JP2008508247A5 - - Google Patents
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- Publication number
- JP2008508247A5 JP2008508247A5 JP2007523160A JP2007523160A JP2008508247A5 JP 2008508247 A5 JP2008508247 A5 JP 2008508247A5 JP 2007523160 A JP2007523160 A JP 2007523160A JP 2007523160 A JP2007523160 A JP 2007523160A JP 2008508247 A5 JP2008508247 A5 JP 2008508247A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- formula
- benzylidene
- piperidin
- acetamide
- 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.)
- Granted
Links
- QMQNIKYRPSFQKB-UHFFFAOYSA-N 4-benzylidenepiperidine Chemical class C1CNCCC1=CC1=CC=CC=C1 QMQNIKYRPSFQKB-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims 8
- -1 cyano, nitro, amino Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 230000003287 optical effect Effects 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000969 carrier Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010058019 Cancer Pain Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010011878 Deafness Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229960003920 cocaine Drugs 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003995 emulsifying agent Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 claims 2
- 235000013355 food flavoring agent Nutrition 0.000 claims 2
- 239000003205 fragrance Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 230000010370 hearing loss Effects 0.000 claims 2
- 231100000888 hearing loss Toxicity 0.000 claims 2
- 208000016354 hearing loss disease Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 231100000878 neurological injury Toxicity 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 230000003204 osmotic effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 210000001525 retina Anatomy 0.000 claims 2
- 210000000278 spinal cord Anatomy 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- 230000008736 traumatic injury Effects 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 238000009736 wetting Methods 0.000 claims 2
- 239000000080 wetting agent Substances 0.000 claims 2
- UMURLIQHQSKULR-UHFFFAOYSA-N 1,3-oxazolidine-2-thione Chemical compound S=C1NCCO1 UMURLIQHQSKULR-UHFFFAOYSA-N 0.000 claims 1
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 claims 1
- GHNQWLARMUQQSN-UHFFFAOYSA-N 2-(4-benzylidenepiperidin-1-yl)-2-oxo-n-(2-oxo-3h-1,3-benzothiazol-6-yl)acetamide Chemical compound C=1C=C2NC(=O)SC2=CC=1NC(=O)C(=O)N(CC1)CCC1=CC1=CC=CC=C1 GHNQWLARMUQQSN-UHFFFAOYSA-N 0.000 claims 1
- DZGFNFKXJJEZGU-UHFFFAOYSA-N 2-(4-benzylidenepiperidin-1-yl)-2-oxo-n-(2-oxo-3h-1,3-benzoxazol-6-yl)acetamide Chemical compound C=1C=C2NC(=O)OC2=CC=1NC(=O)C(=O)N(CC1)CCC1=CC1=CC=CC=C1 DZGFNFKXJJEZGU-UHFFFAOYSA-N 0.000 claims 1
- DAMUKLHPRBOHSI-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-1,3-dihydrobenzimidazol-5-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3NC(=O)NC3=CC=2)CC1 DAMUKLHPRBOHSI-UHFFFAOYSA-N 0.000 claims 1
- RAJOLCMXEZCRSR-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-3h-1,3-benzothiazol-6-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3SC(=O)NC3=CC=2)CC1 RAJOLCMXEZCRSR-UHFFFAOYSA-N 0.000 claims 1
