KR950032094A - 3개의 환상 화합물로 치환된 하이드록삼산 유도체 - Google Patents
3개의 환상 화합물로 치환된 하이드록삼산 유도체 Download PDFInfo
- Publication number
- KR950032094A KR950032094A KR1019950009577A KR19950009577A KR950032094A KR 950032094 A KR950032094 A KR 950032094A KR 1019950009577 A KR1019950009577 A KR 1019950009577A KR 19950009577 A KR19950009577 A KR 19950009577A KR 950032094 A KR950032094 A KR 950032094A
- Authority
- KR
- South Korea
- Prior art keywords
- lower alkyl
- hydroxycarbamoyl
- trimethyl
- ethyl
- propionyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001923 cyclic compounds Chemical class 0.000 title 1
- -1 amino, carboxy Chemical group 0.000 claims abstract 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract 46
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 9
- 125000003118 aryl group Chemical group 0.000 claims abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 201000008482 osteoarthritis Diseases 0.000 claims abstract 7
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 125000006239 protecting group Chemical group 0.000 claims abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 14
- 230000002265 prevention Effects 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 230000005764 inhibitory process Effects 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 125000006267 biphenyl group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 1
- LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 claims 1
- PJQCUMVGSKEOMN-UHFFFAOYSA-N 3-cyclohexylpyrrolidine Chemical compound C1NCCC1C1CCCCC1 PJQCUMVGSKEOMN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000001594 aberrant effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- DNGMYXZLJGHHOM-UHFFFAOYSA-N thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCCCN1 DNGMYXZLJGHHOM-UHFFFAOYSA-N 0.000 claims 1
- 101000645291 Bos taurus Metalloproteinase inhibitor 2 Proteins 0.000 abstract 1
- 229940122097 Collagenase inhibitor Drugs 0.000 abstract 1
- 101000669513 Homo sapiens Metalloproteinase inhibitor 1 Proteins 0.000 abstract 1
- 102100039364 Metalloproteinase inhibitor 1 Human genes 0.000 abstract 1
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000002442 collagenase inhibitor Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—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
- C07D233/66—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 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/44—Two oxygen atoms
-
- 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
- C07D401/06—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
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
본 발명은 하기 일반식(Ⅰ)의 하이드록삼산 유도체 및 그의 약학적으로 허용가능한 염을 제공하며, 상기 화합물은 퇴행성 관절 질환, 예를들어 류마티스성 관절염 및 골관절염의 억제 또는 예방, 또는 침습성 종양, 즉 상동맥경화증 또는 다발성 경화증의 치료에 유용한 콜라게나제 억제제이다 :
상기식에서, R1은 사이클로프로필, 사이클로부틸, 사이클로펜틸 또는 사이클로헥실을 나타내고; R2는 N원자를 통해 결합된, 포화된 5-내지 8-원의 모노사이클릭 또는 가교된 N-헤테로사이클릭 고리를 나타내며, 상기 고리가 모노사이클릭인 경우, 고리원으로서 NR4, O, S, SO 또는 SO2를 임의로 함유하고/하거나 하나이상의 C원자가 하이드록시, 저급 알킬, 저급 알콕시, 옥소, 케탈화된 옥소, 아미노, 모노(저급 알킬)아미노, 디(저급 알킬)아미노, 카복시, 저급 알콕시카보닐, 하이드록시메틸, 저급 알콕시메틸, 카바모일, 모노(저급 알킬)카바모일, 디(저급 알킬)카바모일 또는 하이드록시이미노에 의해 임의로 치환되고; R3는 (a) N원자를 통해 결합되고, (b) 추가의 고리원으로서 N, O 및/또는 S, SO 또는 S02를 임의로 함유하고, (C) 결합하는 N원자에 인접한 하나 또는 2개의 C원자 모두가 옥소에 의해 치환되고, (d) 임의로 벤즈융합되거나, 또는 하나 이상의 다른 C원자가 저급 알킬 또는 옥소에 의해 임의로 치환되고/되거나 임의의 추가의 N원자(들)가 저급 알킬 또는 아릴에 의해 임의로 치환된 5-또는 6-원의 N-헤테로사이클릭 고리를 나타내고; R4는 수소, 저급알킬, 아릴, 아르알킬 또는 보호 그룹을 나타내고; m은 1 또는 2를 나타내고; n은 1 내지 4를 나타낸다.
