RU98118568A - TRIARY CONNECTIONS - Google Patents

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Publication number
RU98118568A
RU98118568A RU98118568/04A RU98118568A RU98118568A RU 98118568 A RU98118568 A RU 98118568A RU 98118568/04 A RU98118568/04 A RU 98118568/04A RU 98118568 A RU98118568 A RU 98118568A RU 98118568 A RU98118568 A RU 98118568A
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Prior art keywords
methoxy
biphenyl
phenyl
aryl
pyridine
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RU98118568/04A
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Russian (ru)
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RU2194035C2 (en
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Уилльям Мэнли Пол
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Новартис Аг
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1. (4-окси-3-(арил)фенил)азарильное соединение или (4-окси-3-(арил)фенил)арилкарбонилоксисоединение в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли, предназначенное для применения в качестве фармацевтического препарата.1. (4-hydroxy-3- (aryl) phenyl) azaryl compound or (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compound in free form or in the form of a pharmaceutically acceptable acid addition salt, intended for use as a pharmaceutical preparation . 2. Фармацевтическая композиция, содержащая (4-окси-3-(арил)фенил)-азарильное соединение или (4-окси-3-(арил)фенил)арилкарбонилоксисоединение в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли. 2. A pharmaceutical composition comprising a (4-hydroxy-3- (aryl) phenyl) -azaryl compound or (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compound in free form or in the form of a pharmaceutically acceptable acid addition salt. 3. Применение (4-окси-3-(арил)фенил)азарильного соединения или (4-окси-3-(арил)фенил)арилкарбонилоксисоединения в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли при изготовлении лекарственного средства, предназначенного для лечения или профилактики воспалительного заболевания. 3. The use of (4-hydroxy-3- (aryl) phenyl) azaryl compound or (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compounds in free form or in the form of a pharmaceutically acceptable acid additive salt in the manufacture of a medicine intended for treating or preventing inflammatory disease. 4. Способ лечения или профилактики воспалительного заболевания, включающий введение эффективного количества (4-окси-3-(арил)фенил)-азарильного соединения или (4-окси-3-(арил)фенил)арилкарбонилоксисоединения в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли пациенту, нуждающемуся в такой терапии. 4. A method of treating or preventing an inflammatory disease, comprising administering an effective amount of (4-hydroxy-3- (aryl) phenyl) -azaryl compound or (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compounds in free form or in pharmaceutically acceptable form. acid additive salt to a patient in need of such therapy. 5. (4-окси-3-(арил)фенил)азарильное соединение или (4-окси-3-(арил)фенил)арилкарбонилоксисоединение в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли, при условии: что 3-арильный фрагмент не обозначает незамещеный фенил, когда фрагмент арилкарбонилокси обозначает фенил-4-карбоновую кислоту или фенил-4-метилкарбоксилат, или азарильный фрагмент обозначает 5-метилтиазол-2-ил, или при условии, что 3-арильный фрагмент не обозначает незамещенный фенил или 2-метоксифен-1-ил, когда азарильный фрагмент обозначает незамещенный 2-хинолин или 2-хинолин, замещенный метилом или фенилом в положении 3 и/или карбоксигруппой в положении 4. 5. (4-hydroxy-3- (aryl) phenyl) azaryl compound or (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compound in free form or in the form of a pharmaceutically acceptable acid addition salt, provided that: 3-aryl the moiety does not denote unsubstituted phenyl, when the arylcarbonyloxy moiety is phenyl-4-carboxylic acid or phenyl-4-methylcarboxylate, or the asaryl moiety is 5-methylthiazol-2-yl, or with the proviso that the 3-aryl moiety does not mean unsubstituted phenyl or 2 -methoxyphen-1-yl, when the azaryl moiety is unsubstituted ny 2-quinoline or 2-quinoline substituted by methyl or phenyl at position 3 and / or by carboxy at position 4. 6. (4-окси-3-(арил)фенил)азарильное соединение по п. 1 или 5. 6. (4-hydroxy-3- (aryl) phenyl) azaryl compound according to claim 1 or 5. 7. (4-окси-3-(арил)фенил)арилкарбонилоксисоединение по п. 1 или 5. 7. (4-hydroxy-3- (aryl) phenyl) arylcarbonyloxy compound according to claim 1 or 5. 8. Соединение по пп. 1, 5, 6 или 7 формулы Ia или формулы Ib:
Figure 00000001

