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 PDF

Info

Publication number: NO327602B1
Authority: NO; Norway
Prior art keywords: alkyl; phenyl; imidazol; piperidine; alkyloxy
Prior art date: 2001-10-15

Application number

NO20041666A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041666L (no

Inventor

Theo Frans Meert

Frans Eduard Janssens

Joseph Elisabeth Leenaerts

Ndez-Gadea Francisco Javier Fern

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date 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 date listed.)

2001-10-15

Filing date

2004-04-22

Publication date

2009-08-31

2004-04-22 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2004-04-22 Publication of NO20041666L publication Critical patent/NO20041666L/no

2009-08-31 Publication of NO327602B1 publication Critical patent/NO327602B1/no

Links

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
230000000241 respiratory effect Effects 0.000 claims description 4
208000000094 Chronic Pain Diseases 0.000 claims description 3
208000006561 Cluster Headache Diseases 0.000 claims description 3
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208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
206010027603 Migraine headaches Diseases 0.000 claims description 3
206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
230000009692 acute damage Effects 0.000 claims description 3
208000005298 acute pain Diseases 0.000 claims description 3
206010003246 arthritis Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
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
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
230000004064 dysfunction Effects 0.000 claims description 3
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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229910052717 sulfur Inorganic materials 0.000 claims description 3
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206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
TXWOTCVSUZXJMH-UHFFFAOYSA-N 2-methoxy-1-[4-phenyl-4-[1-(1-phenylethyl)imidazol-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1(C=1C=CC=CC=1)C1=NC=CN1C(C)C1=CC=CC=C1 TXWOTCVSUZXJMH-UHFFFAOYSA-N 0.000 claims description 2
DTIMTKCIDGMMKY-UHFFFAOYSA-N 4-[[2-(1-benzoyl-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(=O)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DTIMTKCIDGMMKY-UHFFFAOYSA-N 0.000 claims description 2
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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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208000026137 Soft tissue injury Diseases 0.000 claims description 2
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
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
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LJZHXWZDNFILOV-UHFFFAOYSA-N ethyl 4-[1-[(4-methoxycarbonylphenyl)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(C(=O)OC)C=C1 LJZHXWZDNFILOV-UHFFFAOYSA-N 0.000 claims description 2
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
AZPCCLQAOVOOKT-UHFFFAOYSA-N ethyl 4-phenyl-4-[1-(1-phenylethyl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C=1C=CC=CC=1)C1=NC=CN1C(C)C1=CC=CC=C1 AZPCCLQAOVOOKT-UHFFFAOYSA-N 0.000 claims description 2
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125000005842 heteroatom Chemical group 0.000 claims description 2
239000011630 iodine Substances 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
MYVZSNZLGIJIOS-UHFFFAOYSA-N propyl 4-(1-benzylimidazol-2-yl)-4-phenylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCCC)CCC1(C=1C=CC=CC=1)C1=NC=CN1CC1=CC=CC=C1 MYVZSNZLGIJIOS-UHFFFAOYSA-N 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
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230000001562 ulcerogenic effect Effects 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
150000004885 piperazines Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
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238000011533 pre-incubation Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
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150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000002731 protein assay Methods 0.000 description 1
239000011546 protein dye Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
239000001397 quillaja saponaria molina bark Substances 0.000 description 1
238000007347 radical substitution reaction Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000004044 response Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
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150000007949 saponins Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
241000894007 species Species 0.000 description 1
NYKCGQQJNVPOLU-ONTIZHBOSA-N spiradoline Chemical compound C([C@@H]([C@H](C1)N2CCCC2)N(C)C(=O)CC=2C=C(Cl)C(Cl)=CC=2)C[C@]21CCCO2 NYKCGQQJNVPOLU-ONTIZHBOSA-N 0.000 description 1
229950006495 spiradoline Drugs 0.000 description 1
150000003413 spiro compounds Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- 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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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (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)
Nutrition Science (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO20041666A 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 NO327602B1 (no)