상기 화합물들은 상응하는 신규한 카복실산을 하이드록스아미드화시키거나 또는 상응하는 신규한 벤질옥시카바모일 화합물을 탈보호시킴으로써 제조할수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (27)
- 하기 일반식(Ⅰ)의 화합물 및 그의 약학적으로 허용가능한 염 :상기식에서, R1은 사이클로프로필, 사이클로부틸, 사이클로펜틸 또는 사이클로헥실을 나타내고; R2는 N원자를 통해 결합된, 포화된 5-내지 8-원의 모노사이클릭 또는 가교된 N-헤테로사이클릭 고리를 나타내며, 상기 고리가 모노사이클릭인 경우, 고리원으로서 NR4, O, S, SO 또는SO2를 임의로 함유하고/하거나 하나이상의 C원자가 하이드록시, 저급 알킬, 저급 알콕시, 옥소, 케탈화된 옥소, 아미노, 모노(저급 알킬)아미노, 디(저급 알킬)아미노, 카복시, 저급 알콕시카보닐, 하이드록시메틸, 저급 알콕시메틸, 카바모일, 모노(저급 알킬)카바모일, 디(저급 알킬)카바모일 또는 하이드록시이미노에 의해 임의로 치환되고; R3는 (a) N원자를 통해 결합되고, (b) 추가의 고리원으로서 N, O 및/또는 S, SO 또는 S02를 임의로 함유하고, (c) 결합하는 N원자에 인접한 하나또는2개의 C원자 모두가 옥소에 의해 치환되고, (d) 임의로 벤즈융합되거나, 또는 하나 이상의 다른 C원자가 저급 알킬 또는 옥소에 의해 임의로 치환되고/되거나 임의의 추가의 N원자(들)가 저급 알킬 또는 아릴에 의해 임의로 치환된 5-또는6-원의 N-헤테로사이클릭 고리를 나타내고; R4는 수소, 저급알킬, 아릴, 아르알킬 또는 보호 그룹을 나타내고; m은 1 또는 2률 나타내고; n은 1 내지 4를 나타낸다.
- 제1항에 있어서, R1은 사이클로프로필, 사이클로부틸 또는 사이클로펜틸 나타내고; R2가 N원자를 통해 결합된, -5-, 6-또는7-원의 모노사이클릭 또는 가교된 N-헤테로사이클릭 고리를나타내며, 상기 고리가 모노사이클릭인 경우, 고리원으로서 NR4, O, S, SO 또는 SO2를 임의로 함유하고/하거나 하나 이상의 C원자가 하이드록시, 저급알킬, 저급알콕시, 옥소, 케탈화된 옥소, 아미노, 모노(저급알킬)아미노, 디(저급알킬)아미노, 카복시, 저급 알콕시카보닐, 하이드록시메틸, 저급 알콕시메틸, 카바모일, 모노(저급 알킬)카바모일, 디(저급 알킬)카바모일 또는 하이드록시이미노에 의해 임의로 치환되고; R3가 (a) N원자를 통해 결합되고,(b) 결합하는 N원자에 인접하지 않은 위치 또는 위치들에 추가의 고리원으로서 N, O 및/또는 S를 임의로 함유하고, (c) 결합하는 N원자에 인접한 하나 또는 2개의 C원자 모두가 옥소에 의해 치환되고, (d) 임의로 벤즈융합되거나, 또는 하나이상의 다른 C원자가 저급 알킬 또는 옥소에 의해 임의로 치환되고/되거나 임의의 추가의 N원자(들)가 저급 알킬 또는 아릴에 의해 임의로 치환된 5-또는6-원의 N-헤테로사이클릭 고리를 나타내고; R4가 수소, 저급 알킬 또는 보호 그룹을 나타내는 화합물.