Figure 00000002

где в формуле Ia W обозначает N или C-CO-R,
где R обозначает ОН, О-С1-С6алкил или NR3R4,
где R3 и R4, которые могут иметь одинаковые или различные значения, обозначают Н или С1-С6алкил, или
в формуле Ib Az обозначает азарильную группу, содержащую один или несколько атомов азота, такую, как хинолин, изохинилин, индол, имидазопиридин, например, имидазо[1,2-а] пиридин, и в обеих формулах Iа и Ib R1 обозначает С1-С4алкил, предпочтительно метил; R2 обозначает фенильный фрагмент, например, формулы II
Figure 00000003

где R5 и R6 независимо друг от друга обозначают Н, нитро, галоген (например, хлор), трифторметил, С1-С4алкокси, циано или фенокси; или R5 и R6 вместе образуют мостик, имеющий длину 3-5 атомов, где атомы мостика выбирают из группы, включающей S, О, N и С, например, -ОСН2О-, или пропилен; или R2 обозначает 2,5-циклогексадиен-3,4-илидин-1-иловый фрагмент, например, формулы III
Figure 00000004

где R7 и R8 вместе образуют ароматический мостик, имеющий длину 3-5 атомов, где атомы мостика выбирают из группы, включающей S, О, N и С, например, =N-O-N=;
в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли.8. Connection on PP. 1, 5, 6 or 7 of formula Ia or formula Ib:
Figure 00000001

Figure 00000002

where in formula Ia W denotes N or C-CO-R,
where R is OH, OC 1 -C 6 alkyl or NR 3 R 4 ,
where R 3 and R 4 , which may have the same or different meanings, are H or C 1 -C 6 alkyl, or
in formula Ib, Az means an asaric group containing one or more nitrogen atoms, such as quinoline, isoquiniline, indole, imidazopyridine, for example, imidazo [1,2-a] pyridine, and in both formulas Ia and Ib R 1 is C 1 -C 4 alkyl, preferably methyl; R 2 denotes a phenyl fragment, for example, of formula II
Figure 00000003

where R 5 and R 6 independently of one another denote H, nitro, halogen (for example, chlorine), trifluoromethyl, C 1 -C 4 alkoxy, cyano or phenoxy; or R 5 and R 6 together form a bridge having a length of 3-5 atoms, where the atoms of the bridge are selected from the group consisting of S, O, N and C, for example, -OCH 2 O-, or propylene; or R 2 denotes a 2,5-cyclohexadiene-3,4-ylidin-1-yl fragment, for example, of formula III
Figure 00000004

