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RU2353621C2 - Substituted quiinobenzoxazin analogues - Google Patents

Substituted quiinobenzoxazin analogues Download PDF

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Publication number
RU2353621C2
RU2353621C2 RU2005134206/04A RU2005134206A RU2353621C2 RU 2353621 C2 RU2353621 C2 RU 2353621C2 RU 2005134206/04 A RU2005134206/04 A RU 2005134206/04A RU 2005134206 A RU2005134206 A RU 2005134206A RU 2353621 C2 RU2353621 C2 RU 2353621C2
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RU
Russia
Prior art keywords
heterocyclic ring
compound
compound according
substituted
group
Prior art date
Application number
RU2005134206/04A
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Russian (ru)
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RU2005134206A (en
Inventor
Джеффри П. ВИТТЕН (US)
Джеффри П. ВИТТЕН
Майкл ШВАЕБИ (US)
Майкл ШВАЕБИ
Адам СИДДИКЬЮ-ДЖЕЙН (US)
Адам СИДДИКЬЮ-ДЖЕЙН
Терранс МОРАН (US)
Терранс МОРАН
Original Assignee
Силин Фармасьютикалз, Инк.
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Publication of RU2005134206A publication Critical patent/RU2005134206A/en
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Publication of RU2353621C2 publication Critical patent/RU2353621C2/en

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Abstract

FIELD: chemistry.
SUBSTANCE: claimed invention relates to quinobenzoxazin analogues with general formula (1)
Figure 00000455
where V represents H, halo-, or NR1R2; NH2, or NR1-(CR1 2)n-NR3R4; A represents H, fluoro-, or NR1 2; Z represents O, S, NR1 or CH2; U represents NR1R2; X represents NR1R2 or halo-; n=1-6; where in NR1R2, R1 and R2 can form 5-7-member heterocyclic ring which is optionally substituted and has 1-2 heteroatoms, selected from group consisting of N, O and S; R1 represents H or C1-6alkyl; R2 represents C1-10alkyl optionally including one or more non-adjacent heteroatoms N or O and is optionally substituted with if necessary substituted 3-6-member carbocyclic or 5-14-member heterocyclic ring; or R2 is 5-14-member heterocyclic ring, which has 1-2 heteroatoms, selected from group consisting of N, O or S, 6-member aryl or 5-7member heteroaryl ring, which contains 1-3 heteroatoms, selected from group consisting of N, O and S, each of which can be, if necessary, substituted; R3 represents H or C1-6alkyl; R4 represents H, C1-6alkyl, optionally substituted with 3-6 carbocyclic or 5-14-member heterocyclic ring, or 6-member aryl, R4 and R3, if necessary, can form optionally 5-7-member substituted heterocyclic ring, which contains 1-2 heteroatoms selected from N and O; W represents substituent, such as described in i.1 of invention formula, where Q, Q1, Q2, and Q3 represents independently CH or N; Y represents independently O or CH; R5 represents substituent in any position of closed ring in form of H or OR2; on condition that U is not morpholinyl or 2,4-difluoroaniline, when X represents F or pyrrolidinyl, A is F, Z represents O, and W represents phenylene; each obligatorily substituted fragment being substituted with one or more halogen, C1-6-alkoxy, amino, carbamate, C1-10alkyl, C2-10alkenyl, each of which is optionally substituted with halogen, =O, 6-member aryl or one or more heteroatom, selected from N and O; 6-member aryl, 3-6-member carbocyclic ring or 5-7-member heterocyclic ring containing 1-2 heteroatoms, selected from group, consisting of N and O; or its pharmaceutically acceptable salts. Invention also relates to pharmaceutical composition based on formula (1) compound and to method of treatment of proliferative cell diseases using formula (1) compounds.
EFFECT: obtaining novel quinobenzoxazin analogues possessing useful biological properties.
48 cl, 3 tbl, 50 ex

Description

Текст описания приведен в факсимильном виде.

