FI120403B - 4-(2-amino-6-(syklopropyyliamino)-9H-purin-9-yyli)-2-syklopenteeni-1-metanoli-sukkinaatti viruksia torjuvana aineena - Google Patents
4-(2-amino-6-(syklopropyyliamino)-9H-purin-9-yyli)-2-syklopenteeni-1-metanoli-sukkinaatti viruksia torjuvana aineena Download PDFInfo
- Publication number
- FI120403B FI120403B FI970786A FI970786A FI120403B FI 120403 B FI120403 B FI 120403B FI 970786 A FI970786 A FI 970786A FI 970786 A FI970786 A FI 970786A FI 120403 B FI120403 B FI 120403B
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- Finland
- Prior art keywords
- compound
- amino
- purin
- cyclopropylamino
- active ingredient
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Seasonings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9417249 | 1994-08-26 | ||
| GB9417249A GB9417249D0 (en) | 1994-08-26 | 1994-08-26 | A novel salt |
| PCT/GB1995/002014 WO1996006844A1 (en) | 1994-08-26 | 1995-08-25 | 4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)-2-cyclopentene-1-methanol succinate as antiviral agent |
| GB9502014 | 1995-08-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970786L FI970786L (fi) | 1997-02-25 |
| FI970786A0 FI970786A0 (fi) | 1997-02-25 |
| FI120403B true FI120403B (fi) | 2009-10-15 |
Family
ID=10760434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970786A FI120403B (fi) | 1994-08-26 | 1997-02-25 | 4-(2-amino-6-(syklopropyyliamino)-9H-purin-9-yyli)-2-syklopenteeni-1-metanoli-sukkinaatti viruksia torjuvana aineena |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0777669B1 (da) |
| JP (1) | JPH10505593A (da) |
| KR (1) | KR100376240B1 (da) |
| CN (1) | CN1051550C (da) |
| AT (1) | ATE220067T1 (da) |
| AU (1) | AU702618B2 (da) |
| BR (1) | BR9508629A (da) |
| CA (1) | CA2198010C (da) |
| DE (1) | DE69527294T2 (da) |
| DK (1) | DK0777669T3 (da) |
| ES (1) | ES2179110T3 (da) |
| FI (1) | FI120403B (da) |
| GB (1) | GB9417249D0 (da) |
| HU (1) | HU221302B1 (da) |
| IL (1) | IL115074A (da) |
| MX (1) | MX9701273A (da) |
| NO (1) | NO315200B1 (da) |
| NZ (1) | NZ291862A (da) |
| PT (1) | PT777669E (da) |
| RU (1) | RU2145324C1 (da) |
| SI (1) | SI0777669T1 (da) |
| WO (1) | WO1996006844A1 (da) |
| ZA (1) | ZA957166B (da) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY115461A (en) | 1995-03-30 | 2003-06-30 | Wellcome Found | Synergistic combinations of zidovudine, 1592u89 and 3tc |
| EP1019056A1 (en) * | 1997-05-17 | 2000-07-19 | Glaxo Group Limited | Antiviral combinations containing the carbocyclic nucleoside 1592u89 |
| BR9809127A (pt) * | 1997-05-17 | 2000-08-01 | Glaxo Group Ltd | Combinação, formulação farmacêutica, processo para o tratamento de uma infecção por hiv em um animal infectado, uso de (-) -(1s,4r)-4-[2-amino-6-(ciclopropil amino)-9h-purin-9-il)-2-ciclopenteno-1-metanol, e, pacote de paciente |
| GB9709945D0 (en) * | 1997-05-17 | 1997-07-09 | Glaxo Group Ltd | A novel salt |
| CZ298144B6 (cs) * | 1997-11-27 | 2007-07-04 | Lonza Ag | Zpusob výroby (1S,4R)- nebo (1R,4S)-4-(2-amino-6-chlor-9-H-purin-9-yl)-2-cyklopenten-1-methanolu |
| GB9802472D0 (en) * | 1998-02-06 | 1998-04-01 | Glaxo Group Ltd | Pharmaceutical compositions |
| GB9903091D0 (en) * | 1999-02-12 | 1999-03-31 | Glaxo Group Ltd | Therapeutic nucleoside compound |
| GB9918035D0 (en) * | 1999-07-30 | 1999-09-29 | Novartis Ag | Organic compounds |
| BR0109602A (pt) * | 2000-03-30 | 2004-06-29 | Bristol Myers Squibb Co | Glóbulos de liberação controlada contendo estavudina |
| NZ524252A (en) * | 2000-07-20 | 2004-03-26 | Lauras As | Cox-2 inhibitors for treating HIV and AIDS |
| US7462733B2 (en) | 2001-07-30 | 2008-12-09 | University Of Southern California | Preparation and use of α-keto phosphonates |
| RU2242243C2 (ru) * | 2001-09-27 | 2004-12-20 | Вертелецкий Павел Васильевич | Композиции и способы потенцирования терапевтических эффектов интерферонов |
| AU2004287416C1 (en) * | 2003-10-27 | 2010-09-09 | Merck Sharp & Dohme Corp. | CCR-2 antagonist salt |
| EP1905772A1 (en) * | 2006-09-28 | 2008-04-02 | Esteve Quimica, S.A. | Process for the preparation of abacavir |
