RU96108907A - NITROESTERS, possessing anti-inflammatory and / or analgesic activity, and method of their production - Google Patents

NITROESTERS, possessing anti-inflammatory and / or analgesic activity, and method of their production

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Publication number
RU96108907A
RU96108907A RU96108907/04A RU96108907A RU96108907A RU 96108907 A RU96108907 A RU 96108907A RU 96108907/04 A RU96108907/04 A RU 96108907/04A RU 96108907 A RU96108907 A RU 96108907A RU 96108907 A RU96108907 A RU 96108907A
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Russia
Prior art keywords
hydrogen
equal
derivatives
linear
nitroesters
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RU96108907/04A
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Russian (ru)
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RU2136653C1 (en
Inventor
Солдато Пьеро Дел
Original Assignee
Никокс С.А.
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Priority claimed from GB9320599A external-priority patent/GB2283238B/en
Priority claimed from ITMI940916A external-priority patent/IT1269735B/en
Application filed by Никокс С.А. filed Critical Никокс С.А.
Priority claimed from PCT/EP1994/003182 external-priority patent/WO1995009831A1/en
Publication of RU96108907A publication Critical patent/RU96108907A/en
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Publication of RU2136653C1 publication Critical patent/RU2136653C1/en

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Claims (18)

1. Производные пропионовой кислоты, 1-(п-хлорбензоил)-5-метокси-2-метил-3-индолилуксусной кислоты, 5-бензоил-1,2-дигидро-3Н-пирроло[1,2-а] пиррол-1-карбоновой кислоты, 6-метокси-2-нафтилуксусной кислоты, которые имеют следующую общую формулу:
Figure 00000001

где A и B - водород, линейный или разветвленный, замещенный или незамещенный алкил,
M выбран из
Figure 00000002

Figure 00000003

Figure 00000004

Figure 00000005

где R выбран из
Figure 00000006

Figure 00000007

Figure 00000008

Y - кислород, NH, NR1, где R1 означает линейную или разветвленную алкильную группу, и n = 1 - 10.1. Propionic acid derivatives, 1- (p-chlorobenzoyl) -5-methoxy-2-methyl-3-indolylacetic acid, 5-benzoyl-1,2-dihydro-3H-pyrrolo [1,2-a] pyrrol-1 -carboxylic acid, 6-methoxy-2-naphthylacetic acid, which have the following general formula:
Figure 00000001

where A and B is hydrogen, linear or branched, substituted or unsubstituted alkyl,
M is selected from
Figure 00000002

Figure 00000003

Figure 00000004

Figure 00000005

where R is selected from
Figure 00000006

Figure 00000007

Figure 00000008

Y is oxygen, NH, NR 1 , where R 1 means a linear or branched alkyl group, and n = 1 - 10. 2. Нитроэфиры по п.1, отличающиеся тем, что фрагмент
Figure 00000009

является линейной, разветвленной или циклической алкиленовой группой C2 - C10.2. Nitroesters according to claim 1, characterized in that the fragment
Figure 00000009

is a linear, branched or cyclic alkylene group C 2 - C 10 . 3. Производное пропионовой кислоты по п.1, отличающееся тем, что M равно
Figure 00000010

где R означает
Figure 00000011

A и B - водород;
Y - кислород;
n = 4.3. A derivative of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000010

where r means
Figure 00000011

A and B are hydrogen;
Y is oxygen;
n = 4. 4. Производное пропионовой кислоты по п.1, отличающееся тем, что M равен
Figure 00000012

где R равен
Figure 00000013

A и B - водород;
Y - NH;
n = 4.4. A derivative of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000012

where R is equal to
Figure 00000013

A and B are hydrogen;
Y - NH;
n = 4. 5. Производное пропионовой кислоты по п.1, отличающееся тем, что M равен
Figure 00000014

где R равен
Figure 00000015

Y - кислород;
A и B - водород;
n = 4.5. A derivative of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000014

where R is equal to
Figure 00000015

Y is oxygen;
A and B are hydrogen;
n = 4. 6. Производное пропионовой кислоты по п.1, отличающееся тем, что M равен
Figure 00000016

