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 (https=) | 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 (https=) |
| EP (1) | EP1165523B1 (https=) |
| JP (1) | JP4743463B2 (https=) |
| AT (1) | ATE377592T1 (https=) |
| AU (1) | AU4331400A (https=) |
| CA (1) | CA2368843C (https=) |
| DE (1) | DE60037013T2 (https=) |
| WO (1) | WO2000061562A1 (https=) |
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 |
| KR100608414B1 (ko) | 2002-02-13 | 2006-08-02 | 에프. 호프만-라 로슈 아게 | 신규한 피리딘- 및 피리미딘-유도체 |
| 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 |
| CN1930135B (zh) * | 2004-03-05 | 2011-12-28 | 弗·哈夫曼-拉罗切有限公司 | 作为p2x3和p2x2/3拮抗剂的二氨基嘧啶 |
| EP1871420A4 (en) * | 2005-04-15 | 2010-09-22 | Univ North Carolina | PROCESS FOR ENABLING CELL SURVIVAL VIA NEUROTROPHINE MIMETICS |
| US20110230479A1 (en) * | 2005-04-15 | 2011-09-22 | Longo Frank M | Neurotrophin mimetics and uses thereof |
| WO2006133353A2 (en) | 2005-06-08 | 2006-12-14 | The University Of North Carolina At Chapel Hill | Methods of facilitating neural cell survival using non-peptide and peptide bdnf neurotrophin mimetics |
| CA2620129C (en) | 2005-09-01 | 2014-12-23 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| JP4850914B2 (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 |
| WO2007025900A1 (en) * | 2005-09-01 | 2007-03-08 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p3x2/3 modulators |
| CA2619919C (en) * | 2005-09-01 | 2014-04-01 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| US9150507B2 (en) | 2006-04-28 | 2015-10-06 | Shionogi & Co., Ltd. | Amine derivative having NPY Y5 receptor antagonistic activity |
| RU2433119C2 (ru) * | 2006-04-28 | 2011-11-10 | Шионоги Энд Ко., Лтд. | Производное амина, обладающее антагонистической активностью в отношении рецептора npy y5 |
| CN101479238B (zh) * | 2006-04-28 | 2013-08-21 | 盐野义制药株式会社 | 具有npyy5受体拮抗活性的胺衍生物 |
| 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 |
| US10273219B2 (en) | 2009-11-12 | 2019-04-30 | Pharmatrophix, Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
| ES2712752T3 (es) | 2009-11-12 | 2019-05-14 | Pharmatrophix Inc | Formas cristalinas de compuestos miméticos de neurotrofina y sus sales |
| HUE055286T2 (hu) | 2011-04-08 | 2021-11-29 | Janssen Sciences Ireland Unlimited Co | Pirimidinszármazékok vírusfertõzések kezelésére |
| RS57851B1 (sr) | 2011-11-09 | 2018-12-31 | Janssen Sciences Ireland Uc | Purinski derivati za tretman viralnih infekcija |
| CA2874800C (en) | 2012-07-13 | 2021-04-06 | Janssen R&D Ireland | Macrocyclic purines for the treatment of viral infections |
| CN104781239B (zh) * | 2012-08-10 | 2019-03-01 | 爱尔兰詹森科学公司 | 用于治疗病毒感染和另外的疾病的烷基嘧啶衍生物 |
| LT2906563T (lt) | 2012-10-10 | 2018-06-11 | Janssen Sciences Ireland Uc | Pirolo[3,2-d]pirimidino dariniai virusinių infekcijų ir kitų ligų gydymui |
| EP2925729B1 (en) | 2012-11-16 | 2017-10-18 | Janssen Sciences Ireland UC | Heterocyclic substituted 2-amino-quinazoline derivatives for the treatment of viral infections |
| WO2014128189A1 (en) | 2013-02-21 | 2014-08-28 | Janssen R&D Ireland | 2-aminopyrimidine derivatives for the treatment of viral infections |
| JP2016519668A (ja) | 2013-03-15 | 2016-07-07 | ファーマトロフィックス， インコーポレイテッド | 非ペプチドｂｄｎｆニューロトロフィン模倣化合物 |
| RU2015141934A (ru) | 2013-03-15 | 2017-04-20 | Фарматрофикс, Инк. | Непептидные миметики нейротрофина bdnf |
| AU2014242954B2 (en) | 2013-03-29 | 2018-03-15 | Janssen Sciences Ireland Uc | Macrocyclic deaza-purinones for the treatment of viral infections |
| SG11201509520QA (en) | 2013-05-24 | 2015-12-30 | Janssen Sciences Ireland Uc | Pyridone derivatives for the treatment of viral infections and further diseases |
| BR112015032546B1 (pt) | 2013-06-27 | 2022-05-17 | Janssen Sciences Ireland Uc | Derivados de pirrolo[3,2-d]pirimidina e composição farmacêutica que os compreende para o tratamento de infecções virais e outras doenças |
| KR102322425B1 (ko) | 2013-07-30 | 2021-11-05 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염의 치료를 위한 티에노[3,2-d]피리미딘 유도체 |
| AU2017289418B2 (en) | 2016-07-01 | 2021-06-03 | Janssen Sciences Ireland Unlimited Company | Dihydropyranopyrimidines for the treatment of viral infections |
| JP7274415B2 (ja) | 2016-09-29 | 2023-05-16 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | ウイルス感染症および他の疾患を処置するためのピリミジンプロドラッグ |
| TW202415645A (zh) | 2018-03-01 | 2024-04-16 | 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 |
| SG11202101085PA (en) | 2018-08-27 | 2021-03-30 | Sumitomo Dainippon Pharma Co Ltd | Optically active azabicyclic derivative |
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 (https=) * | 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 |
| FI934565A7 (fi) | 1991-04-17 | 1993-10-15 | Pfizer | Pyrimidiinijohdannaisia kasvaimenvastaisen vaikutuksen lisäämiseksi |
| 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 |
| WO1994014780A1 (en) | 1992-12-18 | 1994-07-07 | The Wellcome Foundation Limited | Pyrimidine, pyridine, pteridinone and indazole derivatives as enzyme inhibitors |
| EP0640599B1 (en) | 1993-08-26 | 1998-03-04 | Ono Pharmaceutical Co., Ltd. | 4-Aminopyrimidine derivatives |
| 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 |
| CA2217034A1 (en) | 1995-04-03 | 1996-10-10 | Sumitomo Pharmaceuticals Company, Limited | Novel pyrimidine derivatives effective 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 JP JP2000610837A patent/JP4743463B2/ja not_active Expired - Fee Related
- 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 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 WO PCT/US2000/009108 patent/WO2000061562A1/en not_active Ceased
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