- IIZXZAAOKBKQLD-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-3h-1,3-benzoxazol-6-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3OC(=O)NC3=CC=2)CC1 IIZXZAAOKBKQLD-UHFFFAOYSA-N 0.000 claims 1
- BTBPBRIJFCHIFF-UHFFFAOYSA-N 2-[4-[(4-fluorophenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-3h-1,3-benzoxazol-6-yl)acetamide Chemical compound C1=CC(F)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3OC(=O)NC3=CC=2)CC1 BTBPBRIJFCHIFF-UHFFFAOYSA-N 0.000 claims 1
- RLCNRHZFIAILRX-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-1,3-dihydrobenzimidazol-5-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3NC(=O)NC3=CC=2)CC1 RLCNRHZFIAILRX-UHFFFAOYSA-N 0.000 claims 1
- GDTHRASRLWBZGJ-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-3h-1,3-benzothiazol-6-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3SC(=O)NC3=CC=2)CC1 GDTHRASRLWBZGJ-UHFFFAOYSA-N 0.000 claims 1
- HVMZDPDWJRXJDP-UHFFFAOYSA-N 2-[4-[(4-methylphenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-1,3-dihydrobenzimidazol-5-yl)acetamide Chemical compound C1=CC(C)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3NC(=O)NC3=CC=2)CC1 HVMZDPDWJRXJDP-UHFFFAOYSA-N 0.000 claims 1
- GEEIIFVFHLEMRY-UHFFFAOYSA-N 2-[4-[(4-methylphenyl)methylidene]piperidin-1-yl]-2-oxo-n-(2-oxo-3h-1,3-benzothiazol-6-yl)acetamide Chemical compound C1=CC(C)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=C3SC(=O)NC3=CC=2)CC1 GEEIIFVFHLEMRY-UHFFFAOYSA-N 0.000 claims 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical group O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims 1
- 102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 claims 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 1
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 108010038912 Retinoid X Receptors Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- WGIZGGQKPDSPIN-UHFFFAOYSA-N n-[4-(methanesulfonamido)phenyl]-2-[4-[(4-methoxyphenyl)methylidene]piperidin-1-yl]-2-oxoacetamide Chemical compound C1=CC(OC)=CC=C1C=C1CCN(C(=O)C(=O)NC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 WGIZGGQKPDSPIN-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- IMWUREPEYPRYOR-UHFFFAOYSA-N pyrrolidine-2-thione Chemical compound S=C1CCCN1 IMWUREPEYPRYOR-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- KRXIEYCCUDELMI-NTCAYCPXSA-N CCOC(C(NCC/C(/C(C)C)=C\c1ccccc1)=O)=O Chemical compound CCOC(C(NCC/C(/C(C)C)=C\c1ccccc1)=O)=O KRXIEYCCUDELMI-NTCAYCPXSA-N 0.000 description 1
- YOHGHCLOZIQZPZ-UHFFFAOYSA-N OC(C(N(CC1)CCC1=Cc1ccccc1)=O)=O Chemical compound OC(C(N(CC1)CCC1=Cc1ccccc1)=O)=O YOHGHCLOZIQZPZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0401522A HUP0401522A2 (en) | 2004-07-29 | 2004-07-29 | New 4-benzylidene-piperidine derivatives, pharmaceutical compositions containing the same and process for their preparation |
| HUP0401522 | 2004-07-29 | ||
| PCT/HU2005/000077 WO2006010964A1 (en) | 2004-07-29 | 2005-07-21 | New 4-benzylidene-piperidin derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008508247A JP2008508247A (ja) | 2008-03-21 |
| JP2008508247A5 true JP2008508247A5 (enExample) | 2008-05-15 |
| JP4814880B2 JP4814880B2 (ja) | 2011-11-16 |
Family
