RU99110944A - THYENOPYRIMIDINES WITH INHIBITING ACTION WITH RESPECT TO PHOSPHODYSTRASE V (PDE V) - Google Patents

THYENOPYRIMIDINES WITH INHIBITING ACTION WITH RESPECT TO PHOSPHODYSTRASE V (PDE V)

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Publication number
RU99110944A
RU99110944A RU99110944/04A RU99110944A RU99110944A RU 99110944 A RU99110944 A RU 99110944A RU 99110944/04 A RU99110944/04 A RU 99110944/04A RU 99110944 A RU99110944 A RU 99110944A RU 99110944 A RU99110944 A RU 99110944A
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Russia
Prior art keywords
formula
pyrimidin
physiologically acceptable
compound
acceptable salts
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RU99110944/04A
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Russian (ru)
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RU2197492C2 (en
Inventor
Рохус ЙОНАС
Пирре ШЕЛЛИНГ
Мариа ХРИШТАДЛЕР
Франц-Вернер КЛУКСЕН
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Мерк Патент Гмбх
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Priority claimed from DE19644228A external-priority patent/DE19644228A1/en
Application filed by Мерк Патент Гмбх filed Critical Мерк Патент Гмбх
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Publication of RU2197492C2 publication Critical patent/RU2197492C2/en

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Claims (9)

1. Соединение формулы I
Figure 00000001

в которой R1, R2 каждый независимо друг от друга обозначает H, A, OA, алкенил, алкинил, CF3 или Hal, причем один из остатков R1 или R2 во всех случаях имеет значение, отличное от H,
R1 и R2 вместе обозначают также алкилен с 3 - 5 C-атомами,
R3, R4 каждый независимо друг от друга обозначает H, A, OA, NO2, NH2, NHA, NAA' или Hal,
R3 и R4 вместе обозначают также -O-CH2-CH2-, -O-CH2-O- или -O-CH2-CH2-O-,
X представляет собой одно- или двукратно замещенное остатком R5 5-7-членное насыщенное гетероциклическое кольцо либо одно- или двукратно замещенное остатком R5 5-7-членное ненасыщенное или насыщенное изоциклическое кольцо,
R5 обозначает COOH, COOA, CONH2, CONAA', CONHA, CN, CH2COOH или CH2CH2COOH,
A, A' каждый независимо друг от друга обозначает H или алкил с 1 - 6 C-атомами,
Hal обозначает F, Cl, Br или I и
n обозначает 0, 1, 2 или 3,
а также их физиологически приемлемые соли.1. The compound of formula I
Figure 00000001

in which R 1 , R 2 each independently of one another denotes H, A, OA, alkenyl, quinil, CF 3 or Hal, and one of the residues R 1 or R 2 in all cases has a meaning other than H,
R 1 and R 2 together denote also alkylene with 3-5 carbon atoms,
R 3 , R 4 each independently of one another denotes H, A, OA, NO 2 , NH 2 , NHA, NAA 'or Hal,
R 3 and R 4 together are also —O — CH 2 —CH 2 -, —O — CH 2 —O— or —O — CH 2 —CH 2 —O—,
X is a mono- or disubstituted by R 5 moiety a 5-7 membered saturated heterocyclic ring or mono- or disubstituted by R 5 moiety a 5-7 membered unsaturated or saturated isocyclic ring,
R 5 is COOH, COOA, CONH 2 , CONAA ', CONHA, CN, CH 2 COOH or CH 2 CH 2 COOH,
A, A 'each independently of the other denotes H or alkyl with 1-6 C-atoms,
Hal means F, Cl, Br or I and
n represents 0, 1, 2 or 3,
and their physiologically acceptable salts. 2. Соединения формулы I по п.1 из группы, включающей
(а) 4-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(б) 4-[4-(3,4-метилендиоксибензиламино)-6-метилтиено[2,3-d] пиримидин-2-ил]бензойную кислоту,
(в) 4-[4-(3,4-метилендиоксибензиламино)-5,6-диметилтиено[2,3-d] пиримидин-2-ил]бензойную кислоту,
(г) 4-[4-(3,4-метилендиоксибензиламино)-6-хлортиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(д) 4-[4-(3-хлор-4-метоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(е) 1-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]пиперидин-4-карбоновую кислоту,
(ж) 1-[4-(3,4-метилендиоксибензиламино)-6-метилтиено[2,3-d] пиримидин-2-ил]пиперидин-4-карбоновую кислоту,
(з) 4-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]циклогексанкарбоновую кислоту,
а также их физиологически приемлемые соли.2. The compounds of formula I according to claim 1 from the group including
(a) 4- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(b) 4- [4- (3,4-methylenedioxybenzylamino) -6-methylthieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(c) 4- [4- (3,4-methylenedioxybenzylamino) -5,6-dimethylthieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(d) 4- [4- (3,4-methylenedioxybenzylamino) -6-chlorothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(e) 4- [4- (3-chloro-4-methoxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(e) 1- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] piperidine-4-carboxylic acid,
(g) 1- [4- (3,4-methylenedioxybenzylamino) -6-methylthieno [2,3-d] pyrimidin-2-yl] piperidine-4-carboxylic acid,
(h) 4- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] cyclohexanecarboxylic acid,
and their physiologically acceptable salts. 3. Способ получения
а) соединений формулы I по п.1 и их солей, где X представляет собой одно- или двукратно замещенное остатком R5 насыщенное 5-7-членное гетероциклическое кольцо, связанное через N, отличающийся тем, что соединение формулы II
Figure 00000002

