JP2002541245A5 - - Google Patents
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- Publication number
- JP2002541245A5 JP2002541245A5 JP2000610837A JP2000610837A JP2002541245A5 JP 2002541245 A5 JP2002541245 A5 JP 2002541245A5 JP 2000610837 A JP2000610837 A JP 2000610837A JP 2000610837 A JP2000610837 A JP 2000610837A JP 2002541245 A5 JP2002541245 A5 JP 2002541245A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- amino
- pyrimidine
- chlorophenoxy
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 description 41
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 15
- -1 heptamethyleneimino Chemical group 0.000 description 15
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000012453 solvate Substances 0.000 description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 11
- 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005505 thiomorpholino group Chemical group 0.000 description 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- WDRVZKJGSJDXON-CHWSQXEVSA-N (1r,2r)-2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound N([C@H]1[C@@H](CCCC1)O)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 WDRVZKJGSJDXON-CHWSQXEVSA-N 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- WRUUUVBVOHWJPV-UHFFFAOYSA-N 1-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]propan-2-ol Chemical compound CC(O)CNC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 WRUUUVBVOHWJPV-UHFFFAOYSA-N 0.000 description 1
- HIXIKQQUYWMVPC-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 HIXIKQQUYWMVPC-UHFFFAOYSA-N 0.000 description 1
- IQVXQPDVICCRMK-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]-2-methylpropan-1-ol Chemical compound OCC(C)(C)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 IQVXQPDVICCRMK-UHFFFAOYSA-N 0.000 description 1
- QCJXZNLZFCDTSJ-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]butan-1-ol Chemical compound CCC(CO)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 QCJXZNLZFCDTSJ-UHFFFAOYSA-N 0.000 description 1
- UDDJXYHPSUBHLP-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]ethanol Chemical compound OCCNC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UDDJXYHPSUBHLP-UHFFFAOYSA-N 0.000 description 1
- AWUVVMYYNWXAKH-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]propan-1-ol Chemical compound OCC(C)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 AWUVVMYYNWXAKH-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- OETOQMORKGXZAN-UHFFFAOYSA-N 4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]-2-chlorophenol Chemical compound C=1C=C(O)C(Cl)=CC=1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 OETOQMORKGXZAN-UHFFFAOYSA-N 0.000 description 1
- REFUFYATTVIZSM-UHFFFAOYSA-N 4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]-3-chlorophenol Chemical compound C=1C=C(O)C=C(Cl)C=1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 REFUFYATTVIZSM-UHFFFAOYSA-N 0.000 description 1
- YXAONWAIFKGGRJ-UHFFFAOYSA-N 4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 YXAONWAIFKGGRJ-UHFFFAOYSA-N 0.000 description 1
- UFSPXXMLIZPAOR-UHFFFAOYSA-N 4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]phenol Chemical compound C=1C=C(O)C=CC=1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UFSPXXMLIZPAOR-UHFFFAOYSA-N 0.000 description 1
- UZCYYVJRMMNKRT-UHFFFAOYSA-N 5-(4-chlorophenoxy)-4-n-cyclohexylpyrimidine-2,4-diamine Chemical compound C1CCCCC1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UZCYYVJRMMNKRT-UHFFFAOYSA-N 0.000 description 1
