RU2009133846A - Новые производные гидантоина в качестве ингибиторов металлопротеиназ - Google Patents
Новые производные гидантоина в качестве ингибиторов металлопротеиназ Download PDFInfo
- Publication number
- 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
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- methyl
- acceptable salt
- Prior art date
Links
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
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.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0403086-2 | 2004-12-17 | ||
| SE0403086A SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007126745/04A Division RU2378269C2 (ru) | 2004-12-17 | 2005-12-14 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009133846A true RU2009133846A (ru) | 2011-03-20 |
Family
ID=34075236
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007126745/04A RU2378269C2 (ru) | 2004-12-17 | 2005-12-14 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
| RU2009133846/04A RU2009133846A (ru) | 2004-12-17 | 2009-09-10 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007126745/04A RU2378269C2 (ru) | 2004-12-17 | 2005-12-14 | Новые производные гидантоина в качестве ингибиторов металлопротеиназ |
Country Status (20)
| 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 |
| US7648992B2 (en) * | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| MX2007011378A (es) * | 2005-03-16 | 2008-03-18 | Sensus Metering Systems Inc | Metodo, sistema, aparato y producto de programa de computadora para determinar la ubicacion fisica de un 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 |
| JP5539965B2 (ja) | 2008-04-28 | 2014-07-02 | レバレジオ コーポレイション | 多発性硬化症を治療するための組成物および方法 |
| 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 |
| EP3321256A4 (en) * | 2015-07-09 | 2019-04-03 | Mitsubishi Tanabe Pharma Corporation | NOVEL IMIDE DERIVATIVES AND THEIR USE AS A MEDICINE |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2327890A (en) | 1940-04-17 | 1943-08-24 | Parke Davis & Co | Substituted phenoxyalkyl ethers |
| US2745875A (en) | 1953-06-30 | 1956-05-15 | Hoechst Ag | Preparation of nu-acylamino-phenylpropane diols |
| US3452040A (en) | 1966-01-05 | 1969-06-24 | American Home Prod | 5,5-disubstituted hydantoins |
| US3529019A (en) | 1968-04-23 | 1970-09-15 | Colgate Palmolive Co | Alkylaryloxy alanines |
| US3849574A (en) | 1971-05-24 | 1974-11-19 | Colgate Palmolive Co | Alpha-substituted-beta-arylthioalkyl amino-acids,for increasing heart rate |
| US4315031A (en) | 1977-09-01 | 1982-02-09 | Science Union Et Cie | Thiosubstituted amino acids |
| GB1601310A (en) | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| JPS6172762A (ja) | 1984-09-17 | 1986-04-14 | Kanegafuchi Chem Ind Co Ltd | 光学活性ヒダントイン類の製造法 |
| JPS61212292A (ja) | 1985-03-19 | 1986-09-20 | Mitsui Toatsu Chem Inc | Ｄ−α−アミノ酸の製造方法 |
| CA1325222C (en) | 1985-08-23 | 1993-12-14 | Lederle (Japan), Ltd. | Process for producing 4-biphenylylacetic acid |
| GB8618559D0 (en) | 1986-07-30 | 1986-09-10 | Genetics Int Inc | Rhodococcus bacterium |
| US4983771A (en) | 1989-09-18 | 1991-01-08 | Hexcel Corporation | Method for resolution of D,L-alpha-phenethylamine with D(-)mandelic acid |
| NL9000386A (nl) | 1990-02-16 | 1991-09-16 | Stamicarbon | Werkwijze voor de bereiding van optisch aktief aminozuuramide. |
| DK161690D0 (da) | 1990-07-05 | 1990-07-05 | Novo Nordisk As | Fremgangsmaade til fremstilling af enantiomere forbindelser |