- 제1항 또는 제2항에 있어서, R2가, 하나이상의 C원자가 하이드록시, 저급 알킬, 저급 알콕시, 케틸화된 옥소 또는 모노(저급 알킬)-카바모일에 의해 임의로 치환된 1-피졸리디닐, 피페리디노, 4-아릴-1-피페라지닐, 모르폴리노, 테트라하이드로-1,4-티아진-4-일, 테트라하이드로-1,4-티아진-4-일 1,1-디옥사이드, 티아졸리딘 -3-일, 헥사하이드로아제피노 또는 옥타하이드로아조시노; 또는 및 3-아자비사이클로〔3,2,2〕노난을 나타내는 화합물.
- 제3항에 있어서, R2가 피페리디노 또는 하이드록시피페리디노를 나타내는 화합물.
- 제4항에 있어서, 상기 하이드록시피페리디노가 4-하이드록시피페리디노인 화합물.
- 제1항 내지 5항중 어느 한 항에 있어서, R3가 하기 일반식들의 그룹을 나타내는 화합물 :상기식들에서, R5및 R6는 각각 수소를 나타내거나, 또는 함께 추가의 결합 또는 융합된 벤젠 고리의 나머지 부분을 나타내고; R7은 수소, 저급 알킬 또는 아릴을 나타내고; X는 -CO-, -CH2-, -CH(저급 알킬)-, -C(저급 알킬)2-, -NH-, -N(저급 알킬)-또는 -O-를 나타내거나; 또는 R7이 저급 알킬을 나타내고 X가 -N(저급 알킬)-을 나타내는 경우, 상기 저급 알킬 그룹들은 결합하여 5-, 6-또는 7-원 고리를 형성할 수 있으며; Z는 S, SO 또는 SO2를 나타낸다.
- 제6항에 있어서, R3가 일반식 c)의 그룹을 나타내고, R7이 저급 알킬을 나타내고, X가 -C(저급 알킬)2-를 나타내는 화합물.
- 제7항에 있어서, R3가 3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐을 나타내는 화합물.
- 제1항 내지 8항중 어느 한 항에 있어서, m 및 n이 1을 나타내는 화합물.
- 1-〔3-사이클로프로필-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕피페리딘.
- 1-〔3-사이클로프로필-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-4-피페리디놀.
- 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5 -디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕피페리딘.
- 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-4-피페리디놀.
- 1-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-4-피페리디놀.
- 1-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕피페리딘.
- 제2항에 있어서, 3-〔3-사이클로부틸-2(R)-〔1(R또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-3-아자비사이클로〔3,2,2〕노난, 3-〔3-사이클로프로필-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-3-아자비사이클로〔3,2,2〕노난, 및 3-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일12열)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-3-아자비사이클로〔3,2,2〕노난중에서 선택된 화합물.
- 제1항에 있어서, 1-〔3-사이클로헥실-2(R)-〔1(R또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-l-이미다졸리디닐)에틸〕프로피오닐〕피페리딘, 4-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕테트라하이드로-1,4-티아진,4-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕테트라하이드로-1,4-티아진 S,S-디옥사이드, 4-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕테트라하이드로-1,4-티아진, 4-〔3-사이클로헥실-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕테트라하이드로-1,4-티아진, 3-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-5,5-디메틸-N-프로필-4(R)-티아졸리딘카복스아미드, 4-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕모르폴린, 3-〔3-사이클로펜틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-N,5,5-트리메틸-4(R)-티아졸리딘카복스아미드, 4-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-4-페닐피페라진, 4-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕모르폴린, 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕피롤리딘, 8-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-1,4-디옥사-8-아자스피로〔4,5〕데칸,1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸一2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕-4-메톡시피페리딘, 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕옥타하이드로아조신, 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(5,5-디메틸-2,4-디옥소-3-옥사졸리디닐)에틸〕프로피오닐〕피페리딘, 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-(3,4,4-트리메틸-2,5-디옥소-1-이미다졸리디닐)에틸〕프로피오닐〕헥사하이드로아제핀,1-〔3-사이클로부틸-2(R)-〔2-(헥사하이드로-1,3-디옥소피라졸로〔1,2-a〕〔1,2,4〕트리아졸-2-일)-1(R 또는 S)-(하이드록시카바모일)에틸〕프로피오닐〕피페리딘, 및 1-〔3-사이클로부틸-2(R)-〔1(R 또는 S)-(하이드록시카바모일)-2-프탈이미도에틸〕프로피오닐〕피페리딘중에서 선택된 화합물.
