NO327602B1 - Nye substituerte 4-fenyl-4-[1H-imidazol-2-yl]-piperidinderivater og deres anvendelse som selektive ikke-peptide delta-opoid-agonister - Google Patents
Nye substituerte 4-fenyl-4-[1H-imidazol-2-yl]-piperidinderivater og deres anvendelse som selektive ikke-peptide delta-opoid-agonister Download PDFInfo
- Publication number
- NO327602B1 NO327602B1 NO20041666A NO20041666A NO327602B1 NO 327602 B1 NO327602 B1 NO 327602B1 NO 20041666 A NO20041666 A NO 20041666A NO 20041666 A NO20041666 A NO 20041666A NO 327602 B1 NO327602 B1 NO 327602B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- phenyl
- imidazol
- piperidine
- alkyloxy
- Prior art date
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- 239000000556 agonist Substances 0.000 title description 9
- 108090000765 processed proteins & peptides Proteins 0.000 title description 3
- GBANLFWFVPIRMO-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)-4-phenylpiperidine Chemical class C1CNCCC1(C=1C=CC=CC=1)C1=NC=CN1 GBANLFWFVPIRMO-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 208000002193 Pain Diseases 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- -1 2-pyridyl-thiazol-4-yl Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
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- 201000006549 dyspepsia Diseases 0.000 claims description 3
- IDNSINQXOXDMHW-UHFFFAOYSA-N ethyl 4-(1-benzylimidazol-2-yl)-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C=1C=CC=CC=1)C1=NC=CN1CC1=CC=CC=C1 IDNSINQXOXDMHW-UHFFFAOYSA-N 0.000 claims description 3
- KPOBZMXBVODHGB-UHFFFAOYSA-N ethyl 4-[1-[(4-hydroxyphenyl)methyl]imidazol-2-yl]-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C=1C=CC=CC=1)C1=NC=CN1CC1=CC=C(O)C=C1 KPOBZMXBVODHGB-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
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- KIUPRXNMBOSLIU-UHFFFAOYSA-N 4-[[2-[1-(1,3-benzoxazol-2-yl)-4-phenylpiperidin-4-yl]imidazol-1-yl]methyl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(CN2C(=NC=C2)C2(CCN(CC2)C=2OC3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 KIUPRXNMBOSLIU-UHFFFAOYSA-N 0.000 claims description 2
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- XHGVOFUYLQFSIW-UHFFFAOYSA-N [4-(1-benzylimidazol-2-yl)-4-phenylpiperidin-1-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1(C=1C=CC=CC=1)C1=NC=CN1CC1=CC=CC=C1 XHGVOFUYLQFSIW-UHFFFAOYSA-N 0.000 claims description 2
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- NIXTVCWNTYCMHM-UHFFFAOYSA-N ethyl 4-[1-[1-(4-ethoxycarbonylphenyl)ethyl]imidazol-2-yl]-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C=1C=CC=CC=1)C1=NC=CN1C(C)C1=CC=C(C(=O)OCC)C=C1 NIXTVCWNTYCMHM-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011737 fluorine Substances 0.000 claims description 2
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- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- JXUWRZZEVUREMV-UHFFFAOYSA-N phenyl-[4-phenyl-4-[1-(1-phenylethyl)imidazol-2-yl]piperidin-1-yl]methanone Chemical compound C1=CN=C(C2(CCN(CC2)C(=O)C=2C=CC=CC=2)C=2C=CC=CC=2)N1C(C)C1=CC=CC=C1 JXUWRZZEVUREMV-UHFFFAOYSA-N 0.000 claims description 2
- LFIFXAGOMGUFLO-UHFFFAOYSA-N propan-2-yl 4-(1-benzylimidazol-2-yl)-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C=1C=CC=CC=1)C1=NC=CN1CC1=CC=CC=C1 LFIFXAGOMGUFLO-UHFFFAOYSA-N 0.000 claims description 2
