JP2011500815A5 - - Google Patents
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- JP2011500815A5 JP2011500815A5 JP2010531069A JP2010531069A JP2011500815A5 JP 2011500815 A5 JP2011500815 A5 JP 2011500815A5 JP 2010531069 A JP2010531069 A JP 2010531069A JP 2010531069 A JP2010531069 A JP 2010531069A JP 2011500815 A5 JP2011500815 A5 JP 2011500815A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- heterocycloalkyl
- halogen
- amino
- 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.)
- Granted
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- -1 —C (O) O-alkyl Chemical group 0.000 claims description 285
- 125000000217 alkyl group Chemical group 0.000 claims description 145
- 229910052736 halogen Inorganic materials 0.000 claims description 120
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 118
- 150000002367 halogens Chemical group 0.000 claims description 116
- 125000003545 alkoxy group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000004663 dialkyl amino 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
- 201000010099 disease Diseases 0.000 claims description 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 14
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 14
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 14
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 101710113864 Heat shock protein 90 Proteins 0.000 claims description 11
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical group N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
- 108020004491 Antisense DNA Proteins 0.000 claims description 4
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- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 208000035473 Communicable disease Diseases 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
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- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 208000034578 Multiple myelomas Diseases 0.000 claims description 4
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
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- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003816 antisense DNA Substances 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003184 complementary RNA Substances 0.000 claims description 4
- 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 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 241001493065 dsRNA viruses Species 0.000 claims description 4
- 210000002472 endoplasmic reticulum Anatomy 0.000 claims description 4
- 230000000893 fibroproliferative effect Effects 0.000 claims description 4
- 208000019622 heart disease Diseases 0.000 claims description 4
- 208000002672 hepatitis B Diseases 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims description 4
- 230000003938 response to stress Effects 0.000 claims description 4
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- 241000712461 unidentified influenza virus Species 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims description 2
- AAFJXZWCNVJTMK-GUCUJZIJSA-N (1s,2r)-1-[(2s)-oxiran-2-yl]-2-[(2r)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@H](O)[C@H](O)[C@H]2OC2)O1 AAFJXZWCNVJTMK-GUCUJZIJSA-N 0.000 claims description 2
- HJFONKSERLWIGE-DEOSSOPVSA-N (2s)-2-[[4-[4-(1-benzofuran-2-carbonylamino)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2O1 HJFONKSERLWIGE-DEOSSOPVSA-N 0.000 claims description 2
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims description 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
- NVKGVBZZSJFQLM-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitrosourea Chemical compound NC(=O)N(N=O)CCCl NVKGVBZZSJFQLM-UHFFFAOYSA-N 0.000 claims description 2
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims description 2
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-SFIIULIVSA-N 1H-benzimidazole Chemical group C1=CC=C2N[11CH]=NC2=C1 HYZJCKYKOHLVJF-SFIIULIVSA-N 0.000 claims description 2
- XIFVTSIIYVGRHJ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n-pentamethyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N(C)C)=NC(N(C)C)=N1 XIFVTSIIYVGRHJ-UHFFFAOYSA-N 0.000 claims description 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 claims description 2
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
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- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 claims description 2
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- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
- FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 claims description 2
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- JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 claims description 2
- MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 claims description 2
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- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
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- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
