ES2251121T3 - (4)-aril(piperidin-4-il) aminobenzamidas que se unen al receptor opioide delta. - Google Patents
(4)-aril(piperidin-4-il) aminobenzamidas que se unen al receptor opioide delta.Info
- Publication number
- ES2251121T3 ES2251121T3 ES98964871T ES98964871T ES2251121T3 ES 2251121 T3 ES2251121 T3 ES 2251121T3 ES 98964871 T ES98964871 T ES 98964871T ES 98964871 T ES98964871 T ES 98964871T ES 2251121 T3 ES2251121 T3 ES 2251121T3
- Authority
- ES
- Spain
- Prior art keywords
- baselineskip
- compound
- group
- propyl
- butyl
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 claims abstract description 19
- 108700023159 delta Opioid Receptors Proteins 0.000 claims abstract description 19
- 102000048124 delta Opioid Receptors Human genes 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 18
- 229940079593 drug Drugs 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 7
- 208000007882 Gastritis Diseases 0.000 claims abstract description 7
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 7
- 229940121363 anti-inflammatory agent Drugs 0.000 claims abstract description 7
- 229960003444 immunosuppressant agent Drugs 0.000 claims abstract description 7
- 239000003018 immunosuppressive agent Substances 0.000 claims abstract description 7
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 7
- 239000002327 cardiovascular agent Substances 0.000 claims abstract description 6
- 229940125692 cardiovascular agent Drugs 0.000 claims abstract description 6
- 206010013654 Drug abuse Diseases 0.000 claims abstract description 5
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
- -1 cyano, amino Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 3
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- 230000000241 respiratory effect Effects 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 238000006254 arylation reaction Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 201000009032 substance abuse Diseases 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000001861 immunosuppressant effect Effects 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 abstract description 10
- 229940044601 receptor agonist Drugs 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000556 agonist Substances 0.000 abstract description 5
- 239000002464 receptor antagonist Substances 0.000 abstract description 5
- 229940044551 receptor antagonist Drugs 0.000 abstract description 5
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract description 5
- 208000007848 Alcoholism Diseases 0.000 abstract description 4
- 206010001584 alcohol abuse Diseases 0.000 abstract description 4
- 208000025746 alcohol use disease Diseases 0.000 abstract description 4
- 229940035676 analgesics Drugs 0.000 abstract description 4
- 239000005557 antagonist Substances 0.000 abstract description 4
- 239000000730 antalgic agent Substances 0.000 abstract description 4
- 208000023504 respiratory system disease Diseases 0.000 abstract description 4
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
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- 239000002287 radioligand Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- 239000000203 mixture Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 4
- 102000051367 mu Opioid Receptors Human genes 0.000 description 4
- JFPHICCUJHJABY-UHFFFAOYSA-N n,n-diethyl-4-(3-hydroxy-n-(1-propylpiperidin-4-yl)anilino)benzamide Chemical compound C1CN(CCC)CCC1N(C=1C=C(O)C=CC=1)C1=CC=C(C(=O)N(CC)CC)C=C1 JFPHICCUJHJABY-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 108020001612 μ-opioid receptors Proteins 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- LDUPVXSXLZOQAF-UHFFFAOYSA-N 4-bromo-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(Br)C=C1 LDUPVXSXLZOQAF-UHFFFAOYSA-N 0.000 description 3