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The text of the description is given in facsimile form.
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Claims (48)

1. Соединение формулы (1)
Figure 00000429

где V обозначает Н, гало-, или NR1R2; NH2, или NR1-(CR1 2)n-NR3R4;
А обозначает Н, фторо-, или NR1 2;
Z обозначает О, S, NR1 или СН2;
U обозначает NR1R2;
X обозначает NR1R2 или гало-;
n=1-6;
где в NR1R2, R1 и R2 могут формировать 5-7-членное гетероциклическое кольцо, которое является необязательно замещенным и имеет 1-2 гетероатома, выбранные из группы, состоящей из N, О и S;
R1 обозначает Н или C1-6алкил;
R2 обозначает С1-10алкил, необязательно включающий один и более несмежных гетероатомов N или О, и является необязательно замещенным при необходимости замещенным 3-6-членным карбоциклическим или 5-14-членным гетероциклическим кольцом; или R2 является 5-14-членным гетероциклическим кольцом, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из N, О или S, 6-членным арилом или 5-7-членным гетероарильным кольцом, которое содержит 1-3 гетероатома, выбранные из группы, состоящей из N, О и S, каждый из которых может быть при необходимости замещен;
R3 обозначает Н или C1-6 алкил;
R4 обозначает Н, C1-6 алкил, необязательно замещенный 3-6-членным карбоциклическим или 5-14-членным гетероциклическим кольцом, или 6-членный арил, причем R3 и R4 при необходимости могут образовывать необязательно 5-7-членное замещенное гетероциклическое кольцо, которое содержит 1-2 гетероатома, выбранные из N и О;
W обозначает заместитель, выбираемый из группы:
Figure 00000430
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Figure 00000435
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Figure 00000437
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Figure 00000443
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Figure 00000446

Figure 00000447
Figure 00000448
Figure 00000449

Figure 00000450
Figure 00000451
Figure 00000452

где Q, Q1, Q2, и Q3 обозначает независимо СН или N;
Y обозначает независимо О или СН;
R5 означает заместитель в любом положении замкнутого кольца в виде Н или OR2;
при условии, что U не является морфолинилом или 2,4-дифторанилином, когда X означает F или пирролидинил, А является F, Z означает О, и W означает фенилен;
причем каждый обязательно замещенный фрагмент является замещенным одним или более галогеном, С1-6-алкокси, амино, карбаматом, С1-10алкилом, С2-10алкенилом, каждый из которых необязательно замещен галогеном, =O, 6-членным арилом или одним или более гетероатомом, выбранным из N и О; 6-членным арилом, 3-6-членным карбоциклическим кольцом или 5-7-членным гетероциклическим кольцом, содержащим 1-2 гетероатома, выбранные из группы, состоящей из N и О;
или его фармацевтически пригодные соли.1. The compound of formula (1)
Figure 00000429

where V is H, halo, or NR 1 R 2 ; NH 2 or NR 1 - (CR 1 2 ) n -NR 3 R 4 ;
A is H, fluoro, or NR 1 2 ;
Z is O, S, NR 1 or CH 2 ;
U is NR 1 R 2 ;
X is NR 1 R 2 or halo;
n is 1-6;
where in NR 1 R 2 , R 1 and R 2 can form a 5-7 membered heterocyclic ring which is optionally substituted and has 1-2 heteroatoms selected from the group consisting of N, O and S;
R 1 is H or C 1-6 alkyl;
R 2 is C 1-10 alkyl, optionally including one or more non-adjacent N or O heteroatoms, and is optionally substituted with optionally substituted 3-6 membered carbocyclic or 5-14 membered heterocyclic ring; or R 2 is a 5-14 membered heterocyclic ring that has 1-2 heteroatoms selected from the group consisting of N, O or S, a 6 membered aryl or a 5-7 membered heteroaryl ring that contains 1-3 heteroatoms selected from the group consisting of N, O and S, each of which may be optionally substituted;
R 3 is H or C 1-6 alkyl;
R 4 is H, C 1-6 alkyl optionally substituted with a 3-6 membered carbocyclic or 5-14 membered heterocyclic ring, or a 6 membered aryl, wherein R 3 and R 4 may optionally form a 5-7 membered a substituted heterocyclic ring that contains 1-2 heteroatoms selected from N and O;
W denotes a Deputy selected from the group:
Figure 00000430
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Figure 00000435
Figure 00000436