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

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ID=8181080

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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 (de)
EP (1)	EP1438304B1 (de)
JP (1)	JP4417108B2 (de)
KR (1)	KR100898562B1 (de)
CN (1)	CN100354273C (de)
AR (1)	AR037506A1 (de)
AT (1)	ATE347549T1 (de)
AU (1)	AU2002346994B2 (de)
BR (1)	BR0213327A (de)
CA (1)	CA2462953C (de)
CY (1)	CY1106356T1 (de)
DE (1)	DE60216627T2 (de)
EA (1)	EA006507B1 (de)
ES (1)	ES2278065T3 (de)
HR (1)	HRP20040324A2 (de)
HU (1)	HUP0600447A3 (de)
IL (2)	IL161348A0 (de)
MX (1)	MXPA04003479A (de)
MY (1)	MY137356A (de)
NO (1)	NO327602B1 (de)
NZ (1)	NZ531679A (de)
PL (1)	PL367967A1 (de)
PT (1)	PT1438304E (de)
UA (1)	UA76224C2 (de)
WO (1)	WO2003033486A1 (de)
ZA (1)	ZA200402818B (de)

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AU2002363369B2 (en) *	2001-10-15	2008-08-21	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
AU2003301864A1 (en)	2002-05-08	2004-06-07	Neurogen Corporation	Substituted imidazolylmethyl pyridine and pyrazine derivatives and their use as gabaa receptor ligands
US20060128752A1 (en) *	2002-07-03	2006-06-15	Giuseppe Alvaro	Chemical compounds
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
AU2004278414B2 (en)	2003-10-01	2012-05-24	Adolor Corporation	Spirocyclic heterocyclic derivatives and methods of their use
HUE029852T2 (en)	2004-03-15	2017-04-28	Janssen Pharmaceutica Nv	Opioid receptor modulators
AU2013205089B2 (en) *	2004-03-15	2013-12-19	Janssen Pharmaceutica, N.V.	Novel compounds as opioid receptor modulators
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
EP2399577A1 (de)	2006-09-12	2011-12-28	Adolor Corporation	Verwendung von N-haltigen Spiroverbindungen zur Verbesserung der kognitiven Funktion
IT1396951B1 (it) *	2009-12-18	2012-12-20	Neuroscienze Pharmaness S C A R L	Composti farmaceutici
US20170119786A1 (en)	2011-03-08	2017-05-04	3-V Biosciences, Inc.	Heterocyclic modulators of lipid synthesis
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
HUE070649T2 (hu)	2017-10-19	2025-06-28	Teijin Pharma Ltd	Benzimidazol-származékok és felhasználásuk
EP4353309A4 (de) *	2021-05-26	2025-05-07	Sumitomo Pharma Co., Ltd.	Phenylharnstoffderivat

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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
DE69430373T2 (de)	1993-08-06	2002-12-12	Smithkline Beecham S.P.A., Baranzate Di Bollate	Hydroisochinolinderivate
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
HK1043128B (zh)	1998-12-19	2007-01-19	詹森药业有限公司	抗组胺的螺环化合物
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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

2002
- 2002-10-10 ES ES02782881T patent/ES2278065T3/es not_active Expired - Lifetime
- 2002-10-10 UA UA20040503667A patent/UA76224C2/uk unknown
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- 2002-10-10 IL IL16134802A patent/IL161348A0/xx unknown
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- 2002-10-10 MX MXPA04003479A patent/MXPA04003479A/es active IP Right Grant
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- 2002-10-10 US US10/491,379 patent/US7282508B2/en not_active Expired - Fee Related
- 2002-10-10 EP EP02782881A patent/EP1438304B1/de not_active Expired - Lifetime
- 2002-10-10 PT PT02782881T patent/PT1438304E/pt unknown
- 2002-10-10 BR BR0213327-0A patent/BR0213327A/pt not_active IP Right Cessation
- 2002-10-10 CN CNB028203275A patent/CN100354273C/zh not_active Expired - Fee Related
- 2002-10-10 JP JP2003536226A patent/JP4417108B2/ja not_active Expired - Fee Related
- 2002-10-10 CA CA2462953A patent/CA2462953C/en not_active Expired - Lifetime
- 2002-10-10 WO PCT/EP2002/011372 patent/WO2003033486A1/en not_active Ceased
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- 2002-10-10 NZ NZ531679A patent/NZ531679A/en not_active IP Right Cessation
- 2002-10-10 DE DE60216627T patent/DE60216627T2/de not_active Expired - Lifetime
- 2002-10-10 HU HU0600447A patent/HUP0600447A3/hu unknown
- 2002-10-10 AT AT02782881T patent/ATE347549T1/de active
- 2002-10-11 AR ARP020103837A patent/AR037506A1/es unknown
- 2002-10-11 MY MYPI20023800A patent/MY137356A/en unknown
2004
- 2004-04-13 ZA ZA2004/02818A patent/ZA200402818B/en unknown
- 2004-04-13 IL IL161348A patent/IL161348A/en not_active IP Right Cessation
- 2004-04-22 NO NO20041666A patent/NO327602B1/no not_active IP Right Cessation
2007
- 2007-03-06 CY CY20071100311T patent/CY1106356T1/el unknown
- 2007-05-25 US US11/753,830 patent/US20080096925A1/en not_active Abandoned

