RU2002128004A - Содержащие гетероциклическую боковую цепь ингибиторы металлопротеиназы - Google Patents
Содержащие гетероциклическую боковую цепь ингибиторы металлопротеиназыInfo
- Publication number
- RU2002128004A RU2002128004A RU2002128004/04A RU2002128004A RU2002128004A RU 2002128004 A RU2002128004 A RU 2002128004A RU 2002128004/04 A RU2002128004/04 A RU 2002128004/04A RU 2002128004 A RU2002128004 A RU 2002128004A RU 2002128004 A RU2002128004 A RU 2002128004A
- Authority
- RU
- Russia
- Prior art keywords
- group
- heterocycloalkyl
- alkyl
- heteroalkyl
- hydrogen
- Prior art date
Links
- 239000003475 metalloproteinase inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000004404 heteroalkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 15
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 238000009776 industrial production Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
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- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Claims (14)
1. Соединение, имеющее структуру, соответствующую формуле (I)
отличающееся тем, что
(A) R1 выбран из -ОН и -NHOH;
(B) R2 выбран из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкилалкил, гетероциклоалкилалкил, арилалкил и гетероарилалкил;
(C) А означает замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в кольце, из которых 1-3 являются гетероатомами; или А может быть связан с R2, где вместе они образуют замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в кольце, из которых 1-3 являются гетероатомами;
(D) n = 0-4;
(Е) Е выбран из группы, включающей ковалентную связь, С1-С4-алкил, -С(=O)-, -С(=O)O-, C(=O)N(R3)-, -SO2 и -C(=S)N(R3)-, где R3 выбран из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкил, гетероциклоалкил, арил, арилалкил, гетероарил и гетероарилалкил;
(F) X выбран из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, арил, арилалкил, гетероарил, гетероарилалкил, циклоалкил, гетероциклоалкил, -C(=O)R4, -C(=O)OR4, -C(=O)NR4R4’ и -SO2R4, где R4 и R4’ независимо выбраны из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, циклоалкил, гетероциклоалкил, арил, арилалкил, гетероарил и гетероарилалкил; или Х и R3 соединены, образуя замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в кольце, из которых 1-3 являются гетероатомами;
(G) G выбран из группы, включающей: -S-, -О-, -N(R5)-, -C(R5)=C(R5’)-, -N=C(R5)- и -N=N-, где каждый из R5 и R5’ независимо выбраны из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, арил, гетероарил, циклоалкил и гетероциклоалкил;
(Н) Z выбран из группы, включающей (1) циклоалкил и гетероциклоалкил; (2) -L-(CR6R6’)aR7,
где (a) а = 0-4;
(b) L выбран из группы, включающей: -C≡C-, -CH=CH-, -N=N-, -О-, -S- и -SO2-;
(c) каждый из R6 и R6’ независимо выбран из группы, включающей водород, алкил, алкенил, алкинил, арил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил, галоген, галогеналкил, гидрокси и алкокси;
(d) R7 выбран из группы, включающей: водород, арил, гетероарил, алкил, алкенил, алкинил, гетероалкил, галогеналкил, гетероциклоалкил и циклоалкил; и, если L означает -С=С- или -СН=СН-, то R7 может также быть выбран из –C(=O)NR8R8’, где (i) R8 и R8’ независимо выбраны из группы, включающей: водород, алкил, алкенил, алкинил, галогеналкил, гетероалкил, арил, гетероарил, циклоалкил и гетероциклоалкил, или (ii) R8 и R8’, вместе с атомом азота, к которому они присоединены, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 1-3 являются гетероатомами;
(3) –NR9R9’,
где (а) каждый из R9 и R9’ независимо выбран из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, арил, гетероарил, циклоалкил, гетероалкил и -С (=O)-Q-[CR10R10’)bR11,
где (i) b = 0-4;
(ii) Q выбран из ковалентной связи и -N(R12)-;
(iii) каждый из R10 и R10' независимо выбран из группы, включающей: водород, алкил, алкенил, алкинил, арил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил, галоген, галогеналкил, гидрокси и алкокси; R11 и R12 (i) каждый независимо выбран из группы, включающей: водород, алкил, алкенил, алкинил, гетероалкил, галогеналкил, арил, гетероарил, циклоалкил и гетероциклоалкил, или (ii) вместе с атомами, с которыми они связаны, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 1-3 являются гетероатомами; или R9 и R12, вместе с атомами азота, с которыми они связаны, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 2-3 являются гетероатомами; или