где R равен
Figure 00000017

Y - NH;
A и B - водород;
n = 4.6. A derivative of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000016

where R is equal to
Figure 00000017

Y - NH;
A and B are hydrogen;
n = 4. 7. Производные пропионовой кислоты по п.1, отличающееся тем, что M равен
Figure 00000018

где R равен
Figure 00000019

A и B - водород;
Y - кислород;
n = 4.7. Derivatives of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000018

where R is equal to
Figure 00000019

A and B are hydrogen;
Y is oxygen;
n = 4. 8. Производное пропионовой кислоты по п.1, отличающееся тем, что M равен
Figure 00000020

где R равен
Figure 00000021

A и B - водород;
Y - NH;
n = 4.8. A derivative of propionic acid according to claim 1, characterized in that M is equal to
Figure 00000020

where R is equal to
Figure 00000021

A and B are hydrogen;
Y - NH;
n = 4. 9. Производные 5-бензоил-1,2-дигидро-3H-пирроло[1,2-a] пиррол-1-карбоновой кислоты по п.1, отличающиеся тем, что M равен
Figure 00000022

A и B - водород;
Y - кислород;
n = 4.9. Derivatives of 5-benzoyl-1,2-dihydro-3H-pyrrolo [1,2-a] pyrrole-1-carboxylic acid according to claim 1, characterized in that M is equal to
Figure 00000022

A and B are hydrogen;
Y is oxygen;
n = 4. 10. Производные 1-(п-хлорбензоил)-5-метокси-2-метил-3-индолилуксусной кислоты по п.1, отличающиеся тем, что M равен
Figure 00000023

A и B - водород;
Y - кислород;
n = 4.10. Derivatives of 1- (p-chlorobenzoyl) -5-methoxy-2-methyl-3-indolylacetic acid according to claim 1, characterized in that M is equal to
Figure 00000023

A and B are hydrogen;
Y is oxygen;
n = 4. 11. Нитроэфиры по п.1, отличающиеся тем, что они могут быть использованы в фармацевтике как противовоспалительные агенты. 11. Nitroesters according to claim 1, characterized in that they can be used in the pharmaceutical industry as anti-inflammatory agents. 12. Нитроэфиры по п.1, отличающиеся тем, что они могут быть использованы в фармацевтике как анальгетические агенты. 12. Nitroesters according to claim 1, characterized in that they can be used in the pharmaceutical industry as analgesic agents. 13. Нитроэфиры по п.1, отличающиеся тем, что они могут быть использованы для лечения ревматических болезней, для лечения расстройств иммунологической системы и слабых и средних болевых состояний. 13. Nitroesters according to claim 1, characterized in that they can be used to treat rheumatic diseases, to treat disorders of the immune system, and weak and moderate pain conditions. 14. Нитроэфиры по п.1, отличающиеся тем, что они могут быть использованы для лечения болезней сердечно-сосудистой системы, для лечения старческого слабоумия, для лечения ишемии сердечной и головного мозга и в случае артериальных тромбозов. 14. Nitroesters according to claim 1, characterized in that they can be used to treat diseases of the cardiovascular system, to treat senile dementia, to treat ischemia of the heart and brain, and in the case of arterial thrombosis. 15. Способ получения нитроэфиров по п.1, имеющих следующую общую формулу:
Figure 00000024

где A и B - водород, линейный или разветвленный, замещенный или незамещенный алкил;
M выбран из
Figure 00000025

Figure 00000026

Figure 00000027

Figure 00000028

где R выбран из
Figure 00000029

Figure 00000030

Figure 00000031

Y - кислород, NH, NR1, где R1 означает линейный или разветвленный алкил, и n = 1 - 10,
отличающийся тем, что включает следующие стадии:
получение натриевой соли производных, имеющих следующую общую формулу:
Figure 00000032