where R 7 and R 8 together form an aromatic bridge having a length of 3-5 atoms, where the atoms of the bridge are selected from the group comprising S, O, N and C, for example, = NON =;
in free form or in the form of a pharmaceutically acceptable acid addition salt. 9. Соединение, выбранное из группы, включающей
4-[2-(метокси)бифенил-5-ил]пиридин,
4-[2-(метокси)-3'-(нитро)бифенил-5-ил]пиридин,
4-[2-(метокси)-3'-(трифторметил)бифенил-5-ил]пиридин,
4-[2-(метокси)-3',4'-(пропилен)бифенил]пиридин,
4-[4-(метокси)-3-(бензофуразан-5-ил)фенил]пиридин,
4-[2-(метокси)-3'-(циан)бифенил-5-ил]пиридин,
4-[2-(метокси)-3'-(хлор)бифенил-5-ил]пиридин,
4-[2-(метокси)-3',4'-(метилендиокси)бифенил-5-ил]пиридин,
4-[2-(метокси)-3'-(фенокси)бифенил-5-ил]пиридин,
4-[2-(метокси)-4'-(фенокси)бифенил-5-ил]пиридин,
4-[2-(метокси)-3'-(хлор)-4'-(фтор)бифенил-5-ил]пиридин,
4'-метокси-3'-(бензофуразан-5-ил)[1,1'-бифенил]-4-карбоксамид,
этиловый эфир 4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил] -4-карбоновой кислоты,
этиловый эфир 4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил] -3-карбоновой кислоты,
этиловый эфир 4'-метокси-3-метил-3'-(3-нитрофенил)[1,1'-бифенил]-4-карбоновой кислоты,
этиловый эфир 3'-(5-бензофуразанил)-4'-метокси[1,1'-бифенил]-4-карбоновой кислоты,
2,2-диметилпропиловый эфир 3'-(5-бензофуразанил)-4'-метокси[1,1'-бифенил]-4-карбоновой кислоты,
3'-(5-бензофуразанил)-4'-метокси[1,1'-бифенил]-4-карбоновую кислоту,
4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил]-3-карбоновую кислоту,
4'-метокси-3-метил-3'-(3-нитрофенил)[1,1'-бифенил]-4-карбоновую кислоту,
3'-(5-бензофуразанил)-4'-метокси[1,1'-бифенил]-4-карбоновую кислоту,
4'-метокси-3'-(3-хлорфенил)[1,1'-бифенил]-4-карбоновую кислоту,
4'-метокси-3'-(3-цианфенил)[1,1'-бифенил]-4-карбоновую кислоту,
4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил]-4-карбоксамид,
4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил]-3-карбоксамид,
4'-метокси-3-метил-3'-(3-нитрофенил)[1,1'-бифенил]-4-карбоксамид,
N-метил-4'-метокси-3'-(3-нитрофенил)[1,1'-бифенил]-4-карбоксамид,
6-[4-метокси-3-(5-бензофуразанил)фенил]имидазо[1,2-а]пиридин
в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли.9. A compound selected from the group consisting of
4- [2- (methoxy) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 '- (nitro) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 '- (trifluoromethyl) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 ', 4' - (propylene) biphenyl] pyridine,
4- [4- (methoxy) -3- (benzofurazan-5-yl) phenyl] pyridine,
4- [2- (methoxy) -3 '- (cyan) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 '- (chloro) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 ', 4' - (methylenedioxy) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 '- (phenoxy) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -4 '- (phenoxy) biphenyl-5-yl] pyridine,
4- [2- (methoxy) -3 '- (chlorine) -4' - (fluoro) biphenyl-5-yl] pyridine,
4'-methoxy-3 '- (benzofurazan-5-yl) [1,1'-biphenyl] -4-carboxamide,
4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxylic acid ethyl ester,
4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -3-carboxylic acid ethyl ester,
4'-methoxy-3-methyl-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxylic acid ethyl ester,
3 '- (5-benzofurazanyl) -4'-methoxy [1,1'-biphenyl] -4-carboxylic acid ethyl ester,
3'- (5-benzofurazanyl) -4'-methoxy [1,1'-biphenyl] -4-carboxylic acid 2,2-dimethylpropyl ester
3 '- (5-benzofurazanil) -4'-methoxy [1,1'-biphenyl] -4-carboxylic acid,
4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -3-carboxylic acid,
4'-methoxy-3-methyl-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxylic acid,
3 '- (5-benzofurazanil) -4'-methoxy [1,1'-biphenyl] -4-carboxylic acid,
4'-methoxy-3 '- (3-chlorophenyl) [1,1'-biphenyl] -4-carboxylic acid,
4'-methoxy-3 '- (3-cyanophenyl) [1,1'-biphenyl] -4-carboxylic acid,
4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxamide,
4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -3-carboxamide,
4'-methoxy-3-methyl-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxamide,
N-methyl-4'-methoxy-3 '- (3-nitrophenyl) [1,1'-biphenyl] -4-carboxamide,
6- [4-methoxy-3- (5-benzofurazanyl) phenyl] imidazo [1,2-a] pyridine
in free form or in the form of a pharmaceutically acceptable acid addition salt. 10. Способ получения соединения по любому из пп. 1 или 5-9, включающий взаимодействие соединения формулы I'а или формулы I'b:
Figure 00000005

