JP2006508102A5 - - Google Patents
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- Publication number
- JP2006508102A5 JP2006508102A5 JP2004549490A JP2004549490A JP2006508102A5 JP 2006508102 A5 JP2006508102 A5 JP 2006508102A5 JP 2004549490 A JP2004549490 A JP 2004549490A JP 2004549490 A JP2004549490 A JP 2004549490A JP 2006508102 A5 JP2006508102 A5 JP 2006508102A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- imidazol
- ylmethyl
- propyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 35
- 229910052736 halogen Inorganic materials 0.000 claims 22
- -1 nitro, cyano, amino Chemical group 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 102000005962 receptors Human genes 0.000 claims 14
- 108020003175 receptors Proteins 0.000 claims 14
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 13
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 238000003556 assay Methods 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000007831 electrophysiology Effects 0.000 claims 2
- 238000002001 electrophysiology Methods 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- LVPNLQRMQLZNRJ-UHFFFAOYSA-N 2-[1-[(6-methyl-5-propylpyrimidin-4-yl)methyl]imidazol-2-yl]-1,3-thiazole-4-carbonitrile Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2SC=C(N=2)C#N)=NC=C1 LVPNLQRMQLZNRJ-UHFFFAOYSA-N 0.000 claims 1
- IGGHPDQDHZHESP-UHFFFAOYSA-N 2-[1-[(6-methyl-5-propylpyrimidin-4-yl)methyl]imidazol-2-yl]pyridine-3-carbonitrile Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2C(=CC=CN=2)C#N)=NC=C1 IGGHPDQDHZHESP-UHFFFAOYSA-N 0.000 claims 1
- DPUHYMKVRVPMFF-UHFFFAOYSA-N 2-[6-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidin-4-yl]-1,3-thiazole Chemical compound N1=CN=C(C=2SC=CN=2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F DPUHYMKVRVPMFF-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CQWSUQFUXOGROX-UHFFFAOYSA-N 3-[1-[(5-ethyl-6-methylpyrimidin-4-yl)methyl]imidazol-2-yl]benzonitrile Chemical compound CCC1=C(C)N=CN=C1CN1C(C=2C=C(C=CC=2)C#N)=NC=C1 CQWSUQFUXOGROX-UHFFFAOYSA-N 0.000 claims 1
- RXDRQWJPNILHRD-UHFFFAOYSA-N 4-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-5-ethyl-6-methylpyrimidine Chemical compound CCC1=C(C)N=CN=C1CN1C(C=2C(=CC=C(F)C=2)F)=NC=C1 RXDRQWJPNILHRD-UHFFFAOYSA-N 0.000 claims 1
- PMMQEAQIWITGAS-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-5-propylpyrimidine Chemical compound CCCC1=CN=C(C)N=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 PMMQEAQIWITGAS-UHFFFAOYSA-N 0.000 claims 1
- RLBFRGZDFITHTJ-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propyl-6-pyrazin-2-ylpyrimidine Chemical compound N1=CN=C(C=2N=CC=NC=2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F RLBFRGZDFITHTJ-UHFFFAOYSA-N 0.000 claims 1
- GYRJTUNYEMZWFP-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propyl-6-pyrazol-1-ylpyrimidine Chemical compound N1=CN=C(N2N=CC=C2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F GYRJTUNYEMZWFP-UHFFFAOYSA-N 0.000 claims 1
- QXTHTFNMHARPIB-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propyl-6-pyridin-2-ylpyrimidine Chemical compound N1=CN=C(C=2N=CC=CC=2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F QXTHTFNMHARPIB-UHFFFAOYSA-N 0.000 claims 1
- SEHOOVWAIBDEGP-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propyl-6-pyridin-3-ylpyrimidine Chemical compound N1=CN=C(C=2C=NC=CC=2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F SEHOOVWAIBDEGP-UHFFFAOYSA-N 0.000 claims 1
- HGFXMIVRKIKTSF-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propyl-6-pyridin-4-ylpyrimidine Chemical compound N1=CN=C(C=2C=CN=CC=2)C(CCC)=C1CN1C=CN=C1C1=NC=CC=C1F HGFXMIVRKIKTSF-UHFFFAOYSA-N 0.000 claims 1