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- 238000011533 pre-incubation Methods 0.000 description 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203926 | 2001-10-15 | ||
| PCT/EP2002/011372 WO2003033486A1 (en) | 2001-10-15 | 2002-10-10 | Novel substituted 4-phenyl-4-[1h-imidazol-2-yl]-piperidine derivatives and their use as selective non-peptide delta opioid agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20041666L NO20041666L (no) | 2004-04-22 |
| NO327602B1 true NO327602B1 (no) | 2009-08-31 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041666A NO327602B1 (no) | 2001-10-15 | 2004-04-22 | Nye substituerte 4-fenyl-4-[1H-imidazol-2-yl]-piperidinderivater og deres anvendelse som selektive ikke-peptide delta-opoid-agonister |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7282508B2 (ru) |
| EP (1) | EP1438304B1 (ru) |
| JP (1) | JP4417108B2 (ru) |
| KR (1) | KR100898562B1 (ru) |
| CN (1) | CN100354273C (ru) |
| AR (1) | AR037506A1 (ru) |
| AT (1) | ATE347549T1 (ru) |
| AU (1) | AU2002346994B2 (ru) |
| BR (1) | BR0213327A (ru) |
| CA (1) | CA2462953C (ru) |
| CY (1) | CY1106356T1 (ru) |
| DE (1) | DE60216627T2 (ru) |
| EA (1) | EA006507B1 (ru) |
| ES (1) | ES2278065T3 (ru) |
| HR (1) | HRP20040324A2 (ru) |
| HU (1) | HUP0600447A3 (ru) |
| IL (2) | IL161348A0 (ru) |
| MX (1) | MXPA04003479A (ru) |
| MY (1) | MY137356A (ru) |
| NO (1) | NO327602B1 (ru) |
| NZ (1) | NZ531679A (ru) |
| PL (1) | PL367967A1 (ru) |
| PT (1) | PT1438304E (ru) |
| UA (1) | UA76224C2 (ru) |
| WO (1) | WO2003033486A1 (ru) |
| ZA (1) | ZA200402818B (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PL370371A1 (en) * | 2001-10-15 | 2005-05-16 | Janssen Pharmaceutica N.V. | Substituted 4-phenyl-4-(1h-imidazol-2-yl)-piperidine derivatives for reducing ischaemic damage |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| EP1501825A2 (en) | 2002-05-08 | 2005-02-02 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives: gaba a receptor ligands |
| ATE453621T1 (de) * | 2002-07-03 | 2010-01-15 | Glaxo Group Ltd | Substituierte 4-phenylpiperidinamide als tachykininantagonisten und serotoninwiederaufnahmehemmer |
| AR044010A1 (es) * | 2003-04-11 | 2005-08-24 | Janssen Pharmaceutica Nv | Uso de derivados de 4-fenil-4- [1h-imidazol-2-il]- piperidina sustituidos como agonistas delta opioideos no peptidos selectivos, con actividad antidepresiva y ansiolitica |
| NZ546834A (en) | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
| AU2013205089B2 (en) * | 2004-03-15 | 2013-12-19 | Janssen Pharmaceutica, N.V. | Novel compounds as opioid receptor modulators |
| ME02221B (me) | 2004-03-15 | 2016-02-20 | Janssen Pharmaceutica Nv | Postupak za proizvodnju intermedijara jedinjenja korisnih kao modulatori opioidnih receptora |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| AU2007294968A1 (en) | 2006-09-12 | 2008-03-20 | Adolor Corporation | Use of N-containing spirocompounds for the enhancement of cognitive function |
| IT1396951B1 (it) | 2009-12-18 | 2012-12-20 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
| US9675587B2 (en) | 2013-03-14 | 2017-06-13 | Allergan Holdings Unlimited Company | Opioid receptor modulator dosage formulations |
| TWI652264B (zh) * | 2013-09-26 | 2019-03-01 | 東麗股份有限公司 | Cyclic amine derivatives and their medical uses |
| EP3697410A4 (en) | 2017-10-19 | 2021-08-11 | Amgen Inc. | BENZIMIDAZOLE DERIVATIVES AND THEIR USES |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2985322B2 (ja) | 1991-03-01 | 1999-11-29 | 東レ株式会社 | イソキノリン誘導体およびその医薬用途 |