| EP2305680A3 (en) | 2009-09-30 | 2011-05-18 | Aurobindo Pharma Limited | Novel salts of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol |
| CN103282369A (zh) | 2011-04-08 | 2013-09-04 | 劳乐斯实验室私营有限公司 | 抗逆转录病毒化合物与抗氧化酸的固体形式、其制备方法以及其药物组合物 |
| JP6391561B2 (ja) | 2013-02-27 | 2018-09-19 | 国立大学法人京都大学 | がんの予防または治療用医薬組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025492A1 (de) * | 1980-07-04 | 1982-02-04 | Siemens AG, 1000 Berlin und 8000 München | Filterelement fuer die optische nachrichtentechnik |
| IE830186L (en) * | 1982-02-01 | 1983-08-01 | Syntex Inc | Purines |
| US5003462A (en) * | 1988-05-31 | 1991-03-26 | International Business Machines Corporation | Apparatus and method for implementing precise interrupts on a pipelined processor with multiple functional units with separate address translation interrupt means |
| GB8815265D0 (en) * | 1988-06-27 | 1988-08-03 | Wellcome Found | Therapeutic nucleosides |
| MY104575A (en) * | 1989-12-22 | 1994-04-30 | The Wellcome Foundation Ltd | Therapeutic nucleosides. |
| IL104283A (en) * | 1992-12-30 | 1996-12-05 | Agis Ind 1983 Ltd | Non-emulsion antiviral topical pharmaceutical composition comprising acyclovir an aqueous gel agent and an alkali oleate |
-
1994
- 1994-08-26 GB GB9417249A patent/GB9417249D0/en active Pending
-
1995
- 1995-08-25 EP EP95929954A patent/EP0777669B1/en not_active Expired - Lifetime
- 1995-08-25 NZ NZ291862A patent/NZ291862A/en not_active IP Right Cessation
- 1995-08-25 IL IL11507495A patent/IL115074A/en not_active IP Right Cessation
- 1995-08-25 DK DK95929954T patent/DK0777669T3/da active
- 1995-08-25 AU AU33509/95A patent/AU702618B2/en not_active Expired
- 1995-08-25 HU HU9701756A patent/HU221302B1/hu unknown
- 1995-08-25 JP JP8508550A patent/JPH10505593A/ja active Pending
- 1995-08-25 CA CA002198010A patent/CA2198010C/en not_active Expired - Lifetime
- 1995-08-25 ES ES95929954T patent/ES2179110T3/es not_active Expired - Lifetime
- 1995-08-25 MX MX9701273A patent/MX9701273A/es active IP Right Grant
- 1995-08-25 WO PCT/GB1995/002014 patent/WO1996006844A1/en not_active Ceased
- 1995-08-25 KR KR1019970701213A patent/KR100376240B1/ko not_active Expired - Lifetime
- 1995-08-25 CN CN95194789A patent/CN1051550C/zh not_active Expired - Lifetime
- 1995-08-25 PT PT95929954T patent/PT777669E/pt unknown
- 1995-08-25 DE DE69527294T patent/DE69527294T2/de not_active Expired - Lifetime
- 1995-08-25 AT AT95929954T patent/ATE220067T1/de active
- 1995-08-25 ZA ZA9507166A patent/ZA957166B/xx unknown
- 1995-08-25 SI SI9530614T patent/SI0777669T1/xx unknown
- 1995-08-25 RU RU97104483A patent/RU2145324C1/ru active
- 1995-08-25 BR BR9508629A patent/BR9508629A/pt not_active Application Discontinuation
-
1997
- 1997-02-25 NO NO19970847A patent/NO315200B1/no not_active IP Right Cessation
- 1997-02-25 FI FI970786A patent/FI120403B/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR970705563A (ko) | 1997-10-09 |
| DK0777669T3 (da) | 2002-10-28 |
| CA2198010A1 (en) | 1996-03-07 |
| NO315200B1 (no) | 2003-07-28 |
| SI0777669T1 (en) | 2002-12-31 |
| CN1051550C (zh) | 2000-04-19 |
| RU2145324C1 (ru) | 2000-02-10 |
| NO970847L (no) | 1997-02-25 |
| ATE220067T1 (de) | 2002-07-15 |
| NO970847D0 (no) | 1997-02-25 |
| PT777669E (pt) | 2002-11-29 |
| CA2198010C (en) | 2006-05-02 |
| FI970786L (fi) | 1997-02-25 |
| MX9701273A (es) | 1997-05-31 |
| WO1996006844A1 (en) | 1996-03-07 |
| ES2179110T3 (es) | 2003-01-16 |
| HU221302B1 (en) | 2002-09-28 |
| AU3350995A (en) | 1996-03-22 |
| CN1156456A (zh) | 1997-08-06 |
| FI970786A0 (fi) | 1997-02-25 |
| HUT77222A (hu) | 1998-03-02 |
| EP0777669A1 (en) | 1997-06-11 |
| GB9417249D0 (en) | 1994-10-19 |
| AU702618B2 (en) | 1999-02-25 |
| JPH10505593A (ja) | 1998-06-02 |
| ZA957166B (en) | 1997-02-25 |
| KR100376240B1 (ko) | 2003-06-11 |
| EP0777669B1 (en) | 2002-07-03 |
| IL115074A0 (en) | 1995-12-08 |
| NZ291862A (en) | 1998-02-26 |
| IL115074A (en) | 1998-10-30 |
| DE69527294T2 (de) | 2003-02-13 |
| DE69527294D1 (en) | 2002-08-08 |
| BR9508629A (pt) | 1997-11-25 |
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