- 하기 일반식(Ⅱ)의 화합물:상기식에서, R1, R2, R3, m 및 n은 제1항에 나타낸 의미를 갖는다.
- 하기 일반식(Ⅳ)의 화합물:상기식에서, R1, R2, R3, m 및 n은 제1항에 나타낸 의미를 갖는다.
- 치료학적 활성 물질로서, 특히 퇴행성 관절 질환의 억제 또는 예방, 또는 침습성 종양, 죽상동맥경화증 또는 다발성 경화증의 치료에 사용하기 위한, 제1항 내지 17항중 어느 한 항에 따른 화합물.
- (a) 하기 일반식(Ⅱ)의 산을 하기 일반식(Ⅲ)의 화합물과 반응시키고, 경우에 따라 반응 생성물중에 존재하는 임의의 디페닐(저급 알킬)실릴 그룹을 절단시키거나, 또는 (b) 하기 일반식(Ⅳ)의 화합물을 접촉 수소화시켜 하기 일반식(I)의 화합물을 수득하고, 경우에 따라, 수득된 일반식(I)의 화합물을 약학적으로 허용가능한염으로 전환시킴을 포함하는, 제1항 내지 제17항중 어느 한 항에 따른 화합물의 제조 방법 :상기식들에서, R1은 사이클로프로필, 사이클로부틸, 사이클로펜틸 또는 사이클로헥실을 나타내고; R2는 N 원자를 통해 결합된, 포화된 5-내지 8-원의 모노사이클릭 또는 가교된 N-헤테로사이클릭 고리를 나타내며, 상기 고리가 모노사이클릭인 경우, 고리원으로서 NR4, O, S, SO 또는 SO2를 임의로 함유하고/하거나 하나이상의 C원자가 하이드록시, 저급 알킬, 저급 알콕시, 옥소, 케탈화된 옥소, 아미노, 모노(저급 알킬)아미노, 디(저급 알킬)아미노, 카복시, 저급 알콕시카보닐, 하이드록시메틸, 저급 알콕시메틸, 카바모일, 모노(저급 알킬)카바모일, 디(저급 알킬)카바모일 또는 하이드록시이미노에 의해 임의로 치환되고; R3는 (a) N원자를 통해 결합되고, (b) 추가의 고리원으로서 N, O 및/또는 S, SO 또는 S02를 임의로 함유하고, (c) 결합하는 N원자에 인접한 하나 또는 2개의 C원자 모두가 옥소에 의해 치환되고, (d) 임의로 벤즈융합되거나, 또는 하나이상의 다른 C원자가 저급 알킬 또는 옥소에 의해 임의로 치환되고/되거나 임의의 추가의 N원자(들)가 저급 알킬 또는 아릴에 의해 임의로 치환된 5-또는 6-원의 N-헤테로사이클릭 고리를 나타내고; R4수소, 저급 알킬, 아릴, 아르알킬 또는 보호 그룹을 나타내고; m은 1 또는 2를 나타내고; n은 1 내지 4를 나타낸다. R1, R2, R3, m 및 n은 제1항에서 정의한 바와 같고, Z는 수소, 트리(저급 알킬)실릴 또는 디페닐(저급 알킬)실릴을 나타내고, Bz는 벤질을 나타낸다.