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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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Transplantation (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6879497P | 1997-12-24 | 1997-12-24 | |
| US68794P | 1997-12-24 |
Publications (1)
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|---|---|
| ES2251121T3 true ES2251121T3 (es) | 2006-04-16 |
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| ES98964871T Expired - Lifetime ES2251121T3 (es) | 1997-12-24 | 1998-12-23 | (4)-aril(piperidin-4-il) aminobenzamidas que se unen al receptor opioide delta. |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1049676B1 (https=) |
| JP (1) | JP4754068B2 (https=) |
| AT (1) | ATE306472T1 (https=) |
| AU (1) | AU2009799A (https=) |
| CA (1) | CA2316341A1 (https=) |
| DE (1) | DE69831876T2 (https=) |
| DK (1) | DK1049676T3 (https=) |
| ES (1) | ES2251121T3 (https=) |
| TW (1) | TW476755B (https=) |
| WO (1) | WO1999033806A1 (https=) |
| ZA (1) | ZA9811842B (https=) |
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| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| TW548271B (en) | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
| US6974825B1 (en) | 1996-12-20 | 2005-12-13 | Astrazeneca Canada Inc. | Compounds with analgesic effect |
| US6900228B1 (en) | 1998-03-10 | 2005-05-31 | Research Triangle Institute | Opiate compounds, methods of making and methods of use |
| EP1512683B1 (en) * | 1998-03-10 | 2011-08-31 | Research Triangle Institute | Novel opiate compounds, methods of making and methods of use |
| WO2000071518A2 (en) * | 1999-05-25 | 2000-11-30 | Sepracor, Inc. | Heterocyclic analgesic compounds and their use |
| US6677332B1 (en) | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| US7361666B2 (en) | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| SE9904675D0 (sv) * | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
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| SE9904674D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| EP1242421A1 (en) | 1999-12-22 | 2002-09-25 | Ortho-McNeil Pharmaceutical, Inc. | 4-[aryl(8-azabicyclo[3.2.1] octan-3-yl)] aminobenzoic acid derivatives |
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| WO2002048122A2 (en) * | 2000-12-14 | 2002-06-20 | Ortho-Mcneil Pharmaceutical, Inc. | Benzamidine derivatives |
| CN1258529C (zh) * | 2000-12-15 | 2006-06-07 | 阿斯特拉曾尼卡有限公司 | 制备二芳基－4－氨基－哌啶基化合物的方法 |
| US6699890B2 (en) * | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| US7205320B2 (en) | 2001-01-22 | 2007-04-17 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| US7153871B2 (en) | 2001-01-22 | 2006-12-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs |
| MXPA03007261A (es) * | 2001-02-14 | 2006-03-09 | Abbott Lab | Moduladores del receptor de glucocorticoides. |
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| AU2003256616B2 (en) | 2002-07-19 | 2009-08-27 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including N-substituted aniline and diphenylamine analogs |
| DE60325984D1 (de) | 2002-07-19 | 2009-03-12 | Memory Pharmaceutical Corp | 4-aminobenzofuranverbindungen als phosphodiesterase-4-inhibitoren |
| ES2300626T3 (es) | 2002-10-15 | 2008-06-16 | Janssen Pharmaceutica Nv | Compuestos de aminoquinuclidina sustituida y su uso como ligandos del receptor delta-opioide. |
| WO2004035541A1 (en) * | 2002-10-15 | 2004-04-29 | Janssen Pharmaceutica, N.V. | Benzyl substituted (piperidin-4-yl) aminobenzamido derivatives as delta-opiod receptor modulators |
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| CA2506297A1 (en) | 2002-11-19 | 2004-06-03 | Memory Pharmaceuticals Corporation | Pyridine n-oxide compounds as phosphodiesterase 4 inhibitors |
| CN1756746A (zh) * | 2003-03-07 | 2006-04-05 | 伊莱利利公司 | 作为阿片样物质受体拮抗剂的6－取代的烟酰胺衍生物 |
| AU2004253898A1 (en) | 2003-06-27 | 2005-01-13 | Janssen Pharmaceutica N.V. | Tricyclic delta opioid modulators |