- VBZKDFXIJPJHRP-UHFFFAOYSA-N 5-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]pentan-1-ol Chemical compound OCCCCCNC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 VBZKDFXIJPJHRP-UHFFFAOYSA-N 0.000 description 1
- NJOAMWMECUMSCZ-HDJSIYSDSA-N C1=CC(CC)=CC=C1OC1=CN=C(N)N=C1N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=CC(CC)=CC=C1OC1=CN=C(N)N=C1N[C@@H]1CC[C@@H](O)CC1 NJOAMWMECUMSCZ-HDJSIYSDSA-N 0.000 description 1
- XNSDDHKPRDOTSP-SHTZXODSSA-N C1=CC(CC)=CC=C1OC1=CN=CN=C1N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=CC(CC)=CC=C1OC1=CN=CN=C1N[C@@H]1CC[C@@H](O)CC1 XNSDDHKPRDOTSP-SHTZXODSSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- OSKCZMYMADHTLA-SHTZXODSSA-N N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 Chemical compound N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 OSKCZMYMADHTLA-SHTZXODSSA-N 0.000 description 1
- IKTRZJYQWHAZHX-HAQNSBGRSA-N N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 Chemical compound N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 IKTRZJYQWHAZHX-HAQNSBGRSA-N 0.000 description 1
- AWYGONCSOZSLRM-XYPYZODXSA-N N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1Cl Chemical compound N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1Cl AWYGONCSOZSLRM-XYPYZODXSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- PTRZEOYINPNTSI-UHFFFAOYSA-N [4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 PTRZEOYINPNTSI-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/288,495 | 1999-04-08 | ||
| US09/288,495 US6583148B1 (en) | 1999-04-08 | 1999-04-08 | Neurotrophic substituted pyrimidines |
| PCT/US2000/009108 WO2000061562A1 (en) | 1999-04-08 | 2000-04-06 | Neurotrophic substituted pyrimidines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002541245A JP2002541245A (ja) | 2002-12-03 |
| JP2002541245A5 true JP2002541245A5 (enExample) | 2011-02-10 |
| JP4743463B2 JP4743463B2 (ja) | 2011-08-10 |
Family
ID=23107364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000610837A Expired - Fee Related JP4743463B2 (ja) | 1999-04-08 | 2000-04-06 | 神経栄養置換ピリミジン |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6583148B1 (enExample) |
| EP (1) | EP1165523B1 (enExample) |
| JP (1) | JP4743463B2 (enExample) |
| AT (1) | ATE377592T1 (enExample) |
| AU (1) | AU4331400A (enExample) |
| CA (1) | CA2368843C (enExample) |
| DE (1) | DE60037013T2 (enExample) |
| WO (1) | WO2000061562A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1303495T3 (da) * | 2000-07-24 | 2010-09-20 | Krenitsky Pharmaceuticals Inc | Substituerede 5-alkylnylpyrimidiner med neurotrofisk aktivitet |
| BR0307665A (pt) | 2002-02-13 | 2005-01-04 | Hoffmann La Roche | Compostos, processo para a sua manufatura, composições farmacêuticas que compreendem os mesmos, método para o tratamento e/ou profilaxia de enfermidades associadas com dpp iv e utilização dos compostos |
| JP2005232081A (ja) * | 2004-02-19 | 2005-09-02 | Bayer Cropscience Ag | ベンジルピリミジン誘導体の農園芸用殺菌剤としての利用 |
| PL1725540T3 (pl) * | 2004-03-05 | 2013-02-28 | Hoffmann La Roche | Diaminopirymidyny jako antagoniści p2x3 i p2x2/3 |
| EP2594318B1 (en) * | 2005-04-15 | 2020-06-10 | University Of North Carolina At Chapel Hill | Methods of facilitating cell survival using neurotrophin mimetics |
| US20110230479A1 (en) * | 2005-04-15 | 2011-09-22 | Longo Frank M | Neurotrophin mimetics and uses thereof |