- 제1항 내지 17항중 어느 한 항에 따른 화합물을 치료학적 불활성 담체 물질과 혼합하고, 상기 혼합물을 생약 투여 형태로 만드는 것을 포함하는, 퇴행성 관절 질환의 억제 또는 예방, 또는 침습성 종양, 죽상동맥경화증 또는 다발성 경화증의 치료에 사용하기 위한 약제의 제조 방법.
- 제l항 내지 17항중 어느 한 항에 따른 화합물 및 치료학척 불활성 담체 물질을 함유하는 약제.
- 제1항 내지 17항중 어느 한 항에 따른 화합물 및 치료학적 불활성 담체 물질을 함유하는, 퇴행성 관절질환의 억제 또는 예방, 또는 침습성 종양, 죽상동맥경화증 또는 다발성 경화증의 치료에 사용하기 위한 약제.
- 질병의 억제 또는 예방, 특히 퇴행성 관절 질환의 억제 또는 예방, 또는 침슴성 종양, 죽상동맥경화증 또는 다발성 경화증의 치료에 사용하기 위한, 제1항 내지 17항중 어느 한 항에 따른 화합물의 용도.
- 퇴행성 관절 질환의 억제 또는 예방, 또는 침습성 종양, 죽상동맥경화증 또는 다발성 경화증의 치료 약제를 제조하기 위한, 제1항 내지 17항중 어느 한 항에 따른 화합물의 용도.
- 제21항에 따른 방법에 따라 제조되는, 제1항 내지 17항중 어느 한 항에 따른 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9408183.3 | 1994-04-25 | ||
| GB9408183.3 | 1994-04-25 | ||
| GB9408183A GB9408183D0 (en) | 1994-04-25 | 1994-04-25 | Hydroxamic acid derivatives |
| GB9501737.2 | 1995-01-30 | ||
| JP9501737.2 | 1995-01-30 | ||
| GBGB9501737.2A GB9501737D0 (en) | 1994-04-25 | 1995-01-30 | Hydroxamic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR950032094A true KR950032094A (ko) | 1995-12-20 |
| KR100232323B1 KR100232323B1 (ko) | 2000-02-01 |
Family
ID=26304768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950009577A KR100232323B1 (ko) | 1994-04-25 | 1995-04-24 | 3개의 환상 화합물로 치환된 하이드록삼산 유도체 |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US5614625A (ko) |
| EP (1) | EP0684240B1 (ko) |
| JP (1) | JP2833647B2 (ko) |
| KR (1) | KR100232323B1 (ko) |
| CN (2) | CN1060472C (ko) |
| AT (1) | ATE195119T1 (ko) |
| AU (1) | AU695248B2 (ko) |
| BG (1) | BG62653B1 (ko) |
| CA (1) | CA2145835C (ko) |
| CZ (1) | CZ283502B6 (ko) |
| DE (1) | DE69518194T2 (ko) |
| DK (1) | DK0684240T3 (ko) |
| ES (1) | ES2150513T3 (ko) |
| FI (1) | FI951962A (ko) |
| GB (1) | GB9501737D0 (ko) |
| GR (1) | GR3034624T3 (ko) |
| HU (2) | HU9801923D0 (ko) |
| IL (1) | IL113419A (ko) |
| IS (1) | IS4281A (ko) |
| LV (1) | LV11319B (ko) |
| MA (1) | MA23514A1 (ko) |
| MY (1) | MY113058A (ko) |
| NO (1) | NO307215B1 (ko) |
| NZ (1) | NZ270965A (ko) |
| PH (1) | PH31542A (ko) |
| PT (1) | PT684240E (ko) |
| RO (1) | RO117325B1 (ko) |
| RU (1) | RU2131425C1 (ko) |
| SK (1) | SK282002B6 (ko) |
| TW (1) | TW442479B (ko) |
| UA (1) | UA44230C2 (ko) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601042D0 (en) * | 1996-01-17 | 1996-03-20 | Smithkline Beecham Plc | Medical use |
| EP0816341A1 (de) * | 1996-07-04 | 1998-01-07 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von chiralen Bernsteinsäurederivaten |
| GB9621814D0 (en) * | 1996-10-19 | 1996-12-11 | British Biotech Pharm | Metalloproteinase inhibitors |
| US5840974A (en) * | 1996-12-04 | 1998-11-24 | Britisch Biotech Pharmaceuticals, Ltd. | Metalloproteinase inhibitors |
| AU5577498A (en) * | 1997-01-31 | 1998-08-25 | Shionogi & Co., Ltd. | Compounds having metalloprotease inhibitory activity |
| US5952507A (en) * | 1997-03-10 | 1999-09-14 | Hoffmann La Roche | Process for manufacture of chiral succinic acid derivatives |
