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RU97109528A - ORTO-SUBSTITUTED BENZOILGUANIDINES, THE WAY OF THEIR RECEPTION, THEIR USE AS A MEDICINE OR DIAGNOSTIC MEANS AND CONTAINING THEIR MEDICINE - Google Patents

ORTO-SUBSTITUTED BENZOILGUANIDINES, THE WAY OF THEIR RECEPTION, THEIR USE AS A MEDICINE OR DIAGNOSTIC MEANS AND CONTAINING THEIR MEDICINE

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RU97109528A
RU97109528A RU97109528/04A RU97109528A RU97109528A RU 97109528 A RU97109528 A RU 97109528A RU 97109528/04 A RU97109528/04 A RU 97109528/04A RU 97109528 A RU97109528 A RU 97109528A RU 97109528 A RU97109528 A RU 97109528A
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atoms
substituted
ortho
alkyl
hydrogen
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RU97109528/04A
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Russian (ru)
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RU2193025C2 (en
Inventor
Вайхерт Андреас
Брендель Йоахим
Клееманн Хайнц-Вернер
Йохен Ланг Ханс
Шварк Ян-Роберт
Альбус Удо
Шольц Вольфганг
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Хехст АГ
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Publication of RU2193025C2 publication Critical patent/RU2193025C2/en

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Claims (18)

1. Орто-замещенные бензоилгуанидины формулы I
Figure 00000001

где R(1)-R(13)-SOm или R(14)R(15)N-SO2-, где m = 1 или 2; R(13) - алкил с 1-8 С-атомами, перфторалкил с 1-8 С-атомами, алкенил c 3-8 С-атомами или -CnH2n-R(16), где n = 0, 1, 2, 3 или 4; R(16) - циклоалкил с 3-8 С-атомами, фенил, бифенилил или нафтил, причем фенил, бифенилил или нафтил не замещены или замещены 1 - 3 заместителями, выбираемыми из группы, состоящей из F, Cl, CF3, метила, метокси и NR(25)R(26); R(25) и (26) независимо друг от друга - водород, алкил с 1-4 С-атомами или перфторалкил с 1-4 С-атомами; R(14)-водород, алкил с 1-8 С-атомами, перфторалкил с 1-8 С-атомами, алкенил с 3-8 С-атомами или -CnH2n-R(27), где n = 0, 1, 2, 3 или 4; R(27) циклоалкил с 3-8 C-атомами, фенил, бифенилил или нафтил, причем фенил, бифенилил и нафтил не замещены или замещены 1 - 3 заместителями, выбираемыми из группы, состоящей из F, Cl, CF3, метила, метокси и NR(28)R(29), где R(28) и R(29) независимо друг от друга - водород, алкил с 1-4 С-атомами или перфторалкил с 1-4 С-атомами; R(15) - водород, алкил с 1-4 С-атомами или перфторалкил с 1-4 С-атомами или R(14) и R(15) вместе 4 или 5 метиленовых групп, из которых одна СН2-группа может быть заменена через кислород, S, NH, N-CH3 или N-бензил;
один из заместителей R(2) и R(3) - водород, а другой -CHR(30)R(31), где R(30)-(СH)g-(СНОН)h-СН2)i-(СНОНk)-R(32) или (CH2)g-O-(CH2-CH2O)h-R(24); R(24) и R(32) независимо друг от друга - водород или метил; g, h, i одинаковые или различные, 0, 1, 2, 3 или 4; k = 1, 2, 3 или 4, или соответственно другой заместитель R(2) и R(3)-
-C(OH)R(33)R(34); R(31), R(33) и R(34), одинаковые или различные, -водород или алкил с 1-4 C-атомами или R(33) и R(34) вместе циклоалкил с 3-6 С-атомами; или R(33) - СН2ОН;
R(4)-алкил с 1-4 С-атомами, алкокси с 1-4 С-атомами, F, Сl, Br, I, CN, -(СН2)n-(СF2)o-CF3; n = 0 или 1; o = 0, 1 или 2;
и их фармацевтически переносимые соли.1. Ortho-substituted benzoylguanidines of formula I
Figure 00000001

