RU2360912C2 - Замещенные дигидрохиназолины с противовирусными свойствами - Google Patents
Замещенные дигидрохиназолины с противовирусными свойствами Download PDFInfo
- Publication number
- RU2360912C2 RU2360912C2 RU2005137276/04A RU2005137276A RU2360912C2 RU 2360912 C2 RU2360912 C2 RU 2360912C2 RU 2005137276/04 A RU2005137276/04 A RU 2005137276/04A RU 2005137276 A RU2005137276 A RU 2005137276A RU 2360912 C2 RU2360912 C2 RU 2360912C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- hydrogen atom
- compound according
- fluorine
- atoms
- Prior art date
Links
- 230000000840 anti-viral effect Effects 0.000 title claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 32
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 15
- 125000005843 halogen group Chemical group 0.000 claims abstract 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 239000003814 drug Substances 0.000 claims abstract 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 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 abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 208000036142 Viral infection Diseases 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 230000009385 viral infection Effects 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000024697 human cytomegalovirus infection Diseases 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- -1 cyanic group Chemical group 0.000 abstract 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10319612.9 | 2003-05-02 | ||
| DE10319612A DE10319612A1 (de) | 2003-05-02 | 2003-05-02 | Substituierte Dihydrochinazoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005137276A RU2005137276A (ru) | 2006-07-27 |
| RU2360912C2 true RU2360912C2 (ru) | 2009-07-10 |
Family
ID=33305099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005137276/04A RU2360912C2 (ru) | 2003-05-02 | 2004-04-17 | Замещенные дигидрохиназолины с противовирусными свойствами |
Country Status (38)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10319612A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Healthcare Ag | Substituierte Dihydrochinazoline |
| DE10305785A1 (de) * | 2003-02-12 | 2004-08-26 | Bayer Healthcare Ag | Dihydrochinazoline |
| DE10320780A1 (de) * | 2003-05-09 | 2005-01-20 | Bayer Healthcare Ag | Heterocyclyl-substituierte Dihydrochinazoline |
| DE10352499A1 (de) * | 2003-11-11 | 2005-06-09 | Bayer Healthcare Ag | Substituierte Dihydrochinazoline II |
| DE102004022672A1 (de) | 2004-05-07 | 2005-11-24 | Bayer Healthcare Ag | Substituierte Azachinazoline |
| DE102005027517A1 (de) * | 2005-06-15 | 2006-12-21 | Bayer Healthcare Ag | Verfahren zur Herstellung von Dihydrochinazolinen |
| DE102011101446A1 (de) * | 2011-05-10 | 2012-11-15 | Aicuris Gmbh & Co. Kg | Herstellung von "Dense Bodies" (DB) |
| DE102012101680A1 (de) | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung enthaltend ein antiviral wirksames Dihydrochinazolinderivat |
| DE102012101673A1 (de) | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Salze eines Dihydrochinazolinderivats |
| DE102012101659A1 (de) | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Salze eines Dihydrochinazolinderivats |
| ES2730958T3 (es) * | 2013-06-19 | 2019-11-13 | Aicuris Anti Infective Cures Gmbh | Letermovir amorfo y formulaciones farmacéuticas sólidas del mismo para administración oral |
| US9890128B2 (en) | 2013-12-12 | 2018-02-13 | Merck Sharp & Dohme Corp. | Process for making substituted quinazoline compounds |