Figure 00000437
Figure 00000438
Figure 00000439

Figure 00000440
Figure 00000441
Figure 00000442

Figure 00000443
Figure 00000444
Figure 00000445
Figure 00000446

Figure 00000447
Figure 00000448
Figure 00000449

Figure 00000450
Figure 00000451
Figure 00000452

where Q, Q 1 , Q 2 , and Q 3 are independently CH or N;
Y is independently O or CH;
R 5 means a substituent in any position of the closed ring in the form of H or OR 2 ;
with the proviso that U is not morpholinyl or 2,4-difluoroaniline when X is F or pyrrolidinyl, A is F, Z is O, and W is phenylene;
wherein each necessarily substituted moiety is substituted with one or more halogen, C 1-6 alkoxy, amino, carbamate, C 1-10 alkyl, C 2-10 alkenyl, each of which is optionally substituted with halogen, = O, 6-membered aryl or one or more heteroatoms selected from N and O; 6-membered aryl, 3-6-membered carbocyclic ring or 5-7-membered heterocyclic ring containing 1-2 heteroatoms selected from the group consisting of N and O;
or its pharmaceutically acceptable salts. 2. Соединение по п.1, где А и X независимо являются фтором.2. The compound according to claim 1, where A and X are independently fluorine. 3. Соединение по п.2, где А означает фтор.3. The compound according to claim 2, where A means fluorine. 4. Соединение по п.1, где V представляет собой Н.4. The compound according to claim 1, where V represents N. 5. Соединение по п.1, где U и X независимо означают NR1R2.5. The compound according to claim 1, where U and X independently mean NR 1 R 2 . 6. Соединение по п.5, где R1 является Н, a R2 означает С1-10алкил, необязательно содержащий один или более несмежных гетероатомов N или О и необязательно замещенный необязательно замещенными С3-6циклоалкилом, 6-членным арилом или 5-14-членным гетероциклическим кольцом, содержащим 1-3 гетероатома, выбранные из группы, состоящей из N, О или S.6. The compound according to claim 5, where R 1 is H, a R 2 means C 1-10 alkyl, optionally containing one or more non-adjacent heteroatoms N or O and optionally substituted with optionally substituted C 3-6 cycloalkyl, 6-membered aryl or 5-14 membered heterocyclic ring containing 1-3 heteroatoms selected from the group consisting of N, O or S. 7. Соединение по п.6, где упомянутое 5-14-членное гетероциклическое кольцо выбирается из группы: тетрагидрофуран, 1,3-диоксолан, 2,3-дигидрофуран, тетрагидропиран, бензофуран, изобензофуран, 1,3-дигидроизобензофуран, изоксазол, 4,5-дигидроизоксазол, пиперидин, пирролидин, пирролидин-2-он, пиррол, пиридин, пиримидин, октагидропирроло[3,4-b]пиридин, пиперазин, пиразин, морфолин, тиоморфолин, имидазол, имидазолидин-2,4-дион, бензимидазол, 1,3-дигидробензимидазол-2-он, индол, тиазол, бензотиазол, тиадиазол, тиофен, тетрагидротиофен-1,1-диоксид, диазепин, триазол, гуанидин, диазабицикло[2.2.1]гептан, 2,5-диазабицикло[2.2.1]гептан и 2,3,4,4а,9,9а-гексадигидро-1H-β-карболин.7. The compound according to claim 6, where the aforementioned 5-14 membered heterocyclic ring is selected from the group: tetrahydrofuran, 1,3-dioxolane, 2,3-dihydrofuran, tetrahydropyran, benzofuran, isobenzofuran, 1,3-dihydroisobenzofuran, isoxazole, 4 , 5-dihydroisoxazole, piperidine, pyrrolidine, pyrrolidin-2-one, pyrrole, pyridine, pyrimidine, octahydropyrrolo [3,4-b] pyridine, piperazine, pyrazine, morpholine, thiomorpholine, imidazole, imidazolidine-2,4-dione , 1,3-dihydrobenzimidazol-2-one, indole, thiazole, benzothiazole, thiadiazole, thiophene, tetrahydrothiophene-1,1-dioxide, diazepine, triazole , guanidine, diazabicyclo [2.2.1] heptane, 2,5-diazabicyclo [2.2.1] heptane and 2,3,4,4a, 9,9a-hexadihydro-1H-β-carboline. 