| EP0911324A1 (de) * | 1997-10-03 | 1999-04-28 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von chiralen Bernsteinsäurederivaten |
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| US6239151B1 (en) * | 1998-06-26 | 2001-05-29 | Hoffmann-La Roche Inc. | Compounds as inhibitor of tumor necrosis factor alpha release |
| FR2780402B1 (fr) * | 1998-06-30 | 2001-04-27 | Adir | Nouveaux composes acides carboxyliques et hydroxamiques inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6222039B1 (en) | 1998-07-13 | 2001-04-24 | Hoffman-La Roche Inc. | Process for the preparation of chiral lactones |
| EP0974590A1 (en) * | 1998-07-13 | 2000-01-26 | F. Hoffmann-La Roche Ag | Process for the preparation of chiral lactones by asymetrical hydrogenation |
| US6316633B1 (en) | 1998-09-15 | 2001-11-13 | Hoffman-La Roche Inc. | Process for manufacture of chiral succinic acid derivatives |
| AU4753700A (en) * | 1999-05-11 | 2000-11-21 | F. Hoffmann-La Roche Ag | Process for obtaining a hydroxamic acid |
| JO2258B1 (en) * | 1999-05-11 | 2004-10-07 | اف . هوفمان لاروش ايه جي | Method for preparing hydroxamic acids |
| US6696456B1 (en) | 1999-10-14 | 2004-02-24 | The Procter & Gamble Company | Beta disubstituted metalloprotease inhibitors |
| US6797820B2 (en) | 1999-12-17 | 2004-09-28 | Vicuron Pharmaceuticals Inc. | Succinate compounds, compositions and methods of use and preparation |
| CA2403778A1 (en) * | 2000-03-21 | 2001-09-27 | The Procter & Gamble Company | Carbocyclic side chain containing metalloprotease inhibitors |
| RU2245876C2 (ru) * | 2000-03-21 | 2005-02-10 | Дзе Проктер Энд Гэмбл Компани | Производные сульфонамидов и фармацевтическая композиция на их основе |
| AU2001245862A1 (en) * | 2000-03-21 | 2001-10-03 | The Procter & Gamble Company | Difluorobutyric acid metalloprotease inhibitors |
| WO2002102791A1 (en) * | 2001-06-15 | 2002-12-27 | Vicuron Pharmaceuticals Inc. | Pyrrolidine bicyclic compounds |
| AR036053A1 (es) | 2001-06-15 | 2004-08-04 | Versicor Inc | Compuestos de n-formil-hidroxilamina, un proceso para su preparacion y composiciones farmaceuticas |
| PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| ATE399012T1 (de) | 2002-04-03 | 2008-07-15 | Topotarget Uk Ltd | Carbaminsäurederivate enthaltend eine piperazin verknüpfung als hdac-inhibitoren |
| WO2004065354A1 (en) | 2003-01-17 | 2004-08-05 | Topotarget Uk Limited | Carbamic acid compounds comprising an ester or ketone linkage as hdac inhibitors |
| DK1660471T3 (da) | 2003-08-23 | 2011-08-08 | Vernalis R&D Ltd | Derivater af hydroxamsyre som metalloproteinaseinhibitorer |
| GB0319917D0 (en) * | 2003-08-23 | 2003-09-24 | British Biotech Pharm | Metalloproteinase inhibitors |
| DE102004025901A1 (de) | 2004-05-27 | 2005-12-22 | Consortium für elektrochemische Industrie GmbH | Verfahren zur Herstellung optisch aktiver 3-Alkylcarbonsäuren |