| US10392353B2 (en) * | 2015-11-24 | 2019-08-27 | Merck Sharp & Dohme Corp. | Processes for making substituted quinazoline compounds using hydrogen bonding catalysts |
| WO2018028556A1 (zh) * | 2016-08-08 | 2018-02-15 | 南京明德新药研发股份有限公司 | 抗hcmv病毒化合物 |
| AU2019218150B2 (en) | 2018-02-08 | 2021-05-13 | Phaeno Therapeutics Co., Ltd. | Crystal form of 3,4-dihydrothieno[3,2-d]pyrimidine compound and preparation method therefor |
| EP3527209A1 (en) * | 2018-02-16 | 2019-08-21 | UCB Biopharma SPRL | Pharmaceutical 6,5 heterobicyclic ring derivatives |
| WO2020053654A1 (en) | 2018-09-12 | 2020-03-19 | Novartis Ag | Antiviral pyridopyrazinedione compounds |
| JP7417715B2 (ja) | 2019-09-26 | 2024-01-18 | ノバルティス アーゲー | 抗ウイルスピラゾロピリジノン化合物 |
| AR121437A1 (es) | 2020-02-27 | 2022-06-08 | Aic246 Gmbh & Co Kg | Sal de potasio del ácido 2-[(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5-(trifluorometil)fenil]-4h-quinazolin-4-il]acético |
| AR121440A1 (es) | 2020-02-27 | 2022-06-08 | Aic246 Gmbh & Co Kg | Un método de preparación de 2-[(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5-(trifluorometil)fenil]-4h-quinazolin-4-il] acetato de sodio monohidrato, dicho compuesto y el uso del mismo para el tratamiento de infecciones virales |
| AR121439A1 (es) | 2020-02-27 | 2022-06-08 | Aic246 Gmbh & Co Kg | Un método para producir una forma cristalina de 2-[(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5-(trifluorometil)fenil]-4h-quinazolin-4-il]acetato de sodio trihidrato |
| UY39095A (es) | 2020-02-27 | 2021-09-30 | Aic246 Gmbh & Co Kg | Composiciones farmacéuticas que comprenden acetato de 2- [(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5- (trifluorometil)fenil]-4h-quinazolin-4-il] e iones de sodio |
| UY39099A (es) | 2020-02-27 | 2021-08-31 | Aic246 Gmbh & Co Kg | 2-[(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5-(trifluorometil)fenil]-4h-quinazolin-4-il] acetato de sodio y composiciones farmacéuticas del mismo |
| EP3906929A1 (en) | 2020-05-08 | 2021-11-10 | AiCuris GmbH & Co. KG | Letermovir for use in the prevention and the treatment of coronavirus infections |
| CA3189271A1 (en) | 2020-08-17 | 2022-02-24 | Girij Pal Singh | A precipitation process for amorphous letermovir |
| CN115403528B (zh) * | 2021-05-27 | 2025-01-07 | 南京正大天晴制药有限公司 | 无定形3,4-二氢喹唑啉衍生物的制备方法 |
| CN114031560B (zh) * | 2021-11-16 | 2022-10-04 | 山东诚创蓝海医药科技有限公司 | 一种来特莫韦钠盐的制备方法 |
| AR128035A1 (es) | 2021-12-21 | 2024-03-20 | Aic246 Ag & Co Kg | Composiciones farmacéuticas que comprenden acetato de 2-[(4s)-8-fluoro-2-[4-(3-metoxifenil)piperazin-1-il]-3-[2-metoxi-5-(trifluorometil)fenil]-4h-quinazolin-4-il] e iones de potasio |
| WO2023185597A1 (zh) * | 2022-04-01 | 2023-10-05 | 上海迪赛诺化学制药有限公司 | 莱特莫韦中间体及其制备方法 |
| CN115322157B (zh) * | 2022-06-02 | 2023-12-05 | 浙江车头制药股份有限公司 | 来特莫韦中间体化合物及其制备方法和应用 |
| CN117229223A (zh) * | 2022-06-08 | 2023-12-15 | 苏州远智医药科技有限公司 | 一种杂环衍生物及其药物组合物、应用 |
| WO2025133248A1 (en) | 2023-12-21 | 2025-06-26 | Aic246 Ag & Co. Kg | Diastereomeric aminoalcohol and aminoether salts of 2-[(4r,s)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl]acetic acid and their use for enantiomeric separation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2198879C2 (ru) * | 1996-09-25 | 2003-02-20 | Зенека Лимитед | Производные хиназолина, способы их получения, содержащие их фармацевтические композиции, способ достижения антиангиогенного и/или эффекта снижения проницаемости кровеносных сосудов у теплокровного животного |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4320347A1 (de) | 1993-06-19 | 1994-12-22 | Boehringer Mannheim Gmbh | Quinazolin-Derivate und diese enthaltende Arzneimittel |