8. Соединение по п.5, где R1 является Н, a R2 означает 6-членный арил или 5-14-членное гетероциклическое кольцо, содержащее 1-3 гетероатома, выбранные из группы, состоящей из N, О или S, каждый из которых необязательно замещен амином или другим 5-7-членным гетероциклическим кольцом, которое содержит 1-2 гетероатома, выбранные из группы, состоящей из О и N.8. The compound according to claim 5, where R 1 is H, a R 2 means a 6-membered aryl or 5-14-membered heterocyclic ring containing 1-3 heteroatoms selected from the group consisting of N, O or S, each of which are optionally substituted with an amine or other 5-7 membered heterocyclic ring that contains 1-2 heteroatoms selected from the group consisting of O and N. 9. Соединение по п.8, где упомянутое 5-14-членное гетероциклическое кольцо выбирается из группы: тетрагидрофуран, 1,3-диоксолан, 2,3-дигидрофуран, тетрагидропиран, бензофуран, изобензофуран, 1,3-дигидроизобензофуран, изоксазол, 4,5-дигидроизоксазол, пиперидин, пирролидин, пирролидин-2-он, пиррол, пиридин, пиримидин, октагидропирроло[3,4-b]пиридин, пиперазин, пиразин, морфолин, тиоморфолин, имидазол, имидазолидин-2,4-дион, бензимидазол, 1,3-дигидробензимидазол-2-он, индол, тиазол, бензотиазол, тиадиазол, тиофен, тетрагидротиофен-1,1-диоксид, диазепин, триазол, гуанидин, диазабицикло[2.2.1]гептан, 2,5-диазабицикло[2.2.1]гептан и 2,3,4,4а,9,9а-гексагидро-1Н-β-карболин.9. The compound of claim 8, wherein said 5-14 membered heterocyclic ring is selected from the group: tetrahydrofuran, 1,3-dioxolane, 2,3-dihydrofuran, tetrahydropyran, benzofuran, isobenzofuran, 1,3-dihydroisobenzofuran, isoxazole, 4 , 5-dihydroisoxazole, piperidine, pyrrolidine, pyrrolidin-2-one, pyrrole, pyridine, pyrimidine, octahydropyrrolo [3,4-b] pyridine, piperazine, pyrazine, morpholine, thiomorpholine, imidazole, imidazolidine-2,4-dione , 1,3-dihydrobenzimidazol-2-one, indole, thiazole, benzothiazole, thiadiazole, thiophene, tetrahydrothiophene-1,1-dioxide, diazepine, triazole , guanidine, diazabicyclo [2.2.1] heptane, 2,5-diazabicyclo [2.2.1] heptane and 2,3,4,4a, 9,9a-hexahydro-1H-β-carboline. 10. Соединение по п.5, где R1 и R2 в NR1R2 формируют замещенное или незамещенное 5-7-членное гетероциклическое кольцо, содержащее 1-2 гетероатома, выбранные из группы, содержащей N, О или S.10. The compound according to claim 5, where R 1 and R 2 in NR 1 R 2 form a substituted or unsubstituted 5-7 membered heterocyclic ring containing 1-2 heteroatoms selected from the group consisting of N, O or S. 11. Соединение по п.10, где NR1R2 означает морфолин, тиоморфолин, пиперазин, пиперидин или диазепин, каждый из которых является необязательно замещенным.11. The compound of claim 10, where NR 1 R 2 means morpholine, thiomorpholine, piperazine, piperidine or diazepine, each of which is optionally substituted. 12. Соединение по п.1, где U и X независимо имеют формулу
Figure 00000453

