CA2444489C - Benzimidazolone compounds - Google Patents
Benzimidazolone compounds Download PDFInfo
- Publication number
- CA2444489C CA2444489C CA2444489A CA2444489A CA2444489C CA 2444489 C CA2444489 C CA 2444489C CA 2444489 A CA2444489 A CA 2444489A CA 2444489 A CA2444489 A CA 2444489A CA 2444489 C CA2444489 C CA 2444489C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- benzimidazol
- piperidinyl
- octahydro
- group
- 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 - Fee Related
Links
- 150000008641 benzimidazolones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- -1 -CH2OH Chemical group 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 102000005962 receptors Human genes 0.000 claims description 27
- 108020003175 receptors Proteins 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 108010020615 nociceptin receptor Proteins 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 230000004044 response Effects 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000000144 pharmacologic effect Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 108090000137 Opioid Receptors Proteins 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 102000003840 Opioid Receptors Human genes 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 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 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 230000036407 pain Effects 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 15
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 32
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 20
- 239000003814 drug Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
- 239000000556 agonist Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 239000006186 oral dosage form Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- 208000000094 Chronic Pain Diseases 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 5
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- 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 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 4
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- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
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- JQSAYKKFZOSZGJ-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCN(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JQSAYKKFZOSZGJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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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Landscapes
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- Cardiology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28466501P | 2001-04-18 | 2001-04-18 | |
| US60/284,665 | 2001-04-18 | ||
| PCT/US2002/012375 WO2002085361A1 (en) | 2001-04-18 | 2002-04-18 | Benzimidazolone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2444489A1 CA2444489A1 (en) | 2002-10-31 |
| CA2444489C true CA2444489C (en) | 2010-06-22 |
Family
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Family Applications (1)
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|---|---|---|---|
| CA2444489A Expired - Fee Related CA2444489C (en) | 2001-04-18 | 2002-04-18 | Benzimidazolone compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6872733B2 (enExample) |
| EP (3) | EP2172468A1 (enExample) |
| JP (1) | JP4401076B2 (enExample) |
| AT (2) | ATE403431T1 (enExample) |
| AU (1) | AU2002338424B2 (enExample) |
| CA (1) | CA2444489C (enExample) |
| CY (2) | CY1108456T1 (enExample) |
| DE (2) | DE60228072D1 (enExample) |
| DK (2) | DK1385518T3 (enExample) |
| ES (2) | ES2340441T3 (enExample) |
| PT (2) | PT1975164E (enExample) |
| SI (2) | SI1385518T1 (enExample) |
| WO (1) | WO2002085361A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003220886A1 (en) | 2002-03-29 | 2003-10-13 | Mitsubishi Pharma Corporation | Remedy for sleep disturbance |
| US20100028339A1 (en) | 2004-03-29 | 2010-02-04 | Cheng Jin Q | Compositions including triciribine and trastuzumab and methods of use thereof |