where R (1) -R (13) -SO m or R (14) R (15) N — SO 2 -, where m = 1 or 2; R (13) is alkyl with 1-8 C-atoms, perfluoroalkyl with 1-8 C-atoms, alkenyl with 3-8 C-atoms or -C n H 2n -R (16), where n = 0, 1, 2, 3 or 4; R (16) is cycloalkyl with 3-8 C-atoms, phenyl, biphenylyl or naphthyl, and phenyl, biphenylyl or naphthyl is not substituted or substituted by 1-3 substituents selected from the group consisting of F, Cl, CF 3 , methyl, methoxy and NR (25) R (26); R (25) and (26) independently of each other - hydrogen, alkyl with 1-4 C-atoms or perfluoroalkyl with 1-4 C-atoms; R (14) is hydrogen, alkyl with 1-8 C-atoms, perfluoroalkyl with 1-8 C-atoms, alkenyl with 3-8 C-atoms or -C n H 2n -R (27), where n = 0, 1, 2, 3, or 4; R (27) cycloalkyl with 3-8 C-atoms, phenyl, biphenylyl or naphthyl, and phenyl, biphenylyl and naphthyl are not substituted or substituted by 1-3 substituents selected from the group consisting of F, Cl, CF 3 , methyl, methoxy and NR (28) R (29), where R (28) and R (29) independently of each other are hydrogen, alkyl with 1-4 C-atoms or perfluoroalkyl with 1-4 C-atoms; R (15) is hydrogen, alkyl with 1-4 C-atoms or perfluoroalkyl with 1-4 C-atoms or R (14) and R (15) together 4 or 5 methylene groups, of which one CH 2 group can be replaced by oxygen, S, NH, N-CH 3 or N-benzyl;
one of the substituents R (2) and R (3) is hydrogen, and the other is —CHR (30) R (31), where R (30) - (CH) g - (CHOH) h —CH 2 ) i - (CHOH k ) -R (32) or (CH 2 ) g -O- (CH 2 -CH 2 O) h -R (24); R (24) and R (32) independently of one another are hydrogen or methyl; g, h, i are the same or different, 0, 1, 2, 3, or 4; k = 1, 2, 3 or 4, or respectively another substituent R (2) and R (3) -
-C (OH) R (33) R (34); R (31), R (33) and R (34), the same or different, is hydrogen or alkyl with 1-4 C atoms or R (33) and R (34) together with cycloalkyl with 3-6 C atoms; or R (33) is CH 2 OH;
R (4) -alkyl with 1-4 C-atoms, alkoxy with 1-4 C-atoms, F, Cl, Br, I, CN, - (CH 2 ) n - (CF 2 ) o -CF 3 ; n = 0 or 1; o = 0, 1 or 2;
and their pharmaceutically tolerable salts. 2. Орто-замещенные бензоилгуанидины по п. 1 формулы I, где R(1)-R(13)-SO2, или R(14)R(15)N-SO2-; R(13)-алкил с 1-4 С-атомами, перфторалкил с 1-4 С-атомами, алкенил с 3 или 4 С-атомами или -CnH2n-R(16), n = 0, 1, 2, 3 или 4; R(16) - циклоалкил с 3-6 С-атомами, фенил, бифенилил или нафтил, причем фенил, бифенилил и нафтил не замещены или замещены 1-3 заместителями, выбираемыми из группы, состоящей из F, Cl, CF3, метила или метокси; R(14) - водород, алкил с 1-4 С-атомами, перфторалкил с 1-4 С-атомами, алкенил с 3 или 4 С-атомами или -CnH2n-R(27), где n = 0, 1, 2, 3 или 4; R(27) циклоалкил c 3-8 C-атомами, фенил, бифенилил или нафтил, причем фенил, бифенилил и нафтил не замещены или замещены 1-3 заместителями, выбираемыми из группы, состоящей из F, Cl, CF3, метила или метокси; R(15) - водород, алкил с 1-4 С-атомами или перфторалкил с 1-4 С-атомами; или R(14) и R(15) вместе 4 или 5 метиленовых групп, из которых одна СН2-группа может быть заменена через кислород, S, NH, N-CH3 или N-бензил;
