RU2009133846A - Новые производные гидантоина в качестве ингибиторов металлопротеиназ - Google Patents
Новые производные гидантоина в качестве ингибиторов металлопротеиназ Download PDFInfo
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- RU2009133846A RU2009133846A RU2009133846/04A RU2009133846A RU2009133846A RU 2009133846 A RU2009133846 A RU 2009133846A RU 2009133846/04 A RU2009133846/04 A RU 2009133846/04A RU 2009133846 A RU2009133846 A RU 2009133846A RU 2009133846 A RU2009133846 A RU 2009133846A
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- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical class O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 230000003993 interaction Effects 0.000 claims abstract 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- RNKWPUZHQPNTNU-LJQANCHMSA-N (5s)-5-[[6-(4-chlorophenyl)-3,4-dihydro-1h-2,7-naphthyridin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=CC(Cl)=CC=3)=NC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O RNKWPUZHQPNTNU-LJQANCHMSA-N 0.000 claims abstract 2
- ICQYHSNJHJJYCT-HXUWFJFHSA-N (5s)-5-[[6-(4-chlorophenyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=CC(Cl)=CC=3)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O ICQYHSNJHJJYCT-HXUWFJFHSA-N 0.000 claims abstract 2
- BUQOYLRBXGPDSU-LJQANCHMSA-N (5s)-5-methyl-5-[(6-pyridin-3-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC=CC=3)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O BUQOYLRBXGPDSU-LJQANCHMSA-N 0.000 claims abstract 2
- YOECDUXBAFEAQP-GOSISDBHSA-N (5s)-5-methyl-5-[[6-[2-(trifluoromethyl)pyrimidin-5-yl]-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C(F)(F)F)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O YOECDUXBAFEAQP-GOSISDBHSA-N 0.000 claims abstract 2
- DZUUXTVUBNSYHE-JOCHJYFZSA-N 2-[4-[2-[[(4s)-4-methyl-2,5-dioxoimidazolidin-4-yl]methylsulfonyl]-3,4-dihydro-1h-isoquinolin-6-yl]phenyl]acetonitrile Chemical compound C1CC2=CC(C=3C=CC(CC#N)=CC=3)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O DZUUXTVUBNSYHE-JOCHJYFZSA-N 0.000 claims abstract 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 3
- 230000000414 obstructive effect Effects 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 claims 1
- 101000990902 Homo sapiens Matrix metalloproteinase-9 Proteins 0.000 claims 1
- 102100027998 Macrophage metalloelastase Human genes 0.000 claims 1
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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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
- C07D401/12—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 chain containing hetero atoms as chain links
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61P19/00—Drugs for skeletal disorders
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P35/00—Antineoplastic agents
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- C07D401/14—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 three or more hetero rings
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Abstract
1. Соединение формулы (I) или его фармацевтически приемлемая соль ! ! где R1 представляет собой H, галоген, CF3 или CH2CN; ! R2 представляет собой C1-3алкил и ! каждый из A, A1 и B независимо представляет собой CH или N. ! 2. Соединение по п.1, где R1 представляет собой хлоро. ! 3. Соединение по п.1, где R1 представляет собой CF3. ! 4. Соединение по п.1, где R2 представляет собой метил или этил. ! 5. Соединение по п.1, где каждый из A и A1 представляет собой N. ! 6. Соединение по п.1, выбранное из группы, состоящей из: ! (5S)-5-метил-5-({[6-[2-(трифторметил)пиримидин-5-ил]-3,4-дигидроизохинолин-2(1H)-ил]сульфонил}метил)имидазолидин-2,4-диона; ! (5S)-5-({[6-(4-хлорфенил)-3,4-дигидроизохинолин-2(1Н)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона; ! {4-[2-({[(4S)-4-метил-2,5-диоксоимидазолидин-4-ил]метил}сульфонил)-1,2,3,4-тетрагидроизохинолин-6-ил]фенил}ацетонитрила; ! (5S)-5-метил-5-{[(6-пиридин-3-ил-3,4-дигидроизохинолин-2(1H)-ил)сульфонил]метил}имидазолидин-2,4-диона; ! (5S)-5-({[6-(4-хлорфенил)-3,4-дигидро-2,7-нафтиридин-2(1H)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона; ! и его фармацевтически приемлемые соли. ! 7. Способ получения соединения формулы (I), как определено в п.1, или его фармацевтически приемлемой соли, включающий: ! а) взаимодействие соединения формулы (II) ! ! где R2 такой, как определено в формуле (I), и L1 представляет собой уходящую группу, с соединением формулы (III) (или его солью) ! ! где R1, A, A1 и B такие, как определено в формуле (I); или ! б) взаимодействие соединения формулы (V) ! ! где R2 и B такие, как определено в формуле (I), и LG представляет собой уходящую группу; с производным бороновой кислоты формулы (XII) ! ! где R1, A и A1 такие, как определено в формуле (I); или ! в) взаимодействие соединения формулы (IX) !