ID=89985407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007523160A Expired - Fee Related JP4814880B2 (ja) | 2004-07-29 | 2005-07-21 | 新規な４−ベンジリデン−ピペリジン誘導体 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US8008326B2 (enExample) |
| EP (1) | EP1773810B1 (enExample) |
| JP (1) | JP4814880B2 (enExample) |
| KR (1) | KR20070058428A (enExample) |
| CN (1) | CN1989128A (enExample) |
| AP (1) | AP2074A (enExample) |
| AT (1) | ATE387440T1 (enExample) |
| AU (1) | AU2005266159B2 (enExample) |
| BR (1) | BRPI0513902A (enExample) |
| CA (1) | CA2574148A1 (enExample) |
| CY (1) | CY1107368T1 (enExample) |
| DE (1) | DE602005005064T2 (enExample) |
| DK (1) | DK1773810T3 (enExample) |
| EA (1) | EA011241B1 (enExample) |
| ES (1) | ES2302214T3 (enExample) |
| GE (1) | GEP20084492B (enExample) |
| HR (1) | HRP20080127T3 (enExample) |
| HU (1) | HUP0401522A2 (enExample) |
| IL (1) | IL179484A0 (enExample) |
| MA (1) | MA28816B1 (enExample) |
| MX (1) | MX2007001055A (enExample) |
| NO (1) | NO20071108L (enExample) |
| NZ (1) | NZ552137A (enExample) |
| PL (1) | PL1773810T3 (enExample) |
| PT (1) | PT1773810E (enExample) |
| RS (1) | RS50573B (enExample) |
| SI (1) | SI1773810T1 (enExample) |
| TN (1) | TNSN07018A1 (enExample) |
| UA (1) | UA87862C2 (enExample) |
| WO (1) | WO2006010964A1 (enExample) |
| ZA (1) | ZA200700320B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007099828A1 (ja) | 2006-02-23 | 2007-09-07 | Shionogi & Co., Ltd. | 環式基で置換された含窒素複素環誘導体 |
| CN101426381A (zh) * | 2006-04-21 | 2009-05-06 | 西诺米克斯公司 | 含有高效鲜味调料的可食用组合物及其制备方法 |
| DE602007007759D1 (de) * | 2006-06-08 | 2010-08-26 | Bristol Myers Squibb Co | Alken-piperidin-derivate als antivirale wirkstoffe |
| JP2011527689A (ja) * | 2008-07-08 | 2011-11-04 | リヒター ゲデオン エヌワイアールティー． | ２−［４−（４−フルオロ−ベンジル）−ピペリジン−１−イル］−２−オキソ−ｎ−（２−オキソ−２，３−ジヒドロ−ベンゾオキサゾール−６−イル）−アセトアミドの結晶形態 |
| AU2011216950A1 (en) | 2010-02-16 | 2012-08-23 | Pfizer Inc. | (R)-4-((4-((4-(tetrahydrofuran-3-yloxy) benzo[d]isoxazol-3-yloxy)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-ol, a partial agonist of 5-HT4 receptors |
| WO2012033069A1 (ja) | 2010-09-07 | 2012-03-15 | 大鵬薬品工業株式会社 | プロスタグランジンd合成酵素を阻害するピペリジン化合物 |
| US20120322824A1 (en) * | 2011-01-04 | 2012-12-20 | Surratt Christopher K | Cocaine Antagonist/Antidepressant Pharmaceutical Preparations |
| ES2627541T3 (es) | 2012-04-20 | 2017-07-28 | Ucb Pharma, S.A. | Métodos para tratar la enfermedad de Parkinson |
| BR112017003658B1 (pt) | 2014-08-28 | 2022-12-06 | Asceneuron Sa | Composto, mistura, método para inibição de uma glicosidase, e, composição farmacêutica |
| US10913733B2 (en) | 2015-12-18 | 2021-02-09 | Alectos Therapeutics Inc. | Substituted piperidines thiazolyl acetamides as glycosidase inhibitors and uses thereof |
| EP3585783A2 (en) | 2016-02-25 | 2020-01-01 | Asceneuron SA | Sulfoximine glycosidase inhibitors |
| AU2017222964B2 (en) | 2016-02-25 | 2020-01-02 | Asceneuron S. A. | Glycosidase inhibitors |
| EP3419976B1 (en) | 2016-02-25 | 2021-04-07 | Asceneuron SA | Acid addition salts of piperazine derivatives |
| US11612599B2 (en) | 2016-02-25 | 2023-03-28 | Asceneuron Sa | Glycosidase inhibitors |
| US9486444B1 (en) | 2016-03-21 | 2016-11-08 | King Saud University | Anti-cancer compound |
