WO1999067243A1 - Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine - Google Patents
Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine Download PDFInfo
- Publication number
- WO1999067243A1 WO1999067243A1 PCT/EP1999/003863 EP9903863W WO9967243A1 WO 1999067243 A1 WO1999067243 A1 WO 1999067243A1 EP 9903863 W EP9903863 W EP 9903863W WO 9967243 A1 WO9967243 A1 WO 9967243A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pyrazolo
- pyrimidin
- formula
- pyrimidine
- thione
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Definitions
- the invention relates to pyrazolo [3,4-d] pyrimidin-4 (5H) -ones and pyrazolo [3,4-d] pyrimidin-4 (5H) -thiones and their tautomers which contain a benzyl radical in the 2-position , Process for their preparation and their use as medicaments, in particular for the treatment of both epilepsy of various forms and of allergic diseases such as bronchial asthma, allergic rhinoconjunctivitis or atopic dermatitis.
- the adenosine receptor is a target for influencing disregulations in various organ systems (e.g. central nervous system, respiratory tract, etc.)
- Pyrazolo [3,4-d] pyrimidines are pharmacologically interesting compounds due to their structural similarities to adenine.
- Benzyl radical in the 2-position are also not known.
- Amino-pyrazole-4-carboxylic acid esters can be obtained by benzylating 3-aminopyrazole-4-carboxylic acid esters [S. Senda, K. Hirota, G.-N. Yang,
- bronchial asthma Various forms of allergic / asthmatic diseases, such as bronchial asthma, can also not be adequately treated with the existing medication. Various forms of allergic / asthmatic diseases, such as bronchial asthma, can also not be adequately treated with the existing medication.
- the invention is therefore based on the object of providing compounds with favorable pharmacological properties which can be used as medicaments, in particular for the treatment of epilepsy and various allergic / asthmatic diseases.
- these new compounds are 2-ar (alkyl) -pyrazolo [3,4-d] pyrimidin-4 (5H) -one and 2-ar (alkyl) -pyrazolo [3,4-d] pyrimidin-4 (5H) -thione of the general formula 1
- X is oxygen and sulfur
- Y is halogen, dC-alkyl, -CC 4 alkoxy, trifluoromethyl or trifluoromethoxy.
- the process for the preparation of compounds of formula 1 and their tautomers with X equal to oxygen is based on the cyclization of 3-aminopyrazole-4-carboxylic acid esters or 3-aminopyrazole-4-carboxylic acid amides of the general formula 2 in formamide at temperatures between 100 and 180 ° C. .
- Z is hydroxy, alkoxy or amino
- Y is halogen, dC 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, trifluoromethoxy.
- the process for the preparation of compounds of formula 1 and their tautomers with X equal to sulfur is based on the substitution of compounds of formula 1 and their tautomers with X equal to oxygen by sulfur using phosphorus pentasulfide or 2,4-bis- (4-methoxyphenyl) -1 , 3-dithia-2,4-diphosphetane-2,4-disulfide.
- the process for the preparation of compounds of formula 2 is based on 3-aminopyrazole-4-carboxylic acid derivatives.
- the compounds of formula 2 are obtained by alkylation under phase transfer conditions with a suitably substituted benzyl halide.
- the compounds according to the invention or their pharmaceutically usable salts are suitable for the preparation of pharmaceutical compositions.
- the pharmaceutical compositions or medicaments can contain one or more of the compounds according to the invention.
- the usual pharmaceutical carriers and auxiliary substances can be used for the production of the pharmaceutical preparations.
- the drugs can be administered, for example, parenterally (e.g. intravenously, intramuscularly subcutaneously), topically (intranasally, by inhalation) or orally.
- the application forms can be prepared by methods which are generally known and customary in pharmaceutical practice.
- the compounds according to the invention have strong anticonvulsant or antiallergic / antiasthmatic effects.
- the compounds according to the invention were in vivo after ip application to mice or rats (po application) according to the international standard (Pharmac.Weekblad, Sc.Ed. 14, 132 (1992) and Antiepileptic Drugs, Third.Ed., Raven Press , New York 1989) tested for their anticonvulsant activity (Table 1). Analogous results were obtained for the oral effect.