| BRPI0417156A (pt) | 2003-12-12 | 2007-03-06 | Lilly Co Eli | composto, composição farmacêutica, e, métodos para bloquear receptor mu, capa, delta ou combinação (heterodìmero) dos mesmos em mamìferos, para tratar e/ou prevenir doenças relacionadas com obesidade e obesidade, para suprimir apetite em um paciente, para efetuar perda de peso em um paciente obeso |
| CA2557794A1 (en) | 2004-03-15 | 2005-10-06 | Eli Lilly And Company | Opioid receptor antagonists |
| KR101234421B1 (ko) | 2004-08-02 | 2013-02-18 | 아스트라제네카 아베 | 디아릴메틸 피페라진 유도체, 이의 제조 방법 및 용도 |
| WO2007030089A1 (en) | 2004-08-05 | 2007-03-15 | Janssen Pharmaceutica N.V. | Tricyclic delta- opioid modulators |
| SE0402485D0 (sv) | 2004-10-13 | 2004-10-13 | Astrazeneca Ab | Polymorph of N,N-Diethyl-4-(3-Fluorophenyl-Piperidin-4-Ylidene-Methyl)-Benzamide Hydrochloride salt |
| BRPI0519201A2 (pt) | 2004-12-22 | 2008-12-30 | Janssen Pharmaceutica Nv | moduladores de delta-opiàide tricÍclico |
| EA011674B1 (ru) | 2004-12-22 | 2009-04-28 | Янссен Фармацевтика Н.В. | ТРИЦИКЛИЧЕСКИЕ δ-ОПИОИДНЫЕ МОДУЛЯТОРЫ |
| AU2006203880A1 (en) | 2005-01-06 | 2006-07-13 | Janssen Pharmaceutica N.V. | Tricyclic delta-opioid modulators |
| JP2008543866A (ja) | 2005-06-16 | 2008-12-04 | 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 | 三環式オピオイドモジュレーター |
| JP2007099761A (ja) * | 2005-09-08 | 2007-04-19 | Mitsui Chemicals Inc | アミド誘導体ならびにその殺虫剤としての使用方法 |
| MY148880A (en) * | 2006-10-20 | 2013-06-14 | Astrazeneca Ab | N-(2-hydroxyethyl)-n-methyl-4-(quinolin-8-yl(1-(thiazol-4-ylmethyl)piperidin-4-ylidene)methyl)benzamide, the process of making it as well as its use for the treatment of pain, anxiety and depression |
| US8846655B2 (en) * | 2009-10-30 | 2014-09-30 | Janssen Pharmaceutica, Nv | 4-substituted-2-phenoxy-phenylamine delta opioid receptor modulators |
| CN113979997A (zh) * | 2021-11-12 | 2022-01-28 | 中国科学院昆明植物研究所 | N,n-(4-哌啶基、芳基)-3-氨基苯酚类衍生物及其药物组合物和其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5019583A (en) * | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
| GB9202238D0 (en) * | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
| IT1275433B (it) * | 1995-05-19 | 1997-08-07 | Smithkline Beecham Farma | Derivati di diarildiammine |
| IT1277597B1 (it) * | 1995-09-15 | 1997-11-11 | Smithkline Beecham Spa | Derivati di diarilalchenilammina |
| SE9504661D0 (sv) * | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| SE9604786D0 (sv) * | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
-
1998
- 1998-12-23 EP EP98964871A patent/EP1049676B1/en not_active Expired - Lifetime
- 1998-12-23 AU AU20097/99A patent/AU2009799A/en not_active Abandoned
- 1998-12-23 AT AT98964871T patent/ATE306472T1/de active
- 1998-12-23 ES ES98964871T patent/ES2251121T3/es not_active Expired - Lifetime
- 1998-12-23 DK DK98964871T patent/DK1049676T3/da active
- 1998-12-23 ZA ZA9811842A patent/ZA9811842B/xx unknown
- 1998-12-23 JP JP2000526490A patent/JP4754068B2/ja not_active Expired - Lifetime
- 1998-12-23 CA CA002316341A patent/CA2316341A1/en not_active Abandoned
- 1998-12-23 WO PCT/US1998/027350 patent/WO1999033806A1/en not_active Ceased
- 1998-12-23 DE DE69831876T patent/DE69831876T2/de not_active Expired - Lifetime
-
1999
- 1999-02-11 TW TW087121577A patent/TW476755B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4754068B2 (ja) | 2011-08-24 |
| DK1049676T3 (da) | 2006-01-16 |
| ZA9811842B (en) | 2000-06-23 |
| JP2001527068A (ja) | 2001-12-25 |
| WO1999033806A1 (en) | 1999-07-08 |
| CA2316341A1 (en) | 1999-07-08 |
| ATE306472T1 (de) | 2005-10-15 |
| EP1049676B1 (en) | 2005-10-12 |
| EP1049676A1 (en) | 2000-11-08 |
| DE69831876D1 (de) | 2006-02-23 |
| AU2009799A (en) | 1999-07-19 |
| DE69831876T2 (de) | 2006-07-27 |
| TW476755B (en) | 2002-02-21 |
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