в которой R1, R2, R3, R4 и n имеют указанные выше значения, а L обозначает Cl, Br, OH, SCH3 или реакционноспособную этерифицированную OH-группу, подвергают взаимодействию с одно- или двукратно замещенным остатком R5 насыщенным 5-7-членным гетероциклическим кольцом, где R5 имеет указанное выше значение, или
б) соединений формулы I по п.1 и их солей, где X представляет собой одно- или двукратно замещенное остатком R5 ненасыщенное или насыщенное 5-7-членное изоциклическое кольцо, связанное через C, отличающийся тем, что соединение формулы III
Figure 00000003

в которой R1, R5 и X имеют указанные выше значения, а L обозначает Cl, Br, OH, SCH3 или реакционноспособную этерифицированную OH-группу, подвергают взаимодействию с соединением по формуле IV
Figure 00000004

в которой R3, R4 и n имеют указанные выше значения, или
в) в соединении формулы I один остаток R3, R4 и/или X трансформируют в другой остаток R3, R4 и/или X путем омыления сложного эфира или восстановления нитрогруппы, и/или что кислое соединение формулы I за счет обработки основанием переводят в одну из его солей.3. The method of obtaining
a) compounds of formula I according to claim 1 and their salts, where X is a single or twofold substituted R 5 saturated 5-7-membered heterocyclic ring linked through N, characterized in that the compound of formula II
Figure 00000002

in which R 1 , R 2 , R 3 , R 4 and n have the above values, and L denotes Cl, Br, OH, SCH 3 or a reactive esterified OH group, is reacted with a single or double substituted R 5 saturated A 5-7 membered heterocyclic ring, wherein R 5 is as defined above, or
b) compounds of the formula I according to claim 1 and their salts, where X is a unsaturated or saturated 5-7-membered isocyclic ring which is singly or twice substituted by R 5 and is bonded through C, characterized in that the compound of formula III
Figure 00000003

in which R 1 , R 5 and X have the above values, and L denotes Cl, Br, OH, SCH 3 or a reactive esterified OH group, is reacted with a compound according to formula IV
Figure 00000004

in which R 3 , R 4 and n have the above values, or
c) in a compound of formula I, one residue R 3 , R 4 and / or X is transformed into another residue R 3 , R 4 and / or X by saponification of the ester or reduction of the nitro group, and / or that the acidic compound of formula I due to treatment with base transferred to one of its salts. 4. Способ получения фармацевтических композиций, отличающийся тем, что соединение формулы I по п. 1 и/или одну из его физиологически приемлемых солей используют вместе с по меньшей мере одним твердым, жидким либо полужидким носителем или вспомогательным веществом для изготовления соответствующей дозированной формы. 4. A method of obtaining pharmaceutical compositions, characterized in that the compound of formula I according to claim 1 and / or one of its physiologically acceptable salts is used together with at least one solid, liquid or semi-liquid carrier or auxiliary substance for the manufacture of an appropriate dosage form. 5. Фармацевтическая композиция, отличающаяся тем, что она содержит в своем составе 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. Соединения формулы I по п.1 и их физиологически приемлемые соли для борьбы с заболеваниями сердечно-сосудистой системы и для лечения и/или терапии нарушения потенции. 6. The compounds of formula I according to claim 1 and their physiologically acceptable salts for combating diseases of the cardiovascular system and for the treatment and / or therapy of disorders of potency. 7. Лекарственные средства формулы I по п.1 и их физиологически приемлемые соли в качестве ингибиторов фосфодиэстеразы V (PDE V). 7. Drugs of the formula I according to claim 1 and their physiologically acceptable salts as phosphodiesterase V (PDE V) inhibitors. 8. Применение соединений формулы I по п.1 и/или их физиологически приемлемых солей для получения лекарственного средства. 8. The use of compounds of the formula I according to claim 1 and / or their physiologically acceptable salts for the manufacture of a medicament. 9. Применение соединений формулы I по п.1 и/или их физиологически приемлемых солей для борьбы с болезнями. 9. The use of compounds of the formula I according to claim 1 and / or their physiologically acceptable salts for the control of diseases.
RU99110944/04A 1996-10-24 1997-10-08 Thienopyrimidines with inhibitory effect with respect to phosphodiesterase v (pde v), method of their synthesis and pharmaceutical composition RU2197492C2 (en)

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DE19644228A DE19644228A1 (en) 1996-10-24 1996-10-24 Thienopyrimidines
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