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RU2011127468A - TECHNETSKY- AND RENIUM-BIS (HETEROARYL) COMPLEXES AND METHODS OF THEIR APPLICATION FOR PSMA INHIBITION - Google Patents

TECHNETSKY- AND RENIUM-BIS (HETEROARYL) COMPLEXES AND METHODS OF THEIR APPLICATION FOR PSMA INHIBITION Download PDF

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Publication number
RU2011127468A
RU2011127468A RU2011127468/04A RU2011127468A RU2011127468A RU 2011127468 A RU2011127468 A RU 2011127468A RU 2011127468/04 A RU2011127468/04 A RU 2011127468/04A RU 2011127468 A RU2011127468 A RU 2011127468A RU 2011127468 A RU2011127468 A RU 2011127468A
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Russia
Prior art keywords
integer
compound according
pharmaceutically acceptable
complex
acceptable salt
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RU2011127468/04A
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Russian (ru)
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RU2532912C2 (en
Inventor
Джон У. БАБИЧ
Крейг ЦИММЕРМАН.
Джон ДЖОЯЛ
Кевин П. МАРЕСКА
Генлианг ЛУ
Шон ХИЛЬЕР
Original Assignee
Моликьюлар Инсайт Фармасьютикалз, Инк.
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Priority claimed from PCT/US2009/066836 external-priority patent/WO2010065902A2/en
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Claims (21)

1. Соединений формулы I, его фармацевтически приемлемая соль или сольват:1. The compounds of formula I, its pharmaceutically acceptable salt or MES:
Figure 00000001
Figure 00000001
 гдеWhere R обозначает Н, ион аммония, ион алкиламмония, ион щелочноземельного металла, ион редкоземельного металла или алкильную группу;R is H, an ammonium ion, an alkylammonium ion, an alkaline earth metal ion, a rare earth metal ion or an alkyl group; W обозначает связь, -NHC(O)-, -CH(NH2)-, -NH-C(O)-NH-, -C(O)-NH-, -C(O)-NH-CH(COOH)-, -O-(CH2)n-O-(CH2)n-, -(CH2)nO(CH2)nO(CH2)n-, -CH(NHFmoc)-;W is a bond, -NHC (O) -, -CH (NH 2 ) -, -NH-C (O) -NH-, -C (O) -NH-, -C (O) -NH-CH (COOH ) -, -O- (CH 2 ) n -O- (CH 2 ) n -, - (CH 2 ) n O (CH 2 ) n O (CH 2 ) n -, -CH (NHFmoc) -; Z обозначает связь, -CO(O)-, -NH-, -NHC(O)-, -NH-C(O)-NH-, -NH-C(O)-(CH2)n-, -NH-C(O)-CH(NH2)-, -C(O)-NH-CH(COOH)-; или -NH-C(O)-C6H4-(CH2)n-NH-;Z is a bond, -CO (O) -, -NH-, -NHC (O) -, -NH-C (O) -NH-, -NH-C (O) - (CH 2 ) n -, -NH -C (O) -CH (NH 2 ) -, -C (O) -NH-CH (COOH) -; or -NH-C (O) -C 6 H 4 - (CH 2 ) n -NH-; NRaRb обозначает хелатор из группы формул:NR a R b denotes a chelator from the group of formulas:
Figure 00000002
,
Figure 00000003
,
Figure 00000004
,
Figure 00000002
,
Figure 00000003
,
Figure 00000004
,
Figure 00000005
,
Figure 00000006
,
Figure 00000007
,
Figure 00000005
,
Figure 00000006
,
Figure 00000007
,
Figure 00000008
,
Figure 00000009
,
Figure 00000010
,
Figure 00000008
,
Figure 00000009
,
Figure 00000010
,
Figure 00000011
или
Figure 00000012
Figure 00000011
or
Figure 00000012
 Rt обозначает H, С1-С8-алкильную группу, ион аммония, ион алкиламмония, или ион щелочного или щелочноземельного металла;R t is H, a C 1 -C 8 alkyl group, an ammonium ion, an alkylammonium ion, or an alkali or alkaline earth metal ion; Rv обозначает алкил;R v is alkyl; е есть целое число от 0 до 15;e is an integer from 0 to 15; f есть целое число от 0 до 15;f is an integer from 0 to 15; g есть целое число от 0 до 15; иg is an integer from 0 to 15; and n есть целое число от 0 до 10n is an integer from 0 to 10 при условии, что когда NRaRb является:provided that when NR a R b is:
