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RU2000104282A - Pyrazole [3,4-D] Pyrimidines with anticonvulsant and anti-allergic / anti-asthmatic effects - Google Patents

Pyrazole [3,4-D] Pyrimidines with anticonvulsant and anti-allergic / anti-asthmatic effects

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Publication number
RU2000104282A
RU2000104282A RU2000104282/04A RU2000104282A RU2000104282A RU 2000104282 A RU2000104282 A RU 2000104282A RU 2000104282/04 A RU2000104282/04 A RU 2000104282/04A RU 2000104282 A RU2000104282 A RU 2000104282A RU 2000104282 A RU2000104282 A RU 2000104282A
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RU
Russia
Prior art keywords
pyrazole
pyrimidin
compound
alkoxy
trifluoromethyl
Prior art date
Application number
RU2000104282/04A
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Russian (ru)
Other versions
RU2194050C2 (en
Inventor
Томас Арнольд
Ганс-Иоахим ЛАНКАУ
Манфред Менцер
Ангелика Росток
Кристине Тобер
Клаус Унферферт
Original Assignee
Арцнаймиттельверк Дрезден Гмбх
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19827679A external-priority patent/DE19827679A1/en
Application filed by Арцнаймиттельверк Дрезден Гмбх filed Critical Арцнаймиттельверк Дрезден Гмбх
Publication of RU2000104282A publication Critical patent/RU2000104282A/en
Application granted granted Critical
Publication of RU2194050C2 publication Critical patent/RU2194050C2/en

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Claims (9)

1. Соединение общей формулы 1
Figure 00000001

или его таутомер, где Х - кислород или сера, Y - галоид, С1-С4-алкил, С1-С4-алкоксигруппа, трифторметил или трифторметоксигруппа, m - 1 или 2.1. The compound of General formula 1
Figure 00000001

or a tautomer thereof, where X is oxygen or sulfur, Y is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy group, trifluoromethyl or trifluoromethoxy group, m is 1 or 2. 2. Соединение по п. 1, отличающееся тем, что оно представляет собой
2-(2-фторбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-хлорбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-бромбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-иодбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-тpифтopмeтилбeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(2-мeтилбeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(3-тpифтopмeтилбeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(2,6-дифторбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-хлор-6-фторбензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2,6-диxлopбeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(2,4-диxлopбeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(4-мeтoкcибeнзил)-пиpaзoл[3,4-d] пиpимидин-4(5H)-oн;
2-(2-хлор-4,5-метилендиоксибензил)-пиразол[3,4-d] пиримидин-4(5Н)-он;
2-(2-хлорбензил)-пиразол[3,4-d] пиримидин-4(5Н)-тион;
2-(2-бромбензил)-пиразол[3,4-d] пиримидин-4(5Н)-тион;
2-(2-иодбензил)-пиразол[3,4-d] пиримидин-4(5Н)-тион;
2-(2-трифторметилбензил)-пиразол[3,4-d] пиримидин-4(5Н)-тион;
2-(2,6-дифторбензил)-пиразол[3,4-d] пиримидин-4(5Н)-тион.2. The compound according to claim 1, characterized in that it represents
2- (2-fluorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-chlorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-bromobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-iodobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-trifluoromethylbenzyl) -pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-methylbenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (3-trifluoromethylbenzyl) -pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2,6-difluorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-chloro-6-fluorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2,6-dichlorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2,4-Dichlorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (4-methoxybenzyl) pyrazole [3,4-d] pyrimidine-4 (5H) -one;
2- (2-chloro-4,5-methylenedioxybenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -one;
2- (2-chlorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -thione;
2- (2-bromobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -thione;
2- (2-iodobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -thione;
2- (2-trifluoromethylbenzyl) -pyrazole [3,4-d] pyrimidin-4 (5H) -thione;
2- (2,6-difluorobenzyl) pyrazole [3,4-d] pyrimidin-4 (5H) -thion. 3. Соединение по п. 1 или 2 для приготовления лекарственных средств для лечения, в частности, различных форм эпилепсии. 3. The compound according to claim 1 or 2 for the preparation of medicines for the treatment of, in particular, various forms of epilepsy. 4. Соединение по п. 1 или 2 для приготовления лекарственных средств для лечения, в частности, аллергических/астматических заболеваний. 4. The compound according to claim 1 or 2 for the preparation of medicines for the treatment of, in particular, allergic / asthmatic diseases. 5. Способ получения соединения общей формулы 1
Figure 00000002

или его таутомера,
где Х - кислород, Y - галоид, С1-С4-алкил, С1-С4-алкоксигруппа, трифторметил или трифторметоксигруппа, m - 1 или 2,
отличающийся тем, что соединение формулы 2
Figure 00000003

где Z - гидроксил, алкоксигруппа или аминогруппа, Y - галоид, С1-С4-алкил, С1-С4-алкоксигруппа, трифторметил или трифторметоксигруппа, и m - 1 или 2,
подвергают циклизации с формамидом.5. A method of obtaining a compound of General formula 1
Figure 00000002

or his tautomer,
where X is oxygen, Y is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl or trifluoromethoxy, m is 1 or 2,
characterized in that the compound of formula 2
Figure 00000003

where Z is hydroxyl, alkoxy or amino, Y is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl or trifluoromethoxy, and m is 1 or 2,
subjected to cyclization with formamide. 6. Способ по п. 5, отличающийся тем, что для циклизации упомянутых амидов 3-аминопиразол-4-карбоновой кислоты формулы 2 используют сложные эфиры ортомуравьиной кислоты или смеси муравьиной кислоты с уксусным ангидридом. 6. The method according to p. 5, characterized in that for the cyclization of the mentioned amides of 3-aminopyrazole-4-carboxylic acid of formula 2, esters of orthoformic acid or a mixture of formic acid with acetic anhydride are used. 7. Способ получения соединения общей формулы 1
Figure 00000004