| EP3672959A1 (en) | 2017-08-24 | 2020-07-01 | Asceneuron SA | Linear glycosidase inhibitors |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| US11731972B2 (en) | 2018-08-22 | 2023-08-22 | Asceneuron Sa | Spiro compounds as glycosidase inhibitors |
| EP3841093B1 (en) | 2018-08-22 | 2023-06-21 | Asceneuron SA | Succinate and fumarate acid addition salts of piperazine derivatives useful as glycosidase inhibitors |
| US12016852B2 (en) | 2018-08-22 | 2024-06-25 | Asceneuron Sa | Pyrrolidine glycosidase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA9610738B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| TW498067B (en) * | 1996-07-19 | 2002-08-11 | Hoffmann La Roche | 4-hydroxy-piperidine derivatives |
| CA2220649C (en) | 1996-12-03 | 2007-02-13 | F. Hoffmann-La Roche Ag | 4-hydroxy-piperidine derivatives |
| ATE408611T1 (de) * | 2001-07-24 | 2008-10-15 | Richter Gedeon Nyrt | Piperidine als nmda-rezeptorantagonisten |
-
2004
- 2004-07-29 HU HU0401522A patent/HUP0401522A2/hu unknown
-
2005
- 2005-07-21 PL PL05763197T patent/PL1773810T3/pl unknown
- 2005-07-21 MX MX2007001055A patent/MX2007001055A/es active IP Right Grant
- 2005-07-21 DE DE602005005064T patent/DE602005005064T2/de not_active Expired - Lifetime
- 2005-07-21 AU AU2005266159A patent/AU2005266159B2/en not_active Ceased
- 2005-07-21 SI SI200530213T patent/SI1773810T1/sl unknown
- 2005-07-21 HR HR20080127T patent/HRP20080127T3/xx unknown
- 2005-07-21 EA EA200700367A patent/EA011241B1/ru not_active IP Right Cessation
- 2005-07-21 US US11/658,789 patent/US8008326B2/en not_active Expired - Fee Related
- 2005-07-21 EP EP05763197A patent/EP1773810B1/en not_active Expired - Lifetime
- 2005-07-21 WO PCT/HU2005/000077 patent/WO2006010964A1/en not_active Ceased
- 2005-07-21 ES ES05763197T patent/ES2302214T3/es not_active Expired - Lifetime
- 2005-07-21 RS RSP-2008/0123A patent/RS50573B/sr unknown
- 2005-07-21 NZ NZ552137A patent/NZ552137A/xx not_active IP Right Cessation
- 2005-07-21 CN CNA2005800243746A patent/CN1989128A/zh active Pending
- 2005-07-21 PT PT05763197T patent/PT1773810E/pt unknown
- 2005-07-21 CA CA002574148A patent/CA2574148A1/en not_active Abandoned
- 2005-07-21 BR BRPI0513902-3A patent/BRPI0513902A/pt not_active IP Right Cessation
- 2005-07-21 AT AT05763197T patent/ATE387440T1/de active
- 2005-07-21 DK DK05763197T patent/DK1773810T3/da active
- 2005-07-21 KR KR1020077000262A patent/KR20070058428A/ko not_active Ceased
- 2005-07-21 AP AP2006003839A patent/AP2074A/en active
- 2005-07-21 UA UAA200702171A patent/UA87862C2/ru unknown
- 2005-07-21 GE GEAP20059892A patent/GEP20084492B/en unknown
- 2005-07-21 JP JP2007523160A patent/JP4814880B2/ja not_active Expired - Fee Related
-
2006
- 2006-11-22 IL IL179484A patent/IL179484A0/en unknown
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2007
- 2007-01-11 ZA ZA200700320A patent/ZA200700320B/en unknown
- 2007-01-17 TN TNP2007000018A patent/TNSN07018A1/en unknown
- 2007-02-22 MA MA29703A patent/MA28816B1/fr unknown
- 2007-02-27 NO NO20071108A patent/NO20071108L/no not_active Application Discontinuation
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2008
- 2008-03-27 CY CY20081100349T patent/CY1107368T1/el unknown
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