RU99104796A - THIENOPYRIMIDINES - Google Patents

THIENOPYRIMIDINES

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Publication number
RU99104796A
RU99104796A RU99104796/04A RU99104796A RU99104796A RU 99104796 A RU99104796 A RU 99104796A RU 99104796/04 A RU99104796/04 A RU 99104796/04A RU 99104796 A RU99104796 A RU 99104796A RU 99104796 A RU99104796 A RU 99104796A
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RU
Russia
Prior art keywords
formula
compound
pyrimidine
physiologically acceptable
acceptable salts
Prior art date
Application number
RU99104796/04A
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Russian (ru)
Other versions
RU2199541C2 (en
Inventor
Йонас Рохус
Пьер ШЕЛЛИНГ
Франц-Вернер КЛУКСЕН
Мария Кристадлер
Original Assignee
Мерк Патент Гмбх
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Publication date
Priority claimed from DE19632423A external-priority patent/DE19632423A1/en
Application filed by Мерк Патент Гмбх filed Critical Мерк Патент Гмбх
Publication of RU99104796A publication Critical patent/RU99104796A/en
Application granted granted Critical
Publication of RU2199541C2 publication Critical patent/RU2199541C2/en

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Claims (9)

1. Соединения формулы I
Figure 00000001

где R1, R2 независимо друг от друга обозначают H, A, OA, алкилен, алкинил, NO2, CF3 или Nal, причем один из остатков R1 или R2 всегда не является H,
R1 и R2 совместно обозначают также алкилен с 3 - 5 атомами углерода,
R3, R4 независимо друг от друга обозначают H, A, OA, Nal, NO2, NH2, NHA или NAA',
R3 и R4 совместно обозначают также -O-CH2-CH2-, -O-CH2-O или -O-CH2CH2-O-,
A, A', независимо друг от друга обозначают алкил с 1 - 6 атомами углерода,
X обозначает незамещенный или одно-, двух- или трехкратно замещенный A, Nal или CF3-группой ненасыщенный 5 - 70членный гетероцикл с 1 - 4 атомами N, O и/или S, где дополнительно могут быть замещены другие CH2-группы на NH, NA, S или O, связанные через N или C,
Nal обозначает F, Cl, Br или I,
n обозначает 0, 1, 2 или 3,
а также их физиологически приемлемые соли.1. The compounds of formula I
Figure 00000001