| CA2708281A1 (en) | 2007-12-11 | 2009-08-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| US11192883B2 (en) | 2018-10-26 | 2021-12-07 | University Of South Alabama | Functionalized materials and compounds |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2572072B1 (fr) * | 1984-10-18 | 1989-04-14 | Basf Ag | Procede de preparation de derives d'indole |
| US4743587A (en) * | 1985-09-10 | 1988-05-10 | G. D. Searle & Co. | Hydroxamic acid based collagenase inhibitors |
| IT1230595B (it) * | 1988-10-24 | 1991-10-28 | Ausimont Srl | Perossiacidi immido derivati |
| GB8827308D0 (en) * | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| JP3065636B2 (ja) * | 1989-06-29 | 2000-07-17 | 塩野義製薬株式会社 | ［ジ―ｔｅｒｔ―ブチル（ヒドロキシ）フェニルチオ］置換ヒドロキサム酸誘導体 |
| GB8919251D0 (en) * | 1989-08-24 | 1989-10-04 | British Bio Technology | Compounds |
| CA2073513A1 (en) * | 1990-12-03 | 1992-06-04 | John Robert Porter | Peptidyl derivatives |
| JPH05125029A (ja) * | 1991-11-06 | 1993-05-21 | Yamanouchi Pharmaceut Co Ltd | 新規なアミド化合物又はその塩 |
| US5318964A (en) * | 1992-06-11 | 1994-06-07 | Hoffmann-La Roche Inc. | Hydroxamic derivatives and pharmaceutical compositions |
| AU666727B2 (en) * | 1992-06-25 | 1996-02-22 | F. Hoffmann-La Roche Ag | Hydroxamic acid derivatives |
| AU6554294A (en) * | 1993-04-07 | 1994-10-24 | Glycomed Incorporated | Synthetic matrix metalloprotease inhibitors and uses thereof |
| DE69414396T2 (de) * | 1993-08-09 | 1999-07-15 | Kanebo Ltd | Acylphenylglycin-derivat und dieses als aktivbestandteil enthaltendes vorbeugungs -und heilmittel gegen durch erhöhte collagenaseaktivität verursachte krankheiten |
| WO1995010202A1 (en) * | 1993-10-15 | 1995-04-20 | The Procter & Gamble Company | Elastically extensible mechanical fastening system |
-
1995
- 1995-01-30 GB GBGB9501737.2A patent/GB9501737D0/en active Pending
- 1995-03-29 CA CA002145835A patent/CA2145835C/en not_active Expired - Fee Related
- 1995-04-04 AU AU16271/95A patent/AU695248B2/en not_active Ceased
- 1995-04-05 US US08/417,317 patent/US5614625A/en not_active Expired - Fee Related
- 1995-04-07 TW TW084103323A patent/TW442479B/zh not_active IP Right Cessation
- 1995-04-12 DK DK95105495T patent/DK0684240T3/da active
- 1995-04-12 DE DE69518194T patent/DE69518194T2/de not_active Expired - Fee Related
- 1995-04-12 EP EP95105495A patent/EP0684240B1/en not_active Expired - Lifetime
- 1995-04-12 PT PT95105495T patent/PT684240E/pt unknown
- 1995-04-12 AT AT95105495T patent/ATE195119T1/de not_active IP Right Cessation
- 1995-04-12 ES ES95105495T patent/ES2150513T3/es not_active Expired - Lifetime
- 1995-04-14 MA MA23842A patent/MA23514A1/fr unknown
- 1995-04-18 JP JP7092570A patent/JP2833647B2/ja not_active Expired - Fee Related
- 1995-04-19 IL IL11341995A patent/IL113419A/xx not_active IP Right Cessation
- 1995-04-19 HU HU9801923A patent/HU9801923D0/hu unknown
- 1995-04-19 HU HU9501103A patent/HU216838B/hu not_active IP Right Cessation
- 1995-04-19 SK SK506-95A patent/SK282002B6/sk unknown