| US5854245A (en) * | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE19802437A1 (de) | 1998-01-23 | 1999-07-29 | Bayer Ag | Verwendung von substituierten Sulfonamiden als anitvirale Mittel und neue Stoffe |
| AU748087B2 (en) | 1998-02-17 | 2002-05-30 | Tularik Inc. | Anti-viral pyrimidine derivatives |
| KR20010113820A (ko) | 1999-04-19 | 2001-12-28 | 시오노 요시히코 | 옥사디아졸 고리를 갖는 술폰아미드 유도체 |
| DE19930075A1 (de) | 1999-06-30 | 2001-01-04 | Bayer Ag | Neue Amino- und Amidosulfonamide als antivirale Mittel |
| US6730682B2 (en) * | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| DK1325008T3 (da) * | 2000-07-31 | 2006-02-13 | Hoffmann La Roche | Piperazinderivater |
| EP1201765A3 (en) * | 2000-10-16 | 2003-08-27 | Axxima Pharmaceuticals Aktiengesellschaft | Cellular kinases involved in cytomegalovirus infection and their inhibition |
| WO2002085869A1 (de) | 2001-04-19 | 2002-10-31 | Bayer Aktiengesellschaft | Arylsulfonamide als antivirale mittel |
| DE10138578A1 (de) | 2001-08-06 | 2003-02-27 | Bayer Ag | Heterocyclylarylsulfonamide |
| DE10251914A1 (de) | 2002-11-08 | 2004-05-19 | Bayer Ag | Substituierte Chinazoline |
| DE10319612A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Healthcare Ag | Substituierte Dihydrochinazoline |
| DE10305785A1 (de) * | 2003-02-12 | 2004-08-26 | Bayer Healthcare Ag | Dihydrochinazoline |
| DE10320780A1 (de) | 2003-05-09 | 2005-01-20 | Bayer Healthcare Ag | Heterocyclyl-substituierte Dihydrochinazoline |
| DE10352499A1 (de) * | 2003-11-11 | 2005-06-09 | Bayer Healthcare Ag | Substituierte Dihydrochinazoline II |
| KR100610731B1 (ko) | 2004-02-24 | 2006-08-09 | 한국과학기술연구원 | Ｔ-형 칼슘 채널 차단제로서 유용한 ３,４-디히드로퀴나졸린유도체 및 그의 제조 방법 |
| DE102004022672A1 (de) * | 2004-05-07 | 2005-11-24 | Bayer Healthcare Ag | Substituierte Azachinazoline |
| AU2006208084B2 (en) * | 2005-01-25 | 2012-07-26 | Prolexys Pharmaceuticals, Inc. | Quinoxaline Derivatives as Antitumor Agents |
| DE102005027517A1 (de) | 2005-06-15 | 2006-12-21 | Bayer Healthcare Ag | Verfahren zur Herstellung von Dihydrochinazolinen |
| BRPI0613604A2 (pt) * | 2005-07-21 | 2011-01-18 | Hoffmann La Roche | compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento terapêutico e/ou profilático de enfermidades que são moduladas por inibidores de ptp-1b, e utilização dos compostos |
| DE102006009928A1 (de) | 2006-03-03 | 2007-09-06 | Aicuris Gmbh & Co. Kg | Substituierte Arylsulfonamide |
| DE102012101680A1 (de) * | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung enthaltend ein antiviral wirksames Dihydrochinazolinderivat |
| DE102012101673A1 (de) | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Salze eines Dihydrochinazolinderivats |
| DE102012101659A1 (de) * | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Salze eines Dihydrochinazolinderivats |
| ES2730958T3 (es) * | 2013-06-19 | 2019-11-13 | Aicuris Anti Infective Cures Gmbh | Letermovir amorfo y formulaciones farmacéuticas sólidas del mismo para administración oral |
-
2003
- 2003-05-02 DE DE10319612A patent/DE10319612A1/de not_active Withdrawn
-
2004
- 2004-04-17 DE DE502004003052T patent/DE502004003052D1/de not_active Expired - Lifetime
- 2004-04-17 PL PL04728119T patent/PL1622880T6/pl unknown
- 2004-04-17 NZ NZ543317A patent/NZ543317A/en not_active IP Right Cessation
- 2004-04-17 UA UAA200511418A patent/UA82519C2/uk unknown