where R 1 , R 2 independently of one another denote H, A, OA, alkylene, alkynyl, NO 2 , CF 3 or Nal, and one of the residues R 1 or R 2 is not always H,
R 1 and R 2 together also denote alkylene with 3-5 carbon atoms,
R 3 , R 4 independently of one another denote H, A, OA, Nal, NO 2 , NH 2 , NHA or NAA ',
R 3 and R 4 together denote also-O-CH 2 -CH 2 -, -O-CH 2 -O or-O-CH 2 CH 2 -O-,
A, A ', independently of one another, denotes alkyl with 1-6 carbon atoms,
X is unsubstituted or one-, two- or three-fold substituted by an A, Nal or CF 3 -group unsaturated 5- to 70-membered heterocycle with 1 to 4 N, O and / or S atoms, where other CH 2 -groups may additionally be substituted with NH , NA, S or O, linked through N or C,
Nal is F, Cl, Br or I,
n represents 0, 1, 2 or 3,
and their physiologically acceptable salts. 2. Соединения формулы I по п.1, представляющие собой ; (а) 2-(1-имидазолил)-6-метил-4-(3,4-метилендиокси-бензиламино)-тиено-[2,3-d]-пиримидин;
(б) 2-(1-имидазолил)-5,6-диметил-4-(3,4-метилендиоксибензиламино)-тиано-[2,3-d]-пиримидин;
(в) 2-(1-имидазолил)-4-(3,4метилендиокси-бензиламино)-6,6,7,8-тетрагидро-[2,3-d]-пиримидин;
(г) 2-(1-имидазолил)-5-хлор-4-(3,4-метилендиокси-бензиламино)-тиено-[2,3-d]-пиримидин;
(д) 2-(1-имидазолил)-6-хлор-4-(3,4метилендиокси-бензиламино)-тиено-[2,3-d]-пиримидин;
(е) 2-(1,2,4-триазол-1-ил)-4-(3,4-метилендиокси-бензил-амино)-5,6,7,8-тетрагидро-[1]-бензотиено-[2,3-d]-пиримидин;
(ж) 2-(пиразол-1-ил)-4-(3,4-метилендиокси-бензиламино)-5,6,7,8-тетрагидро-[1]-бензотиено-[2,3-d]-пиримидин;
(з) 2-(пиридин-3-ил)-4-(3,4-метилендиокси-бензиламино)-5,6,7,8-тетрагидро-[1]-бензотиено-[2,3-d]-пиримидин.2. The compounds of formula I according to claim 1, which are; (a) 2- (1-imidazolyl) -6-methyl-4- (3,4-methylenedioxy-benzylamino) thieno [2,3-d] pyrimidine;
(b) 2- (1-imidazolyl) -5,6-dimethyl-4- (3,4-methylenedioxybenzylamino) thiano- [2,3-d] pyrimidine;
(c) 2- (1-imidazolyl) -4- (3,4 methylenedioxy-benzylamino) -6,6,7,8-tetrahydro- [2,3-d] pyrimidine;
(g) 2- (1-imidazolyl) -5-chloro-4- (3,4-methylenedioxy-benzylamino) thieno [2,3-d] pyrimidine;
(e) 2- (1-imidazolyl) -6-chloro-4- (3,4 methylenedioxy-benzylamino) thieno [2,3-d] pyrimidine;
(e) 2- (1,2,4-triazol-1-yl) -4- (3,4-methylenedioxybenzyl-amino) -5,6,7,8-tetrahydro [1] benzothieno- [ 2,3-d] pyrimidine;
(g) 2- (pyrazol-1-yl) -4- (3,4-methylenedioxy-benzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidine ;
(h) 2- (pyridin-3-yl) -4- (3,4-methylenedioxy-benzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidine . 3. Способ получения
а) соединений формулы I по п.1, а также их солей, в которых X связан через N,
отличающийся тем, что соединение формулы II
Figure 00000002

где R1, R2, R3, R4 и n имеют указанные значения, и
L обозначает, Cl, Br, OH, SCH3 или реакционно-способную этерифицированную OH-группу, подвергают взаимодействию с незамещенным или одно-, двух- или трехкратно замещенным A, Nal, CF2-группой ненасыщенным 5-7-членным гетероциклом с, по меньшей мере, одной NH-группой, при этом дополнительно могут быть замещены другие CH2-группы на группы NH, NA, S или O, или
b) соединение формулы I по п.1, а также их солей в которых X связан через C,
отличающийся тем, что соединение формулы III
Figure 00000003

где R1, R2 и X имеют указанные значения, и
L обозначает Cl, Br, OH, SCH3 или реакционно-способную этерифицированную OH-группу,
подвергают взаимодействию с соединением формулы IV
Figure 00000004

где R3, R4 и n имеют указанные значения, или
с) в соединении формулы I один остаток R1, R2, R3 и/или R4 превращают в другой остаток R1>, R2, R3 и/или R4, тем что восстанавливают нитрогруппу, превращают первичную или вторичную аминогруппу путем восстановительного аминирования в алкилированный амин или ацилируют,
и/или основное соединение формулы I путем обработки кислотой переводят в одну из его солей.3. The method of obtaining
a) compounds of formula I according to claim 1, as well as their salts, in which X is linked through N,
characterized in that the compound of formula II
Figure 00000002

where R 1 , R 2 , R 3 , R 4 and n have the indicated meanings, and
L means, Cl, Br, OH, SCH 3 or a reactive esterified OH group, is reacted with an unsubstituted or one, two or three times substituted A, Nal, CF 2 group with an unsaturated 5-7 membered heterocycle, at least one NH group; in addition, other CH 2 groups can be further substituted with NH, NA, S or O groups, or
b) a compound of formula I according to claim 1, as well as salts thereof, in which X is linked through C,
characterized in that the compound of formula III
Figure 00000003

