SK15152002A3 - Cyklohexylamínový derivát ako subtyp selektívnych antagonistov NMDA receptora - Google Patents
Cyklohexylamínový derivát ako subtyp selektívnych antagonistov NMDA receptora Download PDFInfo
- Publication number
- SK15152002A3 SK15152002A3 SK1515-2002A SK15152002A SK15152002A3 SK 15152002 A3 SK15152002 A3 SK 15152002A3 SK 15152002 A SK15152002 A SK 15152002A SK 15152002 A3 SK15152002 A3 SK 15152002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- cyclohexyl
- phenol
- alkyl
- trans
- group
- Prior art date
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- 229940127523 NMDA Receptor Antagonists Drugs 0.000 title description 3
- 150000003946 cyclohexylamines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims abstract description 18
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 8
- 206010008118 cerebral infarction Diseases 0.000 claims abstract description 5
- 201000006474 Brain Ischemia Diseases 0.000 claims abstract description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 4
- -1 4- [4- (5-pentylamino) cyclohexyl] phenol Chemical compound 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- MFZGWTAJGYWBEU-UHFFFAOYSA-N 4-[4-(3-phenylpropylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCCCC=2C=CC=CC=2)CC1 MFZGWTAJGYWBEU-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- FFZAFMWWOKKINB-UHFFFAOYSA-N 4-[4-(3-phenylprop-2-ynylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCC#CC=2C=CC=CC=2)CC1 FFZAFMWWOKKINB-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
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- 239000002552 dosage form Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
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- ZSCFHZMQBFWBIC-UHFFFAOYSA-N 4-[4-(2-anilinoethylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCCNC=2C=CC=CC=2)CC1 ZSCFHZMQBFWBIC-UHFFFAOYSA-N 0.000 claims description 4
- AGKKZDATHXMERD-UHFFFAOYSA-N 4-[4-(4-phenylbutylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCCCCC=2C=CC=CC=2)CC1 AGKKZDATHXMERD-UHFFFAOYSA-N 0.000 claims description 4
- RQCPNEISYJHKDD-UHFFFAOYSA-N 4-[4-[3-phenylpropyl(propan-2-yl)amino]cyclohexyl]phenol Chemical compound C1CC(C=2C=CC(O)=CC=2)CCC1N(C(C)C)CCCC1=CC=CC=C1 RQCPNEISYJHKDD-UHFFFAOYSA-N 0.000 claims description 4
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- QSTLSWKQEWGRHB-UAPYVXQJSA-N Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCc1cccnc1 Chemical compound Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCCc1cccnc1 QSTLSWKQEWGRHB-UAPYVXQJSA-N 0.000 claims description 4
- QUFRMUUIEDVKFC-RUCARUNLSA-N Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCc1ccc(F)cc1 Chemical compound Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCCc1ccc(F)cc1 QUFRMUUIEDVKFC-RUCARUNLSA-N 0.000 claims description 4
- HOUYDKWVSLWILI-JCNLHEQBSA-N Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCc1cccnc1 Chemical compound Oc1ccc(cc1)[C@H]1CC[C@@H](CC1)NCc1cccnc1 HOUYDKWVSLWILI-JCNLHEQBSA-N 0.000 claims description 4
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- YMDDQVXNITZOQA-UHFFFAOYSA-N methyl n-[4-(4-hydroxyphenyl)cyclohexyl]-n-(3-phenylpropyl)carbamate Chemical compound C1CC(C=2C=CC(O)=CC=2)CCC1N(C(=O)OC)CCCC1=CC=CC=C1 YMDDQVXNITZOQA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- ZYCLAUOWJSDGTO-UHFFFAOYSA-N 4-[4-[benzyl(3-phenylpropyl)amino]cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(N(CCCC=2C=CC=CC=2)CC=2C=CC=CC=2)CC1 ZYCLAUOWJSDGTO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- LHPSNJNPZAFCLK-UHFFFAOYSA-N 4-[4-(2-phenylsulfanylethylamino)cyclohexyl]phenol Chemical compound C1=CC(O)=CC=C1C1CCC(NCCSC=2C=CC=CC=2)CC1 LHPSNJNPZAFCLK-UHFFFAOYSA-N 0.000 claims description 2
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- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19976200P | 2000-04-26 | 2000-04-26 | |
| PCT/US2001/013176 WO2001081295A1 (en) | 2000-04-26 | 2001-04-24 | Cyclohexylamine derivative as subtype selective nmda receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK15152002A3 true SK15152002A3 (sk) | 2003-05-02 |