где M выбран из (XXX), (XXXI), (XXXII),
Figure 00000033

где R выбран из следующих структур:
Figure 00000034

Figure 00000035

Figure 00000036

или получение производных (VIA), замещенных по карбоксильной группе, таких как хлорангидриды, ангидриды или подобные,
реакцию натриевой соли вышеуказанных производных (VIA) или вышеуказанных производных (VIA), замещенных по карбоксильной группе, с соединением, имеющим следующую общую формулу:
Figure 00000037

где R4 - хлор, бром, NHR5 с R5 - водород, линейный или разветвленный алкил;
A и B - водород, линейный или разветвленный, замещенный или незамещенный алкил;
R3 - хлор, бром, иод;
n = 1 - 10,
с получением таким путем соответствующих эфиров или соответствующих амидов;
реакцию вышеуказанных эфиров или вышеуказанных амидов с нитрующим агентом, таким как AgNO3 или подобным, с получением в результате нитроэфиров (IA).15. The method of producing nitroesters according to claim 1, having the following general formula:
Figure 00000024

where A and B are hydrogen, linear or branched, substituted or unsubstituted alkyl;
M is selected from
Figure 00000025

Figure 00000026

Figure 00000027

Figure 00000028

where R is selected from
Figure 00000029

Figure 00000030

Figure 00000031

Y is oxygen, NH, NR 1 , where R 1 means a linear or branched alkyl, and n = 1 - 10,
characterized in that it includes the following stages:
obtaining the sodium salt of derivatives having the following general formula:
Figure 00000032

where M is selected from (XXX), (XXXI), (XXXII),
Figure 00000033

where R is selected from the following structures:
Figure 00000034

Figure 00000035

Figure 00000036

or obtaining derivatives (VIA), substituted by a carboxyl group, such as acid chlorides, anhydrides or the like,
the reaction of the sodium salt of the above derivatives (VIA) or the above derivatives (VIA), substituted by a carboxyl group, with a compound having the following general formula:
Figure 00000037

where R 4 is chlorine, bromine, NHR 5 with R 5 is hydrogen, linear or branched alkyl;
A and B are hydrogen, linear or branched, substituted or unsubstituted alkyl;
R 3 - chlorine, bromine, iodine;
n = 1 - 10,
thus obtaining the corresponding esters or the corresponding amides;
reacting the above esters or the above amides with a nitrating agent such as AgNO 3 or the like to result in nitroesters (IA). 16. Способ получения нитроэфиров по п.1, имеющих следующую общую формулу:
Figure 00000038

где A и B - водород, линейный или разветвленный, замещенный или незамещенный алкил;
M выбран из
Figure 00000039

Figure 00000040

Figure 00000041

Figure 00000042

где R выбран из
Figure 00000043

Figure 00000044

Figure 00000045

Y - кислород, NH, NR1, где R1 означает линейную или разветвленную алкильную группу;
n = 1 - 10,
отличающийся тем, что он включает следующие стадии:
получение натриевой соли производных, имеющих следующую общую формулу:
Figure 00000046

где M выбран из (XXX), (XXXI), (XXXII),
Figure 00000047

где R выбран из следующих структур:
Figure 00000048

Figure 00000049

Figure 00000050

или получение производных (VIA), замещенных по карбоксильной группе, таких как хлорангидриды, ангидриды или подобные;
реакцию натриевой соли вышеуказанных производных (VIA) или вышеуказанных производных (VIA), замещенных по карбоксильной группе, с соединением, имеющим следующую общую формулу:
Figure 00000051

где R4 - хлор, бром, NHR5 с R5 - водород, линейный или разветвленный алкил;
A и B - водород, линейный или разветвленный, замещенный или незамещенный алкил,
n = 1 - 10,
с получением таким образом соответствующих эфиров или соответствующих амидов;
реакцию вышеуказанных эфиров или вышеуказанных амидов с галоидирующим соединением, таким как PBr3 или подобным, с получением таким образом продуктов вышеуказанных эфиров или вышеуказанных амидов, характеризующихся наличием концевой галоидной группой;
реакцию вышеуказанных эфиров или вышеуказанных амидов, характеризующихся наличием концевой галоидной группы, с нитрующим агентом, таким как AgNO3 или подобным, с получением таким образом нитроэфиров (IA).16. The method of producing nitroesters according to claim 1, having the following general formula:
Figure 00000038

where A and B are hydrogen, linear or branched, substituted or unsubstituted alkyl;
M is selected from
Figure 00000039