- 2004-04-17 BR BRPI0410029A patent/BRPI0410029B8/pt not_active IP Right Cessation
- 2004-04-17 WO PCT/EP2004/004103 patent/WO2004096778A1/de active IP Right Grant
- 2004-04-17 DK DK04728119.1T patent/DK1622880T6/da active
- 2004-04-17 AU AU2004233978A patent/AU2004233978B2/en active Active
- 2004-04-17 MX MXPA05011707A patent/MXPA05011707A/es active IP Right Grant
- 2004-04-17 EP EP04728119.1A patent/EP1622880B3/de not_active Expired - Lifetime
- 2004-04-17 JP JP2006505178A patent/JP4733631B2/ja not_active Expired - Lifetime
- 2004-04-17 AT AT04728119T patent/ATE355280T1/de active
- 2004-04-17 PT PT04728119T patent/PT1622880E/pt unknown
- 2004-04-17 CN CNB2004800119284A patent/CN100393706C/zh not_active Expired - Lifetime
- 2004-04-17 SI SI200430301T patent/SI1622880T1/sl unknown
- 2004-04-17 CA CA2524069A patent/CA2524069C/en not_active Expired - Lifetime
- 2004-04-17 KR KR1020057020720A patent/KR100927063B1/ko not_active Expired - Lifetime
- 2004-04-17 ES ES04728119.1T patent/ES2284007T7/es active Active
- 2004-04-17 RU RU2005137276/04A patent/RU2360912C2/ru active
- 2004-04-23 AR ARP040101391A patent/AR044078A1/es active IP Right Grant
- 2004-04-26 US US10/832,109 patent/US7196086B2/en not_active Ceased
- 2004-04-28 UY UY28294A patent/UY28294A1/es not_active IP Right Cessation
- 2004-04-29 HN HN2004000146A patent/HN2004000146A/es unknown
- 2004-04-29 MY MYPI20041603A patent/MY144616A/en unknown
- 2004-04-30 PE PE2004000432A patent/PE20050145A1/es active IP Right Grant
- 2004-04-30 TW TW093112100A patent/TWI335912B/zh active
- 2004-04-30 CL CL200400930A patent/CL2004000930A1/es unknown
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2005
- 2005-10-20 IL IL171513A patent/IL171513A/en active IP Right Grant
- 2005-10-27 ZA ZA2005/08710A patent/ZA200508710B/en unknown
- 2005-10-29 EG EGNA2005000688 patent/EG25273A/xx active
- 2005-11-01 EC EC2005006138A patent/ECSP056138A/es unknown
- 2005-11-02 CO CO05111848A patent/CO5700764A2/es active IP Right Grant
- 2005-11-08 MA MA28581A patent/MA27794A1/fr unknown
- 2005-11-30 NO NO20055649A patent/NO333265B3/no active Protection Beyond IP Right Term
-
2007
- 2007-03-26 US US11/728,896 patent/US8513255B2/en active Active
- 2007-05-25 CY CY20071100709T patent/CY1106476T1/el unknown
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2015
- 2015-04-09 US US14/682,512 patent/USRE46791E1/en active Active
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2018
- 2018-04-17 NL NL300933C patent/NL300933I2/nl unknown
- 2018-04-21 HU HUS1800018C patent/HUS1800018I1/hu unknown
- 2018-06-15 HU HUS1800028C patent/HUS1800028I1/hu unknown
- 2018-06-29 CY CY2018019C patent/CY2018019I2/el unknown
- 2018-07-04 NO NO2018022C patent/NO2018022I1/no unknown
- 2018-07-06 FR FR18C1029C patent/FR18C1029I2/fr active Active
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2020
- 2020-07-21 US US16/934,363 patent/USRE49698E1/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2198879C2 (ru) * | 1996-09-25 | 2003-02-20 | Зенека Лимитед | Производные хиназолина, способы их получения, содержащие их фармацевтические композиции, способ достижения антиангиогенного и/или эффекта снижения проницаемости кровеносных сосудов у теплокровного животного |
Non-Patent Citations (1)
| Title |
|---|
| GRIBAUDO G. et al. The anticytomegaloviral aktivity of raltitrexed is abrogated in quiescent mouse fibroblasts that overexpress thymidylate synthase. VIRUS RESEARCH, 2001, 73(1), 57-65. * |
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