Claims (15)
1. Соединение формулы (I) или его фармацевтически приемлемая соль
где R1 представляет собой H, галоген, CF3 или CH2CN;
R2 представляет собой C1-3алкил и
каждый из A, A1 и B независимо представляет собой CH или N.
2. Соединение по п.1, где R1 представляет собой хлоро.
3. Соединение по п.1, где R1 представляет собой CF3.
4. Соединение по п.1, где R2 представляет собой метил или этил.
5. Соединение по п.1, где каждый из A и A1 представляет собой N.
6. Соединение по п.1, выбранное из группы, состоящей из:
(5S)-5-метил-5-({[6-[2-(трифторметил)пиримидин-5-ил]-3,4-дигидроизохинолин-2(1H)-ил]сульфонил}метил)имидазолидин-2,4-диона;
(5S)-5-({[6-(4-хлорфенил)-3,4-дигидроизохинолин-2(1Н)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона;
{4-[2-({[(4S)-4-метил-2,5-диоксоимидазолидин-4-ил]метил}сульфонил)-1,2,3,4-тетрагидроизохинолин-6-ил]фенил}ацетонитрила;
(5S)-5-метил-5-{[(6-пиридин-3-ил-3,4-дигидроизохинолин-2(1H)-ил)сульфонил]метил}имидазолидин-2,4-диона;
(5S)-5-({[6-(4-хлорфенил)-3,4-дигидро-2,7-нафтиридин-2(1H)-ил]сульфонил}метил)-5-метилимидазолидин-2,4-диона;
и его фармацевтически приемлемые соли.
7. Способ получения соединения формулы (I), как определено в п.1, или его фармацевтически приемлемой соли, включающий:
а) взаимодействие соединения формулы (II)
где R2 такой, как определено в формуле (I), и L1 представляет собой уходящую группу, с соединением формулы (III) (или его солью)
где R1, A, A1 и B такие, как определено в формуле (I); или
б) взаимодействие соединения формулы (V)
где R2 и B такие, как определено в формуле (I), и LG представляет собой уходящую группу; с производным бороновой кислоты формулы (XII)
где R1, A и A1 такие, как определено в формуле (I); или
в) взаимодействие соединения формулы (IX)
где R1, R2, A, A1 и B такие, как определено в формуле (I);
с карбонатом аммония и цианидом калия;
и возможно после этого получение его фармацевтически приемлемой соли.
8. Фармацевтическая композиция, содержащая соединение формулы (I) или его фармацевтически приемлемую соль по любому из пп.1-6 вместе с фармацевтически приемлемым вспомогательным веществом, разбавителем или носителем.
9. Способ получения фармацевтической композиции по п.8, включающий смешивание соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6 с фармацевтически приемлемым вспомогательным веществом, разбавителем или носителем.
10. Соединение формулы (I) или его фармацевтически приемлемая соль по любому из пп.1-6 для применения в терапии.
11. Применение соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6 в изготовлении лекарственного средства для применения в лечении обструктивного заболевания дыхательных путей.
12. Применение по п.11, где обструктивное заболевание дыхательных путей представляет собой астму или хроническое обструктивное заболевание легких.
13. Применение соединения (I) или его фармацевтически приемлемой соли по любому из пп.1-6 в изготовлении лекарственного средства для применения в лечении ревматоидного артрита, остеоартрита, атеросклероза, рака или рассеянного склероза.
14. Способ лечения заболевания или состояния, опосредованного ММР12 и/или ММР9, включающий введение пациенту терапевтически эффективного количества соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6.
15. Способ лечения обструктивного заболевания дыхательных путей, включающий введение пациенту терапевтически эффективного количества соединения формулы (I) или его фармацевтически приемлемой соли по любому из пп.1-6.
