ZA200505186B - Diarylmethylidene piperidine derivatives, preperations thereof and uses thereof - Google Patents
Diarylmethylidene piperidine derivatives, preperations thereof and uses thereof Download PDFInfo
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- ZA200505186B ZA200505186B ZA200505186A ZA200505186A ZA200505186B ZA 200505186 B ZA200505186 B ZA 200505186B ZA 200505186 A ZA200505186 A ZA 200505186A ZA 200505186 A ZA200505186 A ZA 200505186A ZA 200505186 B ZA200505186 B ZA 200505186B
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- South Africa
- Prior art keywords
- nrc
- hydrogen
- independently
- compound
- phenyl
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- 150000003053 piperidines Chemical class 0.000 title 1
- -1 N-oxido-pyridyl Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001246 bromo group Chemical group Br* 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 208000027520 Somatoform disease Diseases 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 208000027753 pain disease Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- AOIABXSUGFHWJJ-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(1,3-thiazol-4-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC=2N=CSC=2)CC1 AOIABXSUGFHWJJ-UHFFFAOYSA-N 0.000 claims 1
- UQVGNSHSQHAAFS-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(furan-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC=2OC=CC=2)CC1 UQVGNSHSQHAAFS-UHFFFAOYSA-N 0.000 claims 1
- VGNVIKBFRCEHRY-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(pyridin-2-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC=2N=CC=CC=2)CC1 VGNVIKBFRCEHRY-UHFFFAOYSA-N 0.000 claims 1
- MDVVKIYWARQZNM-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(pyridin-3-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC=2C=NC=CC=2)CC1 MDVVKIYWARQZNM-UHFFFAOYSA-N 0.000 claims 1
- FFIPMCKXTBYFQV-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(pyridin-4-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC=2C=CN=CC=2)CC1 FFIPMCKXTBYFQV-UHFFFAOYSA-N 0.000 claims 1
- XNMIACUFNRTUPM-UHFFFAOYSA-N 4-[(3-acetamidophenyl)-[1-(thiophen-3-ylmethyl)piperidin-4-ylidene]methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(C=1C=C(NC(C)=O)C=CC=1)=C1CCN(CC2=CSC=C2)CC1 XNMIACUFNRTUPM-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000556 agonist Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102000003840 Opioid Receptors Human genes 0.000 description 2
- 108090000137 Opioid Receptors Proteins 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 238000001949 anaesthesia Methods 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (1)
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SE0300105A SE0300105D0 (sv) | 2003-01-16 | 2003-01-16 | Diarylmethylidene piperdine derivatives, preparations thereof and uses thereof |
Publications (1)
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ZA200505186B true ZA200505186B (en) | 2006-04-26 |
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ZA200505186A ZA200505186B (en) | 2003-01-16 | 2005-06-27 | Diarylmethylidene piperidine derivatives, preperations thereof and uses thereof |
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US (1) | US20060154964A1 (zh) |
EP (1) | EP1587790A2 (zh) |
JP (1) | JP2006516559A (zh) |
KR (1) | KR20050096137A (zh) |
CN (1) | CN100422151C (zh) |
AR (1) | AR042887A1 (zh) |
AU (1) | AU2004204390B2 (zh) |
BR (1) | BRPI0406614A (zh) |
CA (1) | CA2510382A1 (zh) |
IL (1) | IL169366A0 (zh) |
IS (1) | IS7980A (zh) |
MX (1) | MXPA05007484A (zh) |
NO (1) | NO20053809L (zh) |
NZ (1) | NZ540758A (zh) |
PL (1) | PL378336A1 (zh) |
RU (1) | RU2324680C2 (zh) |
