JP2014506590A5 - - Google Patents
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- JP2014506590A5 JP2014506590A5 JP2013554966A JP2013554966A JP2014506590A5 JP 2014506590 A5 JP2014506590 A5 JP 2014506590A5 JP 2013554966 A JP2013554966 A JP 2013554966A JP 2013554966 A JP2013554966 A JP 2013554966A JP 2014506590 A5 JP2014506590 A5 JP 2014506590A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally substituted
- group
- methyl
- alkynyl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 113
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 103
- 125000000623 heterocyclic group Chemical group 0.000 claims 50
- -1 cyano, hydroxy Chemical group 0.000 claims 38
- 125000001072 heteroaryl group Chemical group 0.000 claims 37
- 125000003342 alkenyl group Chemical group 0.000 claims 30
- 125000000304 alkynyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000000547 substituted alkyl group Chemical group 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 24
- 125000001424 substituent group Chemical group 0.000 claims 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 125000004043 oxo group Chemical group O=* 0.000 claims 18
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 16
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 16
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000003107 substituted aryl group Chemical group 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 208000010877 cognitive disease Diseases 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 208000028698 Cognitive impairment Diseases 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 210000004204 blood vessel Anatomy 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 210000004558 lewy body Anatomy 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- OVXJXUQIGIWHEK-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)-4-methyl-3-(4-piperidin-1-ylsulfonylphenyl)thiophen-2-yl]propan-1-one Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 OVXJXUQIGIWHEK-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JIXVXTOJWFELIT-UHFFFAOYSA-N 4-[2-acetyl-5-(4-chlorophenyl)-4-methylthiophen-3-yl]benzenesulfonamide Chemical compound CC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 JIXVXTOJWFELIT-UHFFFAOYSA-N 0.000 claims 1
- UFFRPOINLQRCOO-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-1,4-dimethyl-2-propanoylpyrrol-3-yl]benzenesulfonamide Chemical compound CN1C(C(=O)CC)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C(C)=C1C1=CC=C(Cl)C=C1 UFFRPOINLQRCOO-UHFFFAOYSA-N 0.000 claims 1
- RDOQYOYVSYMZDJ-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-1-ethyl-4-methyl-2-propanoylpyrrol-3-yl]benzenesulfonamide Chemical compound CCN1C(C(=O)CC)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C(C)=C1C1=CC=C(Cl)C=C1 RDOQYOYVSYMZDJ-UHFFFAOYSA-N 0.000 claims 1
- YSTWQCSMRHVGPN-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-2-propanoylthiophen-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=CC=1C1=CC=C(S(N)(=O)=O)C=C1 YSTWQCSMRHVGPN-UHFFFAOYSA-N 0.000 claims 1
- UTYKABNJDPLOIC-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-(dimethylamino)-2-propanoylthiophen-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(N(C)C)C=1C1=CC=C(S(N)(=O)=O)C=C1 UTYKABNJDPLOIC-UHFFFAOYSA-N 0.000 claims 1
- DBRXYUZKHRHRMW-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-[(dimethylamino)methyl]-2-propanoylthiophen-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(CN(C)C)C=1C1=CC=C(S(N)(=O)=O)C=C1 DBRXYUZKHRHRMW-UHFFFAOYSA-N 0.000 claims 1
- QEQXBTYYHGIUCK-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-methyl-2-propanoyl-1h-pyrrol-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1NC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 QEQXBTYYHGIUCK-UHFFFAOYSA-N 0.000 claims 1
- RRMNYWQOHCDIOK-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-methyl-2-propanoylthiophen-3-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(=O)(=O)N(C)C)C=C1 RRMNYWQOHCDIOK-UHFFFAOYSA-N 0.000 claims 1
- WFNYBPJRPXJGRK-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-methyl-2-propanoylthiophen-3-yl]-n-methylbenzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(=O)(=O)NC)C=C1 WFNYBPJRPXJGRK-UHFFFAOYSA-N 0.000 claims 1
- DYIIYIJHDMIABW-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-4-methyl-2-propanoylthiophen-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 DYIIYIJHDMIABW-UHFFFAOYSA-N 0.000 claims 1
- RNMYKOMXUBBUGJ-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)-4-methyl-2-propanoylthiophen-3-yl]benzenesulfonamide Chemical compound CCC(=O)C=1SC(C=2C=CC(OC)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 RNMYKOMXUBBUGJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- QOXQGDILIPAINR-UHFFFAOYSA-N 5-(4-chlorophenyl)-n,n,1,4-tetramethyl-3-(4-sulfamoylphenyl)pyrrole-2-carboxamide Chemical compound CN1C(C(=O)N(C)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C(C)=C1C1=CC=C(Cl)C=C1 QOXQGDILIPAINR-UHFFFAOYSA-N 0.000 claims 1
- VHCJGVRILQNFDJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n,n,4-trimethyl-3-(4-sulfamoylphenyl)thiophene-2-carboxamide Chemical compound CN(C)C(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 VHCJGVRILQNFDJ-UHFFFAOYSA-N 0.000 claims 1