- the compounds according to the invention were tested in vivo after oral administration to the male guinea pig for an anti-asthmatic effect, the inhibition of the immigration of the eosinophilic granulocytes into the lungs being determined.
- the eosinophilic granulocytes were counted microscopically in a Neubauer chamber.
- the Becton Dickinson Test kit No. 5877 for eosinophils was used for staining.
- the test kit uses phloxin B as a selective stain for eosinophils.
- the eosinophils were counted in the BAL and the eosinophils were calculated in million / animal.
- the test substances were administered orally 2 hours before the allergen challenge.
- compound 3 at a dose of 100 mg / kg inhibits the bronchial asthma characteristic migration of eosinophilic granulocytes into the lungs by 74%.
- the compounds according to the invention are suitable, for example, for the treatment of bronchial asthma, rhinoconjunctivitis and atopic dermatitis.
- the compounds of the invention bind subtype-specifically (A3) to the adenosine receptor.
- Adenosine A 3 receptor antagonists can prevent mediator release by blocking their receptors. It has recently been shown that adenosine A 3 receptor antagonists prevent the lowering of the intracellular cAMP concentration in the eosinophilic granulocytes and thereby also suppress the release of the cytokines and other mediators from these cells (Jacobson et al., 1995). On the one hand, this can alleviate the uncomfortable acute symptoms that severely impair the quality of life and, on the other hand, suppress the inflammatory processes underlying the disease.
- the precipitated crude product is purified from a suitable solvent, preferably ethanol, by means of recrystallization (UK).
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9906552-5A BR9906552A (pt) | 1998-06-22 | 1999-06-04 | Pirazolo (3,4-d) pirimidinas com efeito anticonvulsivo e antialérgico/antiasmático |
CA002301107A CA2301107A1 (en) | 1998-06-22 | 1999-06-04 | Pyrazolo(3,4-d)pyrimidines with anticonvulsive and antiallergic/antiasthmatic action |
SK225-2000A SK283506B6 (sk) | 1998-06-22 | 1999-06-04 | Pyrazolo(3,4-d)pyrimidín, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a použitie tejto zlúčeniny |
EA200000249A EA002768B1 (ru) | 1998-06-22 | 1999-06-04 | ПИРАЗОЛО [3,4-d] ПИРИМИДИНЫ С ПРОТИВОКОНВУЛЬСИВНЫМ, ПРОТИВОАЛЛЕРГИЧЕСКИМ/ПРОТИВОАСТМАТИЧЕСКИМ ДЕЙСТВИЕМ |
DK99929137T DK1005471T3 (da) | 1998-06-22 | 1999-06-04 | Antikonvulsivt og antiallergisk/antiastmatisk virkende pyrazolo(3,4-D)pyrimidiner |
EP99929137A EP1005471B1 (de) | 1998-06-22 | 1999-06-04 | Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine |
DE59902538T DE59902538D1 (de) | 1998-06-22 | 1999-06-04 | Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine |
KR1020007001746A KR100350823B1 (ko) | 1998-06-22 | 1999-06-04 | 항경련 효과와 항알레르기/항천식 효과를 갖는피라졸로(3,4-d)피리미딘 |
JP2000555896A JP2002518499A (ja) | 1998-06-22 | 1999-06-04 | 抗痙攣作用および抗アレルギー/抗喘息作用を有するピラゾロ(3,4−d)ピリミジン |
AT99929137T ATE223412T1 (de) | 1998-06-22 | 1999-06-04 | Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine |
NZ502880A NZ502880A (en) | 1998-06-22 | 1999-06-04 | Pyrazolo(3,4-d)pyrimidines with anticonvulsive and antiallergic/antiasthmatic action |