| US20100009928A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and taxanes and methods of use thereof |
| US20100009929A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and bortezomib and derivatives thereof and methods of use thereof |
| US20100173864A1 (en) | 2004-03-29 | 2010-07-08 | Cheng Jin Q | Compositions including triciribine and one or more platinum compounds and methods of use thereof |
| US20110008327A1 (en) * | 2004-03-29 | 2011-01-13 | Cheng Jin Q | Compositions including triciribine and epidermal growth factor receptor inhibitor compounds or salts thereof and methods of use thereof |
| EP1737472B1 (en) | 2004-03-29 | 2014-08-13 | University Of South Florida | Effective treatment of tumors and cancer with triciribine |
| EP1937670A1 (en) * | 2005-09-30 | 2008-07-02 | Glaxo Group Limited | Benzimidazolones which have activity at m1 receptor |
| WO2007036718A2 (en) * | 2005-09-30 | 2007-04-05 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| DE602006019119D1 (de) * | 2005-09-30 | 2011-02-03 | Glaxo Group Ltd | Verbindungen mit aktivität am m1-rezeptor und ihre verwendung in der medizin |
| CN1870631B (zh) * | 2005-11-11 | 2010-04-14 | 华为技术有限公司 | 媒体网关的门控方法 |
| TW200813018A (en) | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| WO2008089201A2 (en) | 2007-01-16 | 2008-07-24 | Purdue Pharma L.P. | Heterocyclic-substituted piperidine as orl-1 ligands |
| GB0706188D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
| JP5554709B2 (ja) * | 2007-08-31 | 2014-07-23 | パーデュー、ファーマ、リミテッド、パートナーシップ | 置換キノキサリンタイプピペリジン化合物とその使用 |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| GB0718415D0 (en) * | 2007-09-20 | 2007-10-31 | Glaxo Group Ltd | Compounds |
| RU2500678C2 (ru) | 2008-07-21 | 2013-12-10 | Пэдью Фарма Л.П. | Замещенные хиноксалинового типа мостиковые пиперидиновые соединения и их применение |
| WO2014102594A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| WO2014102589A1 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Quinazolin-4(3h)-one-type piperidine compounds and uses thereof |
| US9963458B2 (en) | 2012-12-27 | 2018-05-08 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| WO2014102590A1 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted piperidin-4-amino-type compounds and uses thereof |
| RS66574B1 (sr) | 2016-07-29 | 2025-03-31 | Janssen Pharmaceutica Nv | Niraparib za upotrebu u postupku lečenja raka prostate |
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| US3161645A (en) | 1962-12-18 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds |
| US3318900A (en) | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| US3325499A (en) | 1964-11-02 | 1967-06-13 | Mcneilab Inc | 1-(1-hydrocarbyl-4-piperdyl)-2-indolinone |
| DE2609645A1 (de) | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| US4329353A (en) | 1980-10-22 | 1982-05-11 | Janssen Pharmaceutica, N.V. | 1-(4-Aryl-cyclohexyl)piperidine derivatives, method of use thereof and pharmaceutical compositions thereof |
| US4410528A (en) | 1980-05-16 | 1983-10-18 | Kyowa Hakko Kogyo Co., Ltd. | Hypotensive piperidine derivatives |
| JPS58180481A (ja) | 1982-04-15 | 1983-10-21 | Kyowa Hakko Kogyo Co Ltd | 新規なピペリジン誘導体 |
| JPS60120872A (ja) | 1983-12-01 | 1985-06-28 | Kyowa Hakko Kogyo Co Ltd | 新規なヘテロ環状化合物及び強心剤 |
| WO1995028397A1 (en) | 1994-04-14 | 1995-10-26 | Merck & Co., Inc. | Alpha1c adrenergic receptor antagonists |
| FR2722190B1 (fr) | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
| US5767118A (en) | 1994-10-26 | 1998-06-16 | Merck & Co., Inc. | 4-Heterocyclic peperidines promote release of growth hormone |
| US5574044A (en) | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| AU6111796A (en) | 1995-06-12 | 1997-01-09 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5 -lipoxygenase inhibitor |
| EP0974583B1 (en) | 1995-09-13 | 2002-05-29 | Kyowa Hakko Kogyo Co., Ltd. | Phenylpiperidine derivatives |
| AU2388697A (en) | 1996-04-19 | 1997-11-12 | Neurosearch A/S | 1-(4-piperidyl)-benzimidazoles having neurotrophic activity |
| US6063796A (en) | 1997-04-04 | 2000-05-16 | Merck & Co., Inc. | Somatostatin agonists |