SE (1) | SE0300105D0 (zh) |
TW (1) | TW200504059A (zh) |
UA (1) | UA80012C2 (zh) |
WO (1) | WO2004062562A2 (zh) |
ZA (1) | ZA200505186B (zh) |
Families Citing this family (12)
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KR100885100B1 (ko) | 2001-05-18 | 2009-02-20 | 아스트라제네카 아베 | 4(페닐-피페라지닐-메틸)벤즈아미드 유도체 및 통증,불안증 또는 위장관 장애 치료를 위한 이들의 용도 |
SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203301D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
EP1641757A1 (en) * | 2003-05-16 | 2006-04-05 | AstraZeneca AB | Diarylmethylidene piperidine derivatives, preparations thereof and uses thereof |
CN100549004C (zh) | 2003-10-01 | 2009-10-14 | 阿得罗公司 | 螺环杂环衍生物及其应用方法 |
DK1781631T3 (da) | 2004-08-02 | 2012-05-14 | Astrazeneca Ab | Diarylmethylpiperazinderivater, præparater dermed og anvendelser deraf |
EP1856076A1 (en) * | 2005-02-28 | 2007-11-21 | AstraZeneca AB | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
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 |
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 |
CN111825654A (zh) * | 2019-04-19 | 2020-10-27 | 北京酷瓴生物技术有限公司 | 苯甲烯哌啶衍生物及其制备方法、中间体和用途 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US2898339A (en) * | 1957-07-29 | 1959-08-04 | Wm S Merrell Co | N-substituted benzhydrol, benzhydryl, and benzhydrylidene piperidine |
US4581171A (en) * | 1983-07-27 | 1986-04-08 | Janssen Pharmaceutica, N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders |
US4816586A (en) * | 1987-07-29 | 1989-03-28 | Regents Of The University Of Minnesota | Delta opioid receptor antagonists |
US5140029A (en) * | 1989-01-09 | 1992-08-18 | Janssen Pharmaceutica N.V. | 2-aminopyrimidinone derivatives |
US4939137A (en) * | 1989-06-28 | 1990-07-03 | Ortho Pharmaceutical Corporation | Ring-fused thienopyrimidinedione derivatives |
US5683998A (en) * | 1991-04-23 | 1997-11-04 | Toray Industries, Inc. | Tricyclic triazolo derivatives, processes for producing the same and the uses of the same |
US5574159A (en) * | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
TW548271B (en) * | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
BR0108965A (pt) * | 2000-03-03 | 2002-11-26 | Ortho Mcneil Pharm Inc | Derivados de 3-(diarilmetileno)-8-azabiciclo[3,2,1]octano |
US6556387B1 (en) * | 2000-03-31 | 2003-04-29 | Seagate Technology Llc | Controlling mechanical response characteristics of a disc drive actuator by adjusting a fastener engaging the actuator shaft to vary axial force on the bearing assembly |
SE0001207D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
SE0101766D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
EP1644373A1 (en) * | 2003-06-27 | 2006-04-12 | Janssen Pharmaceutica N.V. | Tricyclic delta opioid modulators |
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RU2005121491A (ru) | 2006-02-10 |
IS7980A (is) | 2005-08-12 |
AU2004204390B2 (en) | 2007-09-06 |
EP1587790A2 (en) | 2005-10-26 |
CN100422151C (zh) | 2008-10-01 |
PL378336A1 (pl) | 2006-03-20 |
UA80012C2 (en) | 2007-08-10 |
NZ540758A (en) | 2008-03-28 |
AR042887A1 (es) | 2005-07-06 |
JP2006516559A (ja) | 2006-07-06 |
WO2004062562A2 (en) | 2004-07-29 |
TW200504059A (en) | 2005-02-01 |
BRPI0406614A (pt) | 2005-12-06 |
KR20050096137A (ko) | 2005-10-05 |
AU2004204390A1 (en) | 2004-07-29 |
CA2510382A1 (en) | 2004-07-29 |
SE0300105D0 (sv) | 2003-01-16 |
NO20053809D0 (no) | 2005-08-12 |
MXPA05007484A (es) | 2005-09-21 |
NO20053809L (no) | 2005-10-17 |
WO2004062562A3 (en) | 2004-09-16 |
US20060154964A1 (en) | 2006-07-13 |
RU2324680C2 (ru) | 2008-05-20 |
IL169366A0 (en) | 2007-07-04 |
CN1738801A (zh) | 2006-02-22 |
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