или его таутомера,
где Х - сера, Y - галоид, С1-С4-алкил, С1-С4-алкоксигруппа, трифторметил или трифторметоксигруппа, m - 1 или 2,
отличающийся тем, что соединение общей формулы 1
Figure 00000005

или его таутомер,
где Х - кислород, Y - галоид, С1-С4-алкил, С1-С4-алкоксигруппа, трифторметил или трифторметоксигруппа, m - 1 или 2,
вводят в реакцию с пятисернистым фосфором или 2,4-бис(4-метоксифенил)-1,3-дитиа-2,4-дифосфэтан-2,4-дисульфидом.7. A method of obtaining a compound of General formula 1
Figure 00000004

or his tautomer,
where X is sulfur, Y is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl or trifluoromethoxy, m is 1 or 2,
characterized in that the compound of general formula 1
Figure 00000005

or its tautomer,
where X is oxygen, Y is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl or trifluoromethoxy, m is 1 or 2,
enter into reaction with pentasulfide phosphorus or 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphethane-2,4-disulfide. 8. Фармацевтическая композиция, содержащая активное вещество в сочетании с одним или несколькими физиологически переносимыми вспомогательными веществами и/или носителями и при необходимости с разбавителем, отличающаяся тем, что активным веществом является один или несколько пиразол[3,4-d] пиримидинов по п. 1 либо их фармацевтически приемлемые соли. 8. A pharmaceutical composition containing an active substance in combination with one or more physiologically tolerable excipients and / or carriers and, if necessary, a diluent, characterized in that the active substance is one or more pyrazole [3,4-d] pyrimidines according to claim 1 or their pharmaceutically acceptable salts. 9. Фармацевтическая композиция по п. 8, отличающаяся тем, что активным веществом является один или несколько пиразол[3,4-d] пиримидинов по п. 2 либо их фармацевтически приемлемые соли. 9. The pharmaceutical composition according to claim 8, characterized in that the active substance is one or more pyrazole [3,4-d] pyrimidines according to claim 2 or their pharmaceutically acceptable salts.
RU2000104282/04A 1998-06-22 1999-06-04 Pyrazole[3,4-d]pyrimidines showing anticonvulsant and antiallergic/antiasthmatic effect, methods of their synthesis (variants) and pharmaceutical composition RU2194050C2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19827679.6 1998-06-22
DE19827679A DE19827679A1 (en) 1998-06-22 1998-06-22 New pyrazolo(3,4-d)pyrimidine derivative adenosine A3 receptor antagonists, used for treating epilepsy, asthma or allergy
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 (2)

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RU2000104282A true RU2000104282A (en) 2002-03-27
RU2194050C2 RU2194050C2 (en) 2002-12-10

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US (1) US6054460A (en)
EP (1) EP1005471B1 (en)
JP (1) JP2002518499A (en)
CN (1) CN1126753C (en)
AT (1) ATE223412T1 (en)
AU (1) AU748090B2 (en)
BG (1) BG104150A (en)
BR (1) BR9906552A (en)
CA (2) CA2301107A1 (en)
CZ (1) CZ288195B6 (en)
DE (2) DE19827679A1 (en)
DK (1) DK1005471T3 (en)
EA (1) EA002768B1 (en)
ES (1) ES2182541T3 (en)
HU (1) HUP0003783A3 (en)
IL (1) IL134439A0 (en)
NO (1) NO314760B1 (en)
NZ (1) NZ502880A (en)
PL (1) PL338897A1 (en)
PT (1) PT1005471E (en)
RU (1) RU2194050C2 (en)
SK (1) SK283506B6 (en)
TR (1) TR200000473T1 (en)
TW (1) TW449476B (en)
WO (1) WO1999067243A1 (en)
ZA (1) ZA200000742B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10042092A1 (en) * 2000-08-26 2002-03-07 Dresden Arzneimittel Anticonvulsant 2,5-dihydro-pyrazolo (3,4-d) pyrimidin-4-ones and process for their preparation
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 (en) * 2016-12-07 2019-04-05 青岛科技大学 A kind of [1,2,4]-triazole simultaneously [1,5-a] Pyrimdinone heterocyclic compound, Its Preparation Method And Use

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* Cited by examiner, † Cited by third party
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
DE3712735A1 (en) * 1987-04-15 1988-11-10 Boehringer Mannheim Gmbh NEW PYRAZOLO (3,4-D) PYRIMIDINE, METHOD FOR THE PRODUCTION AND USE THEREOF AS A MEDICINAL PRODUCT
GB9114760D0 (en) * 1991-07-09 1991-08-28 Pfizer Ltd Therapeutic agents
DE19649460A1 (en) * 1996-11-26 1998-05-28 Bayer Ag New substituted pyrazole derivatives

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