- SORIWIPTILYMLG-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidine Chemical compound CCCC1=CN=CN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 SORIWIPTILYMLG-UHFFFAOYSA-N 0.000 claims 1
- OONDWEIREXIPPA-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methyl-5-propylpyrimidine Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 OONDWEIREXIPPA-UHFFFAOYSA-N 0.000 claims 1
- YLEQBUIDVGAHOB-UHFFFAOYSA-N 4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-propan-2-yloxy-5-propylpyrimidine Chemical compound N1=CN=C(OC(C)C)C(CCC)=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 YLEQBUIDVGAHOB-UHFFFAOYSA-N 0.000 claims 1
- MVQGTCVMJMAMRJ-UHFFFAOYSA-N 4-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidine Chemical compound CCCC1=CN=CN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 MVQGTCVMJMAMRJ-UHFFFAOYSA-N 0.000 claims 1
- GTUBRXFVNOIVLZ-UHFFFAOYSA-N 4-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methoxy-5-propylpyrimidine Chemical compound N1=CN=C(OC)C(CCC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 GTUBRXFVNOIVLZ-UHFFFAOYSA-N 0.000 claims 1
- PFKQDCHWZNGVRY-UHFFFAOYSA-N 4-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methyl-5-propylpyrimidine Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 PFKQDCHWZNGVRY-UHFFFAOYSA-N 0.000 claims 1
- DOOMJOTXYRUNHE-UHFFFAOYSA-N 4-chloro-6-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-5-propylpyrimidine Chemical compound CCCC1=C(Cl)N=C(C)N=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 DOOMJOTXYRUNHE-UHFFFAOYSA-N 0.000 claims 1
- XWXPSQYSSKCHSM-UHFFFAOYSA-N 4-chloro-6-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidine Chemical compound CCCC1=C(Cl)N=CN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 XWXPSQYSSKCHSM-UHFFFAOYSA-N 0.000 claims 1
- FIPOFHABVOQICE-UHFFFAOYSA-N 4-chloro-6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-2-methyl-5-propylpyrimidine Chemical compound CCCC1=C(Cl)N=C(C)N=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 FIPOFHABVOQICE-UHFFFAOYSA-N 0.000 claims 1
- AZNBUWWLYBFJIK-UHFFFAOYSA-N 4-methyl-5-propyl-6-[[2-[6-(trifluoromethyl)pyridin-2-yl]imidazol-1-yl]methyl]pyrimidine Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2N=C(C=CC=2)C(F)(F)F)=NC=C1 AZNBUWWLYBFJIK-UHFFFAOYSA-N 0.000 claims 1
- ASYVLNSLBMHJQD-UHFFFAOYSA-N 5-(3-fluoropropyl)-4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-methylpyrimidine Chemical compound CC1=NC=NC(CN2C(=NC=C2)C=2C(=CC=CN=2)F)=C1CCCF ASYVLNSLBMHJQD-UHFFFAOYSA-N 0.000 claims 1
- SCBXXFKWEQIEOM-UHFFFAOYSA-N 5-(3-fluoropropyl)-4-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]pyrimidine Chemical compound FCCCC1=CN=CN=C1CN1C(C=2C(=CC=CN=2)F)=NC=C1 SCBXXFKWEQIEOM-UHFFFAOYSA-N 0.000 claims 1
- WBGKERRYKLYBLB-UHFFFAOYSA-N 6-[1-[(5-propylpyrimidin-4-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound CCCC1=CN=CN=C1CN1C(C=2N=C(C=CC=2)C#N)=NC=C1 WBGKERRYKLYBLB-UHFFFAOYSA-N 0.000 claims 1
- RXWUGDCJFPONDU-UHFFFAOYSA-N 6-[1-[(6-methyl-5-propylpyrimidin-4-yl)methyl]imidazol-2-yl]pyridine-2-carbonitrile Chemical compound CCCC1=C(C)N=CN=C1CN1C(C=2N=C(C=CC=2)C#N)=NC=C1 RXWUGDCJFPONDU-UHFFFAOYSA-N 0.000 claims 1
- XFXGHXOOVFSOMW-UHFFFAOYSA-N 6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidin-4-amine Chemical compound CCCC1=C(N)N=CN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 XFXGHXOOVFSOMW-UHFFFAOYSA-N 0.000 claims 1