где R1 и R3 означает независимо Н или C1-6алкил;
n=1-6;
R4 обозначает Н или C1-6алкил, необязательно замещенный 3-6-членным карбоциклическим или 5-14-членным гетероциклическим кольцом;
и где в NR3R4 R3 и R4 могут формировать замещенное или незамещенное 5-7-членное гетероциклическое кольцо, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из О и N.12. The compound according to claim 1, where U and X independently have the formula
Figure 00000453

where R 1 and R 3 mean independently H or C 1-6 alkyl;
n is 1-6;
R 4 is H or C 1-6 alkyl optionally substituted with a 3-6 membered carbocyclic or 5-14 membered heterocyclic ring;
and where in NR 3 R 4 R 3 and R 4 can form a substituted or unsubstituted 5-7 membered heterocyclic ring that has 1-2 heteroatoms selected from the group consisting of O and N. 13. Соединение по п.12, где n равно 2-3.13. The compound according to item 12, where n is 2-3. 14. Соединение по п.12, где NR3R4 означает ациклический амин или гуанидинил, или его таутомер; или же R3 и R4 необязательно формируют замещенное 5-7-членное гетероциклическое кольцо, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из N и О.14. The compound of claim 12, wherein NR 3 R 4 is an acyclic amine or guanidinyl, or a tautomer thereof; or R 3 and R 4 optionally form a substituted 5-7 membered heterocyclic ring that has 1-2 heteroatoms selected from the group consisting of N and O. 15. Соединение по п.12, где NR3R4 означает морфолин, имидазол, пирролидин, пиперазин, пиридин или пиперидин, каждый из которых является необязательно замещенным.15. The compound according to item 12, where NR 3 R 4 means morpholine, imidazole, pyrrolidine, piperazine, pyridine or piperidine, each of which is optionally substituted. 16. Соединение по п.1, где X означает NR1R2, a U имеет формулу
Figure 00000453

где R1 и R2 означает как определено в п.1;
R3 обозначает Н или C1-6алкил;
n=1-6;
R4 обозначает Н или С1-6алкил, необязательно замещенный 3-6-членным карбоциклическим или 5-14-членным гетероциклическим кольцом, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из О и N;
и где R1 и R2 в NR1R2, a R3 и R4 в NR3R4 каждый независимо могут формировать замещенное 5-7-членное гетероциклическое кольцо, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из N и О.16. The compound according to claim 1, where X is NR 1 R 2 , and U has the formula
Figure 00000453