where R 1 , R 2 and X have the indicated meanings, and
L denotes Cl, Br, OH, SCH 3 or reactive esterified OH group,
subjected to interaction with the compound of formula IV
Figure 00000004

where R 3 , R 4 and n have the indicated meanings, or
c) in the compound of formula I, one residue R 1 , R 2 , R 3 and / or R 4 is converted to another residue R 1 >, R 2 , R 3 and / or R 4 , by reducing the nitro group, by transforming the primary or secondary amino group by reductive amination to alkylated amine or acylated,
and / or the basic compound of formula I is transferred to one of its salts by treatment with acid. 4. Способ получения фармацевтических композиций, отличающийся тем, что соединение формулы I по п. 1 и/или одну из его физиологически приемлемых солей вместе с по меньшей мере одним твердым, жидким или полужидким носителем или вспомогательным веществом приводят в подходящую форму дозирования. 4. A method for preparing pharmaceutical compositions, characterized in that a compound of formula I according to claim 1 and / or one of its physiologically acceptable salts, together with at least one solid, liquid or semi-liquid carrier or auxiliary substance, is brought into a suitable dosage form. 5. Фармацевтическая композиция, отличающаяся тем, что она содержит, по меньшей мере, одно соединение формулы I по п.1 и/или одну из его физиологически приемлемых солей. 5. Pharmaceutical composition, characterized in that it contains at least one compound of formula I according to claim 1 and / or one of its physiologically acceptable salts. 6. Соединение формулы I по п.1 и их физиологически приемлемые соли для лечения заболеваний сердечно-сосудистой системы и для терапии нарушений потенции. 6. The compound of formula I according to claim 1 and their physiologically acceptable salts for the treatment of diseases of the cardiovascular system and for the treatment of disorders of potency. 7. Лекарственное средство формулы I по п.1 и их физиологически приемлемые соли в качестве ингибиторов фосфодиэстеразы V. 7. The drug of formula I according to claim 1 and their physiologically acceptable salts as inhibitors of phosphodiesterase V. 8. Соединение формулы I по п.1 и/или их физиологически приемлемые соли, применяемые для получения лекарственного средства. 8. The compound of formula I according to claim 1 and / or their physiologically acceptable salts used to obtain the drug. 9. Соединение формулы I по п.1 и/или их физиологически приемлемые соли, применяемые для лечения заболеваний. 9. The compound of formula I according to claim 1 and / or their physiologically acceptable salts used for the treatment of diseases.
RU99104796/04A 1996-08-12 1997-07-30 Thienopyrimidines, method of their synthesis (versions), pharmaceutical composition and method of its preparing RU2199541C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19632423.8 1996-08-12
DE19632423A DE19632423A1 (en) 1996-08-12 1996-08-12 Thienopyrimidines

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RU99104796A true RU99104796A (en) 2001-01-20
RU2199541C2 RU2199541C2 (en) 2003-02-27

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EP (1) EP0920431B1 (en)
JP (1) JP4405593B2 (en)
KR (1) KR100502271B1 (en)
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AR (1) AR009052A1 (en)
AT (1) ATE233265T1 (en)
AU (1) AU725227B2 (en)
BR (1) BR9711062A (en)
CA (1) CA2263561C (en)
CZ (1) CZ287772B6 (en)
DE (2) DE19632423A1 (en)
DK (1) DK0920431T3 (en)
ES (1) ES2191192T3 (en)
HK (1) HK1021731A1 (en)
HU (1) HUP0001607A3 (en)
IL (1) IL128504A (en)
NO (1) NO990643D0 (en)
NZ (1) NZ334600A (en)
PL (1) PL190174B1 (en)
PT (1) PT920431E (en)
RU (1) RU2199541C2 (en)
SI (1) SI0920431T1 (en)
SK (1) SK282823B6 (en)
TR (1) TR199900308T2 (en)
TW (1) TW359672B (en)
UA (1) UA55421C2 (en)
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