AU46054/99A AU748090B2 (en) | 1998-06-22 | 1999-06-04 | Pyrazolo(3,4-d)pyrimidines with anticonvulsive and antiallergic/antiasthmatic action |
HU0003783A HUP0003783A3 (en) | 1998-06-22 | 1999-06-04 | Pyrazolo[3,4-d]pyrimidines with anticonvulsive and antiallergic/antiasthmatic action and process for the preparation thereof |
PL99338897A PL338897A1 (en) | 1998-06-22 | 1999-06-04 | Anticonvulsant and antiallergic/antihistaminic pyrazol-[3,4-d]pyrimidines exhibiting affinity in respect to an adenosine receptor and method of obtaining them |
IL13443999A IL134439A0 (en) | 1998-06-22 | 1999-06-04 | Pyrazolo (3,4-d) pyrimidines with anticonvulsive and antiallergic/antiasthmatic action |
BG104150A BG104150A (en) | 1998-06-22 | 2000-02-10 | PYRAZOLO(3,4-d)PYRIMIDINES WITH ANTICONVULSIVE AND ANTIALLERGIC/ANTIASTHMATIC EFFECT |
NO20000748A NO314760B1 (no) | 1998-06-22 | 2000-02-15 | Pyrazolo(3,4-d)pyrimidiner, fremgangsmåte for fremstilling, farmasöytiske sammensetninger inneholdende disse, samt anvendelse av pyrimidinene |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19827679A DE19827679A1 (de) | 1998-06-22 | 1998-06-22 | Adenosinrezeptoraffine, antikonvulsiv und antiallergisch/antiasthmatisch wirkende Pyrazolo[3,4-d]pyrimidine und Verfahren zu deren Herstellung |
DE19827679.6 | 1998-06-22 | ||
CZ2000594A CZ288195B6 (en) | 1998-06-22 | 1999-06-04 | Derivative of pyrazolo[3,4-d]pyrimidines exhibiting anticonvulsive a antiallergic/anti-asthmatic activity, process of its preparation and use |
CA002297706A CA2297706A1 (en) | 1998-06-22 | 2000-02-02 | Anticonvulsive and antiallergic/anti-asthmatic pyrazolo-(3,4-d)pyrimidines having affinity for the adenosine receptor, and process for their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999067243A1 true WO1999067243A1 (de) | 1999-12-29 |
Family
ID=27171156
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/003863 WO1999067243A1 (de) | 1998-06-22 | 1999-06-04 | Antikonvulsiv und antiallergisch/antiasthmatisch wirkende pyrazolo(3,4-d)pyrimidine |
Country Status (26)
Country | Link |
---|---|
US (1) | US6054460A (de) |
EP (1) | EP1005471B1 (de) |
JP (1) | JP2002518499A (de) |
CN (1) | CN1126753C (de) |
AT (1) | ATE223412T1 (de) |
AU (1) | AU748090B2 (de) |
BG (1) | BG104150A (de) |
BR (1) | BR9906552A (de) |
CA (2) | CA2301107A1 (de) |
CZ (1) | CZ288195B6 (de) |
DE (2) | DE19827679A1 (de) |
DK (1) | DK1005471T3 (de) |
EA (1) | EA002768B1 (de) |
ES (1) | ES2182541T3 (de) |
HU (1) | HUP0003783A3 (de) |
IL (1) | IL134439A0 (de) |
NO (1) | NO314760B1 (de) |
NZ (1) | NZ502880A (de) |
PL (1) | PL338897A1 (de) |
PT (1) | PT1005471E (de) |
RU (1) | RU2194050C2 (de) |
SK (1) | SK283506B6 (de) |
TR (1) | TR200000473T1 (de) |
TW (1) | TW449476B (de) |
WO (1) | WO1999067243A1 (de) |
ZA (1) | ZA200000742B (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10042092A1 (de) * | 2000-08-26 | 2002-03-07 | Dresden Arzneimittel | Antikonvulsiv wirkende 2,5-Dihydro-pyrazolo(3,4-d)pyrimidin-4-one und Verfahren zu deren Darstellung |
WO2012125400A1 (en) * | 2011-03-14 | 2012-09-20 | Acorn Biomedical, Inc. | Compositions and methods using adenosine a3 receptor antagonists for the treatment of inflammatory eye diseases |