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 тогда, если W-связь Z не является -C(O)-NH- или -NHC(O)-;then if the W bond of Z is not —C (O) —NH— or —NHC (O) -; и если Z является связью, W не является связью, -C(O)-NH- или -NHC(O)-.and if Z is a bond, W is not a bond, —C (O) —NH— or —NHC (O) -. 2. Соединение по п.1, у которого Rv обозначает метил, этил, н-пропил, изопропил, н-бутил, изобутил или трет-бутил.2. The compound according to claim 1, wherein R v is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl. 3. Соединение по п.2, у которого Rv обозначает метил.3. The compound according to claim 2, in which R v denotes methyl. 4. Соединение по п.1, у которого каждый Rt независимо обозначает Н или трет-бутил.4. The compound according to claim 1, in which each R t independently represents H or tert-butyl. 5. Соединение по п.4, у которого Rt обозначает Н.5. The compound according to claim 4, in which R t denotes N. 6. Соединение по п.1, у которого е есть целое число от 0 до 4, f есть целое число от 0 до 12 и g есть целое число от 0 до 6.6. The compound of claim 1, wherein e has an integer from 0 to 4, f is an integer from 0 to 12, and g is an integer from 0 to 6. 7. Соединение по п.1, у которого W обозначает -C(O)-NH-.7. The compound according to claim 1, in which W is —C (O) —NH—. 8. Соединение по п.1, представляющее:8. The compound according to claim 1, representing:
Figure 00000013
,
Figure 00000014
,
Figure 00000013
,
Figure 00000014
,
Figure 00000015
,
Figure 00000016
,
Figure 00000015
,
Figure 00000016
,
Figure 00000017
,
Figure 00000018
,
Figure 00000017
,
Figure 00000018
,
Figure 00000019
,
Figure 00000020
,
Figure 00000019
,
Figure 00000020
,
Figure 00000021
,
Figure 00000022
Figure 00000021
,
Figure 00000022
Figure 00000023
,
Figure 00000024
,
Figure 00000023
,
Figure 00000024
,
Figure 00000025
,
Figure 00000026
,
Figure 00000025
,
Figure 00000026
,
Figure 00000027
,
Figure 00000028
,
Figure 00000027
,
Figure 00000028
,
Figure 00000029
,
Figure 00000030
или
Figure 00000029
,
Figure 00000030
or
Figure 00000031
или
Figure 00000031
or или его фармацевтически приемлемую соль или сольват;or a pharmaceutically acceptable salt or solvate thereof; е есть целое число от 0 до 10;e is an integer from 0 to 10; f есть целое число от 0 до 12;f is an integer from 0 to 12; g есть целое число от 0 до 12; иg is an integer from 0 to 12; and n есть целое число от 0 до 10.n is an integer from 0 to 10. 9. Соединение по п.1, у которого Z обозначает -NH-C(O)-.9. The compound according to claim 1, wherein Z is —NH — C (O) -. 10. Соединение по п.1, у которого Z обозначает -C(O)-NH-CH(COOH)-.10. The compound according to claim 1, wherein Z is —C (O) —NH — CH (COOH) -. 11. Соединение по п.1, у которого Z обозначает -NH-C(O)-CH(NH2)-.11. The compound according to claim 1, wherein Z is —NH — C (O) —CH (NH 2 ) -. 12. Комплекс, содержащий металл и соединение по п.1.12. The complex containing metal and the compound according to claim 1. 13. Комплекс по п.12, у которого металлом является Re, Тс, Y, Lu, Ga, In или Cu.13. The complex according to item 12, in which the metal is Re, Tc, Y, Lu, Ga, In or Cu. 14. Комплекс по п.12, у которого металлом является какой-либо радионуклид.14. The complex of claim 12, wherein the metal is any radionuclide. 15. Комплекс по п.14, у которого металлом является технеций-99m, рений-186 или рений-188.15. The complex of claim 14, wherein the metal is technetium-99m, rhenium-186 or rhenium-188. 16. Комплекс по п.12, у которого NRaRb представляет16. The complex according to item 12, in which NR a R b represents