| EP1893192A4 (en) | 2005-06-08 | 2010-03-31 | Univ North Carolina | METHOD FOR ENABLING SURVIVAL OF NERVE CELLS BASED ON NON-PEPTIDIC AND PEPTIDIC BDNF NEUROTROPHINE MIMETICS |
| KR101012926B1 (ko) * | 2005-09-01 | 2011-02-09 | 에프. 호프만-라 로슈 아게 | Ｐ2ｘ3 및 ｐ2ｘ2/3 조정자로서의 다이아미노피리미딘 |
| JP4850912B2 (ja) * | 2005-09-01 | 2012-01-11 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐ２ｘ３およびｐ３ｘ２／３モジュレーターとしてのジアミノピリミジン |
| CN101300235B (zh) | 2005-09-01 | 2011-12-07 | 弗·哈夫曼-拉罗切有限公司 | 作为p2x3和p2x2/3调节剂的二氨基嘧啶类化合物 |
| JP4850911B2 (ja) * | 2005-09-01 | 2012-01-11 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐ２ｘ３およびｐ２ｘ２／３モジュレーターとしてのジアミノピリミジン |
| RU2433119C2 (ru) * | 2006-04-28 | 2011-11-10 | Шионоги Энд Ко., Лтд. | Производное амина, обладающее антагонистической активностью в отношении рецептора npy y5 |
| ZA200809146B (en) * | 2006-04-28 | 2009-12-30 | Shionogi & Co | Amine derivative having NPY Y5 receptor antagonist activity |
| AU2007244358B2 (en) * | 2006-04-28 | 2012-06-14 | Shionogi & Co., Ltd. | Amine derivative having NPY Y5 receptor antagonist activity |
| SA08290668B1 (ar) | 2007-10-25 | 2012-02-12 | شيونوجي آند كو.، ليمتد | مشتقات أمين لها نشاط مضاد لمستقبل npy y5 واستخداماتها |
| US8227618B2 (en) | 2009-04-23 | 2012-07-24 | Shionogi & Co., Ltd. | Amine-derivatives having NPY Y5 receptor antagonistic activity and the uses thereof |
| EP2498782B1 (en) | 2009-11-12 | 2019-01-09 | Pharmatrophix Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
| US10273219B2 (en) | 2009-11-12 | 2019-04-30 | Pharmatrophix, Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
| EA027792B1 (ru) | 2011-04-08 | 2017-09-29 | Янссен Сайенсиз Айрлэнд Юси | Производные пиримидина для лечения вирусных инфекций |
| CN104066733A (zh) | 2011-11-09 | 2014-09-24 | 爱尔兰詹森研发公司 | 用于治疗病毒感染的嘌呤衍生物 |
| SG11201408542VA (en) | 2012-07-13 | 2015-02-27 | Janssen Sciences Ireland Uc | Macrocyclic purines for the treatment of viral infections |
| EP2882721B1 (en) * | 2012-08-10 | 2018-12-05 | Janssen Sciences Ireland Unlimited Company | Alkylpyrimidine derivatives for the treatment of viral infections and further diseases |
| KR102280595B1 (ko) | 2012-10-10 | 2021-07-22 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염 및 다른 질환 치료를 위한 피롤로[3,2-d]피리미딘 유도체 |
| CN105051018B (zh) | 2012-11-16 | 2019-09-20 | 爱尔兰詹森科学公司 | 用于治疗病毒性感染的杂环的经取代的2-氨基-喹唑啉衍生物 |
| CN105189468B (zh) | 2013-02-21 | 2018-10-30 | 爱尔兰詹森科学公司 | 用于治疗病毒性感染的2-氨基嘧啶衍生物 |
| BR112015022836A2 (pt) | 2013-03-15 | 2017-07-18 | Pharmatrophix Inc | miméticos de neurotrofina bdnf não peptídicos |
| AU2014227623B2 (en) | 2013-03-15 | 2018-08-16 | Pharmatrophix, Inc. | Non-peptide BDNF Neurotrophin mimetics |
| MX366481B (es) | 2013-03-29 | 2019-07-09 | Janssen Sciences Ireland Uc | Deaza-purinonas macrociclicas para el tratamiento de infecciones virales. |
| DK3004074T3 (da) | 2013-05-24 | 2018-01-29 | Janssen Sciences Ireland Uc | Pyridonderivater til behandling af virusinfektioner og yderligere sygdomme |
| NO3030563T3 (enExample) | 2013-06-27 | 2018-01-06 | ||
| MX368625B (es) | 2013-07-30 | 2019-10-08 | Janssen Sciences Ireland Uc | Derivados de tieno[3,2-d]pirimidinas para el tratamiento de infecciones virales. |
| CA3027471A1 (en) | 2016-07-01 | 2018-01-04 | Janssen Sciences Ireland Unlimited Company | Dihydropyranopyrimidines for the treatment of viral infections |