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| SE0403086-2 | 2004-12-17 | ||
| SE0403086A SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Compounds |
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| RU2007126745/04A Division RU2378269C2 (ru) | 2004-12-17 | 2005-12-14 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
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| RU2009133846/04A RU2009133846A (ru) | 2004-12-17 | 2009-09-10 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
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| Country | Link |
|---|---|
| US (1) | US7700604B2 (ru) |
| EP (1) | EP1831196A4 (ru) |
| JP (1) | JP2008524211A (ru) |
| KR (1) | KR20070090923A (ru) |
| CN (1) | CN101080403B (ru) |
| AR (1) | AR051796A1 (ru) |
| AU (1) | AU2005317287B2 (ru) |
| BR (1) | BRPI0517033A (ru) |
| CA (1) | CA2590843A1 (ru) |
| IL (1) | IL183667A0 (ru) |
| MX (1) | MX2007007025A (ru) |
| NO (1) | NO20073571L (ru) |
| NZ (1) | NZ555832A (ru) |
| RU (2) | RU2378269C2 (ru) |
| SA (1) | SA05260410B1 (ru) |
| SE (1) | SE0403086D0 (ru) |
| TW (1) | TW200635916A (ru) |
| UA (1) | UA89801C2 (ru) |
| WO (1) | WO2006065216A1 (ru) |
| ZA (1) | ZA200705076B (ru) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0100903D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0202539D0 (sv) * | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| US7648992B2 (en) * | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| EP1859356B1 (en) * | 2005-03-16 | 2019-07-10 | Sensus Metering Systems Inc. | Method, system, apparatus, and computer program product for determining a physical location of a sensor |
| TW200740769A (en) * | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| AU2009241365B2 (en) | 2008-04-28 | 2015-01-22 | Revalesio Corporation | Compositions and methods for treating multiple sclerosis |
| AR080375A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamida |
| KR20180041662A (ko) * | 2015-07-09 | 2018-04-24 | 미쓰비시 타나베 파마 코퍼레이션 | 신규 이미드 유도체 및 그 의약으로서의 용도 |
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| SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| TW200740769A (en) | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
-
2004
- 2004-12-17 SE SE0403086A patent/SE0403086D0/sv unknown
-
2005
- 2005-12-14 UA UAA200706363A patent/UA89801C2/ru unknown
- 2005-12-14 US US11/721,590 patent/US7700604B2/en not_active Expired - Fee Related
- 2005-12-14 EP EP05815746A patent/EP1831196A4/en not_active Withdrawn
- 2005-12-14 KR KR1020077013484A patent/KR20070090923A/ko not_active Withdrawn
- 2005-12-14 JP JP2007546610A patent/JP2008524211A/ja active Pending
- 2005-12-14 WO PCT/SE2005/001918 patent/WO2006065216A1/en not_active Ceased
- 2005-12-14 CA CA002590843A patent/CA2590843A1/en not_active Abandoned
- 2005-12-14 NZ NZ555832A patent/NZ555832A/en not_active IP Right Cessation
- 2005-12-14 AU AU2005317287A patent/AU2005317287B2/en not_active Ceased
- 2005-12-14 MX MX2007007025A patent/MX2007007025A/es not_active Application Discontinuation
- 2005-12-14 RU RU2007126745/04A patent/RU2378269C2/ru not_active IP Right Cessation
- 2005-12-14 CN CN2005800434419A patent/CN101080403B/zh not_active Expired - Fee Related
- 2005-12-14 BR BRPI0517033-8A patent/BRPI0517033A/pt not_active IP Right Cessation
- 2005-12-15 AR ARP050105274A patent/AR051796A1/es unknown
- 2005-12-16 TW TW094144601A patent/TW200635916A/zh unknown
- 2005-12-17 SA SA05260410A patent/SA05260410B1/ar unknown
-
2007
- 2007-06-04 IL IL183667A patent/IL183667A0/en unknown
- 2007-06-12 ZA ZA200705076A patent/ZA200705076B/xx unknown
- 2007-07-10 NO NO20073571A patent/NO20073571L/no not_active Application Discontinuation
-
2009
- 2009-09-10 RU RU2009133846/04A patent/RU2009133846A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200635916A (en) | 2006-10-16 |
| UA89801C2 (en) | 2010-03-10 |
| AU2005317287B2 (en) | 2009-02-05 |
| US20080032997A1 (en) | 2008-02-07 |
| ZA200705076B (en) | 2008-12-31 |
| EP1831196A1 (en) | 2007-09-12 |
| US7700604B2 (en) | 2010-04-20 |
| NZ555832A (en) | 2009-02-28 |
| CN101080403A (zh) | 2007-11-28 |
| NO20073571L (no) | 2007-09-12 |
| MX2007007025A (es) | 2007-07-04 |
| IL183667A0 (en) | 2007-09-20 |
| JP2008524211A (ja) | 2008-07-10 |
| CA2590843A1 (en) | 2006-06-22 |
| RU2378269C2 (ru) | 2010-01-10 |
| AU2005317287A1 (en) | 2006-06-22 |
| BRPI0517033A (pt) | 2008-09-30 |
| CN101080403B (zh) | 2010-09-08 |
| RU2007126745A (ru) | 2009-01-27 |
| SE0403086D0 (sv) | 2004-12-17 |
| AR051796A1 (es) | 2007-02-07 |
| EP1831196A4 (en) | 2009-11-04 |
| WO2006065216A1 (en) | 2006-06-22 |
| SA05260410B1 (ar) | 2009-02-28 |
| KR20070090923A (ko) | 2007-09-06 |
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