Figure 00000032
и
Figure 00000032
and металл, выбираемый из группы, состоящей из Y, Ga, Lu, In и Cu.a metal selected from the group consisting of Y, Ga, Lu, In and Cu. 17. Комплекс по п.12, представляющий:17. The complex according to item 12, representing:
Figure 00000033
,
Figure 00000034
,
Figure 00000033
,
Figure 00000034
,
Figure 00000035
,
Figure 00000036
,
Figure 00000035
,
Figure 00000036
,
Figure 00000037
,
Figure 00000038
,
Figure 00000037
,
Figure 00000038
,
Figure 00000039
,
Figure 00000040
,
Figure 00000039
,
Figure 00000040
,
Figure 00000041
,
Figure 00000042
,
Figure 00000041
,
Figure 00000042
,
Figure 00000043
,
Figure 00000044
,
Figure 00000043
,
Figure 00000044
,
Figure 00000045
,
Figure 00000046
,
Figure 00000045
,
Figure 00000046
,
Figure 00000047
,
Figure 00000048
,
Figure 00000047
,
Figure 00000048
,
Figure 00000049
,
Figure 00000050
,
Figure 00000049
,
Figure 00000050
,
Figure 00000051
или
Figure 00000052
или
Figure 00000051
or
Figure 00000052
or или его фармацевтически приемлемую соль или сольват;or a pharmaceutically acceptable salt or solvate thereof; М обозначает Re, Тс, Y, Lu, Ga, In или Cu;M is Re, Tc, Y, Lu, Ga, In or Cu; е есть целое число от 0 до 10;e is an integer from 0 to 10; f есть целое число от 0 до 12;f is an integer from 0 to 12; g есть целое число от 0 до 12; иg is an integer from 0 to 12; and n есть целое число от 0 до 10.n is an integer from 0 to 10. 18. Фармацевтический состав, содержащий соединение по любому из предыдущих пунктов, его фармацевтически приемлемую соль или сольват и фармацевтически приемлемый наполнитель.18. A pharmaceutical composition comprising a compound according to any one of the preceding claims, a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutically acceptable excipient. 19. Метод визуализации какой-либо области у пациента, включающий: введение пациенту диагностически эффективного количества соединения по любому из предыдущих пунктов, его фармацевтически приемлемой соли или сольвата и получение изображения этой области у пациента.19. A method of visualizing a region in a patient, comprising: administering to a patient a diagnostically effective amount of a compound according to any one of the preceding paragraphs, a pharmaceutically acceptable salt or solvate thereof, and obtaining an image of the region in a patient. 20. Метод визуализации ткани, такой как ткань селезенки, ткани почки или экспрессирующая PSMA опухолевая ткань, включающий осуществление контакта ткани с комплексом, содержащим радиоактивный металл и соединение, содержащее группу формулы:20. A method for visualizing tissue, such as spleen tissue, kidney tissue, or PSMA expressing tumor tissue, comprising contacting the tissue with a complex containing a radioactive metal and a compound containing a group of the formula:
Figure 00000053
,
Figure 00000054
или
Figure 00000053
,
Figure 00000054
or ее фармацевтически приемлемую соль или сольват.a pharmaceutically acceptable salt or solvate thereof. 21. Метод по п.20, в котором тканью является экспрессирующая PSMA опухолевая ткань. 21. The method of claim 20, wherein the tissue is PSMA expressing tumor tissue.
RU2011127468/04A 2008-12-05 2009-12-04 Technetium- and rhenium-bis(heteroaryl) complexes and methods for using them for psma inhibition RU2532912C2 (en)

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