where R 1 and R 2 means as defined in claim 1;
R 3 is H or C 1-6 alkyl;
n is 1-6;
R 4 is H or C 1-6 alkyl optionally substituted with a 3-6 membered carbocyclic or 5-14 membered heterocyclic ring which has 1-2 heteroatoms selected from the group consisting of O and N;
and where R 1 and R 2 in NR 1 R 2 , a R 3 and R 4 in NR 3 R 4 each independently can form a substituted 5-7 membered heterocyclic ring that has 1-2 heteroatoms selected from the group consisting of N and O. 17. Соединение по п.16, где R1 и R2 в NR1R2, a R3 и R4 в NR3R4 каждый независимо формируют замещенное 5-7-членное гетероциклическое кольцо, содержащее 1-2 гетероатома, выбранные из группы, состоящей из N и O.17. The compound according to clause 16, where R 1 and R 2 in NR 1 R 2 , a R 3 and R 4 in NR 3 R 4 each independently form a substituted 5-7 membered heterocyclic ring containing 1-2 heteroatoms selected from the group consisting of N and O. 18. Соединение по п.17, где X означает замещенный или не замещенный амином, карбаматом, С1-10алкилом, содержащим один и более несмежных атомов N, О или S, и замещенный или незамещенный 5-7-членным гетероциклическим кольцом, 6-членным арилом или насыщенным или не насыщенным 5-7-членным гетероциклическим кольцом, каждый из которых также необязательно замещен.18. The compound of claim 17, wherein X is substituted or unsubstituted with an amine, carbamate, C 1-10 alkyl containing one or more non-adjacent N, O or S atoms, and substituted or unsubstituted with a 5-7 membered heterocyclic ring, 6 a membered aryl or a saturated or unsaturated 5-7 membered heterocyclic ring, each of which is also optionally substituted. 19. Соединение по п.17, где X замещен гетероциклическим кольцом, выбранным из группы: тетрагидрофуран, 1,3-диоксолан, 2,3-дигидрофуран, тетрагидропиран, бензофуран, изобензофуран, 1,3-дигидроизобензофуран, изоксазол, 4,5-дигидроизоксазол, пиперидин, пирролидин, пирролидин-2-он, пиррол, пиридин, пиримидин, октагидропирроло[3,4-b]пиридин, пиперазин, пиразин, морфолин, тиоморфолин, имидазол, имидазолидин-2,4-дион, бензимидазол, 1,3-дигидробензимидазол-2-он, индол, тиазол, бензотиазол, тиадиазол, тиофен, тетрагидротиофен-1,1-диоксид, диазепин, триазол, гуанидин, диазабицикло[2.2.1]гептан, 2,5-диазабицикло[2.2.1]гептан и 2,3,4,4а,9,9а-гексагидро-1H-β-карболин.19. The compound according to 17, where X is substituted by a heterocyclic ring selected from the group: tetrahydrofuran, 1,3-dioxolane, 2,3-dihydrofuran, tetrahydropyran, benzofuran, isobenzofuran, 1,3-dihydroisobenzofuran, isoxazole, 4,5- dihydroisoxazole, piperidine, pyrrolidine, pyrrolidin-2-one, pyrrole, pyridine, pyrimidine, octahydropyrrolo [3,4-b] pyridine, piperazine, pyrazine, morpholine, thiomorpholine, imidazole, imidazolidine-2,4-dione, 1 3-dihydrobenzimidazol-2-one, indole, thiazole, benzothiazole, thiadiazole, thiophene, tetrahydrothiophene-1,1-dioxide, diazepine, triazole, guanidine, iazabitsiklo [2.2.1] heptane, 2,5-diazabicyclo [2.2.1] heptane, 2,3,4,4a, 9,9a-hexahydro-1H-β-carboline. 20. Соединение по п.17, где X и NR3R4 означает независимо морфолин, имидазол, пирролидин, пиперазин, пиридин или пиперидин, каждый из которых является необязательно замещенным.20. The compound of claim 17, wherein X and NR 3 R 4 are independently morpholine, imidazole, pyrrolidine, piperazine, pyridine or piperidine, each of which is optionally substituted. 21. Соединение по п.20, где X и NR3R4 независимо означают пирролидин, каждый из которых является необязательно замещенным.21. The compound according to claim 20, where X and NR 3 R 4 independently mean pyrrolidine, each of which is optionally substituted. 22. Соединение по п.21, где X замещен пиразином.22. The compound of claim 21, wherein X is substituted with pyrazine. 23. Соединение по п.22, где W означает нафталенил.23. The compound of claim 22, wherein W is naphthalenyl. 24. Соединение по п.1, где W означает бензол, пиридин, дифенил, нафталин, фенантрен, хинолин, изохинолин, хиназолин, циннолин, фталазин, хиноксалин, индол, бензимидазол, бензоксазол, бензтиазол, бензофуран, антрон, ксантон, акридон, флуоренон, карбазолил, пиримидо[4,3-b]фуран, пиридо[4,3-b]индол, пиридо[2,3-b]индол, дибензофурана, акридин или акридизин.24. The compound according to claim 1, where W means benzene, pyridine, diphenyl, naphthalene, phenanthrene, quinoline, isoquinoline, quinazoline, cinnoline, phthalazine, quinoxaline, indole, benzimidazole, benzoxazole, benzthiazole, benzofuran, anthrone, xanthon, acridone, fluoride , carbazolyl, pyrimido [4,3-b] furan, pyrido [4,3-b] indole, pyrido [2,3-b] indole, dibenzofuran, acridine or acridizine. 25. Соединение по п.1, где указанное соединение проявляет хиральные свойства.25. The compound according to claim 1, where the specified compound exhibits chiral properties. 26. Фармацевтическая композиция, полезная для снижения клеточной пролиферации или индукции смерти клеток, включающая соединение по п.1 и приемлемый фармацевтически наполнитель.26. A pharmaceutical composition useful for reducing cell proliferation or inducing cell death, comprising the compound of claim 1 and an acceptable pharmaceutically acceptable excipient. 27. Способ лечения пролиферативных клеточных заболеваний, включающий введение субъекту эффективных количеств соединения по п.1 или его фармацевтической композиции, в результате чего излечиваются вышеупомянутые пролиферативные клеточные заболевания.27. A method of treating proliferative cell diseases, comprising administering to the subject effective amounts of a compound according to claim 1 or a pharmaceutical composition thereof, as a result of which the aforementioned proliferative cell diseases are treated. 