| IL99957A0 (en) | 1990-11-13 | 1992-08-18 | Merck & Co Inc | Piperidinylcamphorsulfonyl oxytocin antagonists and pharmaceutical compositions containing them |
| PH31245A (en) | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5308853A (en) | 1991-12-20 | 1994-05-03 | Warner-Lambert Company | Substituted-5-methylidene hydantoins with AT1 receptor antagonist properties |
| US5246943A (en) | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| NL9201230A (nl) | 1992-07-09 | 1994-02-01 | Dsm Nv | Werkwijze voor de bereiding van optisch aktief methionineamide. |
| EP0640594A1 (en) | 1993-08-23 | 1995-03-01 | Fujirebio Inc. | Hydantoin derivative as metalloprotease inhibitor |
| JPH09505310A (ja) | 1993-11-16 | 1997-05-27 | メルク エンド カンパニー インコーポレーテッド | ピペリジンショウノウスルホニルオキシトシン拮抗剤 |
| EP0709375B1 (en) | 1994-10-25 | 2005-05-18 | AstraZeneca AB | Therapeutic heterocycles |
| ZA96211B (en) | 1995-01-12 | 1996-07-26 | Teva Pharma | Compositions containing and methods of using 1- aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| US6048841A (en) | 1995-11-22 | 2000-04-11 | Darwin Discovery, Ltd. | Peptidyl compounds |
| GB9616643D0 (en) | 1996-08-08 | 1996-09-25 | Chiroscience Ltd | Compounds |
| US5919790A (en) | 1996-10-11 | 1999-07-06 | Warner-Lambert Company | Hydroxamate inhibitors of interleukin-1β converting enzyme |
| ATE212619T1 (de) | 1996-10-22 | 2002-02-15 | Upjohn Co | Alpha-amino sulfonyl hydroxamsäure als matrix metalloproteinase inhibitoren |
| EP0983239A1 (en) | 1997-05-06 | 2000-03-08 | Novo Nordisk A/S | Novel heterocyclic compounds |
| PT877019E (pt) | 1997-05-09 | 2002-05-31 | Hoechst Ag | Acidos diaminocarboxilicos substituidos |
| CN1178906C (zh) | 1997-07-31 | 2004-12-08 | 艾博特公司 | 基质金属蛋白酶的逆异羟肟酸盐抑制剂 |
| TW514634B (en) | 1997-10-14 | 2002-12-21 | Lilly Co Eli | Process to make chiral compounds |
| WO1999024399A1 (en) | 1997-11-12 | 1999-05-20 | Darwin Discovery Limited | Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity |
| NZ505968A (en) | 1998-02-04 | 2003-03-28 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix- degrading metallproteinases |
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| JP2002514644A (ja) | 1998-05-14 | 2002-05-21 | デュポン ファーマシューティカルズ カンパニー | メタロプロテイナーゼ阻害剤としての置換アリールヒドロキサム酸 |
| WO1999062880A1 (en) | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of n-heterocyclic carboxylic acids or carboxylic acid isosteres |
| CA2333554A1 (en) | 1998-06-17 | 1999-12-23 | Chu-Baio Xue | Cyclic hydroxamic acids as metalloproteinase inhibitors |
| FR2782082B3 (fr) | 1998-08-05 | 2000-09-22 | Sanofi Sa | Formes cristallines de (r)-(+)-n-[[3-[1-benzoyl-3-(3,4- dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4 -yl]-n-methylacetamide (osanetant) et procede pour la preparation dudit compose |
| US6339101B1 (en) | 1998-08-14 | 2002-01-15 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders |
| JP2002523492A (ja) | 1998-08-29 | 2002-07-30 | ブリティッシュ バイオテック ファーマシューティカルズ リミテッド | タンパク質分解酵素阻害剤としてのヒドロキサム酸誘導体 |
| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| EP1117616B1 (en) | 1998-10-07 | 2003-04-23 | Yazaki Corporation | Sol-gel process using porous mold |
| US6114361A (en) | 1998-11-05 | 2000-09-05 | Pfizer Inc. | 5-oxo-pyrrolidine-2-carboxylic acid hydroxamide derivatives |
| CZ20012006A3 (cs) | 1998-12-18 | 2002-03-13 | Axys Pharmaceuticals, Inc. | Sloučenina a farmaceutický prostředek |
| AU1817700A (en) | 1998-12-31 | 2000-07-24 | Aventis Pharmaceuticals Inc. | 1-carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of mmp-12 |