(b) R9 и R9’, вместе с атомом азота, с которым они связаны, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 1-3 являются гетероатомами; и
где (a) Е’ и М независимо выбраны из группы, включающей -СН- и -N-;
(b) L’ выбран из группы, включающей -S-, -О-, -N(R14)-, -С(R14)=С(R14’),-N=C(R14)- и -N=N-, где каждый из R14 и R14’ независимо выбран из группы, включающей водород, алкил, алкенил, алкинил, гетероалкил, арил, гетероарил, циклоалкил и гетероциклоалкил;
(c) с = 0-4;
(d) каждый из R13 и R13’ независимо выбран из группы, включающей водород, алкил, алкенил, алкинил, арил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил, галоген, галогеналкил, гидрокси и алкокси;
(e) А’ выбран из группы, включающей ковалентную связь, -О-, -SOd-, -C(=O)-, -C(=O)N(R15)-, -N(R15)- и -N(R15)С(=O)-; где d равно 0-2 и R15 выбран из группы, включающей: водород, алкил, алкенил, алкинил, арил, гетероарил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил и галогеналкил;
(f) G’ означает - (CR16R16’)e-R17,
где е равно 0-4;
каждый из R16 и R16’ независимо выбран из группы, включающей: водород, алкил, алкенил, алкинил, арил, гетероалкил, гетероарил, циклоалкил, гетероциклоалкил, галоген, галогеналкил, гидрокси, алкокси и арилокси; и R17 выбран из группы, включающей: водород, алкил, алкенил, алкинил, галоген, гетероалкил, галогеналкил, арил, гетероарил, циклоалкил и гетероциклоалкил; или R16 и R17, вместе с атомами, с которыми они связаны, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 1-3 являются гетероатомами; или R13 и R17, вместе с атомами, с которыми они связаны, объединены с образованием необязательно замещенного гетероцикла с 5-8 атомами в кольце, из которых 1-3 являются гетероатомами;
или оптический изомер, диастереомер или энантиомер для формулы (I), или их фармацевтически приемлемая соль, или биогидролизуемый амид, сложный эфир или имид.
2. Соединение по п.1, отличающееся тем, что А и R2 не объединяются с образованием кольца, и что А означает замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в кольце и 1-3 гетероатомами в кольце.
3. Соединение по п.1, отличающееся тем, что А и R2 вместе образуют замещенный или незамещенный моноциклический гетероциклоалкил с 3-8 атомами в кольце и 1-3 гетероатомами в кольце.
4. Соединение по любому из пп.1, 2 или 3, отличающееся тем, что Х выбран из группы, включающей водород, алкил, гетероалкил, арил, арилалкил, гетероарил, гетероарилалкил, циклоалкил или гетероциклоалкил.
5. Соединение по любому из пп.1, 2 или 3, отличающееся тем, что Х и R3 объединены с образованием замещенного или незамещенного моноциклического гетероциклоалкила с 3-8 атомами в кольце и 1-3 гетероатомами в кольце.
6. Соединение по любому из предшествующих пунктов, отличающееся тем, что G выбран из -S- и -СН=СН-.
8. Соединение по любому из предшествующих пунктов, отличающееся тем, что Е выбран из группы, включающей ковалентную связь, C1-С3-алкил, -С(=O), -С(=O)O-, -C(=O)N(R3)-и –SO2-.
9. Соединение по любому из предшествующих пунктов, отличающееся тем, что R2 выбран из группы, включающей водород и алкил.
10. Соединение по любому из предшествующих пунктов, отличающееся тем, что n = 0 или 1.
11. Фармацевтическая композиция, включающая (a) безопасное и эффективное количество соединения по любому из предшествующих пунктов и (b) фармацевтически приемлемый носитель.
12. Применение соединения по любому из предшествующих пунктов для промышленного получения лекарственного средства для лечения заболевания, связанного с нежелательной активностью металлопротеаз в организме млекопитающего.
13. Применение по п.12, отличающееся тем, что указанным заболеванием является артрит и оно выбрано из группы, включающей остеоартрит и ревматоидный артрит.
14. Применение по п.12, отличающееся тем, что указанным нарушением является раковая опухоль, и данное лечение предупреждает или останавливает рост опухолей и метастазов.
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US20030171400A1 (en) | 2003-09-11 |
AR033356A1 (es) | 2003-12-17 |
CA2404076A1 (en) | 2001-09-27 |
WO2001070690A1 (en) | 2001-09-27 |
MA25782A1 (fr) | 2003-07-01 |
AU2001245863A1 (en) | 2001-10-03 |
CZ20023180A3 (cs) | 2003-02-12 |
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MXPA02009312A (es) | 2003-03-12 |
NO20024521D0 (no) | 2002-09-20 |
HUP0300262A2 (hu) | 2003-06-28 |
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