- WJXTVWLBDVTBPV-UHFFFAOYSA-N 6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-n,n-dimethyl-5-propylpyrimidin-4-amine Chemical compound N1=CN=C(N(C)C)C(CCC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 WJXTVWLBDVTBPV-UHFFFAOYSA-N 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 238000000376 autoradiography Methods 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- VWZWVOKGBLPJEQ-UHFFFAOYSA-N n-ethyl-6-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-5-propylpyrimidin-4-amine Chemical compound N1=CN=C(NCC)C(CCC)=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 VWZWVOKGBLPJEQ-UHFFFAOYSA-N 0.000 claims 1
- VTWJSXSCJVTOMB-UHFFFAOYSA-N n-methyl-6-[[2-[3-(methylamino)pyridin-2-yl]imidazol-1-yl]methyl]-5-propylpyrimidin-4-amine Chemical compound N1=CN=C(NC)C(CCC)=C1CN1C(C=2C(=CC=CN=2)NC)=NC=C1 VTWJSXSCJVTOMB-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 230000006403 short-term memory Effects 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 230000007781 signaling event Effects 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42494502P | 2002-11-08 | 2002-11-08 | |
| PCT/IB2003/004978 WO2004041808A1 (en) | 2002-11-08 | 2003-11-04 | 4-imidazol-1-ylmethyl-pyrimidine derivatives_as ligands for gabaa receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006508102A JP2006508102A (ja) | 2006-03-09 |
| JP2006508102A5 true JP2006508102A5 (https=) | 2006-12-21 |
Family
ID=32312901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004549490A Pending JP2006508102A (ja) | 2002-11-08 | 2003-11-04 | Ｇａｂａａ受容体のリガンドとしての４−イミダゾール−１−イルメチル−ピリミジン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6951864B2 (https=) |
| EP (1) | EP1560822B1 (https=) |
| JP (1) | JP2006508102A (https=) |
| AT (1) | ATE335732T1 (https=) |
| AU (1) | AU2003276514A1 (https=) |
| CA (1) | CA2495708A1 (https=) |
| DE (1) | DE60307499T2 (https=) |
| ES (1) | ES2268488T3 (https=) |
| WO (1) | WO2004041808A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100579579C (zh) | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
| EP1594848A1 (en) | 2003-02-19 | 2005-11-16 | Neurogen Corporation | Aryl acid pyrimidinyl methyl amides, pyridazinyl methyl amides and related compounds |
| CA2524376A1 (en) * | 2003-05-05 | 2004-12-16 | Neurogen Corporation | Substituted imidazolopyrazine and triazolopyrazyne derivatives: gabaa receptor ligands |
| WO2005012306A2 (en) | 2003-07-25 | 2005-02-10 | Neurogen Corporation | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
| KR101170925B1 (ko) * | 2004-06-18 | 2012-08-07 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 암 치료용 키네신 방추 단백질 (ｋｓｐ) 억제제로서의ｎ-(1-(1-벤질-4-페닐-1ｈ-이미다졸-2-일)-2,2-디메틸프로필)벤자미드 유도체 및 관련 화합물 |
| AU2008205169B2 (en) | 2007-01-05 | 2012-02-02 | Novartis Ag | Imidazole derivatives as kinesin spindle protein inhibitors (Eg-5) |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8535601A1 (es) * | 2000-12-21 | 2002-11-28 | Pfizer | Derivados benzimidazol y piridilimidazol como ligandos para gabaa |
| ATE338758T1 (de) * | 2001-03-23 | 2006-09-15 | Merck Sharp & Dohme | Imidazopyrimidin-derivate als liganden für gaba- rezeptoren |
| CN100579579C (zh) * | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
-
2003
- 2003-11-04 AT AT03810562T patent/ATE335732T1/de not_active IP Right Cessation
- 2003-11-04 DE DE60307499T patent/DE60307499T2/de not_active Expired - Fee Related
- 2003-11-04 JP JP2004549490A patent/JP2006508102A/ja active Pending
- 2003-11-04 EP EP03810562A patent/EP1560822B1/en not_active Expired - Lifetime
- 2003-11-04 CA CA002495708A patent/CA2495708A1/en not_active Abandoned
- 2003-11-04 ES ES03810562T patent/ES2268488T3/es not_active Expired - Lifetime
- 2003-11-04 WO PCT/IB2003/004978 patent/WO2004041808A1/en not_active Ceased
- 2003-11-04 AU AU2003276514A patent/AU2003276514A1/en not_active Abandoned
- 2003-11-06 US US10/702,629 patent/US6951864B2/en not_active Expired - Fee Related
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