| CN109790154B (zh) | 2016-09-29 | 2023-06-23 | 爱尔兰詹森科学公司 | 用于治疗病毒感染和另外的疾病的嘧啶前药 |
| TW201945003A (zh) | 2018-03-01 | 2019-12-01 | 愛爾蘭商健生科學愛爾蘭無限公司 | ２，４－二胺基喹唑啉衍生物及其醫學用途 |
| WO2020045334A1 (ja) | 2018-08-27 | 2020-03-05 | 大日本住友製薬株式会社 | 光学活性なアザビシクロ環誘導体 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691655A (en) | 1952-05-24 | 1954-10-12 | Burroughs Wellcome Co | 2-amino-4-substituted amino-6-aryl pyrimidines and process of preparing same |
| GB951432A (en) | 1959-03-17 | 1964-03-04 | Wellcome Found | Pyrimidine derivatives and the manufacture thereof |
| US3862190A (en) | 1972-09-08 | 1975-01-21 | Pfizer | 5-(unsubstituted and substituted phenoxy)-4-amino pyrimidines |
| DK397574A (enExample) * | 1973-08-24 | 1975-04-28 | Ciba Geigy Ag | |
| GB1523274A (en) | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
| FR2358148A1 (fr) | 1976-07-12 | 1978-02-10 | Dick Pr | Derives de 2,4-diaminopyrimidines et leur mise en solution en association avec des sulfamides |
| FR2397407A2 (fr) | 1977-07-11 | 1979-02-09 | Dick Pierre | Derives de 2,4-diamino pyrimidines et leur mise en solution en association avec des sulfamides |
| FI895821A7 (fi) | 1988-12-07 | 1990-06-08 | The Wellcome Foundation Ltd | Farmaseuttisesti aktivisia CNS-yhdisteitä |
| GB9012316D0 (en) | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
| IE912114A1 (en) | 1990-07-02 | 1992-01-15 | Union Pharma Scient Appl | Novel pyrimidine derivatives which are angiotensin ii¹receptor antagonists, their methods of preparation and¹pharmaceutical compositions in which they are present |
| US5075305A (en) | 1991-03-18 | 1991-12-24 | Warner-Lambert Company | Compound, composition and use |
| DE69201559T2 (de) | 1991-04-17 | 1995-07-13 | Pfizer | Pyrimidinderivate zur erhöhung der antitumoraktivität. |
| US5336677A (en) | 1991-10-24 | 1994-08-09 | American Home Products Corporation | Substituted aminopyrimidines as antihypertensives |
| GB9125842D0 (en) | 1991-12-04 | 1992-02-05 | Ici Plc | Heterocyclic derivatives |
| JPH08504798A (ja) | 1992-12-18 | 1996-05-21 | ザ ウエルカム ファウンデーション リミテッド | 酵素阻害薬としての，ピリミジン，ピリジン，プテリジノンおよびインダゾール誘導体 |
| DE69408750T2 (de) | 1993-08-26 | 1998-07-23 | Ono Pharmaceutical Co | 4-Aminopyrimidin Derivate |
| JPH08283246A (ja) | 1994-06-01 | 1996-10-29 | Nippon Soda Co Ltd | ピリミジン誘導体、その製造方法及び有害生物防除剤 |
| WO1996031488A1 (en) | 1995-04-03 | 1996-10-10 | Sumitomo Pharmaceuticals Company, Limited | Novel pyrimidine derivatives efficacious as psychotropic drug and process for the production thereof |
| US6440965B1 (en) | 1997-10-15 | 2002-08-27 | Krenitsky Pharmaceuticals, Inc. | Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system |
-
1999
- 1999-04-08 US US09/288,495 patent/US6583148B1/en not_active Expired - Fee Related
-
2000
- 2000-04-06 CA CA002368843A patent/CA2368843C/en not_active Expired - Fee Related
- 2000-04-06 AU AU43314/00A patent/AU4331400A/en not_active Abandoned
- 2000-04-06 WO PCT/US2000/009108 patent/WO2000061562A1/en not_active Ceased
- 2000-04-06 US US09/958,511 patent/US6916820B1/en not_active Expired - Fee Related
- 2000-04-06 DE DE60037013T patent/DE60037013T2/de not_active Expired - Lifetime
- 2000-04-06 AT AT00923138T patent/ATE377592T1/de not_active IP Right Cessation
- 2000-04-06 EP EP00923138A patent/EP1165523B1/en not_active Expired - Lifetime
- 2000-04-06 JP JP2000610837A patent/JP4743463B2/ja not_active Expired - Fee Related
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