CN106749271B (zh) * | 2016-12-07 | 2019-04-05 | 青岛科技大学 | 一类[1,2,4]-三氮唑并[1,5-a]嘧啶酮类杂环化合物、其制备方法及其用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988000192A1 (en) * | 1986-06-26 | 1988-01-14 | Warner-Lambert Company | 5-SUBSTITUTED PYRAZOLO[4,3-d]PYRIMIDIN-7-ONES |
DE19649460A1 (de) * | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
-
1998
- 1998-06-22 DE DE19827679A patent/DE19827679A1/de not_active Withdrawn
-
1999
- 1999-06-04 IL IL13443999A patent/IL134439A0/xx unknown
- 1999-06-04 AU AU46054/99A patent/AU748090B2/en not_active Ceased
- 1999-06-04 PL PL99338897A patent/PL338897A1/xx unknown
- 1999-06-04 CN CN99801435A patent/CN1126753C/zh not_active Expired - Fee Related
- 1999-06-04 PT PT99929137T patent/PT1005471E/pt unknown
- 1999-06-04 ES ES99929137T patent/ES2182541T3/es not_active Expired - Lifetime
- 1999-06-04 TR TR2000/00473T patent/TR200000473T1/xx unknown
- 1999-06-04 CZ CZ2000594A patent/CZ288195B6/cs not_active IP Right Cessation
- 1999-06-04 CA CA002301107A patent/CA2301107A1/en not_active Abandoned
- 1999-06-04 EP EP99929137A patent/EP1005471B1/de not_active Expired - Lifetime
- 1999-06-04 WO PCT/EP1999/003863 patent/WO1999067243A1/de active IP Right Grant
- 1999-06-04 DE DE59902538T patent/DE59902538D1/de not_active Expired - Fee Related
- 1999-06-04 HU HU0003783A patent/HUP0003783A3/hu unknown
- 1999-06-04 NZ NZ502880A patent/NZ502880A/en unknown
- 1999-06-04 SK SK225-2000A patent/SK283506B6/sk unknown
- 1999-06-04 EA EA200000249A patent/EA002768B1/ru not_active IP Right Cessation
- 1999-06-04 BR BR9906552-5A patent/BR9906552A/pt not_active IP Right Cessation
- 1999-06-04 RU RU2000104282/04A patent/RU2194050C2/ru not_active IP Right Cessation
- 1999-06-04 AT AT99929137T patent/ATE223412T1/de not_active IP Right Cessation
- 1999-06-04 DK DK99929137T patent/DK1005471T3/da active
- 1999-06-04 JP JP2000555896A patent/JP2002518499A/ja active Pending
- 1999-06-15 US US09/333,709 patent/US6054460A/en not_active Expired - Fee Related
- 1999-06-17 TW TW088110197A patent/TW449476B/zh active
-
2000
- 2000-01-01 ZA ZA200000742A patent/ZA200000742B/xx unknown
- 2000-02-02 CA CA002297706A patent/CA2297706A1/en not_active Abandoned
- 2000-02-10 BG BG104150A patent/BG104150A/xx unknown
- 2000-02-15 NO NO20000748A patent/NO314760B1/no not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988000192A1 (en) * | 1986-06-26 | 1988-01-14 | Warner-Lambert Company | 5-SUBSTITUTED PYRAZOLO[4,3-d]PYRIMIDIN-7-ONES |
DE19649460A1 (de) * | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
Non-Patent Citations (3)
Title |
---|
EISENAECHER TH ET AL: "UEBER NEUE PYRAZOLVERBINDUNGEN: 6. MITTEILUNG: PYRAZOLO 3,4 -DPYRIMIDINYLESSIGSAEUREDERIVATE", PHARMAZIE, vol. 46, no. 10, 1 October 1991 (1991-10-01), pages 747/748, XP002040530, ISSN: 0031-7144 * |
EL HEDI JELLALI M ET AL: "Acylation and alkylation of 4-aminopyrazolo[3,4-d]pyrimidine", TETRAHEDRON (TETRAB);1975; VOL.31 (6); PP.587-91, Inst. Chim. Subst. Nat.;Gif-sur-Yvette; Fr., XP002115520 * |
GATTA F ET AL: "Pyrazolo[3,4-d]pyrimidines related to lonidamine", J. HETEROCYCL. CHEM. (JHTCAD,0022152X);1989; VOL.26 (3); PP.613-18, Ist. Super. Sanita;Lab. Chim. Farm.; Rome; 00161; Italy (IT), XP002115519 * |
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