Figure 00000006

где X обозначает галоген или уходящую группу, a R1, W и Az имеют значения, указанные в п. 8, с активированным арильным соединением формулы IIа или IIIа:
Figure 00000007

Figure 00000008

где Y обозначает галоген (предпочтительно бром) или уходящую группу, такую, как олово- или борсодержащую группу (предпочтительно -В(ОН)2), a R-группы имеют значения, указанные в п. 8, и выделение образовавшегося соединения в свободной форме или в форме фармацевтически приемлемой кислотно-аддитивной соли.10. The method of obtaining compounds according to any one of paragraphs. 1 or 5-9, including the interaction of the compounds of formula Ia or formula Ib:
Figure 00000005

Figure 00000006

where X denotes a halogen or leaving group, a R 1 , W and Az have the meanings indicated in paragraph 8, with an activated aryl compound of the formula IIa or IIIa:
Figure 00000007

Figure 00000008

where Y is halogen (preferably bromine) or a leaving group, such as a tin or boron group (preferably -B (OH) 2 ), a R-groups have the meanings indicated in paragraph 8, and the release of the resulting compound in free form or in the form of a pharmaceutically acceptable acid addition salt. 11. Соединение формул I'а или I'b
Figure 00000009

Figure 00000010

где Х обозначает галоген (предпочтительно бром) или уходящую группу, такую, как олово- или борсодержащую группу (предпочтительно -В(ОН)2), a R1 W и Az имеют значения, указанные в п. 8, при условии, что
когда Х обозначает бром и R1 обозначает метил, W не обозначает C-COOCH3,
когда Х обозначает хлор или бром и R1 обозначает метил, этил, пропил или бутил, W не обозначает С-СООН,
когда Х обозначает хлор и R1 обозначает метил, W не обозначает C-COOCH2CH3 или C-COOCH2CH2CH3 и,
когда R1 обозначает метил и Az обозначает замещенный хинолин или незамещенную или замещенную индольную группу, Х не обозначает фтор.11. Compound formulas of I'a or I'b
Figure 00000009

Figure 00000010

where X denotes halogen (preferably bromine) or a leaving group, such as a tin or boron group (preferably -B (OH) 2 ), a R 1 W and Az have the meanings indicated in paragraph 8, provided that
when X is bromine and R 1 is methyl, W is not C-COOCH 3 ,
when X is chlorine or bromine and R 1 is methyl, ethyl, propyl or butyl, W is not C-COOH,
when X is chlorine and R 1 is methyl, W is not C-COOCH 2 CH 3 or C-COOCH 2 CH 2 CH 3 and,
when R 1 is methyl and Az is substituted quinoline or an unsubstituted or substituted indole group, X is not fluorine. 12. Способ
а) понижающей регуляции или ингибирования выделения TNF-α,
б) ингибирования активности изофермента PDE типа IV,
в) осуществления иммуносупрессии,
г) лечения воспалительного заболевания, или
д) лечения любого конкретного состояния или заболевания, указанного выше,
у пациента, нуждающего в таком лечении, включающий введение пациенту эффективного количества агента по изобретению.12. Method
a) down regulation or inhibition of secretion of TNF-α,
b) inhibiting the activity of PDE isoenzyme type IV,
c) the implementation of immunosuppression,
d) treating an inflammatory disease, or
e) treating any particular condition or disease indicated above,
in a patient in need of such treatment, comprising administering to the patient an effective amount of an agent according to the invention.
RU98118568/04A 1996-03-08 1997-03-07 Triaryl compounds, method of their synthesis, pharmaceutical composition based on thereof, method of treatment and intermediates substances RU2194035C2 (en)

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