Family
ID=22738909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1515-2002A SK15152002A3 (sk) | 2000-04-26 | 2001-04-24 | Cyklohexylamínový derivát ako subtyp selektívnych antagonistov NMDA receptora |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6919377B2 (is) |
| EP (1) | EP1278716B1 (is) |
| JP (1) | JP2003531187A (is) |
| KR (1) | KR20020093950A (is) |
| CN (1) | CN1441773A (is) |
| AP (1) | AP2002002664A0 (is) |
| AT (1) | ATE337292T1 (is) |
| AU (1) | AU2001255620A1 (is) |
| BG (1) | BG107258A (is) |
| BR (1) | BR0110247A (is) |
| CA (1) | CA2406272A1 (is) |
| CZ (1) | CZ20023479A3 (is) |
| DE (1) | DE60122495T2 (is) |
| EA (1) | EA200200952A1 (is) |
| EE (1) | EE200200612A (is) |
| ES (1) | ES2267759T3 (is) |
| HU (1) | HUP0300600A2 (is) |
| IL (1) | IL152424A0 (is) |
| IS (1) | IS6569A (is) |
| MA (1) | MA26895A1 (is) |
| MX (1) | MXPA02009659A (is) |
| NO (1) | NO20025136L (is) |
| OA (1) | OA12253A (is) |
| PL (1) | PL358584A1 (is) |
| SK (1) | SK15152002A3 (is) |
| WO (1) | WO2001081295A1 (is) |
| ZA (1) | ZA200208177B (is) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0100623D0 (en) * | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical compounds IV |
| US7064211B2 (en) * | 2002-03-22 | 2006-06-20 | Eisai Co., Ltd. | Hemiasterlin derivatives and uses thereof |
| WO2004054579A1 (en) * | 2002-12-17 | 2004-07-01 | Pfizer Japan Inc. | 2-pyridyl and 2-pyrimidyl cycloalkylene amide compounds as nr2b receptor antagonists |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| NZ551603A (en) | 2004-06-24 | 2010-11-26 | Incyte Corp | N-substituted piperidines and their use as pharmaceuticals |
| EP1768954A4 (en) * | 2004-06-24 | 2008-05-28 | Incyte Corp | 2-METHYLPROPANAMIDES AND THEIR USE AS PHARMACEUTICALS |
| EA200700251A1 (ru) * | 2004-08-10 | 2007-08-31 | Инсайт Корпорейшн | Амидосоединения и их применение в качестве фармацевтических средств |
| JP5379692B2 (ja) | 2006-11-09 | 2013-12-25 | プロビオドルグ エージー | 潰瘍、癌及び他の疾患の治療のためのグルタミニルシクラーゼの阻害薬としての3−ヒドロキシ−1,5−ジヒドロ−ピロール−2−オン誘導体 |
| US9126987B2 (en) | 2006-11-30 | 2015-09-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| AU2008220785B2 (en) | 2007-03-01 | 2013-02-21 | Vivoryon Therapeutics N.V. | New use of glutaminyl cyclase inhibitors |
| JP5667440B2 (ja) | 2007-04-18 | 2015-02-12 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのチオ尿素誘導体 |
| BRPI0816690A2 (pt) * | 2007-09-12 | 2016-11-01 | Merz Pharma Gmbh & Co Kgaa | derivados 1-amino-alquilciclohexano para tratamento e a prevenção da perda da audição |
| RU2438658C2 (ru) * | 2007-09-12 | 2012-01-10 | Мерц Фарма Гмбх Унд Ко. Кгаа | Производные 1-аминоалкилциклогексана для лечения кохлеарного тиннитуса |
| JP5551597B2 (ja) * | 2008-08-22 | 2014-07-16 | 第一三共株式会社 | シクロアルキルアミン誘導体 |
| NZ598685A (en) | 2009-09-11 | 2013-05-31 | Probiodrug Ag | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
| JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤 |
| DK2545047T3 (da) | 2010-03-10 | 2014-07-28 | Probiodrug Ag | Heterocycliske inhibitorer af glutaminylcyclase (QC, EC 2.3.2.5) |
| EP2560953B1 (en) | 2010-04-21 | 2016-01-06 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| US8530670B2 (en) | 2011-03-16 | 2013-09-10 | Probiodrug Ag | Inhibitors |
| CA2931313C (en) | 2013-11-21 | 2022-04-05 | Marquette University | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
| US9187506B2 (en) | 2014-01-09 | 2015-11-17 | Bristol-Myers Squibb Company | (R)-3-((3S,4S)-3-fluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one and its prodrugs for the treatment of psychiatric disorders |
| US9221796B2 (en) * | 2014-01-09 | 2015-12-29 | Bristol-Myers Squibb Company | Selective NR2B antagonists |
| KR20190004743A (ko) * | 2016-05-04 | 2019-01-14 | 브리스톨-마이어스 스큅 컴퍼니 | 인돌아민 2,3-디옥시게나제의 억제제 및 그의 사용 방법 |