Figure 00000040

Figure 00000041

Figure 00000042

where R is selected from
Figure 00000043

Figure 00000044

Figure 00000045

Y is oxygen, NH, NR 1 , where R 1 means a linear or branched alkyl group;
n = 1 - 10,
characterized in that it includes the following stages:
obtaining the sodium salt of derivatives having the following general formula:
Figure 00000046

where M is selected from (XXX), (XXXI), (XXXII),
Figure 00000047

where R is selected from the following structures:
Figure 00000048

Figure 00000049

Figure 00000050

or preparing derivatives (VIAs) substituted at the carboxyl group, such as acid chlorides, anhydrides or the like;
the reaction of the sodium salt of the above derivatives (VIA) or the above derivatives (VIA), substituted by a carboxyl group, with a compound having the following general formula:
Figure 00000051

where R 4 is chlorine, bromine, NHR 5 with R 5 is hydrogen, linear or branched alkyl;
A and B are hydrogen, linear or branched, substituted or unsubstituted alkyl,
n = 1 - 10,
thus obtaining the corresponding esters or the corresponding amides;
reacting the above esters or the above amides with a halogenating compound, such as PBr 3 or the like, to thereby obtain products of the above esters or above amides characterized by the presence of a terminal halide group;
reacting the above esters or the above amides, characterized by the presence of a terminal halide group, with a nitrating agent such as AgNO 3 or the like, thus obtaining nitroesters (IA). 17. Фармацевтические композиции, обладающие противовоспалительной активностью, отличающиеся тем, что они включают по крайней мере один нитроэфир по п.1 в качестве активного ингредиента. 17. Pharmaceutical compositions having anti-inflammatory activity, characterized in that they include at least one nitro ester according to claim 1 as an active ingredient. 18. Фармацевтические композиции, обладающие анальгетической активностью, отличающиеся тем, что они включают по крайней мере один нитроэфир по п.1 в качестве активного ингредиента. 18. Pharmaceutical compositions having analgesic activity, characterized in that they include at least one nitro ester according to claim 1 as an active ingredient.
RU96108907A 1993-10-06 1994-09-23 Nitroesters exhibiting anti-inflammatory and/or analgetic activity, methods of their synthesis, pharmaceutical compositions RU2136653C1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB9320599A GB2283238B (en) 1993-10-06 1993-10-06 Nitric esters of derivatives of propionic acid and process for their preparation
GB9320599.5 1993-10-06
ITMI94/A000916 1994-05-10
ITM194/A000916 1994-05-10
ITMI940916A IT1269735B (en) 1994-05-10 1994-05-10 Products having a terminal nitroester group with anti- inflammatory and/or analgesic activity
PCT/EP1994/003182 WO1995009831A1 (en) 1993-10-06 1994-09-23 Nitric esters having anti-inflammatory and/or analgesic activity and process for their preparation

Publications (2)

Publication Number Publication Date
RU96108907A true RU96108907A (en) 1998-08-20
RU2136653C1 RU2136653C1 (en) 1999-09-10

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EP (1) EP0722434B1 (en)
JP (1) JP3775796B2 (en)
KR (1) KR100343243B1 (en)
AT (1) ATE168986T1 (en)
AU (1) AU678063B2 (en)
BR (1) BR9407749A (en)
CA (1) CA2173582C (en)
DE (1) DE69412109T2 (en)
DK (1) DK0722434T3 (en)
ES (1) ES2120070T3 (en)
HU (1) HU218923B (en)
RU (1) RU2136653C1 (en)
SI (1) SI0722434T1 (en)
WO (1) WO1995009831A1 (en)

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