| US6340691B1 (en) | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| WO2000044770A1 (fr) | 1999-01-28 | 2000-08-03 | Chugai Seiyaku Kabushiki Kaisha | Derives phenethylamine substitues |
| US6294694B1 (en) | 1999-06-04 | 2001-09-25 | Wisconsin Alumni Research Foundation | Matrix metalloproteinase inhibitors and method of using same |
| GB9916562D0 (en) | 1999-07-14 | 1999-09-15 | Pharmacia & Upjohn Spa | 3-Arylsulfonyl-2-(substituted-methyl) propanoic acid derivatives as matrix metalloproteinase inhibitora |
| US20020006920A1 (en) | 1999-07-22 | 2002-01-17 | Robinson Ralph Pelton | Arylsulfonylamino hydroxamic acid derivatives |
| US6266453B1 (en) | 1999-07-26 | 2001-07-24 | Computerized Medical Systems, Inc. | Automated image fusion/alignment system and method |
| PT1078923E (pt) | 1999-08-02 | 2006-07-31 | Hoffmann La Roche | Processo para a preparacao de derivados de benzotiofeno |
| EE200200065A (et) | 1999-08-12 | 2003-04-15 | Pharmacia Italia S.P.A. | 3-aminopürasooli derivaadid, nende valmistamine ja kasutamine vähivastaste toimeainetena ning neid sisaldav farmatseutiline kompositsioon |
| SE9904044D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US20020065219A1 (en) | 2000-08-15 | 2002-05-30 | Naidu B. Narasimhulu | Water soluble thiazolyl peptide derivatives |
| US20020091107A1 (en) | 2000-09-08 | 2002-07-11 | Madar David J. | Oxazolidinone antibacterial agents |
| EP1191024A1 (en) | 2000-09-22 | 2002-03-27 | Harald Tschesche | Thiadiazines and their use as inhibitors of metalloproteinases |
| CN1509275A (zh) * | 2001-03-15 | 2004-06-30 | 金属蛋白酶抑制剂 | |
| SE0100903D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| CA2447475A1 (en) | 2001-05-25 | 2002-12-05 | Chu-Biao Xue | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| GB0114004D0 (en) | 2001-06-08 | 2001-08-01 | Glaxo Group Ltd | Chemical compounds |
| SE0103710D0 (sv) | 2001-11-07 | 2001-11-07 | Astrazeneca Ab | Compounds |
| CA2486350A1 (en) | 2002-06-05 | 2003-12-24 | Kaneka Corporation | Process for producing optically active .alpha.-methylcysteine derivative |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0202693D0 (sv) * | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| GB0221246D0 (en) | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
| US7041693B2 (en) * | 2002-10-04 | 2006-05-09 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| US7132432B2 (en) * | 2003-06-05 | 2006-11-07 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) |
| US20040266832A1 (en) | 2003-06-26 | 2004-12-30 | Li Zheng J. | Crystal forms of 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl pyridine |
| TWI220073B (en) | 2003-07-24 | 2004-08-01 | Au Optronics Corp | Method for manufacturing polysilicon film |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| SE0401763D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Compounds |
| US7648992B2 (en) | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| 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 EP EP05815746A patent/EP1831196A4/en not_active Withdrawn
- 2005-12-14 RU RU2007126745/04A patent/RU2378269C2/ru not_active IP Right Cessation
- 2005-12-14 CA CA002590843A patent/CA2590843A1/en not_active Abandoned
- 2005-12-14 AU AU2005317287A patent/AU2005317287B2/en not_active Ceased
- 2005-12-14 UA UAA200706363A patent/UA89801C2/ru unknown
- 2005-12-14 BR BRPI0517033-8A patent/BRPI0517033A/pt not_active IP Right Cessation
- 2005-12-14 JP JP2007546610A patent/JP2008524211A/ja active Pending
