379432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011544892A Abandoned JP2012515152A (ja) | 2009-01-12 | 2010-01-12 | 代謝調節型グルタミン酸レセプターのポジティブアロステリックモジュレーターとしてのヘテロ三環式化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8697744B2 (https=) |
| EP (1) | EP2382219A1 (https=) |
| JP (1) | JP2012515152A (https=) |
| AU (1) | AU2010204283A1 (https=) |
| CA (1) | CA2748843A1 (https=) |
| GB (1) | GB0900404D0 (https=) |
| WO (1) | WO2010079238A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012006104A2 (en) | 2010-06-28 | 2012-01-12 | Academia Sinica, Taiwan | Compounds and methods for treating tuberculosis infection |
| EP2593277A4 (en) * | 2010-07-14 | 2014-09-03 | Addex Pharmaceuticals Sa | Novel condensed pyrazoline derivatives and their use as allosmetic modulators of metabotropic glutamate receptors |
| GB201011831D0 (en) | 2010-07-14 | 2010-09-01 | Addex Pharmaceuticals Sa | New compounds 5 |
| WO2012008999A2 (en) * | 2010-07-14 | 2012-01-19 | Merck Sharp & Dohme Corp. | Tricyclic compounds as allosteric modulators of metabotropic glutamate receptors |
| US20120129811A1 (en) * | 2010-11-18 | 2012-05-24 | Aihua Wang | Tricyclic inhibitors of pro-matrix metalloproteinase activation |
| US20140349994A1 (en) * | 2012-01-18 | 2014-11-27 | Addex Pharma S.A. | Novel 2-Amino-4,5,6,8-Tetrahydropyrazolo[3,4-b]Thiazolo [4,5-d]Azepine Derivatives and Their Use as Allosteric Modulators of Metabotropic Glutamate Receptors |
| EP2853532B1 (en) | 2013-09-28 | 2020-12-09 | Instytut Farmakologii Polskiej Akademii Nauk | 1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III |
| CN113444108B (zh) * | 2021-07-19 | 2022-03-25 | 成都大学 | 含二氢苯并呋喃结构的1,4-硫桥多环化合物、其制备方法及用途 |
| WO2023064857A1 (en) | 2021-10-14 | 2023-04-20 | Incyte Corporation | Quinoline compounds as inhibitors of kras |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945417A (en) | 1995-07-31 | 1999-08-31 | Novo Nordisk | Heterocyclic compounds, their preparation and use |
| WO2005007096A2 (en) | 2003-07-11 | 2005-01-27 | Merck & Co., Inc. | Treatment of movement disorders with a metabotropic glutamate 4 receptor positive allosteric modulator |
| KR20070064660A (ko) | 2004-10-07 | 2007-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｐｉ３ 키나제 |
| US7687501B2 (en) | 2005-08-19 | 2010-03-30 | Schering Corporation | Pyridothienopyridazinone derivatives as mGluR1 antagonists |
| US20100144756A1 (en) | 2007-07-13 | 2010-06-10 | Bolea Christelle | Novel heteroaromatic derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors |
| WO2009070871A1 (en) | 2007-12-04 | 2009-06-11 | Mds Analytical Technologies, A Business Unit Of Mds Inc. Doing Business Through Its Sciex Division | Systems and methods for analyzing substances using a mass spectrometer |
-
2009
- 2009-01-12 GB GBGB0900404.5A patent/GB0900404D0/en not_active Ceased
-
2010
- 2010-01-12 CA CA2748843A patent/CA2748843A1/en not_active Abandoned
- 2010-01-12 EP EP10700980A patent/EP2382219A1/en not_active Withdrawn
- 2010-01-12 JP JP2011544892A patent/JP2012515152A/ja not_active Abandoned
- 2010-01-12 WO PCT/EP2010/050304 patent/WO2010079238A1/en not_active Ceased
- 2010-01-12 AU AU2010204283A patent/AU2010204283A1/en not_active Abandoned
- 2010-01-12 US US12/998,955 patent/US8697744B2/en not_active Expired - Fee Related