и один из заместителей R(2) и R(3) - водород, а другой -CHR(30)R(31); R(30)-(CH2)g-(CHOH)h-(CH2)i-(CHOH)k-R(32) или -(CH2)g-O-(CH2-CH2O)h-R(24); R(24) и R(32) независимо друг от друга - водород или метил; g, h, i одинаковые или различные, -0, 1 или 2; k = 1 или 2;
или соответственно другой заместитель R(2) и R(3)- -C(OH)R(33)R(34); R(33) и R(34) одинаковые или различные - водород или алкил с 1-4 С-атомами или R(33) и R(34) вместе - циклоалкил с 3-6 С-атомами; или R(33) - СН2ОН;
R(4)-алкил с 1-4 С-атомами, алкокси с 1-4 С-атомами, F, Cl, CN или (СF2)o-CF3; 0, 1 или 2.2. Ortho-substituted benzoylguanidines according to claim 1 of formula I, where R (1) -R (13) -SO 2 , or R (14) R (15) N — SO 2 -; R (13) -alkyl with 1-4 C-atoms, perfluoroalkyl with 1-4 C-atoms, alkenyl with 3 or 4 C-atoms or -C n H 2n -R (16), n = 0, 1, 2 , 3 or 4; R (16) is cycloalkyl with 3-6 C-atoms, phenyl, biphenylyl or naphthyl, and phenyl, biphenylyl and naphthyl are not substituted or substituted by 1-3 substituents selected from the group consisting of F, Cl, CF 3 , methyl or methoxy; R (14) is hydrogen, alkyl with 1-4 C-atoms, perfluoroalkyl with 1-4 C-atoms, alkenyl with 3 or 4 C-atoms or -C n H 2n -R (27), where n = 0, 1, 2, 3, or 4; R (27) cycloalkyl with 3-8 C-atoms, phenyl, biphenylyl or naphthyl, and phenyl, biphenylyl and naphthyl not substituted or substituted by 1-3 substituents selected from the group consisting of F, Cl, CF 3 , methyl or methoxy ; R (15) is hydrogen, alkyl with 1-4 C-atoms or perfluoroalkyl with 1-4 C-atoms; or R (14) and R (15) together 4 or 5 methylene groups, of which one CH 2 group can be replaced via oxygen, S, NH, N-CH 3 or N-benzyl;
and one of the substituents R (2) and R (3) is hydrogen, and the other is CHR (30) R (31); R (30) - (CH 2 ) g - (CHOH) h - (CH 2 ) i - (CHOH) k -R (32) or - (CH 2 ) g -O- (CH 2 -CH 2 O) h -R (24); R (24) and R (32) independently of one another are hydrogen or methyl; g, h, i are the same or different, -0, 1, or 2; k = 1 or 2;
or, respectively, another substituent R (2) and R (3) - —C (OH) R (33) R (34); R (33) and R (34) are the same or different - hydrogen or alkyl with 1-4 C-atoms or R (33) and R (34) together - cycloalkyl with 3-6 C-atoms; or R (33) is CH 2 OH;
R (4) -alkyl with 1-4 C-atoms, alkoxy with 1-4 C-atoms, F, Cl, CN or (CF 2 ) o -CF 3 ; 0, 1 or 2. 3. Орто-замещенные бензоилгуанидины по п. 1 или 2 формулы I, где R(1) - R(13)-SO2; R(13) алкил с 1-4 С-атомами, и соответственно другой заместитель R(2) и R(3)-С(ОН)(СН3)-СН2ОН, -СН(СН3)-СН2OН или С(ОН)(СН3)2;
R(4)- алкил с 1-4 С-атомами, алкокси с 1-4 С-атомами, F, Cl, CN или -CF3.3. Ortho-substituted benzoylguanidines according to claim 1 or 2 of the formula I, where R (1) is R (13) —SO 2 ; R (13) alkyl with 1-4 C-atoms, and respectively another substituent R (2) and R (3) -C (OH) (CH 3 ) -CH 2 OH, -CH (CH 3 ) -CH 2 OH or C (OH) (CH 3 ) 2 ;
R (4) is alkyl with 1-4 C-atoms, alkoxy with 1-4 C-atoms, F, Cl, CN or -CF 3 . 4. Способ для получения орто-замещенных бензоилгуанидинов формулы I по п. 1, отличающийся тем, что соединение формулы II
Figure 00000002