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| US8129390B2 (en) * | 2007-12-12 | 2012-03-06 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds and methods for using the same |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| UY32940A (es) | 2009-10-27 | 2011-05-31 | Bayer Cropscience Ag | Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas |
| US9145425B2 (en) | 2010-04-05 | 2015-09-29 | Shionogi & Co., Ltd. | Cephem compound having catechol group |
| WO2012068096A2 (en) | 2010-11-15 | 2012-05-24 | Exelixis, Inc. | Benzoxazepines as inhibitors of pi3k/mtor and methods of their use and manufacture |
| EP2740474A1 (en) | 2012-12-05 | 2014-06-11 | Instituto Europeo di Oncologia S.r.l. | Cyclopropylamine derivatives useful as inhibitors of histone demethylases kdm1a |
| WO2014107718A2 (en) * | 2013-01-07 | 2014-07-10 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Heat shock protein (hsp) inhibition and monitoring effectiveness thereof |
| HK1225716A1 (zh) | 2013-08-21 | 2017-09-15 | Alios Biopharma, Inc. | 抗病毒化合物 |
| JP2016538574A (ja) * | 2013-11-18 | 2016-12-08 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール中の不純物のｈｐｌｃ分析 |
| EP2949648A1 (en) | 2014-05-30 | 2015-12-02 | IEO - Istituto Europeo di Oncologia Srl | Cyclopropylamine derivatives as histone demethylase inhibitors |
| EP3148974B1 (en) | 2014-05-30 | 2018-09-26 | Istituto Europeo di Oncologia S.r.l. | Cyclopropylamine compounds as histone demethylase inhibitors |
| TW201625243A (zh) | 2014-10-14 | 2016-07-16 | 艾克塞里克斯公司 | 用於治療黑素瘤之藥物組合 |
| US20180200392A1 (en) * | 2015-07-16 | 2018-07-19 | Akuru Pharma Ab | Detection and treatment of renal cell carcinoma with a slc6a3 ligand linked to a label, cytotoxic or immunomodulatory group |
| EP3588064B1 (en) * | 2017-02-23 | 2022-09-07 | IHI Corporation | Oh radical detection probe, oh radical measurement device, and oh radical measurement method |
| CN108164529B (zh) * | 2017-12-25 | 2020-04-24 | 三峡大学 | 一种小分子抑制剂sld9059及其在制药中的应用 |
| DK3737677T3 (da) | 2018-01-10 | 2022-01-10 | Allinky Biopharma | Tetrahydroisoquinolinforbindelser |
| CN111825702A (zh) * | 2019-04-22 | 2020-10-27 | 成都科岭源医药技术有限公司 | 一种氮杂*并吲唑类衍生物及其制备方法和用途 |
| CN110698395B (zh) * | 2019-10-22 | 2021-05-25 | 杭州百诚医药科技股份有限公司 | 一种托吡司特的中间体的制备方法 |
| CN112920078A (zh) * | 2019-12-05 | 2021-06-08 | 武汉珈汇精化科技有限公司 | 一种制备4-氰基苯甲酸甲酯的方法和一种制备4-氰基苯甲酸的方法 |
| TW202136238A (zh) * | 2020-01-06 | 2021-10-01 | 大陸商廣東東陽光藥業有限公司 | RORγt抑制劑及其製備方法和用途 |
| EP4229053A1 (en) * | 2020-10-14 | 2023-08-23 | Ranok Therapeutics (Hangzhou) Co. Ltd. | Methods and compositions for targeted protein degradation |
| CN114591192B (zh) * | 2020-12-04 | 2024-06-21 | 江西仰立新材料有限公司 | 一种n-环丙甲基苯胺类化合物的制备方法 |
| US20240083910A1 (en) * | 2020-12-18 | 2024-03-14 | Merck Sharp & Dohme Llc | Amido-substituted pyridyl compounds and methods of use thereof for the treatment of herpesviruses |
| CN112707809B (zh) * | 2020-12-30 | 2023-08-29 | 丽珠集团新北江制药股份有限公司 | 一种制备噁唑啉杀虫剂氟雷拉纳中间体的方法 |
| MX2024001265A (es) * | 2021-07-26 | 2024-02-14 | Zoetis Services Llc | Compuestos inhibidores de serotonina 5-ht2b. |
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| EP0101641A3 (en) | 1982-07-22 | 1984-03-28 | Beecham Group Plc | Sulfonylamino-aza-bicyclo-alkyl derivatives |
| FR2738569B1 (fr) | 1995-09-12 | 1997-11-28 | Pf Medicament | Nouveaux derives naphtamide de 3 beta-amino azabicyclo octane ou nonane, leur procede de preparation, leur utilisation a titre de medicament antipsychotique |
| JP4169368B2 (ja) * | 1996-01-15 | 2008-10-22 | 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 | 脈管形成阻害性ピリダジンアミン |
| HUP0202001A2 (hu) * | 2002-06-14 | 2005-08-29 | Sanofi-Aventis | DDP-IV gátló hatású azabiciklooktán- és nonánszármazékok |
| US7358244B2 (en) * | 2003-05-28 | 2008-04-15 | Theravance, Inc. | Azabicycloalkane compounds |
| CA2530023A1 (en) * | 2003-06-24 | 2004-12-29 | Neurosearch A/S | Novel 8-aza-bicyclo[3.2.1]octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| GB0323236D0 (en) * | 2003-10-03 | 2003-11-05 | Pfizer Ltd | Chemical compounds |
| EP1682545B1 (en) * | 2003-10-03 | 2007-12-12 | Pfizer Limited | Imidazopyridine substituted tropane derivatives with ccr5 receptor antagonist activity for the treatment of hiv and inflammation |
| PT1731518E (pt) * | 2004-03-31 | 2014-09-18 | Nippon Soda Co | Composto amina cíclico e agente de controlo de pragas |
| FR2873693B1 (fr) * | 2004-07-29 | 2006-09-15 | Sanofi Synthelabo | Derives d'amino-tropane, leur preparation et leur application en therapeutique |
| US7713990B2 (en) | 2005-01-13 | 2010-05-11 | Neurosearch A/S | 3,8-substituted 8-AZA-bicyclo[3.2.1]octane derivatives and their use as monomine neurotransmitter re-uptake inhibitors |
| EP2251341A1 (en) * | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| WO2007040280A1 (ja) * | 2005-10-06 | 2007-04-12 | Nippon Soda Co., Ltd. | 環状アミン化合物および有害生物防除剤 |
| BRPI0716240B8 (pt) * | 2006-09-01 | 2019-09-17 | Oat Agrio Co Ltd | composto de n-piridilpiperidina, método para a sua produção, e agente de controle de pestes |
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