| US5354863A (en) | 1992-01-21 | 1994-10-11 | G. D. Searle & Co. | Opioid agonist compounds |
| GB9202238D0 (en) | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
| ES2173921T3 (es) | 1993-08-06 | 2002-11-01 | Glaxosmithkline Spa | Derivados de hidroisoquinolina. |
| US5618934A (en) | 1994-05-17 | 1997-04-08 | Merck & Co., Inc. | Boronic acid compound |
| AU4458996A (en) | 1995-01-20 | 1996-08-07 | Nippon Shinyaku Co. Ltd. | Ethylamine derivatives and drugs |
| IT1307327B1 (it) | 1995-09-12 | 2001-10-30 | Smithkline Beecham Spa | Derivati idroisochinolinici sostituiti |
| TW548271B (en) | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| DE19805370A1 (de) | 1997-03-14 | 1998-09-17 | Gruenenthal Gmbh | Substituierte Aminoverbindungen und ihre Verwendung als analgetisch wirksame Substanzen |
| GB9709972D0 (en) | 1997-05-19 | 1997-07-09 | Pfizer Ltd | Tetrazoles |
| JP4601175B2 (ja) | 1998-12-19 | 2010-12-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗ヒスタミン性スピロ化合物 |
| EP1038872A1 (en) | 1999-02-22 | 2000-09-27 | Pfizer Products Inc. | 4-Phenyl-4-heteroarylpiperdine derivatives as opioid receptor ligands |
| JP2005231995A (ja) | 1999-12-22 | 2005-09-02 | Meiji Seika Kaisha Ltd | オピオイドδ受容体アゴニスト／アンタゴニストとして有用なスピロ化合物 |
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2002
- 2002-10-10 UA UA20040503667A patent/UA76224C2/uk unknown
- 2002-10-10 AT AT02782881T patent/ATE347549T1/de active
- 2002-10-10 CN CNB028203275A patent/CN100354273C/zh not_active Expired - Fee Related
- 2002-10-10 WO PCT/EP2002/011372 patent/WO2003033486A1/en active IP Right Grant
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- 2002-10-10 PL PL02367967A patent/PL367967A1/xx unknown
- 2002-10-10 CA CA2462953A patent/CA2462953C/en not_active Expired - Lifetime
- 2002-10-10 NZ NZ531679A patent/NZ531679A/en not_active IP Right Cessation
- 2002-10-10 KR KR1020047002381A patent/KR100898562B1/ko not_active IP Right Cessation
- 2002-10-10 DE DE60216627T patent/DE60216627T2/de not_active Expired - Lifetime
- 2002-10-10 MX MXPA04003479A patent/MXPA04003479A/es active IP Right Grant
- 2002-10-10 BR BR0213327-0A patent/BR0213327A/pt not_active IP Right Cessation
- 2002-10-10 PT PT02782881T patent/PT1438304E/pt unknown
- 2002-10-10 HU HU0600447A patent/HUP0600447A3/hu unknown
- 2002-10-10 AU AU2002346994A patent/AU2002346994B2/en not_active Ceased
- 2002-10-10 JP JP2003536226A patent/JP4417108B2/ja not_active Expired - Fee Related
- 2002-10-10 ES ES02782881T patent/ES2278065T3/es not_active Expired - Lifetime
- 2002-10-10 EA EA200400545A patent/EA006507B1/ru not_active IP Right Cessation
- 2002-10-11 MY MYPI20023800A patent/MY137356A/en unknown
- 2002-10-11 AR ARP020103837A patent/AR037506A1/es unknown
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2004
- 2004-04-06 HR HR20040324A patent/HRP20040324A2/xx not_active Application Discontinuation
- 2004-04-13 IL IL161348A patent/IL161348A/en not_active IP Right Cessation
- 2004-04-13 ZA ZA2004/02818A patent/ZA200402818B/en unknown
- 2004-04-22 NO NO20041666A patent/NO327602B1/no not_active IP Right Cessation
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2007
- 2007-03-06 CY CY20071100311T patent/CY1106356T1/el unknown
- 2007-05-25 US US11/753,830 patent/US20080096925A1/en not_active Abandoned
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