где R(1) - R(4) имеют указанное в п. 1 значение;
L обозначает легко замещаемую нуклеофильно летучую группу, вступает во взаимодействие с гуанидином.4. A method for producing ortho-substituted benzoylguanidines of the formula I according to claim 1, characterized in that a compound of formula II
Figure 00000002

where R (1) - R (4) have the meaning specified in paragraph 1;
L stands for easily replaceable nucleophilic volatile group, interacts with guanidine. 5. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или для профилактики вызванных ишемическими состояниями заболеваний. 5. The use of ortho-substituted benzoylguanidines according to claim 1 for preparing a medicament for treating or preventing diseases caused by ischemic conditions. 6. Метод лечения и профилактики, вызванных ишемическими состояниями заболеваний, отличающийся тем, что эффективное количество орто-замещенных бензоилгуанидинов по п. 1 смешивают с обычными добавками и назначают в соответствующей форме введения. 6. The method of treatment and prevention caused by ischemic conditions of diseases, characterized in that the effective amount of ortho-substituted benzoylguanidines according to claim 1 is mixed with the usual additives and is prescribed in the appropriate form of administration. 7. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики инфаркта миокарда и аритмий. 7. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for the treatment or prevention of myocardial infarction and arrhythmias. 8. Применение орто-замещенныхх бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики стенокардии. 8. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for the treatment or prophylaxis of angina pectoris. 9. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики ишемических состояний сердца. 9. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for treating or preventing ischemic conditions of the heart. 10. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики ишемических состояний периферической и центральной нервной системы и инсульта. 10. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for treating or preventing ischemic states of the peripheral and central nervous system and stroke. 11. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики ишемических состояний периферических органов и конечностей. 11. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for the treatment or prevention of ischemic conditions of peripheral organs and limbs. 12. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения состояний шока. 12. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for treating shock conditions. 13. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для применения при хирургических операциях и при трансплантациях органов. 13. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for use in surgical operations and organ transplantation. 14. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента при консервации и хранении трансплантантов для хирургических целей. 14. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for the preservation and storage of transplants for surgical purposes. 15. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения заболеваний, при которых пролиферация клеток представляет первичную или вторичную причину и поэтому его применение в качестве противоатеросклеротического средства, средства против поздних диабетических осложнений, заболеваний раком, фибромных заболеваний, как фиброз легких, фиброз печени или фиброз почек, гиперплазии предстательной железы. 15. The use of ortho-substituted benzoylguanidines according to claim 1 for obtaining a medicament for treating diseases in which cell proliferation is the primary or secondary cause and therefore its use as an anti-atherosclerotic agent, an agent for late diabetic complications, cancer diseases, fibroid diseases like fibrosis lung, liver fibrosis or kidney fibrosis, prostatic hyperplasia. 16. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения научного инструмента торможения Na+/H+-ионообменника для диагноза гипертонии и пролиферативных заболеваний.16. The use of ortho-substituted benzoylguanidines according to claim 1 for obtaining a scientific tool for inhibiting the Na + / H + ion exchanger for the diagnosis of hypertension and proliferative diseases. 17. Применение орто-замещенных бензоилгуанидинов по п. 1 для получения медикамента для лечения или профилактики нарушений жирового обмена веществ. 17. The use of ortho-substituted benzoylguanidines according to claim 1 for the preparation of a medicament for treating or preventing disorders of the fat metabolism. 18. Лекарственное средство, на основе активнодействующего вещества и целевых добавок, отличающееся тем, что в качестве активнодействующего вещества оно включает орто-замещенные бензоилгуанидины общей формулы I по пп. 1-4 в эффективном количестве. 18. Drug, based on the active substance and target additives, characterized in that as the active substance, it includes ortho-substituted benzoylguanidines of general formula I according to claims. 1-4 in effective amount.
RU97109528/04A 1996-06-18 1997-06-17 Ortho-substituted benzoylguanidines and medicinal agent based on thereof RU2193025C2 (en)

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DE19608161A1 (en) * 1996-03-04 1997-09-11 Hoechst Ag Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE19713427A1 (en) * 1997-04-01 1998-10-08 Hoechst Ag Ortho-substituted benzoylguanidines, processes for their preparation, their use as medicaments or diagnostic agents and medicaments containing them
DE10001879A1 (en) 2000-01-19 2001-07-19 Aventis Pharma Gmbh New benzoylguanidine derivatives are Na+/H+ exchange inhibitors useful for the treatment and prevention of e.g. ischemic disorders, infarction, arrhythmia, angina pectoris and stroke
US6641811B1 (en) * 2000-02-10 2003-11-04 Cornell Research Foundation, Inc. Use of angiotensin II inhibitors to prevent malignancies associated with immunosuppression
US7828840B2 (en) * 2007-11-15 2010-11-09 Med Institute, Inc. Medical devices and methods for local delivery of angiotensin II type 2 receptor antagonists

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DE4318658A1 (en) * 1993-06-04 1994-12-08 Hoechst Ag Substituted benzoylguanidines, process for their preparation, their use as medicament or diagnostic agent, and medicament containing them
DE4318756A1 (en) * 1993-06-05 1994-12-08 Hoechst Ag Substituted benzoylguanidines, process for their preparation, their use as medicament or diagnostic agent, and medicament containing them
DE4328869A1 (en) * 1993-08-27 1995-03-02 Hoechst Ag Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE4430213A1 (en) * 1994-08-28 1996-02-29 Merck Patent Gmbh Arylbenzoylguanidine
DE4430916A1 (en) * 1994-08-31 1996-03-07 Merck Patent Gmbh Alkyl benzoylguanidine derivatives
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