- LGHXVLYSCJRRIB-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(2-hydroxyethyl)-4-methyl-n-propyl-3-(4-sulfamoylphenyl)thiophene-2-carboxamide Chemical compound CCCN(CCO)C(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 LGHXVLYSCJRRIB-UHFFFAOYSA-N 0.000 claims 1
- YNRLBJJKFSMVFK-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-methoxy-n,4-dimethyl-3-(4-sulfamoylphenyl)thiophene-2-carboxamide Chemical compound CON(C)C(=O)C=1SC(C=2C=CC(Cl)=CC=2)=C(C)C=1C1=CC=C(S(N)(=O)=O)C=C1 YNRLBJJKFSMVFK-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- OIBXNTRFHALESR-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C(C(=C(S1)C(CC)=O)C=1C(=C(C=CC=1)S(=O)(=O)N)C)C Chemical compound ClC1=CC=C(C=C1)C1=C(C(=C(S1)C(CC)=O)C=1C(=C(C=CC=1)S(=O)(=O)N)C)C OIBXNTRFHALESR-UHFFFAOYSA-N 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 1
- 229940127236 atypical antipsychotics Drugs 0.000 claims 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 229960000074 biopharmaceutical Drugs 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- VEVOECUDDNJOOR-UHFFFAOYSA-L diethyl-methyl-[2-(1-methyl-1-azoniabicyclo[2.2.2]octane-2-carbonyl)oxyethyl]azanium;diiodide Chemical compound [I-].[I-].C1C[N+]2(C)C(C(=O)OCC[N+](C)(CC)CC)CC1CC2 VEVOECUDDNJOOR-UHFFFAOYSA-L 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JIGSWJHMJDWBIL-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoyl-5,6,7,8-tetrahydronaphthalen-1-yl)thiophene-2-carboxylate Chemical compound CC=1C(C=2C=3CCCCC=3C(=CC=2)S(N)(=O)=O)=C(C(=O)OCC)SC=1C1=CC=C(Cl)C=C1 JIGSWJHMJDWBIL-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 230000004112 neuroprotection Effects 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 201000001245 periodontitis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 230000001953 sensory effect Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN242KO2011 | 2011-02-23 | ||
| IN242/KOL/2011 | 2011-02-23 | ||
| IN1184/KOL/2011 | 2011-09-09 | ||
| IN1184KO2011 | 2011-09-09 | ||
| PCT/IB2012/050806 WO2012114285A1 (en) | 2011-02-23 | 2012-02-22 | Heteroaryl derivatives as alpha7 nachr modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014506590A JP2014506590A (ja) | 2014-03-17 |
| JP2014506590A5 true JP2014506590A5 (enExample) | 2015-04-09 |
| JP6118270B2 JP6118270B2 (ja) | 2017-04-19 |
Family
ID=45873193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013554966A Active JP6118270B2 (ja) | 2011-02-23 | 2012-02-22 | アルファ７ｎａｃｈｒモジュレータとしてのヘテロアリール誘導体 |
Country Status (37)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2826792A1 (en) | 2011-02-23 | 2012-08-30 | Lupin Limited | Heteroaryl derivatives as alpha7 nachr modulators |
| CA2866015A1 (en) | 2012-03-06 | 2013-09-12 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| SI3415517T1 (sl) * | 2012-09-28 | 2022-06-30 | Takeda Pharmaceutical Company Limited | Kristalna oblika 1-(4-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6- metoksipiridazin-3-il)-2,4-diokso-1,2,3,4-tetrahidrotieno(2,3-D)- pirimidin-6il)fenil)-3-metoksiurea |
| WO2014072957A1 (en) | 2012-11-12 | 2014-05-15 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| WO2014111839A1 (en) | 2013-01-16 | 2014-07-24 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| AU2014229300A1 (en) | 2013-03-13 | 2015-06-11 | Lupin Limited | Pyrrole derivatives as alpha 7 nAChR modulators |
| TW201446243A (zh) | 2013-06-03 | 2014-12-16 | Lupin Ltd | 4-(5-(4-氯苯基)-2-(2-環丙基乙醯基)-1,4-二甲基-1氫-吡咯-3-基)苯磺醯胺作為α7尼古丁乙醯膽鹼受體調節劑 |
| WO2014203150A1 (en) | 2013-06-17 | 2014-12-24 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| ES2764660T3 (es) | 2014-12-16 | 2020-06-04 | Axovant Sciences Gmbh | Compuestos de amida de quinuclidina sustituida geminal como agonistas de receptores alfa-7 nicotínicos de acetilcolina |
| WO2016201096A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmaceuticals, Inc. | Aminobenzisoxazole compounds as agonists of a7-nicotinic acetylcholine receptors |
| HK1253295A1 (zh) | 2015-08-12 | 2019-06-14 | Axovant Sciences Gmbh | 作为7-烟碱乙酰胆碱受体的激动剂的偕取代的氨基苯并异恶唑化合物 |
| HRP20211960T1 (hr) * | 2016-03-22 | 2022-03-18 | Merck Sharp & Dohme Corp. | Alosterični modulatori nikotinskih acetilcolinskih receptora |
| EP4155293B1 (en) * | 2018-06-07 | 2025-07-30 | The Regents of The University of Michigan | Prc1 inhibitors and methods of treatment therewith |
| TWI823961B (zh) | 2018-07-05 | 2023-12-01 | 德商拜耳廠股份有限公司 | 噻吩基噁唑酮及類似物 |
| WO2021001331A1 (en) | 2019-07-03 | 2021-01-07 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides and derivatives thereof as microbicides |
| EP4077302A1 (en) | 2019-12-20 | 2022-10-26 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof |
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| US3953596A (en) | 1973-06-14 | 1976-04-27 | Ici United States Inc. | 8-Oxa-3-azabicyclo(3.2.1)octane analgesic compositions and method of alleviating pain in animals |
| US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| US4501728A (en) | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| US5019369A (en) | 1984-10-22 | 1991-05-28 | Vestar, Inc. | Method of targeting tumors in humans |
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