28. Способ по п.27, в котором упомянутым пролиферативным клеточным заболеванием является рак.28. The method of claim 27, wherein said proliferative cell disease is cancer. 29. Способ по п.27, в котором угнетается клеточная пролиферация или индуцируется клеточная смерть.29. The method according to item 27, in which cell proliferation is inhibited or cell death is induced. 30. Способ по п.27, в котором упомянутым субъектом является человек или животное.30. The method of claim 27, wherein said subject is a human or animal. 31. Способ угнетения клеточной пролиферации или индукции клеточной смерти, включающий контактирование системы с эффективным количеством соединения по п.1 или его фармацевтической композиции, приводит к угнетению клеточной пролиферации или индукции клеточной смерти в вышеупомянутой системе.31. A method of inhibiting cell proliferation or inducing cell death, comprising contacting the system with an effective amount of a compound according to claim 1 or a pharmaceutical composition thereof, inhibiting cell proliferation or inducing cell death in the aforementioned system. 32. Способ по п.31, где упомянутой системой является клетка или ткань.32. The method of claim 31, wherein said system is a cell or tissue. 33. Способ уменьшения микробных титров, включающий контактирование системы с эффективным количеством соединения по п.1 или его фармацевтической композиции, что приводит к уменьшению микробных титров.33. A method of reducing microbial titers, comprising contacting the system with an effective amount of a compound according to claim 1 or its pharmaceutical composition, which leads to a decrease in microbial titers. 34. Способ по п.33, где системой является клетка или ткань.34. The method according to p, where the system is a cell or tissue. 35. Способ по п.33, в котором микробными титрами являются титры вирусов, бактерий и грибов.35. The method according to p, in which the microbial titers are titers of viruses, bacteria and fungi. 36. Способ лечения микробной инфекции, включающий введение субъекту эффективных количеств соединения по п.1 или его фармацевтической композиции, в результате чего излечивается вышеупомянутая микробная инфекция.36. A method of treating a microbial infection, comprising administering to the subject effective amounts of a compound according to claim 1 or a pharmaceutical composition thereof, as a result of which the aforementioned microbial infection is cured. 37. Способ по п.36, в котором упомянутым объектом является человек или животное.37. The method of claim 36, wherein said object is a human or animal. 38. Способ по п.36, в котором микробной инфекцией является вирусная, бактериальная или грибковая инфекция.38. The method according to clause 36, in which the microbial infection is a viral, bacterial or fungal infection. 39. Соединение по п.1, где V означает NH2 или NR1-(CR1 2)n-NR3R4,
где R1 и R3 являются независимо Н или C1-6алкил;
n=1-6;
R4 означает Н, С1-6алкил, замещенный или незамещенный 3-6-членным карбоциклическим или 5-7-членным гетероциклическим кольцом, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из О и N или 6-членныи арил; и где могут формировать необязательно замещенное 5-7-членное гетероциклическое кольцо, которое имеет 1-2 гетероатома, выбранные из группы, состоящей из О и N.39. The compound according to claim 1, where V means NH 2 or NR 1 - (CR 1 2 ) n -NR 3 R 4 ,
where R 1 and R 3 are independently H or C 1-6 alkyl;
n is 1-6;
R 4 means H, C 1-6 alkyl, substituted or unsubstituted with a 3-6 membered carbocyclic or 5-7 membered heterocyclic ring which has 1-2 heteroatoms selected from the group consisting of O and N or 6 membered aryl ; and where they can form an optionally substituted 5-7 membered heterocyclic ring that has 1-2 heteroatoms selected from the group consisting of O and N. 40. Соединение по п.16, где V означает Н.40. The compound according to clause 16, where V means N. 41. Соединение по п.16, где А означает фторо.41. The compound of claim 16, wherein A is fluoro. 42. Соединение по п.16, где W означает нафталенил.42. The compound according to clause 16, where W means naphthalenyl. 43. Соединение по п.23, где V означает Н, а А - фторо.43. The compound of claim 23, wherein V is H and A is fluoro. 44. Соединение по п.1, где указанное соединение выбирается из соединений, представленных в табл.2.44. The compound according to claim 1, where the specified compound is selected from the compounds shown in table.2. 45. Соединение по п.1, где Z означает О.45. The compound according to claim 1, where Z means O. 46. Соединение по п.1, где соединение выбирают из группы, состоящей из соединений 339, 356, 468, 469, 494 и 516 представленных в табл.2.46. The compound according to claim 1, where the compound is selected from the group consisting of compounds 339, 356, 468, 469, 494 and 516 shown in table 2. 47. Соединение по п.46, где соединением является соединение 516, представленное в табл.2.47. The compound of claim 46, wherein the compound is compound 516 shown in Table 2. 48. Соединение по п.46, где соединением является соединение 494, представленное в табл.2. 48. The compound of claim 46, wherein the compound is compound 494 shown in Table 2.
RU2005134206/04A 2003-04-07 2004-04-07 Substituted quiinobenzoxazin analogues RU2353621C2 (en)