- 2005-12-14 NZ NZ555832A patent/NZ555832A/en not_active IP Right Cessation
- 2005-12-14 MX MX2007007025A patent/MX2007007025A/es not_active Application Discontinuation
- 2005-12-14 CN CN2005800434419A patent/CN101080403B/zh not_active Expired - Fee Related
- 2005-12-14 KR KR1020077013484A patent/KR20070090923A/ko not_active Application Discontinuation
- 2005-12-14 WO PCT/SE2005/001918 patent/WO2006065216A1/en active Application Filing
- 2005-12-14 US US11/721,590 patent/US7700604B2/en not_active Expired - Fee Related
- 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 |
|---|---|
| US7700604B2 (en) | 2010-04-20 |
| AR051796A1 (es) | 2007-02-07 |
| KR20070090923A (ko) | 2007-09-06 |
| JP2008524211A (ja) | 2008-07-10 |
| EP1831196A1 (en) | 2007-09-12 |
| CA2590843A1 (en) | 2006-06-22 |
| US20080032997A1 (en) | 2008-02-07 |
| EP1831196A4 (en) | 2009-11-04 |
| AU2005317287B2 (en) | 2009-02-05 |
| WO2006065216A1 (en) | 2006-06-22 |
| ZA200705076B (en) | 2008-12-31 |
| NO20073571L (no) | 2007-09-12 |
| SE0403086D0 (sv) | 2004-12-17 |
| UA89801C2 (en) | 2010-03-10 |
| SA05260410B1 (ar) | 2009-02-28 |
| RU2007126745A (ru) | 2009-01-27 |
| CN101080403B (zh) | 2010-09-08 |
| BRPI0517033A (pt) | 2008-09-30 |
| RU2378269C2 (ru) | 2010-01-10 |
| MX2007007025A (es) | 2007-07-04 |
| CN101080403A (zh) | 2007-11-28 |
| IL183667A0 (en) | 2007-09-20 |
| TW200635916A (en) | 2006-10-16 |
| NZ555832A (en) | 2009-02-28 |
| AU2005317287A1 (en) | 2006-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2009133846A (ru) | Новые производные гидантоина в качестве ингибиторов металлопротеиназ | |
| RU2007126746A (ru) | Новые производные гидантоина в качестве ингибиторов металлопротеиназ | |
| JP2008524211A5 (ru) | ||
| RU2007101236A (ru) | Новые гидантоиновые производные для лечения обструктивных заболеваний дыхательных путей | |
| RU2394028C2 (ru) | Производные бензилтриазолона в качестве ненуклеозидных ингибиторов обратной транскриптазы | |
| RU2440330C2 (ru) | ПРОИЗВОДНЫЕ 4-(2-АМИНО-1-ГИДРОКСИЭТИЛ)ФЕНОЛА, КАК АГОНИСТЫ β2 АДРЕНЕРГИЧЕСКОГО РЕЦЕПТОРА | |
| RU2373209C2 (ru) | Пирролотриазиновые соединения как ингибиторы киназ | |
| EA200400830A1 (ru) | ПИРИМИДИНОВЫЕ СОЕДИНЕНИЯ, ОТНОСЯЩИЕСЯ К A2b-СЕЛЕКТИВНЫМ АНТАГОНИСТАМ, ИХ СИНТЕЗ И ПРИМЕНЕНИЕ | |
| RU2342383C2 (ru) | ПРОИЗВОДНЫЕ ИМИДАЗОЛ-4-ИЛЭТИНИЛПИРИДИНА, СПОСОБ ИХ ПОЛУЧЕНИЯ (ВАРИАНТЫ) И ПРИМЕНЕНИЕ В КАЧЕСТВЕ АНКСИОЛИТИКА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ЛЕЧЕНИЯ НАРУШЕНИЙ, ОПОСРЕДУЕМЫХ РЕЦЕПТОРОМ mGLuR5 | |
| JP2019529443A5 (ru) | ||
| JP2008524210A5 (ru) | ||
| US20120189580A1 (en) | Anti-infective agents and uses thereof | |
| US20210052585A1 (en) | Substituted 1,1'-biphenyl compounds, analogues thereof, and methods using same | |
| RU2005121667A (ru) | 5-замещенные пиразиновые или пиридиновые активаторы глюкокиназы | |
| JP2005536475A5 (ru) | ||
| RU2009119290A (ru) | Производные гидантоина, используемые в качестве ингибиторов ммр | |
| RU2009133259A (ru) | Производные пиразола в качестве ингибиторов 11-бета-hsd1 | |
| JP2005538955A5 (ru) | ||
| JP2008505874A5 (ru) | ||
| JP4915715B2 (ja) | フェニルピリダジン誘導体及びこれを含有する医薬 | |
| CA2617991A1 (en) | N-phenyl-2-pyrimidine-amine derivatives and process for the preparation thereof | |
| JP2011509290A5 (ru) | ||
| JP2022522312A (ja) | ピロール化合物 | |
| US20230165843A1 (en) | Use and pharmaceutical composition of phenylisoxazolyl methylene-naphthalene-ether derivatives | |
| JP2008509182A5 (ru) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20121001 |