- 1995-04-20 NZ NZ270965A patent/NZ270965A/en unknown
- 1995-04-20 PH PH50366A patent/PH31542A/en unknown
- 1995-04-21 MY MYPI95001058A patent/MY113058A/en unknown
- 1995-04-21 RO RO95-00792A patent/RO117325B1/ro unknown
- 1995-04-24 NO NO951555A patent/NO307215B1/no not_active IP Right Cessation
- 1995-04-24 LV LVP-95-103A patent/LV11319B/en unknown
- 1995-04-24 IS IS4281A patent/IS4281A/is unknown
- 1995-04-24 CZ CZ951045A patent/CZ283502B6/cs not_active IP Right Cessation
- 1995-04-24 CN CN95104555A patent/CN1060472C/zh not_active Expired - Fee Related
- 1995-04-24 RU RU95106673A patent/RU2131425C1/ru active
- 1995-04-24 KR KR1019950009577A patent/KR100232323B1/ko not_active IP Right Cessation
- 1995-04-25 BG BG99599A patent/BG62653B1/bg unknown
- 1995-04-25 FI FI951962A patent/FI951962A/fi unknown
- 1995-04-25 UA UA95048363A patent/UA44230C2/uk unknown
-
1996
- 1996-10-29 US US08/741,157 patent/US5698690A/en not_active Expired - Fee Related
- 1996-10-29 US US08/741,158 patent/US5731441A/en not_active Expired - Fee Related
- 1996-10-29 US US08/741,153 patent/US5710167A/en not_active Expired - Fee Related
-
2000
- 2000-02-03 CN CN00101976A patent/CN1095835C/zh not_active Expired - Fee Related
- 2000-10-13 GR GR20000402310T patent/GR3034624T3/el not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR950032094A (ko) | 3개의 환상 화합물로 치환된 하이드록삼산 유도체 | |
| US5447929A (en) | Method of treating joint disorders using hydroxamic derivatives | |
| AU2001242744B2 (en) | Diphenylalkylamine derivatives useful as opioid delta receptor ligands | |
| CZ173398A3 (cs) | Inhibitory metaloproteinasy, farmaceutické prostředky je obsahující a jejich farmaceutické použití, způsob a meziprodukty pro jejich výrobu | |
| KR940018382A (ko) | 5원 헤테로사이클, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| WO1998024806A2 (en) | Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors | |
| FI112483B (fi) | Menetelmä terapeuttisesti käyttökelpoisten 3-[2-[4-(6-fluori-1,2-bentsisoksatsol-3-yyli) -1-piperidinyyli]etyyli]-2-alkyyli-pyrimidin-4-onijohdannaisten valmistamiseksi | |
| US20050148583A1 (en) | Phenoxyalkylamine derivatives useful as opioid delta receptor ligands | |
| US5556909A (en) | Substituted 2-arylcarbonyloxymethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide derivatives and compositions and method of use thereof | |
| FR2464259A1 (fr) | Nouvelles 5-(2-chlorophenyl)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme anticonvulsivants, et leur procede de preparation | |
| KR100426545B1 (ko) | 세린 프로테아제 억제제 | |
| HRP950251A2 (en) | Hydroxamic acid derivatives with tricyclic substitution | |
| JP2001192398A (ja) | セリンプロテアーゼ阻害剤 | |
| SI9300289A (sl) | Derivati hidroksamske kisline | |
| JPH02286675A (ja) | アゾール―１―アルカンアミドおよびそれらの製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20020822 Year of fee payment: 4 |
|
| LAPS | Lapse due to unpaid annual fee |