| CA2291094C (en) | 1997-05-30 | 2008-02-26 | Banyu Pharmaceutical Co., Ltd. | 2-oxoimidazole derivative |
| JPH10330377A (ja) | 1997-06-02 | 1998-12-15 | Kyowa Hakko Kogyo Co Ltd | ピペリジン誘導体 |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| EP0921125B1 (en) | 1997-12-05 | 2002-01-30 | F. Hoffmann-La Roche Ag | 1,3,8-Triazaspiro[4,5]decan-4-on derivatives |
| US6166209A (en) | 1997-12-11 | 2000-12-26 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| IL137149A0 (en) * | 1998-01-19 | 2001-07-24 | Pfizer | 4-(2-keto-1-benzimidazolinyl) piperidine compounds as orl1-receptor agonists |
| HUP0101275A3 (en) | 1998-03-26 | 2002-12-28 | Japan Tobacco Inc | Amide derivatives and pharmaceutical compositions containing them as nociceptin antagonists |
| AU3809999A (en) | 1998-05-18 | 1999-12-06 | Novo Nordisk A/S | Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| US6262066B1 (en) | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| ID29137A (id) | 1998-07-27 | 2001-08-02 | Schering Corp | Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1 |
| MA26659A1 (fr) * | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| HUP0302475A2 (hu) | 2000-09-06 | 2003-11-28 | Ortho-Mcneil Pharmaceutical, Inc. | Eljárás allergia kezelésére szubsztituált pirazolok alkalmazásával |
-
2002
- 2002-04-18 JP JP2002582934A patent/JP4401076B2/ja not_active Expired - Fee Related
- 2002-04-18 DK DK02764243T patent/DK1385518T3/da active
- 2002-04-18 DK DK08011371.5T patent/DK1975164T3/da active
- 2002-04-18 PT PT08011371T patent/PT1975164E/pt unknown
- 2002-04-18 EP EP10000601A patent/EP2172468A1/en not_active Withdrawn
- 2002-04-18 SI SI200230749T patent/SI1385518T1/sl unknown
- 2002-04-18 ES ES08011371T patent/ES2340441T3/es not_active Expired - Lifetime
- 2002-04-18 CA CA2444489A patent/CA2444489C/en not_active Expired - Fee Related
- 2002-04-18 EP EP02764243A patent/EP1385518B1/en not_active Expired - Lifetime
- 2002-04-18 DE DE60228072T patent/DE60228072D1/de not_active Expired - Lifetime
- 2002-04-18 AT AT02764243T patent/ATE403431T1/de not_active IP Right Cessation
- 2002-04-18 AT AT08011371T patent/ATE456564T1/de not_active IP Right Cessation
- 2002-04-18 AU AU2002338424A patent/AU2002338424B2/en not_active Ceased
- 2002-04-18 PT PT02764243T patent/PT1385518E/pt unknown
- 2002-04-18 SI SI200230894T patent/SI1975164T1/sl unknown
- 2002-04-18 EP EP08011371A patent/EP1975164B1/en not_active Expired - Lifetime
- 2002-04-18 ES ES02764243T patent/ES2312616T3/es not_active Expired - Lifetime
- 2002-04-18 US US10/126,437 patent/US6872733B2/en not_active Expired - Lifetime
- 2002-04-18 DE DE60235274T patent/DE60235274D1/de not_active Expired - Lifetime
- 2002-04-18 WO PCT/US2002/012375 patent/WO2002085361A1/en not_active Ceased
-
2005
- 2005-03-28 US US11/091,229 patent/US20050192307A1/en not_active Abandoned
-
2008
- 2008-10-27 CY CY20081101210T patent/CY1108456T1/el unknown
-
2010
- 2010-04-14 CY CY20101100336T patent/CY1110000T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1975164A3 (en) | 2008-10-08 |
| JP2004531532A (ja) | 2004-10-14 |
| DK1975164T3 (da) | 2010-05-25 |
| PT1385518E (pt) | 2008-10-07 |
| EP1975164B1 (en) | 2010-01-27 |
| CY1108456T1 (el) | 2012-05-23 |
| AU2002338424B2 (en) | 2005-04-21 |
| EP1385518A1 (en) | 2004-02-04 |
| ES2312616T3 (es) | 2009-03-01 |
| SI1385518T1 (sl) | 2009-02-28 |
| SI1975164T1 (sl) | 2010-05-31 |
| DK1385518T3 (da) | 2008-10-27 |
| US20030008886A1 (en) | 2003-01-09 |
| ES2340441T3 (es) | 2010-06-02 |
| DE60235274D1 (de) | 2010-03-18 |
| PT1975164E (pt) | 2010-04-20 |
| CY1110000T1 (el) | 2012-05-23 |
| EP1385518A4 (en) | 2005-10-05 |
| EP1975164A2 (en) | 2008-10-01 |
| ATE403431T1 (de) | 2008-08-15 |
| EP2172468A1 (en) | 2010-04-07 |
| US6872733B2 (en) | 2005-03-29 |
| EP1385518B1 (en) | 2008-08-06 |
| US20050192307A1 (en) | 2005-09-01 |
| WO2002085361A1 (en) | 2002-10-31 |
| DE60228072D1 (de) | 2008-09-18 |
| JP4401076B2 (ja) | 2010-01-20 |
| ATE456564T1 (de) | 2010-02-15 |
| CA2444489A1 (en) | 2002-10-31 |
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