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US46127103P 2003-04-07 2003-04-07
US60/461,271 2003-04-07
US46317103P 2003-04-15 2003-04-15
US60/463,171 2003-04-15
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US4533663A (en) * 1984-04-26 1985-08-06 Abbott Laboratories Quino-benzothiazine antibacterial compounds
US4607032A (en) * 1984-04-26 1986-08-19 Abbott Laboratories Quino-benoxazine antibacterial compounds
US5318965A (en) * 1990-08-24 1994-06-07 Abbott Laboratories Quinobenzoxazine, antineoplastic agents
RU2173318C2 (en) * 1996-02-23 2001-09-10 Байер Акциенгезелльшафт Fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acids, their derivatives and pharmaceutical composition eliciting anti-bacterial activity

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4533663A (en) * 1984-04-26 1985-08-06 Abbott Laboratories Quino-benzothiazine antibacterial compounds
US4607032A (en) * 1984-04-26 1986-08-19 Abbott Laboratories Quino-benoxazine antibacterial compounds
US5318965A (en) * 1990-08-24 1994-06-07 Abbott Laboratories Quinobenzoxazine, antineoplastic agents
RU2173318C2 (en) * 1996-02-23 2001-09-10 Байер Акциенгезелльшафт Fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acids, their derivatives and pharmaceutical composition eliciting anti-bacterial activity

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