| EP3461819B1 (en) | 2017-09-29 | 2020-05-27 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW209868B (is) | 1991-04-04 | 1993-07-21 | Yoshitomi Pharmaceutical | |
| CA2091204C (en) * | 1992-03-11 | 1997-04-08 | Ronald J. Mattson | Antiischemic-piperazinyl and piperidinyl-cyclohexanes |
| DE4438020A1 (de) | 1994-10-25 | 1996-05-02 | Thomae Gmbh Dr K | N-substituierte Arylcyclohexylacylamine, ihre Salze mit physiologisch verträglichen organischen oder anorganischen Säuren, Verfahren zur Herstellung dieser Verbindungen und diese enthaltende Arzneimittel |
| CZ126598A3 (cs) * | 1995-10-26 | 1998-09-16 | Mitsubishi-Tokyo Pharmaceuticals, Inc. | Fenylethanolaminové sloučeniny, způsob jejich výroby a farmaceutické prostředky s jejich obsahem |
| PE20000728A1 (es) * | 1998-06-26 | 2000-08-21 | Cocensys Inc | Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda |
| EP0982026B1 (en) | 1998-08-18 | 2006-05-17 | F. Hoffmann-La Roche Ag | Use of aryl-cyclohexylamine derivatives in the manufacture of NMDA receptor blockers |
-
2001
- 2001-04-24 CN CN01808644A patent/CN1441773A/zh active Pending
- 2001-04-24 EA EA200200952A patent/EA200200952A1/ru unknown
- 2001-04-24 AU AU2001255620A patent/AU2001255620A1/en not_active Abandoned
- 2001-04-24 KR KR1020027014329A patent/KR20020093950A/ko not_active Withdrawn
- 2001-04-24 IL IL15242401A patent/IL152424A0/xx unknown
- 2001-04-24 PL PL01358584A patent/PL358584A1/xx not_active Application Discontinuation
- 2001-04-24 WO PCT/US2001/013176 patent/WO2001081295A1/en not_active Ceased
- 2001-04-24 EP EP01928803A patent/EP1278716B1/en not_active Expired - Lifetime
- 2001-04-24 AT AT01928803T patent/ATE337292T1/de not_active IP Right Cessation
- 2001-04-24 CZ CZ20023479A patent/CZ20023479A3/cs unknown
- 2001-04-24 HU HU0300600A patent/HUP0300600A2/hu unknown
- 2001-04-24 JP JP2001578392A patent/JP2003531187A/ja active Pending
- 2001-04-24 EE EEP200200612A patent/EE200200612A/xx unknown
- 2001-04-24 MX MXPA02009659A patent/MXPA02009659A/es active IP Right Grant
- 2001-04-24 BR BR0110247-8A patent/BR0110247A/pt not_active IP Right Cessation
- 2001-04-24 CA CA002406272A patent/CA2406272A1/en not_active Abandoned
- 2001-04-24 SK SK1515-2002A patent/SK15152002A3/sk unknown
- 2001-04-24 DE DE60122495T patent/DE60122495T2/de not_active Expired - Fee Related
- 2001-04-24 US US10/258,721 patent/US6919377B2/en not_active Expired - Fee Related
- 2001-04-24 ES ES01928803T patent/ES2267759T3/es not_active Expired - Lifetime
- 2001-04-24 AP APAP/P/2002/002664A patent/AP2002002664A0/en unknown
- 2001-04-24 OA OA1200200326A patent/OA12253A/en unknown
-
2002
- 2002-09-27 IS IS6569A patent/IS6569A/is unknown
- 2002-10-10 ZA ZA200208177A patent/ZA200208177B/en unknown
- 2002-10-17 MA MA26873A patent/MA26895A1/fr unknown
- 2002-10-25 NO NO20025136A patent/NO20025136L/no not_active Application Discontinuation
- 2002-11-08 BG BG107258A patent/BG107258A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20025136D0 (no) | 2002-10-25 |
| DE60122495T2 (de) | 2007-03-29 |
| NO20025136L (no) | 2002-12-20 |
| IS6569A (is) | 2002-09-27 |
| MA26895A1 (fr) | 2004-12-20 |
| EP1278716A1 (en) | 2003-01-29 |
| DE60122495D1 (de) | 2006-10-05 |
| AU2001255620A1 (en) | 2001-11-07 |
| EA200200952A1 (ru) | 2003-02-27 |
| BR0110247A (pt) | 2003-03-05 |
| PL358584A1 (en) | 2004-08-09 |
| HUP0300600A2 (hu) | 2003-08-28 |
| AP2002002664A0 (en) | 2002-12-31 |
| KR20020093950A (ko) | 2002-12-16 |
| CN1441773A (zh) | 2003-09-10 |
| IL152424A0 (en) | 2003-05-29 |
| EP1278716B1 (en) | 2006-08-23 |
| US6919377B2 (en) | 2005-07-19 |
| ES2267759T3 (es) | 2007-03-16 |
| WO2001081295A1 (en) | 2001-11-01 |
| BG107258A (bg) | 2003-07-31 |
| MXPA02009659A (es) | 2003-03-10 |
| OA12253A (en) | 2006-05-11 |
| ZA200208177B (en) | 2004-02-11 |
| JP2003531187A (ja) | 2003-10-21 |
| CA2406272A1 (en) | 2001-11-01 |
| EE200200612A (et) | 2004-06-15 |
| ATE337292T1 (de) | 2006-09-15 |
| US20030236286A1 (en) | 2003-12-25 |
| CZ20023479A3 (cs) | 2003-04-16 |
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