Also Published As

Publication number	Publication date
ZA200402818B (en)	2005-06-29
DE60216627D1 (de)	2007-01-18
EA200400545A1 (ru)	2004-08-26
MXPA04003479A (es)	2004-07-30
US7282508B2 (en)	2007-10-16
EA006507B1 (ru)	2005-12-29
IL161348A (en)	2010-11-30
HUP0600447A3 (en)	2008-03-28
US20040260096A1 (en)	2004-12-23
PT1438304E (pt)	2007-03-30
HRP20040324A2 (en)	2005-04-30
AR037506A1 (es)	2004-11-17
HUP0600447A2 (en)	2006-09-28
MY137356A (en)	2009-01-30
PL367967A1 (en)	2005-03-07
IL161348A0 (en)	2004-09-27
NZ531679A (en)	2005-02-25
CA2462953C (en)	2011-01-04
ATE347549T1 (de)	2006-12-15
KR20050035121A (ko)	2005-04-15
CN1568321A (zh)	2005-01-19
BR0213327A (pt)	2004-10-13
CA2462953A1 (en)	2003-04-24
CY1106356T1 (el)	2011-10-12
UA76224C2 (en)	2006-07-17
EP1438304B1 (de)	2006-12-06
AU2002346994B2 (en)	2007-09-06
ES2278065T3 (es)	2007-08-01
DE60216627T2 (de)	2007-09-20
KR100898562B1 (ko)	2009-05-20
NO20041666L (no)	2004-04-22
US20080096925A1 (en)	2008-04-24
EP1438304A1 (de)	2004-07-21
WO2003033486A1 (en)	2003-04-24
JP4417108B2 (ja)	2010-02-17
JP2005505625A (ja)	2005-02-24
CN100354273C (zh)	2007-12-12

Legal Events

Date	Code	Title	Description
2019-05-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US20080096925A1 (en)	2008-04-24	Novel Substituted 4-Phenyl-4[H-Imidazol-2-YL]-Piperidine Derivatived And Their Use As Selective Non-Peptide Delta Opioid Agonists
TWI378096B (en)	2012-12-01	Heterocyclic compound and use thereof
US20040097546A1 (en)	2004-05-20	Acylated piperidine derivatives as melanocortin-4 receptor agonists
JP2002521382A (ja)	2002-07-16	ロータマーゼ酵素の阻害薬としてのヘテロ環式化合物
TW200904433A (en)	2009-02-01	Substituted imidazole compound and use thereof
JPWO2002068407A1 (ja)	2004-06-24	ベンゾイミダゾール化合物
AU2004227835A1 (en)	2004-10-21	Acylated spiropiperidine derivatives as melanocortin-4 receptor agonists
AU2002346994A1 (en)	2003-07-03	Novel substituted 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives and their use as selective non-peptide delta opioid agonists
ES2282858T3 (es)	2007-10-16	Derivados de la 4-fenil-4-(1h-imidazol-2-il)-piperidina y su uso como agonistas opioides delta no peptidicos con actividad antidepresiva y ansiolitica.
CA2462374C (en)	2011-01-18	Substituted 4-phenyl-4-(1h-imidazol-2-yl)-piperidine derivatives for reducing ischaemic damage
AU2016344689A1 (en)	2018-05-17	CGRP receptor antagonists
AU2002363369A1 (en)	2003-07-24	Substituted 4-phenyl-4-(1H-imidazol-2-yl)-piperidine derivatives for reducing ischaemic damage
CZ286992B6 (en)	2000-08-16	Oxadiazole derivatives, process and intermediates of their preparation, their use and pharmaceutical compositions based thereon
HK1072599A (en)	2005-09-02	Novel substituted 4-phenyl-4-[1h-imidazol-2-yl]-piperidine derivatives and their use as selective non-peptide delta opioid agonists
HK1072562B (en)	2007-06-22	Substituted 4-phenyl-4-(1h-imidazol-2-yl)-piperidine derivatives for reducing ischaemic damage
CZ2001236A3 (cs)	2001-06-13	Heterocyklické sloučeniny jako inhibitory rotamasy